As I’ve said before, I grew up in Rockland County, NY.*

*I was there for the first time in a while this past week when I had lunch with my parents in Nyack and Nyack is probably one of the very few places in Rockland that has retained anything resembling what it was like to live there when I was young. I also had a really good meal at the Art Cafe.

Rockland County was probably more interesting than I give it credit for generally, but broadly speaking, it’s a pretty unremarkable suburb of New York City. It had cute little towns and it had good schools and bad schools. It had diversity and some arts and culture. It was, in a word, ordinary.

It also had a local newspaper.

Back then, it was the Rockland Journal News*. It’s still served by what I would call a shell of that paper. It’s now the Journal News, having merged with the Westchester version of the paper when the economics of local news (like the economics of basically local anything) became untenable.

*I know everyone thinks they have the best local sports section, but I cannot stress how amazing the Journal News sports section was. They had the best local, regional and national sports coverage possible about every team and I’m not sure how they did it. I wore out that section every day of my childhood

That’s what we’re here to talk about today. The slow, agonizing decline of independent and local journalism and the role that advertising and content investment plays in that decline and (ideally) the potential revitalization of the discipline.

And the first thing we’re going to do is be honest with ourselves as a group. Especially on LinkedIn, I see a lot of self-aggrandizing posts about how someone’s tech platform or technology is busy supporting the growth and nourishment of independent and fair journalism or (far more often) the Open Internet™*. I don’t believe this to be a lie on its face.

*Related but not relevant, I want to start an open internet-based band. It’s either going to be called The Public Domain or Cache Me Outside and we’re looking for a bass player at a minimum right now. Inquire within

But I do think that there’s a difference between supporting journalism in theory and on professional social media and funding it in practice. The very clear reality is that there’s a misalignment between the incentives* of the advertising, media and technology ecosystem and the actual dedication to the funding of journalism.

*I feel like with everything I think about today, misaligned incentives are at the core of the issue

Ad tech runs on optimization, things like efficiency, scale and outcomes. That’s reasonable. The non-specific goal of advertising is to sell more stuff. That’s not really the issue. The economy generally runs on selling stuff. The issue is that the optimization that ad tech runs on rewards attention that is cheap, scalable and targetable. The important nuance to all this is that it’s not about bad actors or intent* necessarily. It’s about how incentives express themselves.

*Although there’s plenty of that if you know where to look

It’s not a bug. The system is doing what it’s designed to do.

And because it’s doing what it’s designed to do, two different things are happening:

You don’t need to look further than the flow of ad spend to see a massive imbalance and issue. For every dollar of digital ad spend that’s pumped through the machine, Meta, Google, Amazon and TikTok get 80-ish cents. Most of the rest goes to large, consolidated media ecosystems like enormous national content creators.

That’s one thing.

The second thing is that cheap, scalable and targetable attention isn’t really attention at all. It’s reach masquerading as attention. And because people reading local anything are not cheap those eyeballs haven’t been bought through local channels. And because those people aren’t being bought through local channels and are being bought as a reach extension by tech platforms sitting in the middle, they can’t scale. And because they can’t scale, they either shut down (bad) or they get swallowed up by a content conglomerate (probably worse).

This is where it gets a little dicey. Corporations typically have one goal: maximizing profit at the expense of basically anything else. That means a lot of things, but it mostly means that whatever it takes to make profit is fair game, including but not limited to, highly partisan-driven entertainment posing as news, poorly vetted editorial and/or increasingly stunt driven programming.

CBS News is openly partisan media, but ad spend continues to flow through Paramount post-Skydance acquisition despite the editorial integrity of a show like 60 Minutes being degraded and the shuttering of CBS News Radio under the guise of “changing dynamics.”* And the same people now own TikTok and are about to buy CNN. What I’d ask the tech platforms who suggest that they’re funding the open internet and real journalism: are there intentions to do anything about that spend?**

*The actual quote is “a shift in radio station programming strategies, coupled with challenging economic realities, has made it impossible to continue the service,” which honestly, it’s like a woman who made a living on podcasts has never heard of podcasts

**Or in the immortal words of Public Enemy, you gotta fight the powers that be

I wish that was the only example. Jeff Bezos bought the Washington Post in 2013 for $250 million. He could take a fraction of his personal wealth and fund the paper into perpetuity. Instead, leadership slashed the newsroom and editorial staff by 1/3. Something like 30-40% of revenue for the Washington Post comes from advertising. Is there any plan to use spending power to create incentives to protect the newsroom?

Over 100 local newspapers in California shut their doors in 2024 alone. I get a newspaper called The Acorn in my driveway for free every week. It’s news entirely focused on my area, hyper-local, civic-minded, lived-in journalism. It’s not scalable, not optimized and not-programmatic friendly, I’m waiting for the day that it stops coming because they can’t afford to print it anymore. It’s not like there aren’t alternatives either. As a for instance, a company like Flytedesk captures the same engaged audiences online as TikTok (an evergreen 18-25) through small, independent campus newspapers and other campus outlets that are a haven for free speech and debate and have a meaningful impact on campus life. But massive investment continues to flow to Google, TikTok, Meta and Amazon.

I hear “we support the open internet and local, independent journalism” But what I see if “if you want to understand what we value, don’t listen to what we say, look at where the money goes.”

The system doesn’t need villains*. The system does the work itself. Buyers optimize toward performance. Platforms optimize toward engagement. Publishers compete in that environment. To be clear, there’s no explicit choice, but the outcome is still very real. No one deciding. Everyone reinforcing. Over time, systems tell the truth that narratives try to soften.

*Remember the Rogue’s Gallery of Villains from the Justice League of America? No point, just asking.

What if we actually meant what we said when we said we want to fund real journalism? How would that actually work?

There’s an obvious place to start and that’s by shifting the narrative. We need to stop asking “did this campaign work?” and start asking “what did this campaign fund?” That requires no new pipes, no new integrations, no new systems or platforms. It only requires reallocations, even small ones matter. $50,000 isn’t meaningful to Google, but I can promise you it’s meaningful to any one of the multitude of local publications that still exist.

What if we shifted 5-10% of spend toward things like local journalism and independent publishers and verified news environments instead of aggregators who take huge cuts of the spend and conglomerates who swallow it into their bottom line without reinvestment?

We can do that by using the technology that already exists. Leverage PMP and curated marketplace structures to build intentional access to trusted journalistic environments, because that doesn’t just value who sees an ad; it also values where the ad runs. Expand the definition of quality beyond things like viewability and fraud and brand safety and introduce additional vectors like context and contribution - what does this publisher or content partner produce?

Let’s solve some of the internal incentive problems of buyers not being rewarded for supporting journalism by tying KPIs to supply quality and publisher diversity and actual allocation to real journalism.

Let’s be actually transparent either through a report or an industry body so we can expand our understanding the percent of spend that goes to platforms vs. publishers, but also have a sense of how much goes to actual journalism vs. things that pose as such. Maybe a “media impact report” that shows the real direction of spend, publicly for all to see.

More than anything, we have to accept the tradeoff. This may reduce short-term efficiency, but it supports long-term ecosystem health. And if we’re unwilling to trade a few points for truth, then we’ve already made the decision.

If we’re not willing to fund journalism, we should stop saying that we do.

With everything going on, I’ve really leaned back on the things that fill my cup. Writing, volunteering, time with my kids. Sometimes, finding the joy in the small things helps you get through the big ones. I hope you can find the small joys as well.

That’s all for this week. Until next time, friends.

I’m not a sci-fi nerd.*

*That’s coming off as a weird defense from an accusation no one made, but I need a punchy sentence to start these things, so here we are.

I do love the original Star Trek series, which is worth noting, and the Twilight Zone. For a good long while, I was obsessed with the Twilight Zone*. In the NYC-area, WPIX Channel 11 would play a Twilight Zone marathon every July 4th weekend and at this point I’ve probably seen every episode 10 times over. The best sci-fi uses the future to analyze the present. The worst sci-fi is Battlefield Earth.**

*”IT’S A COOKBOOK” never fails with the right audience

**In case the Scientologists come after me, I want it known that I’m healthy and not at all suicidal

So I guess I am a bit of a nerd for sci-fi, because I also love Isaac Asimov’s Foundation novels.* It’s a trilogy so you have to invest a bit of time to get through them but they’re not super long either, so you won’t be reading for the rest of your life. And if you don’t want to read them at all, but don’t want to use AI to summarize them, the AppleTV show is not super true to the novels but is probably one of the top 2 or 3 shows they’ve made.

*And his sideburns. RIP.

If you’re looking for a hyper-short summary of the novels, they’re about a mathematician who predicts the collapse of a galactic empire and creates a hidden plan to shorten the coming dark age. The catch is that the unpredictability of humanity may be the one force his equations can’t account for.

I spoke a lot a couple of weeks ago about the practical impact of AI on the future of work. This is more about how the systems we have in place are ill-equipped to deal with the pace at which a technology like AI evolves, which in the absence of guardrails and a semblance of ethics, is the kind of thing that incites entropy and ultimately sows the seeds that lead to the dismantling of order.

The Galactic Empire in Foundation spans millions of worlds. It believes it is permanent. It believes its bureaucracy creates order. It believes decline is something that happens to other civilizations.

Our world feels similarly stable today. Despite all the polarization, dysfunction, and noise, the general scaffolding of the modern world still stands: nation-states, central banks, universities, multinational corporations.

Bureaucracy slows while exponential systems speed up. The empire in Foundation believed in and relied on the centralization of control. AI by its very nature is decentralized and diffuses power. Those two things are at odds and the conflict of the two is probably the single biggest issue the future of humanity faces at scale in the next 5-10 years.

Asimov’s core insight of the novels is that decline is mathematical, not dramatic. There’s no one thing that takes an empire down, but a series of predictable events that brings whole systems to their knees. Asimov called the science of this psychohistory and its flag bearer in the Foundation novels is a mathematician named Hari Seldon.*. Hari Seldon’s discipline doesn’t predict individuals. His predicts masses. He models social momentum. And the great friction of the novel comes early and sets the stage for the narrative arc, which is that model predicts the fall of the Empire.

*The nearest equivalent to psychohistory that I can think of in the real world is moneyball and the nearest equivalent to Hari Seldon is Billy Beane. It’s a series of ongoing analysis that works in aggregate over the long haul, but the smaller the sample size, the more variability in results. Which why those early 2000s As teams did very well in the regular season relative to the amount they spent on their roster, but tended to fail in the playoffs

Seldon says the Empire’s fall is inevitable not because of villainy, but inertia.

We’ve got plenty villainy in our world, but villainy often arises from inertia. Things are good enough (or the bad stuff is happening to others), so we lose motivation to try to make them better. That’s human nature. And when someone comes along with motivation and takes advantage of that complacency (for good or for bad), they face little resistance until it’s too late. Ultimately, that leads to overextended bureaucracy (takes forever to do things), leaders focused on preservation, not adaptation (far more concerned with keeping their job than doing what they’ve been hired to do), technological stagnation disguised as sophistication and arrogance toward peripheral worlds (difference of opinion leads not to conversation, but being outcast for not adhering to the norm).

I’ll stop burying the lede: AI may be our psychohistorical inflection point.

Why do I think this? Well, look at where we are in the lifecycle. Institutions in general are built for linear change, but with AI, we’re facing exponential growth curves. And given how pervasive the letters A and I are right now, companies are racing to deploy it faster than even our already degraded social norms can absorb it. And governments don’t really understand it, so they’re either scrambling to regulate it without foundational knowledge of what it can do or they’re paralyzed by an inability to act.

It’s like trying to regulate television with printing press-era rules. The Empire in Foundation tried to regulate entropy. AI is entropy at scale.

Ineffective leadership tends to have a control reflex. The Emperors in the novels believe they can suppress the inexorable* march of psychohistorical trends and control the uncontrollable. They believe they can suppress dissent and outmaneuver historical forces by managing perception.

*I’ve been trying to get inexorable into a written sentence since I took the SATs, so let’s cross another thing off my bucket list

The overarching issue is that perception doesn’t reverse decline. Action does.

Like anything else, short-term political gains are far more expedient than long term sustainable policy and technical consequence. Why bother creating a framework for long term success if you can create immediate gains for yourself and blame the long term failure on your opponent and win an election down the road? I recognize that a pretty cynical take, but it’s hard not to see when you look at history.

The tension between world leaders attempting to centralize control just as information transfer and power is truly decentralizing is a completely destabilizing construct. And as systems strain, people retreat to smaller identity groups. This is the tribal turn.

Think about history. After the fall of the Roman Empire*, the world fragmented into smaller nation-states. Think about post-colonization Africa as the continent restructured itself along tribal lines within imperial boundaries. Think about post-financial crisis populism. These are all historical disruptors causing massive realignment.

*I still don’t understand this “X is my Roman Empire” thing. I mean, I get what it means, I’m just not sure why that’s the thing, because I legitimately don’t know a single person obsessed with the Roman Empire. Now, if someone had made it “X is my Breaking Bad” or “X is my CrossFit” it would make sense to me because the people who like those things are OBSESSED with those things

AI is a disruptor. And it will cause uneven disruption of labor markets, create elite technocratic classes and increase mistrust in institutions (which aren’t exactly breaking all-time highs in trust right now). All of this increases polarization and polarization is a precursor to fragmentation. In Foundation, outer systems fall first and the center falls last. This big question I keep asking myself is “have our outer systems fallen already?”

Oceans rise; empires fall*. They centralize and overextend, and then they collapse. And new orders emerge from the rubble. To be clear, that’s not an apocalyptic prediction. It’s just the cycle of history. But I don’t think there’s any question that AI is an accelerant to that cycle. And it will accelerate the collapse of existing hegemonies. What of American global dominance? Western institutional frameworks? Traditional labor structures? All at risk.

*Thanks, Lin-Manuel

But let’s take an optimistic turn here. Collapse isn’t only chaos; it’s reorganization. The point of the Foundation novels isn’t doom; it’s compression. Hari Seldon’s message isn’t only empiric collapse and an extended period of darkness. It’s “here’s a plan to reduce the period of darkness from 30,000 years to 1,000 years”. So if I’m being truly optimistic here, AI as an accelerant may actual shorten our real world era cycle of burn.

AI will almost certainly create a dramatic increase in productivity. It will democratize knowledge. It may solve issues of coordination across entities. And it could even strengthen institutions. After all, going back to the novels and the guy who wrote them, Asimov was a proponent of rational planning. He believed in that. But his caution around technological progress was clear: arrogance is the enemy of true progress.

We’re not Hari Seldon. There’s no vault of holographic messages containing an explanation of why something happened according to the psychohistorical predictions. More pointedly: there’s no guaranteed arc.

Our responsibility is to ask the right questions if we want to create the right framework. Are we strengthening our institutions or are we hollowing them out? As power decentralizes, is it happening responsibly? Or, to be a little on the nose, are we building Foundations or defending Empires?

Every empire believes it’s the exception to history. It won’t fall because of its exceptionalism. But psychohistory suggests otherwise and AI will change the order.

Can we shorten the darkness?

This was part 2 - there’s no part 3. I’ve got a few more of these that are half-done and if I can finish them, I’ll publish next week. Otherwise, we’re probably going to take. quick break here to recharge the creative batteries.

Have thoughts about AI and any of this? I’d love to hear them because it’s my current obsession, not really from a usage perspective - although that’s interesting too - but from a historical trends perspective. Pop into my LinkedIn DMs or hit me up at geoff (at) jpegconsult (dot) com.

That’s all for this week. Until next time, friends.

*I love when people ask me what I’m doing, because you can interpret that question so many different ways. Occasionally, I’ll answer with a Nietzsche quote, but most of the time I just say “Nothing much, what are you doing?”

Right now, I’m sitting in a coffee shop staring at this screen and thinking about the next set of newsletters that I want to push out the door. I’ve got a whole lot of ideas and I just dump them into Substack drafts and then when the mood strikes, I just look at the list and pick away at the one that seems most interesting in the moment.

And I never write any of them all at once. I get one of them part of the way there and then I put it down. And when I’m ready again, I’ll pick another and I’ll get that one moving some of the way through and then put it down. If you’re wondering why one thing is about mourning and then the next one is about Skynet and then the next one is about movies, that’s why. I don’t ever do them in order.*

*As it turns out, I do everything this way. My work, cleaning up, putting things away, etc. etc., which isn’t at all annoying to the people around me. I literally stopped writing this to check my email and there were emails I needed for my taxes, so I read those and logged them. To restate that, I did part of my taxes in the middle of writing this.

That’s my process.

And process is the thing that got me thinking about what I’m writing now. We all have different processes because we’re all different people.* The same way we all have different affinities, desires and talents because we all have different ideas of what we want to get out of the things we experience. To paraphrase Alexis Rose, I love this for us.**

*Not to state the obvious

**Schitt’s Creek did a lot of things for the world, but the best one is the gift of “I love that for you”

However, as you may have figured out, there’s a big, hairy BUT there. This isn’t the end.

We talk a lot about “creators” today. And that’s thing I want to talk about now: how rise of the creator has shifted our focus from the process of creating to the performance of output through algorithms and eyeballs. And I think that when we optimize for algorithms instead of actual attention, the risk is that we trade creativity for consistency.

And my sense is that to recover actual creativity, we probably need to rediscover the discipline of process and the necessity of silence.

30 years ago, if you asked anyone on the street what it meant to be a creator, they’d have had a wildly different answer than if you asked someone the same question today. Before, they might have said “someone who makes things” or “someone who follows their curiosity” or “someone who takes something out of their head and makes it real” or something else that pointed to what people do when they take time to pull something from the head and put it out into the world.

Now it means publishing on schedule, feeding the algorithm, maintaining engagement and building an audience, which has shifted the focus from “what am I exploring?” to “what increasingly inflammatory take should I post next?” And that sometimes subtle, sometimes not-so-subtle shift changes the entire enterprise.

That’s the creator economy. It shifts the mindset of creation from “ars gratia artis” to “ars gratia pecuniae.”* It’s not malicious; it’s structural. The incentive to create for the sake of creating is misaligned with platforms that reward consistency independent of quality, volume and predictability. Creativity requires time to foment in a potentially non-linear way. It favors incubation and iteration.

*”Art for art’s sake” and “art for money’s sake” respectively. I’d love to say I constructed that Latin from my head, but I had to look it up

This has all been bouncing around my head for a while, but what crystallized it for me was listening to Rick Rubin’s book The Creative Act: A Way of Being. It’s a good book, but not a perfect one. Given Rick Rubin’s career*, it would have been super interesting to hear how working with some of the acts he worked with informed or reinforced the worldview that he’s discussing. But the book really focuses on the how of creation, not the what. And that’s super interesting to me.

*I find it nearly impossible to believe that anyone reading this doesn’t know who Rick Rubin is, but he’s a hip-hop pioneer who produced early work by LL Cool J, the Beastie Boys, Run-DMC and Public Enemy, to name a few.

At a high level, Rubin’s argument is that creativity is not about productivity; it’s about attention. I’m gonna bring up Rumi again, because this wouldn’t be a newsletter if I didn’t. Rubin’s version of that famous Rumi quote is “The work reveals itself as you go.” But that means working against the algorithm. It means you have to protect things like silence, space, unfinished ideas and your own intuition.

His perspective is that you shouldn’t optimize for frequency. You should optimize for signal. When you have to constantly produce in order to create relevance in an algorithmic construct, you stop experimenting and taking risks and you start just repeating what works. Your output becomes safer, your perspective narrows and you lose the uniqueness of your voice.

In other words, you don’t feel less creative because you lack ideas. You feel less creative because you lack the space to pursue things that are interesting at the expense of things that will be amplified by the platforms. The result is confusing visibility with creation.

It’s time to recapture the process.

First, we need to separate creating from publishing. The goal should be to create things you’re proud of and want to share, but not everything needs to be shared, in the same way that not everything needs to be optimized for consumption. Creation can be the goal, with publishing the byproduct. If the focus is on the output, the consumption will come naturally.

It’s also important to allow for incubation. Meaningful work needs time. It takes patience. It requires a tolerance for uncertainty. It takes courage. And those aren’t fungible assets. I mentioned this above in the context of how I write, but there is work that has sat in my drafts for very extended periods of time. I’ve been working on a piece called “Healthy, Wealthy and Wise” based on a study I read in 2023. It’s unfinished. It’s pushing back against resolution. And so it sits where it is, not as a personal failure, but as something still coming together.

Protect the silence. Gaps are not failures. Gaps are gestation periods. It takes time to create. What outwardly appears as inactivity is often the inward assembling of something more substantial.

Create things that no one is asking for. Innovation typically doesn’t emerge from demand. The ideas that resonate most often begin as private curiosities, pursued without any certainty that they will find an audience at all.

Let your outcomes surprise you. If you already know how a piece will perform: how it will be received, how it will circulate, you’re falling back on creative safety. Your authentic creativity carries the possibility of discovery, and discovery requires letting go of control over how the work will land (or how it will be amplified). It also carries the possibility of failure, which in turn creates personal growth. The point is not to engineer a reaction; it’s to uncover something that didn’t exist before you began.

The creator economy gave us access, which has in many ways given us democratization of distribution channels. But the platforms that control those channels require delivery on a certain cadence to bring consumption of our creations.

But Rick Rubin reminds us that creativity isn’t production; it’s perception. And my great hope is that the future of creativity won’t belong to the fastest, most optimized or most consistent. My great hope is that it will belong to the most attentive, the most patient and the most willing to sit with something until it’s ready to appear.

That’s my hope for the great return to creation.

My intent was the publish my 2nd AI piece this week, but that’s another super heavy one and in the spirit of this piece, I don’t think it’s quite ready yet. That will ideally come next week, but perhaps not.

Some other news:

• I’ve found myself with some open utilization at JPEG in March, so if you’re in the need of a few hours of consulting in the operational, GTM or sales and marketing spaces, please reach out to me here

• Greg and I will be recording Leadership In Season 2 in mid-March! If you have ideas for guests, feel free to email us here

• Finally, I’ll be in NYC for the week of 3/16 for meetings. Let’s hang!

That’s all for this week. Until next time, friends.

I think I spoke about this somewhere along the way, but I used to run a website that published pop culture fiction and satire.

Well, I didn’t do it alone. I did it with my friends Josh and Nick. We called it Yankee Pot Roast and it’s all still out there if you want to look at it and see what we did*. The background is that we found ourselves getting rejected from the online publications that existed at the time (largely McSweeney’s) and just decided to create our own.

*I would not go to YankeePotRoast.org, as it remains wildly infested with malware, but the good people at the Internet Archive will get you what you need

And boy did we have fun with it. Because it was ours and we could. We published what we want. We did absolutely ridiculous things: we did a feature called “I Love The ‘I Love The’”, where we brought in writers and instead of commenting on the year or decade, we commented on the show about the year or decade. We did our own version of the Skin Project, where we hired a model and wrote a story on her in washable marker. We wrote and published an incredibly underrated book. We were prolific. There were shenanigans. We had fun.*

*The way I typically described our fame back then was that we were cool enough to get invited to a Gawker party, but not cool enough to get invited back

And then we “grew up” - our jobs got bigger and so did our families and that meant less time for things that weren’t work or family.

So we closed our doors. To everything there is a season, all things must pass, sic transit gloria, etc., etc., etc.

All of this is prelude to discuss a very real topic: the original cultural promise of AI and automation. The thing that if it existed 15 years ago when we shuttered our beautiful website (with our logo: the hand drawn Stars and Stripes cauldron in which we made the Yankee Pot Roast) might have saved us from having to move on.

The promise of AI and automation was to take away the drudge work (which it has done to some extent) and free human beings up to do the work of creativity, curiosity, care and culture. IMHO, the core things of what it means to be human.

That’s a pretty common hope for new technology. It nearly always carries the promise of freeing people from the shackles of labor, creating wealth for individuals and for society and allowing people to, you know, enjoy their lives a little instead of toiling endlessly until they’re forced to retire or die on the line. Industrial machinery, computing, the internet all carried hopes similar to what we’re pinning on AI and I’ll be generous and say the results have been a pretty mixed bag.

AI (like other innovations) was supposed to remove the worst parts of work. Spoiler alert: it really hasn’t and, another spoiler alert, doesn’t seem to be trending that way.

Instead, we are watching institutions automate creativity first*, preserve drudgery for humans and treat human labor as a temporary inconvenience. So the core tension (and where the AI revolution begins to lose me) is that we seem to be building a future that has the dual impact of automating the very things that it wasn’t supposed to at the expense of those things it should, creating a future that doesn’t liberate but rather stratifies. It’s happened for time immemorial: a small ruling class gains leverage and time and everyone else gets to kick rocks and keep grinding it out under outdated assumptions of what a work week is supposed to look like.**

*I’m old enough to remember the 2023 SAG-AFTRA strike when famed union organizer and rabble rouser Fran Drescher held firm on actors, and not studios, owning the rights to their digital likeness for this very reason. “They would have the right to use your likeness forever in any form without pay or consent” was how she described the studios’ proposal.

**I really don’t want to get hyper political here, but if you want an example of this, look no further than Dr. Oz, who suggested that the GDP could gain $3T if everyone works another year, which is logic-defying, but perfectly illustrative of the overarching point

AI is not failing us because it can’t free us. It’s failing us because those in power have no interest in what it would require in order to free us.

It feels pretty quaint to even talk about now, but in the middle of the 20th century in the aftermath of World War II, automation was viewed as something that was going to revolutionize the way that we lived our lives. And it has, but certainly not in the way that it was envisioned. Automation was once pitched as efficiency that would create abundance which in turn would create leisure which in turn would drive all manner of new culture and art and advancements in civic life. In 1930, no less an accomplished economist as John Maynard Keynes, said “I expect, ten years hence, that there will be work for only fifteen hours a week.” Of course, the war got in the way of that, but that was not an uncommon idea among economists and futurists:

Buckminster Fuller said “We should do away with the absolutely specious notion that everybody has to earn a living.”

Peter Drucker wasn’t as optimistic as Fuller, but predicted that knowledge work and automation would fundamentally reshape labor structures and reduce manual work demands.

John Kenneth Galbraith argued in The Affluent Society that productivity growth had already reduced the necessity of long work hours and that society could choose more leisure if it prioritized it.

And there’s probably 10 other examples if I wanted to do any more research that I already did, but that is the implicit bargain of automation. We give the machines the repetitive, soul crushing work and we let humans invest more deeply in creativity, strategic problem-solving, intellectual curiosity and emotional and social labor that we all set aside at the expense of the drudgery.

That’s why we all are currently sitting in the scenic locale of our choosing, sipping a beverage of our choosing and debating the relative merits of deconstructionism vs. analytics or whatever it is you folks watch on television.

Or what actually happened, which is that productivity skyrocketed (yay!), wages stagnated (boo!), working hours didn’t budge an inch and the vast majority of the benefits pooled upward.

This failure isn’t accidental; it’s conditioned. And it reveals how power adapts faster than ethics.

But it does shine a light on Parkinson’s Law, which I’m sure everyone has had a great deal of experience with. Simply put, work expands to fill the time available*. And in the real world, that means that even when tasks become easier and more doable, that institutions resist shrinking work itself.

*Related but not relevant: in college, I took a class called History of the Future. Every Friday, we had a paper due. And every Thursday night, we sat down and said, “what are we writing about?” and pulled an all-nighter to finish the paper that we knew at the beginning of the week would be due that coming Friday

And the modern inversion of that is that technology reduces effort but expectations expand and availability replaces productivity. The 40-hour work week keeps on keeping on not because it’s necessary, but because it preserves the veneer of what it means to work and it justifies itself by intimating that mere existence is to be earned if you’re a certain kind of worker.

And it’s already manifesting itself with AI in the workplace. This Harvard Business Review article sums it up pretty succinctly. They studied the implementation of generative AI at a US-based tech company for 8 months and found that employees ended up working longer hours at a faster pace and took on a broader scope of tasks once AI was used routinely, even when it wasn’t mandated. Employees reported feeling busier, not less busy.

The popular assumption is that AI will automate work away. Instead, the study suggests that without intentional organizational design and guardrails, AI can expand expectations for speed and output while increasing multitasking and scope creep and normalizing always-on work culture.

The big threat of AI is not that it removes work, but that it exposes how unnecessary much of it already is.

And if you’re a massive corporation with responsibility to Wall Street around FCF, EIBTDA and unrealistic expectations of growth, what would you do? You’d do exactly what’s happening. Instead of (or in addition to) automating scheduling, compliance, reporting and bureaucracy, you’d automate writing, art, music, content and film development and design. Because creative labor is expensive, it’s unionized and it has opinions. With the exception of potentially very expensive, AI isn’t those things. it’s predictable, controlled and controllable and will iterate practically infinitely without complaining that it’s hungry or its eyes hurt because it’s getting older and it can’t find its readers.*

*This might be top of mind for me personally

Creativity was supposed to be the human dividend. Instead, it’s being treated as cheap, replaceable and good enough when AI-generated. And the quiet insult of all of this is that humans are left with cleaning, moderating, annotating and prompting. Right up until those get automated away too*.

*I find Moltbook profoundly disturbing and I’m not sure why more people don’t

The uncomfortable reality is that AI doesn’t just replace jobs. It replaces advancement. Entry-level work is the first to go because those things are incredibly easy to automate. I don’t need 10 recent college grads to build plans on behalf of my advertisers when Claude can do it in fairly short order and doesn’t need bagels in the breakroom. That alone breaks the cycle of skill transmission and creates structural (not cyclical) unemployment: built into the system and permanent for large swaths of society. There won’t be enough meaningful work for everyone.

And as it was with factories, a small ownership class owns the models and the platforms. Everyone else competes for shrinking relevance and is told to reskill endlessly. The big lie of the meritocracy isn’t a failure of effort; it’s a failure of imagination and policy.

Which brings us to the billionaire problem.

When you have extreme wealth paired with tax avoidance, regulatory capture, unfettered and unrestrained investment in campaign finance, what you end up with is disengagement from civic responsibility. And AI only amplifies this. It has concentrated power faster than previous technologies and rewards ownership over contribution.

Which, to be clear, would be completely and totally fine if it weren’t missing the most important part: reinvestment. There has been no reinvestment in education, the arts, any public goods or universal basic supports of any kind. If anything, those things continue to be hollowed out and criticized as “entitlements”. The billionaires want to capture all of the upside of automation with none of the civic responsibilities that come with it and they rely on an outdated moral framework equating worth with toil.

OK, so that was a lot to get out of my fingers. There’s an obvious question to ask here: what can a creative society even look like? First, let’s reframe the bigger question. We shouldn’t be asking “how do we create more jobs?” We should be asking “What do we want people to be free to do?” or “What, other than some mythical notion of productivity, would add value to community?”

Well, not to be repetitive, but investments that are an alternative to simple “production” would be a good start. Invest in culture and the arts, care, education, building community, exploration and research of any kind. Create some new metrics. Instead of ROI, ROAS, ARPU and other metrics of profit and corporate wealth, how about meaning, well-being, cultural wealth and civic engagement.

AI should be a force multiplier for the human condition and its curiosity, not the replacement for it.

Here’s the reality: AI can either cement a neo-feudal order or it can unlock a new renaissance, one of human creativity.

Technology is not destiny. Policy, power, and values decide outcomes.

The tragedy would not be that machines became creative. It would be that humans were never given the chance.

I have a second AI related piece coming that came from a LinkedIn post that I made about Isaac Asimov’s Foundation novels. That will publish after the next newsletter, probably next week but maybe later.

In the meantime, I’m sitting in a coffee shop finishing this up and watching a man on a computer with two monitors and a mouse conduct a conference call. In a public space. I aspire to this level of main character energy.

That’s all for this week. Until next time, friends.

*When I was growing up, we called this the Chinese New Year, but the Lunar New Year is not limited to just the Chinese - the Vietnamese also use the lunar calendar for cultural holidays, for instance - so we say Lunar New Year now and I’m all for inclusivity, so let’s make it happen

When I was a kid, this always meant going out for Chinese food - sometimes the restaurant would hand you a small red envelope that had a small denomination Yuan bill in it and that was super cool. Also, I remember a lot of places had paper placemats that showed the 12* year cycle and each of the animals represented with a little explanation of what it meant (astrologically) to be born in each year. I was born in the Year of the Dragon, which is obviously** the best.

*Three may be the magic number, but I’ll put 12 in as a strong second

**Not obvious

As I’ve said more than once in this space, I’m entering my hippie era. I spend a lot of time thinking about my place in the world, how I can be better, what it means to be a very small part of a very large and complex cosmos.* And with the Lunar New Year here, I took a minute to remember that placemat and think through the year behind and the year ahead - not on the Gregorian timeline but on the lunar one.

*I’m not going to lie: there are many times this overwhelms me. The vastness of time and space can be a lot for my tiny brain to deal with.

I didn’t remember this until I looked it up, but 2025 was the Year of the Snake: inward and strategic. The Year of the Snake is quiet and uncomfortable, but necessary to set the table for the year that follows: The Year of the Horse. The Year of the Horse is the natural progression from a year of introspection: it’s kinetic, forward-driving, and exposed. It’s about momentum, movement and courage.

So while the snake says “take your time to hunt” or “chart your path,” the horse says “pick a direction and go.”*

*This is a true story. When I was maybe 12-13 years old, my parents bought a 10% stake in a racehorse that competed at the Meadowlands and Yonkers racetracks. The horse’s name was Keep The Tip. It won its first 7 races and then we never heard from it again

Shedding isn’t a glamorous process. It’s slow and clunky. The work of the snake doesn’t look like progress in the way we’re conditioned to recognize progress. There’s no announcement. No rebrand. No sudden burst of hustle or public momentum. In fact, shedding often looks like a standstill, like nothing is happening at all, when in reality, everything is happening.

This kind of change is deeply personal. It’s the quiet dismantling of old roles you’ve always relied on. Identities that brought you safety or comfort but no longer fit the person you’re becoming. Narratives about success, security, or who you’re supposed to be that once made sense and now feel suffocating.

For longer than I’d like to admit, I kept living inside versions of myself that had already expired. Not because they were right, but because they were familiar.

Ultimately, you have to have a hard reality: you don’t outgrow skin delicately. You have to tear yourself free.

I often cite my favorite Rumi quote* “when you walk on the way, the way appears — action precedes clarity.” But this was the opposite. I couldn’t build something new while dragging the old systems with me. Before anything could take shape, I had to let go of a lot: borrowed definitions of success, metrics I didn’t choose, timelines I inherited, structures that felt safe but were ultimately pretty limiting. Walking away from them didn’t feel bold. It felt crazy.

*I’m actually paraphrasing when I say this. The actual quote is “When you let yourself be silently drawn by the strange pull of what you really love, it will not lead you astray.”

Clarity didn’t arrive first. In this case, release did. Only after letting go of the old notions of what it meant to be successful did the outlines begin to emerge. That’s the work of the snake. It strips away the unnecessary urgency and frivolous motion. It slows you down long enough to ask the only question that counts:

What’s worth building even if it stays small?

The answer to that question came through leaning into nonprofit and community work as a big part of what I do.

It required letting go of the idea that contribution has to be transactional or that impact only counts if it’s scalable or tied to some future return on the investment. It meant releasing the belief that ambition and service sit on opposite ends of the success spectrum.

Service helped to ground me. It was a necessary reminder that showing up, consistently and quietly, can matter just as much (and in many cases more) as building something profitable. Contribution became a counterweight to ambition. Not a distraction from it, but a stabilizing force.

With that, when the time comes to run, the horse moves differently. Lighter. Truer. More enduring.

At the beginning of 2025, I thought I knew exactly what I wanted to build with JPEG. It turned out that picture was overly influenced by the concept of what I had been conditioned to believe a business should look like, not what I actually wanted to put together. I needed 2025, needed that Year of the Snake, to get rid of the things that were weighing me down.

And now that we’ve done that work, we’re done with endless refinement and quiet preparation that came in the Year of the Snake. In the Year of the Horse, we don’t linger in analysis. The horse chooses. It commits. It moves. Where the snake turns inward, the horse runs outward: into visibility, into friction, into consequence.

Of course, that outward motion carries risk. Exposure always does. Picking a direction means closing off alternatives. Commitment means accepting that you’ll be judged not by intention, but by execution.

But this kind of movement isn’t reckless. It’s earned.

It comes after the shedding. After the subtraction. After the unnecessary weight has been stripped away. The horse runs because it’s lighter, not because it’s impatient.

You can’t leap into something new while clinging to what no longer fits. Momentum without shedding isn’t progress; it’s drag. A lot of people want the Year of the Horse without ever enduring the Year of the Snake. They want motion without discomfort. But the run only works because of what came before it.

The courage to let go is often quieter than the courage to run. It happens without witnesses, without fanfare, and often without certainty, but it’s the most decisive act in the entire story arc.

Shedding creates the space for movement. It makes commitment possible. It turns intention into momentum.

The horse may get the glory. But the snake does the work.

And you can’t skip it.

Special thanks to amazing human and friend of the newsletter Jay Given for the idea for this issue. This was an outgrowth of a long conversation at CES.

I’ve been spending a lot of time thinking and talking about AI (very unique) and my next two posts will be some of my thoughts around the creative aspect of it and where we are in the lifecycle that inevitably accompanies game-changing technologies.

Also, Notes In Motion has a gala coming up! Can you go? Tickets here! If not, would you like to help us in the mission of bringing the arts to underserved kids? Donate here!

Finally, I’m in NYC for meetings on March 2 and 3. Let’s catch up if you’re around!

*If you’re old like me, you remember halftime performances by marching bands and Up With People and I’m going to tell you right now, you do not want to go back to that.

But I’m now a couple of days removed from it. And I can’t stop thinking about it.

Fighting hate with love is difficult. It requires a level of self-discipline and compassion that most of us can only aspire to - think about any occasion that you’ve been provoked or shouted down or told you’re not just wrong for thinking what you think, but wrong for being who you are. I’d imagine that in most of those cases, you escalated or shouted back or said back “I’m not wrong” in a voice that you don’t break out all that often.

And don’t get me wrong: that’s probably the right strategy sometimes. Sometimes the only thing bullies or jerks or government officials understand and cow to is strength. Sometimes, there’s a necessary use of force when combatting the wrong in the world. I’m not naive - I don’t think Ukraine (as a for instance) should just sit there and get pummeled by Russia and say something like “thank you, sir, may I have another?” But I also think it’s important to recognize that most paths in life aren’t that black and white. In many cases, we get to choose our response. And the ongoing calculus of whether we choose peace or violence is a difficult one that’s often overwhelmed by emotion.

I don’t know that I’ve written about this specifically, but most of my writing points toward one thing*: how do we sit with who we are and how we feel and use that as a guidepost to move through our lives? And that manifests itself in a bunch of different ways: how we handle our response to the unexpected, things like grief and loss, what it means to be humane and kind, how do we look at adversity and use it a mechanism to forge growth instead of shrinking in its face.

*Two things if you count these non-sequiturs and asides

There’s another big part of that as well: inclusion vs. exclusion.

And what Bad Bunny showed us more than anything in his performance is that if we tend toward inclusion, if we look around and appreciate both how we’re the same, but also how we’re different, we’re better for it. And if I’m boiling down most of what I see in the world to one fundamental issue, it’s exactly that. We tend toward exclusion, not inclusion. We tend toward drawing lines and building walls, not opening our doors and welcoming people in. We tend toward finding the places we differ and focusing on those things as dividers, not as things that we can look at and understand.*

*I always find it hilarious when people talk about how much they love to travel and then they go to Tokyo and eat at McDonald’s. The Tokyo McDonald’s was never empty when I walked by it

Bad Bunny chose peace. He chose inclusion. He chose to lean into his culture and show the beauty of it. That made his performance all the more special to me (again, not telling you how to feel). I don’t know much Spanish and he was singing quickly enough that it was challenging for me to even catch a word I do know. But what I can say is that he got me on my feet. He got me moving. And he got me crying.

The aesthetic beauty of that performance was unmistakable*. The music was energetic and fun. The celebrity cameos across the performance were fun and exciting to see how many you could find. The subtle and not-so-subtle messaging through the performance resonated. The messaging was clear, as clear as a Jumbotron in a stadium full of people, the only thing more powerful than hate is love. That’s true, isn’t it? Beauty is truth, truth beauty, - that is all/Ye know on earth, and all ye need to know. At least, that’s what it says in the Bible**.

*Whoever designed that deserves a Nobel Prize or something

**This might be John Keats in Ode To a Grecian Urn

And that message: we’re stronger together than we are apart. That’s powerful. And I think the reaction of seeing that statement as an attack says more about the person who feels attacked than it does about the person saying it. Do you tend toward inclusion or exclusion?

I’m not going to sit here and tell you what to think. This is about explaining how I’m thinking about all of this and how I’m using this to inform how I move through the world. For me, I continue to hang on that question. It’s something that’s been bouncing around my brain for a while. Do you tend toward inclusion or exclusion? The way that you behave in answering that question tells me everything I need to know.

For instance, I volunteer a lot of my time. I sit on the board of the high school’s parent’s association, I sit on the board at ASDT/Notes In Motion, I’ve just joined the board of Feeding Matters. I spend a couple of hours a week helping out at my local library. None of this is meant to do anything other than illustrate that all of those activities, all of that time volunteered focuses on one thing: inclusion. Do you tend toward inclusion or exclusion?

That will continue to be the fundamental question for me,

Bad Bunny did a lot of things during his absolutely transcendent Super Bowl halftime show, but for me, more than anything, he showed that sometimes the best way to respond to hate is just simply showing who you are and inviting the person in. Maybe they’ll accept that invitation and maybe they won’t.

But their response is a pretty easy way to figure out who they are.

Well, I found myself sitting and thinking about what to write here. The essay came off my fingers in 45 minutes today, but this ending isn’t really coming that fast. I’m sad about Catherine O’Hara - I think we all are. I’m joyful about the coming months, which will bring needed respite and also some travel for wonderful conversations with people I deeply respect.

That’s all for this week. Until next time, friends.

It’s who I am. It’s why I love conferences like CES. I love talking to people, asking questions, finding out about who they are and what makes them tick. I lean toward inclusion, not exclusion. I love moving through parties that are loud enough to have energy, but quiet enough to have conversations with people.*

*One thing I’m not, though, is super comfortable talking about myself. I nearly deleted that opening like 6 times

That’s just it. I love people. I wrote late last year that I’ve recommitted myself to a couple of things: bringing back the in-person interactions that the Internet and COVID robbed me of and wishing people a beautiful day when I finish my interaction with them. And I’ll say now, as I said then, it’s changed the flow of my day. It has changed how I looked at people and changed how they look back.

Jean-Paul Sartre is known for a lot of things. He’s a pretty pivotal figure in existentialist philosophy and if you’re my age and reading this, he was alive and doing his thing while you were toddling around in diapers, so he’s more “modern” than you think. But what he’s probably known for more than anything is a famous line from his 1944 play No Exit*: “L’enfer, c’est les autres” - “Hell is other people.”**

*If you haven’t read No Exit, it’s worth your time

**The Seinfeld version of this is an interaction between Jerry and Elaine, where she says, “I will never understand people” and Jerry looks up at her and says, “They’re the worst”

Hell is other people has been wrongly interpreted, misunderstood and meme-ified as “people are the worst” for so long that I’m probably swimming against a current that I’ll never catch up with in trying to work through this, but I’m here and as it says in the description of this thing: I think about things and then I write about them. So here we are.

The reality is that thinking of it that way hollows out the actual meaning, as Sartre himself later clarified:

But what I really mean is something totally different. I mean that if relations with someone else are twisted, vitiated, then that other person can only be hell… when we think about ourselves, when we try to know ourselves, we use the knowledge of us which other people already have… But that does not at all mean that one cannot have relations with other people. It simply brings out the capital importance of all other people for each one of us

This isn’t about hating people. It’s about what happens when we outsource our self-definition. In other words, the same social forces that constrain us are also the ones that make growth, meaning, and freedom possible. This is Sartre’s concept of “the gaze.”

When Sartre talks about the gaze, he talks about how other people see us as static, being seen, judged and then fixed in their minds as whatever they see in that moment. The net effect of that is that it can be impossible to break out of that mold. Anyone who started a job early in their career and stayed for years through life changes knows exactly what I’m talking about. You’re seen as who you were, not who you are, and that’s exactly what can prevent your growth in that organization.

We’re turned into the roles we play (job title, reputation) and versions of our worst moments and given expectations we didn’t choose. These become the work identity that calcifies, the social media algorithm that feeds us only Sabrina Carpenter or a family narrative that we can’t escape.

When you think about it like that, hell isn’t other people; it’s being trapped by how other people define us.

And when Sartre sat down with his biographer John Gerassi in 1971, he expanded on this. Sartre confirmed his quote, but also said “That’s only one side of the coin. The other side, which no one seems to mention, is also ‘Heaven is each other.’” He insists that both are true at the same time. Without others, for instance, we have no language, no system of shared values, no self-understanding.*

*We also wouldn’t have people who take their shoes off on airplanes, so it giveth and it taketh away

The mechanism doesn’t change. The outcome does.

Because we can survive on our own, but we thrive as a community. Think about all of the community you’ve built over time and how it’s helped you form and shape your worldview. Mentors who see the potential in us before we do. Friends who reflect our best selves back to us. Partners who hold us accountable. That’s the other side of the gaze. It’s the constructive gaze. It’s being recognized rather than reduced and being challenged rather than confined.

There’s risk in this type of openness, of course. Being seen fully requires a level of vulnerability that can leave you open to pain. But real growth happens between people, not in isolation and that means that paradise isn’t comfort. Paradise is truth. Paradise is friction. But most importantly, paradise is care.

The gaze is the gaze. It’s out there. It’s happening whether you want it to or not. You can’t escape being seen. But you do have choices. You can choose who gets proximity and access. You can choose whose feedback matters. You can choose the rooms you stay in. And those choices matter.

Through leadership, parenting, community, friendship, we’re constantly shaping hell or paradise for others. And as it says in the Bible “with great power comes great responsibility”* We are each other’s environment, so we all bear the responsibility of creating one that helps to nourish, not to deprive.

*This might be Uncle Ben in Spider-Man

Hell is other people, but that’s only one side of the coin … Heaven is also other people. Hell and Heaven are not opposites; they’re outcomes. The people around us don’t just influence our lives, they help author who we become. They help us create. They help us move through what can be a very confrontational and difficult world. But you can choose whose gaze you internalize.

The question isn’t whether other people matter (or whether they’re the best or the worst).

It’s whether we’re brave enough to show up and choose to be the right kind of people.

We haven’t done a “what I’m reading” section here in a while, so here’s a few interesting things:

Jeff Jarvis’s The Web We Weave about how we create a better internet by taking back control

Liar In a Crowded Theater by Jeff Kosseff about how we can combat the lying liars who take advantage of the First Amendment’s protection of lying

Derek Bayer on disconnecting from Big Tech

That’s all for this week, friends. Until next time.

*Well not everyone, but basically everyone. And my favorite comment about CES ever came from my sister who said “I love it when we all go to Vegas to see the same people we see in New York while we eat at the same restaurants we eat at in New York

And while we were at CES, we all met. And ate. And gambled. And while I was standing and chatting with a friend at the roulette table, I watched #5 hit and a couple of guys who I didn’t know win over $1000 each. I’m a sporting guy and I like when the house loses and people win, so I cheered for them. But while I was cheering, I noticed something.

There was a third zero.*

*If you’re not familiar, there’s a variety of ways to bet on roulette. You can bet the colors, red or black. You can bet even or odd. You can bet groups of numbers. Or you can bet the numbers themselves. But in order to win on the zeroes, you have to bet the zeros. They’re green, so they fall outside of the red/black construct of the game. They’re effectively winning house bets.

So I did some quick research. And as it turns out, at some point in the last few years, many casinos added a third green pocket to the roulette wheel. Now, we all know that the games are tilted to the house. That’s not a surprise. But there’s this social contract that we have the casinos: we come and gamble away some money at reasonable odds - as the payout gets bigger, the odds get longer - and they provide free drinks and sometimes a voucher for the buffet if you win or lose enough money. That’s a fair trade.

But something’s happened over the last few years: auto-shufflers bring cards back in to play more quickly, blackjack pays out at 6 to 5 instead of 3 to 2, progressive sucker bets pay out at way less than the actual odds of hitting them. All of these changes are changing that social contract. They all have one thing in common: they shift the odds further toward the house.

Stated more plainly: that third zero gives away the whole game.

Because this isn’t just about Vegas. Or casinos. Or gambling. It’s about America at large in its late stage of enshittification: everything getting marginally worse and optimized past the point of enjoyment. And unless we decide to do something, the people responsible will keep adding zeros to everything we touch.

If you’re not familiar with the term, enshittification was coined a Canadian journalist and author named Cory Doctorow, who used it to describe how platforms tend to degrade due to greed. First, they coddle users. Then they squeeze them. Then they collapse under the weight of their own greed.

But what started in tech has spread like contagion into nearly every corner of modern life: travel, retail, entertainment, housing, even how we buy a goddamn cup of coffee.*

*Here is a perfect example of non-Internet based enshittification: remember how you used to be able to get a cup of coffee outside of your house for $1 and it was pretty good? Now it’s $4.50 for the same size at Starbucks for empirically worse coffee and you have to wait 15 minutes to get it and the place has lines out the door

The common thread isn’t technology. It’s the mindset of late stage capitalism.

A philosophy that sees customers not as humans or long-term relationships to be nurtured, but as short-term yield opportunities. A belief that if something is working, the correct response is to make it just a little more profitable, forever and ever until there’s either no more money or no more people.

The third zero is emblematic. The house was already winning. They just couldn’t help themselves from trying to win just a little more.

You see the same thinking everywhere. Google had the cleanest, most beloved interface in the world. People happily used it every day. And yet, someone still decided the top of the page needed more ads, more AI answers, more paid placement masquerading as “sponsored links”. Not because users demanded it, asked for it or even thought about it, but because the entire system demanded growth.*

*It’s truly stunning how “Don’t be evil” turned into “Sorry we sold all your personal data to Taco Bell so they could sell a couple more Crunchwrap supremes. Maybe if you weren’t such a fat ass, it wouldn’t have worked”

The product didn’t fail. Restraint did. And the roulette story sticks because it’s such a simple, clean example.

The player remembers losing slowly. The rhythm of the game. The social energy. The that implicit contract that I described: “Yes, the house wins but you’ll have fun doing it. Maybe you’ll get drunk”

Later, they come back and realizes something subtle has changed. The game feels adversarial now. The casino logic is easy to understand: more revenue per minute. Faster churn. Higher yield.

But in a lot of cases the player’s* logic is just as clear: “Yeah, sure, but I’m never coming back.” Or “I’m not coming back as often as I would have.” Or “I’ll just spend my money somewhere else that’s just as enjoyable”

*Assuming they don’t have a serious gambling problem. If you live in NY and think you have a problem, call (877) 846-7369

That’s enshittification in a nutshell. Confusing extraction with strategy.

People don’t mind losing money when they know the rules. They mind feeling tricked. They mind when the system starts to feel predatory instead of playful. Once that trust breaks, the relationship is over.

You see this exact dynamic in ad tech. Buyers don’t mind fees. They mind fees that feel hidden, arbitrary, or untethered from real value creation. When simple take-rate models turn into opaque product bundles and black boxes, the question stops being “Is this effective?” and becomes “Who’s stealing what?”*

*Or in the immortal words of Aretha Franklin “Who’s zooming who?” (or more grammatically correctly, “who’s zooming whom?”. Who, the object of the sentence, zooming whom, the subject

The house was already winning. Someone still wanted to add another zero.

Enshittification shows up differently depending on where you look, but the pattern is the same.

Movies and music feel increasingly beaten to death. Endless sequels*. Music optimized for viral clips instead of emotional resonance. Surprise has been replaced by safety, and safety has been optimized into boredom.

*Since Tobey McGuire’s Spider-Man in 2002, there’s been him, Andrew Garfield and Tom Holland, plus the animated ones. 4 reboots in less than 25 years.

Shopping used to feel like a great convenience. Now it feels like a scavenger hunt with a guy on meth. Amazon went from “you’ll get the best version of this in 48 hours” to “pick one of these 74 indistinguishable products and pray that it’s not a piece of shit.”

Housing and work have followed the same path. Finding a place to live became a financial instrument of sub-prime loans, predatory rates and forced shortage. Jobs became a set of policies designed to protect companies from employees rather than empower them. An entire generation learned (correctly) that loyalty is a one-way street.

Concert tickets have been industrialized*. The show itself feels like a curated retail experience.

*Somehow it felt more fair when I went to the small video store in my town, got a bracelet with a number for a lottery, waited in line, worked with an employee tapping into a mainframe who then printed out your tickets on the spot and handed them to you when you paid

And then there’s everyday life, which seems to carry the same ambient hostility.

And let’s not look past ad tech, which deserves its own footnote here. Programmatic made buying easier. Then we strangled it with fee layers, supply-path gymnastics, arbitrage, and endless “value-added” products that mostly add cost, latency, and confusion. What started as simplification metastasized into complexity—because complexity is where margin hides.

Why does everything get worse? It’s not a mystery. It’s math.

Incentives drive behavior, and our incentives reward “more” at all costs. Corporations are trained to optimize KPIs, not experiences, and those KPIs are almost always profit motivated. Public companies prioritize the next earnings call over customer satisfaction. Leaders who find a way to squeeze another two percent of ARPU get promoted.

Enshittification isn’t a bug; it’s a feature. It’s the logical end state of a system where enough is never enough.

In ad tech, this shows up as an arms race of non-innovation innovation: new products that sound sophisticated, promise differentiation, and quietly extract a little more margin while delivering marginal, if any, incremental value.

You feel it in the tiny questions that now accompany daily life: Do I need to read Yelp reviews for a sandwich? Will this ticket link even work? Is this product real or a knockoff with better SEO?

It’s fucking exhausting. And no one wants to live like that.

So how do we reclaim a decent experience? This doesn’t require utopia. It requires agency.

Spend deliberately. Reward the businesses that still care. Stop tolerating places that treat customers like dollar signs.*

*Watch Buy Now on Netflix. It changed my perspective

Walk away from broken systems. You don’t have to play the 000 table. You don’t have to stay on platforms that treat you like a trapped audience. In ad tech terms, not every impression is worth bidding on.

Rebuild community at a human scale. Find the coffee shop, bookstore, or restaurant that actually remembers your name. Those places become comfort in a world that increasingly feels gross and disconnected.

Make your own joy. Host dinners. Travel intentionally. Take back small pieces of your life from the algorithm.

And yes, push for accountability. Basic fairness. Transparency. Guardrails that reward long-term thinking. The things that used to be table stakes for doing good business.

Enshittification has one fatal flaw: it only works if we keep playing.

If we start demanding better, not necessarily loudly, but consistently, the people designing our systems might finally remember that joy, not extraction, was always the real long-term value.

The house wins when we accept the rules without question. It loses when we remember that enjoyment was always the real long-term value.

And that’s a bet still worth making.

OK, you guys, I’m back with the first installment of my 5th (!) year writing this thing.

As always, there’s a lot of things brewing and we’ll see what pans out, but for sure:

• Season 2 of Leadership In will start recording this winter

• JPEG Consulting will be in NYC in February and March and at Possible in April (will you?)

When I was in my mid-20s and writing regularly, I would submit at least one piece every day to some online publication. And in the early 2000s, there were so many sites that published humor or essays or things like that*. The one that remains the most popular that started way back then is McSweeney’s. In online humor magazines as in business, consolidation comes and it comes quickly.

*Off the top of my head: Haypenny, Kittenpants, Parenthetical Note, The Black Table, Opium Magazine, Eyeshot, Pindeldyboz, Flak Magazine

I would say of the probably 150 things that I wrote and submitted from 2001-2002, approximately 5 got published. And that felt both like an amazing hit rate (there were people who had none published) and was insanely infuriating. I had things to say. And so did my friends Josh and Nick. So we did what most people in the same situation do: we complained about it. A lot. And constantly.

But because we got zero external validation from these other pubs, we decided to start our own. We called it Yankee Pot Roast. And YPR did a lot for us: we got to publish whatever we wanted, including whatever we wrote that we wanted to publish. We got a couple of book deals out of it. We made t-shirts. And we got to the point where we had about 50,000 visitors a month. It was a lot of fun. Eventually, life happened, careers and families grew and we shuttered it*.

*The URL itself is still live, I think, but wildly infected with malware

It also gave us an outlet that we so desperately needed.

As I sit here thinking about YPR, I’m also thinking about a question I’ve been circling for a long time and it sits underneath almost everything I try to build or create:

If the people closest to me don’t believe in what I’m doing, do they still believe in me?

It sounds ridiculous even saying it out loud. That’s me being wildly dramatic and unfair to myself. But I guess also brutally honest. And if you’ve ever put something into the world that mattered to you even a little, you’ve probably felt it too. It’s the faint but unmistakable anxiety that the work you pour your energy into doubles as a referendum on who you are as a human.

This past year:

• I launched JPEG Consulting.

• I kept a newsletter going*.

• I started a podcast with Greg**.

• I put my voice, ideas, and work into the world in a way I hadn’t really done in a meaningful way before.

*I assume to the great shock of the 7 people that read it regularly

**Reminder that Leadership In season 2 is going to be a thing

And as exciting as it is to build something new, it also comes with a level of vulnerability that’s easy to look past. When you’re creating anything, whether a business, a body of work, or even your point of view, you’re not just showing people what you’re doing. You’re showing them who you think you might be capable of becoming.

That’s the space where this question shows up and it’s where my rational mind goes out the fire escape and my irrational mind shows up at the front door.*

*This also happens when I don’t get a text back IMMEDIATELY after sending mine

Whenever we create, we’re operating in this constant back-and-forth between self-belief and self-doubt. Self-belief gets you started. Self-doubt refines the work. And it’s this constant push and pull and it’s never completely obvious which voice is the one you should be listening to.

There are moments in my week, it’s almost always when I’m polishing a newsletter draft or thinking through a strategy for a client, where I’ll pause and feel that familiar jolt of irrational doubt:

Is this any good?
Does this matter?
Is anyone going to care?
Am I convincing myself into thinking this is important?*

*Sometimes, probably not, ehhhhh maybe and very much so

Anyone who tries to make something from scratch: builders, creators, leaders, founders, they know that moment well. But because the moment is real and recurring, external validation becomes powerful. Encouragement hits differently when you’re taking risks.

“This really hit for me” keeps the wind in your sails.
”This isn’t exactly right” can derail the momentum you convinced yourself you had.

We want to believe we’re immune to these things, that our own sense of self-worth can carry us through and internal brief is enough, but we’re not. The people around us matter. Their belief matters. Sometimes more than it should.

There’s a simple reason the opinions of people close to us carry more emotional force: we’ve given them access. They know our insecurities, our ambitions, our blind spots. We trust them with the parts of ourselves that aren’t polished. Their perspective is not neutral; it’s intimate.

So when someone in that inner circle believes in what you’re building, it makes you feel capable. Not perfect, not unstoppable, just capable. And capability is the real fuel of long-term work.

But when someone in that same circle doesn’t believe in what you’re building? Or doesn’t see it? Or doesn’t take it seriously?

It can hit a different part of you. Not the logical part. Not the professional part. A much more personal, much more exposed part. And that’s the thing I’ve had to work through this year.

Here’s where I’ve arrived, slowly and with some resistance:

External belief can be fuel, but it cannot be the engine.

When I first started JPEG Consulting, I leaned heavily on the encouragement of people around me. And that support helped me get started. It gave me a sense of legitimacy I didn’t necessarily feel internally at the time. It made the leap feel less like a freefall.

But as the year went on, I realized something uncomfortable: if I used other people’s belief as the determinant of the value of my work, then other people could just as easily designate its failure.

And that’s not healthy. And it’s definitely not the foundation of a long-term creative or entrepreneurial life where constructive and negative feedback come with the territory.

So I made a shift. Not away from caring what people think, but away from needing it to move forward.

I still care what people think. Of course I do. It would be strange if I didn’t*. And I still feel a lift when people respond positively to something I’ve created. That’s human. That’s part of the relationship between creator and universe.

*I feel like saying your don’t care about what other people think is more of an admission than you want it to be

But I no longer let the presence or absence of that belief dictate the legitimacy of the work.

I’m building what I’m building because I believe in it. The newsletter, the consulting and the podcast aren’t experiments in validation or approbation. They’re expressions of who I am and what I want to contribute to the world.

If others believe in them too, that’s a gift. If they don’t, that’s okay. The work still matters. And so do I.

So the real question isn’t:

“Do you believe in what I’m building?”

The healthier question is:

“Do I believe in what I’m building enough to keep going, even if the support isn’t always there?”

And this year, for the first time in a long time, the answer is yes.

OK, dear readers, I’ve got exactly one more of these in my fingertips. It’ll be out in the next couple of weeks, just in time for the holiday break. I’m closing it down for the year on 12/15.

After that, here’s what Q1 looks like right now:

• CES in January - if you’re going to be there, please reach out! I’d love to see you

• IAB ALM in February - same as above

• Right now, I’ve got two trips to NYC planned. One in February for the Notes In Motion Annual Gala (please keep your eyes open here for ticket info, I’d love to see you there. One in March for the NYC Half Marathon. Let’s also find time to meet in NYC.

That’s all for this week. Until next time, friends.

It meant I got to read a lot and it meant I got to have strong opinions about things. And if you know me, you know that I love to read and I have a lot of strong opinions about things.*

*For instance, ketchup on hot dogs. No. Just … no. Crocs on adults. Again, no.

But one of the unexpected benefits of studying history is that it forces you to spend real time with people who understood the world before we did, people who lived through foundational changes, governmental and institutional collapses, revolutions, and rebirths. People whose warnings are often clearer in hindsight than they ever were in the moment.

One of those voices for me is Václav Havel. Havel’s is a name that, fifteen years after his death, feels increasingly absent from our memory. And that’s a mistake, because I don’t know that anyone saw our current moment with as clearly as he did.

Havel was a lot of things: a playwright, an essayist, a dissident who was imprisoned by a Communist regime that feared the power of truth told plainly*. Then, in one of history’s least predictable career trajectories, he became the last president of Czechoslovakia and the first president of the Czech Republic.

*The power of truth told plainly is feared by a lot of people because a lot of people don’t like telling it and even more don’t want to face it

Havel was a gentle guy, philosophical, as non-ideological as one can get, and had very little interest in power for himself. In spite of that, he became one of the most important political figures of the late 20th century and a symbol of the moral force that helped collapse authoritarianism in Eastern Europe.*

*And let’s just say he’s turning over in his grave at people like Viktor Orban in power

Today, outside Central Europe or certain academic circles, he’s largely forgotten. But on July 4, 1994, just a few years after the fall of the Berlin Wall, Havel delivered a lecture at Independence Hall in Philadelphia (published in the New York Times Op-Ed column under “The New Measure of Man” - subscription required) that reads now like prophecy. Liberal democracy was ascendant. Capitalism was triumphant. The future seemed both pre-destined and bright.

Havel instead saw danger.

He saw a tension between the modern age that he believed had already ended and something post-modern that we were stepping into blindly. And crucially (and very insightfully), he believed we were ill-equipped to confront it.

Havel’s point was that the world we inhabited had exhausted itself. The Enlightenment promised that reason, science, and progress would solve human problems, but had proven incomplete. Yes, modernity had created prosperity and, for many, freedom. But it had also created alienation, spiritual directionlessness, and a loss of meaning.

He described the world as a kind of “civilizational rubble,” a place where new meaning was “painfully being born.”

Years ago, those words felt powerful, if a bit melodramatic. Today, they feel diagnostic.

We live in a world where institutional trust has been eroded, narratives are totally fragmented, and every old certainty that we thought we knew whether political, social or economic feels like it’s lost its pull. We are connected to everything, all the time, and somehow less sure than ever what any of it means or is for.*

*Or in the words of my friend Franky: “Shit is the smartest it’s ever been and shit is still so stupid”

Havel wasn’t describing that moment. He was describing this one.

Havel warned that modern rationalism, while extraordinarily powerful, could only describe “the surface of things.” It could measure, predict, optimize, analyze. But it could not answer the questions of meaning that societies depend on to remain coherent.

Replace “rationalism” with “big data,” “algorithmic feeds,” or “AI,” and you have the present day.

We know more about the “what” than any generation in history. But the “why” feels increasingly out of reach.

This is where our friend Carl Jung again becomes weirdly useful. Jung believed that human beings require shared myths, symbols, and paradigms (what he called the collective unconscious) not in a fairytale sense but as emotional and psychological glue. Without shared narratives that tell us who we are, what matters, and how to live together, societies fracture.

And *gestures broadly*: can’t think of a better word than “fractured” to describe where we are right now*.

*Dumpster fire is also appropriate

Without shared meaning, people retreat into primal identities like political tribes, online factions, conspiracy movements, ethnic nationalism, etc. These aren’t just political phenomena; they are the desperate attempts of our developed human brains to force coherence onto a world that no longer offers it to us.

When nothing feels grounded, people cling to whatever feels firm. Even if it’s rage. Even if it’s false. Even if, sometimes especially if, it’s self-destructive.

This is the crisis Havel foresaw: not a crisis of systems, but a crisis of soul.

Related and relevant, Havel also posited that globalization had transformed only the surface of human life. We built global markets, global information networks, global supply chains, but without any corresponding global ethic, identity, or emotional foundation.

And so we ended up with contradictions that define our current moment:

• We have a global economy but no global sense of responsibility.

• A worldwide internet but completely separate information ecosystems in echo chambers.

• Shared crises (climate change, pandemics, AI, ethnic cleansing) but utterly divergent moral compasses about how to confront them.

We can trade across borders instantly, but we can’t agree on what’s true no matter how basic the truth.

This kind of surface-level connectivity doesn’t unify the world; it actually intensifies cultural friction*. The more contact we have, the more conflict we feel, because the underlying frameworks that should help us interpret one another simply aren’t there.

*In many ways, the internet broadly has done so much to improve lives, but my hot take is that it’s a pretty strong societal net negative

We know of each other. We do not know about each other.

Havel believed that technical solutions like treaties, institutions and policies are necessary but insufficient. Without shared values, technical solutions fail or simply postpone the problem.

We see this in real time:

• Climate agreements stall because nations protect short-term corporate interests.

• Migration crises become political weapons instead of humanitarian priorities.

• Democracies backslide because the rituals remain but the moral commitments fade.

The problem isn’t engineering. The problem is meaning.

Havel proposed that the values we need lie beneath ideology: humility, responsibility, human dignity, reverence for the world. Not partisan values. Human values.

He invoked ideas like the anthropic principle* or the Gaia hypothesis** not as scientific arguments but as attempts to articulate awe and those are reminders that we exist within something much larger than ourselves.

*the proposition that the range of possible observations that could be made about the universe is limited by the fact that observations are only possible in the type of universe that is capable of developing observers in the first place

**that living organisms interact with their inorganic surroundings on Earth to form a synergistic and self-regulating complex system that helps to maintain and perpetuate the conditions for life on the planet. Thanks to Wikipedia for this one

His point wasn’t that these frameworks were correct; it was that they were critical to our survival. Humans require a story about the whole picture. When we lose that story, everything else becomes noise.

So Havel arrived at a radical conclusion: the only real solution is self-transcendence.

That doesn’t mean abandoning identity or dissolving individuality. It means seeing ourselves as part of something larger: our community, our planet, our fragile shared future. It means holding our identities lightly, not wielding them as weapons.

Jung would agree. Individuation, in his sense, is not isolation but integration. It is becoming your full self precisely so you can connect to others without fear.

Self-transcendence is not a spiritual luxury. It is a civic necessity.

Because in an interconnected world, ego is a recipe for conflict. And tribalism is a recipe for collapse. We either learn to rise above ourselves, or we will continue pulling each other down.

This is why Havel matters now, maybe more than ever.

He endured oppression, imprisonment, and surveillance. He found moral clarity in the darkest conditions. And when history unexpectedly handed him power, he led with humility and inclusiveness rather than victory laps and a “mandate”. He governed as someone who believed politics was fundamentally a moral act.

We don’t talk about Havel much anymore, but maybe we should.

Because the world he warned us about is the one we’re living in. It’s a world of fragmentation, alienation, and meaninglessness. And the world he hoped we might build, a world rooted in dignity, humility, shared values, and a sense of the sacred, is still possible.

But not inevitable.

To get there, we have to do something profoundly simple and extraordinarily difficult: recover a sense of meaning, not just for ourselves but for the whole we share.

We have to remember, as Havel wrote, “the miracle of being.”

And we have to embrace it, but also take responsibility for it.

OK, folks, here’s where we’re at:

We’ve got Thanksgiving this week here in the U.S. and we’re all going to take some time to recharge these batteries and focus on ending the year right.

I’ve got one or maybe two more of these in me before I call it for the year.

I’ll also be in NYC for some holiday parties and for the winter break, so let’s maybe get together and say hi to one another. If you’re interested, you know where to find me.

That’s all for this week. Until next time, friends.

In NYC, everyone is guaranteed a spot in public Pre-K, but not everyone is guaranteed a spot in their zone, so when we got a spot at P.S. 9 (our zoned school), it was like we’d won the MegaMillions jackpot. It was amazing. And the Pre-K teacher at the time was a woman named Mrs. Stitham. Mrs. Stitham is exactly what you’re picturing in your head: kindly older woman, been doing it for 30 years, competent guitar player*

*One time while she was holding her guitar, I asked Mrs. Stitham if she knew “Highway to Hell” and it would have been absolutely legendary if she’d stood up and played it. But alas, she didn’t know it. Related but not relevant, I was at a Super Diamond show in Atlantic City once where they asked the crowd for requests and I asked for “Highway to Hell” and THEY PLAYED IT. I’m not a big AC/DC fan, but this is my go to for some reason.

Pre-K is largely about 2 things: getting along with other kids and singing. And Mrs. Stitham’s class was long on both, but especially singing. They sang a lot, but my favorite song that they sang which I still find myself singing around the house sometimes*, was a song called “I Think You’re Wonderful”. You can find the lyrics here. You can also listen to a guy named Red Grammar singing it at that link if you’re inclined. It’s a sweet song with a message that we tend to lose as we get older.

*I sing a lot around the house. Mostly the worst songs of your lifetime, but also evidently Pre-K songs

As adults, we stop saying things like “I think you’re wonderful”. In the workplace, praise tends to be focused on metrics or outcomes: KPIs*, budgets, measurable performance reviews. And those things are important, of course. You can’t run a real world business without actually accomplishing anything other than hollow praise. But this isn’t only a question of outcomes; it’s a question of motivation and leadership. But leadership, at its best, is about seeing people the way a child sings about them, without hesitation or agenda.

*I had just gotten used to KPIs when someone came up with OKRs. Whoever is responsible for this probably deserves an award for their continued dedication to results, but they also get my eternal disdain for making me remember another initialism

What if leadership, true leadership, starts where that song leaves off? With the courage to tell people (and show people) that they’re wonderful?

Somewhere along the way, we forgot how to do that*. Somewhere between our first job and our first leadership role, we learned to ration appreciation. Praise became a performance tool, that being something we give when it drives an outcome or smooths over a hard conversation. We say “nice work” the way we’d offer a handshake.

*I’ve done two things recently: one is that I’ve recommitted to in person interactions and the second is that I tell people to have a beautiful day at the end of the interaction and I have to say it’s been a big value add for me

The problem isn’t that people don’t want to recognize others; it’s that doing so can feel risky. In a culture obsessed with control, efficiency and Wall Street outcomes, genuine vulnerability and looking someone in the eye and saying, “You’re really good at this” can feel almost subversive. On the other side of that is that we’ve reached the point in our society where someone says something nice and our initial reaction is “What’s your angle? What do you want from me?” instead of taking, internalizing and appreciating the praise.

The outcome of that is a culture obsessed with productivity, but starved for belonging. Wonder and being wonderful isn’t about flattery; it’s about attention and seeing the unique potential in someone before they see it themselves.

I talked about this a little bit in an earlier post, when I dissected the word “amateur”*, but wonder has a similar problem. I think the notion of wonder has this connotation now of being associated with daydreaming or a lack of seriousness, rather than the awe or the curiosity that it actually means. But that wonder, that awe, that curiosity allows you to see people not just for what they produce, but for what they might become. And the best leaders see that and treat their admiration as fuel, not reward.

*Nothing brings attention from the ladies like an etymology lesson

All of this has been validated and proved over and over again in my own career. The managers who did the most for me in my career were exclusively those who recognized my skills and translated that vision into specific feedback that showed gratitude for the attention I gave and work that I did. And that meant the world to me. I’ll call out two phenomenal people in my career who embodied this as leaders: Bev Beeson and Trish Lemley, who saw the potential in me at Turner and pulled me into a leadership position on their team. They saw me for what I could be, not just what I was. That type of vision isn’t as common as it should be.

People rise to meet belief. “Wonderful” is a mirror, not a label.

How do you put this into practice? Over time, both as a leader, but also as someone being led, I’ve found that the best leaders embody a few things.

It’s easy to fall into the trap of thinking that people can clearly see their assets*. The reality is that people don’t spend a lot of time thinking about their strengths and weaknesses. They may have a sense of what they do well and what they don’t, but as a leader, you have a unique view into how they work and what they do well. Simply put, don’t assume people know what they’re good at: articulate it clearly to them and do it often.

*Or their opportunities to improve, but that’s a different newsletter

And don’t just say it, but be specific about it: “Your insight reframed that client’s perspective” beats “Good job” every day of the week and twice on Sunday. And using that praise to celebrate in context helps tie recognition to shared purpose: “Your action solved the problem that’s been blocking us.”

My son doesn’t remember that song. We found a video of him singing it and we showed it to him and he smiled, I think largely at the vision of his younger self. He’s in 7th grade now, so his own sense of wonder is beginning to fade in certain spots. I consider it a pretty big part of my job as his father to not let him lose it entirely. And as a leader of teams, I considered it a pretty big part of my job to ask myself what would happen if my teams heard every once in a while that they’re wonderful, not as a song, but as truth?

In leadership, as in life, the simplest phrases are the hardest to say. But sometimes, they’re the ones people remember forever.

And by the way, I’ve been meaning to say: I think you’re wonderful too.

It goes without saying that I took a little time to recharge my creative batteries and focus on a few other things and that’s been great for me. I’m aiming to keep this going for the rest of the year on a semi-regular schedule. I’ve got a few half-written posts teed up.

In the meantime:

• We’re doing great things on the podcast and over at Cognitive Film Society

• I’m extremely excited about Notes in Motion and you’ll hear more from me about this on LinkedIn and in coming newsletters, but I’d love to see you at our gala in February. Specifics to come.

That’s all for this week. Until next time, friends.

*I have very literally never harvested anything in my entire life, unless we’re talking about harvesting feelings of vengeance - in which case, look out 7th grade English teacher Ms. Prisampt

But still: September always sneaks up on me.

The air shifts, the leaves change, the days shorten, and - sometimes gently, sometimes like a punch in the gut - every year around this time I’m reminded that my mother died 6 years ago. There’s a part of me that still thinks she’s alive and kicking because we thought she was going to outlive us all, even though she lived her almost 75 years pretty hard. There’s a part that still expects to pick up the phone and hear some sort of complaint about something. And there’s another part that has grown used to the quiet, that has made some kind of uneasy peace with the absence, despite leaving so many things unsettled.

Grief is strange like that. It isn’t a clean, five-step process or a tidy arc* with a clear beginning and end. It’s like a weather system that rolls in uninvited, at unexpected times, long after the world assumes you’ve moved on. And for me, the hardest thing about grief hasn’t been its intensity, but its slipperiness. I keep wanting to understand it but it refuses to stay still. I want it to be linear, but it wants to throw me curveballs. And I want it to be over, but it really never ends. You simply can’t think your way through it, which feels like the hardest and the most important lesson.

*My therapist says this to me ALL the time. When he and I first started, I kept saying things like “when does denial end because I’m ready to be angry.” He was like “I’ve got good news and bad news …”

What I wanted to write about today is how we navigate not just death, but all kinds of loss, and what it means to keep moving forward without “getting over it.”

I love the Kübler-Ross* stages of grief paradigm. It’s a guide to understand and grapple with what you’re feeling and helps contextualize. But the reality is that it’s a vast oversimplification of what you’re actually going through because it suggests a) you feel all of these things neatly in order and b) there’s a finish line to cross. It feels too neat.

*Denial, Anger, Bargaining, Depression, Acceptance if you are unfamiliar

And life is full of unexpected triggers. You hear a song* or a smell a familiar scent or you’re walking down the street and a random thought pops into your head and you reach for your phone to share it. Those experiences can reset the clock and bring back the emotions full-force. And different emotions can compete for your headspace. You can feel sadness and gratitude, anger and peace, and you can feel them all at the same time. There’s no guidebook.

*This one is the most triggering for me, specifically the song “I Can Dream About You” by Dan Hartman

This messiness is exactly why we have to feel our way through it, not try to intellectualize it away.

And that can be difficult, for me especially. Because I’m a problem-solver. I’m a planner. I want to “make sense” of everything. It took me a while to recognize that some things can’t be solved or fixed; they can only be lived. I think we all have these moments where we try to reason or logic our way out of feelings of loss. For me, I just dove into work. I stayed late and I started early and I worked out like crazy. Then I found myself with a quiet moment in the shower one day where the voices in my head and all the feelings of loss I’d been setting aside caught up to me and I broke down. There’s no amount of distraction that’s enough to outrun the feeling of loss.

My biggest problem in dealing was always that I felt like healing had to mean moving on. Forgetting. That’s why I had to keep running, because if my grief caught up to me and I processed it, that would mean my feelings were gone. And my mother was already gone. It felt impossible to face losing both.

With the help of my support structure, I realized that logic-ing my way through meant denying that emotion plays a role. Feeling my way through meant allowing myself to be sad without a deadline.

And to be clear, loss isn’t limited to death. We can feel a sense of loss for all kinds of things. We tend to be inclined to minimize these types of losses because they seem small or insignificant or we’ve been conditioned to just “be a man” or “deal with it”. That doesn’t mean we don’t mourn things like friendships that faded, jobs that ended, identities we’ve shed, life changes that bring uncertainty. Very recently, I’ve found myself mourning a friendship that I once held dear but that simply faded over time. These things happen sometimes for no other reason than the thing ran its course: it served its purpose for a time and then went away. There’s no judgment there, but there’s still a finality to that, a sense of loss. Grief is not just for death; it’s the process of adjusting to life not being the way you imagined.

Feeling your way through these smaller losses builds emotional muscle for the big ones.

The loss doesn’t shrink, but you grow around it. It’s the “grief as a ball in a box” metaphor. The box has a button that triggers pain and the ball is large, so it’s constantly hitting the button. But over time, the ball shrinks. It still hits the button, but less frequently. Eventually, the button gets hit sparsely, but the pain is still real. The ball may shrink, but it never goes away.

By this point, as usual, you’re asking the logical question: what if anything can we do?

As always, YMMV, but I have a few practical suggestions. First, recognize that your emotions aren't right or wrong. They’re natural and part of you, so let them arrive without judgment. Also for me, finding safe containers for grief like journaling, therapy, or time with your support structure is extremely helpful. And I find it also helps to create some rituals like anniversary dates or telling stories to give shape to the pain.

When you feel your way through loss, you give yourself permission to be fully human. To be unsteady. To be imperfect. To let the ground fall out from under you, trusting that you’ll eventually find a new footing. And in doing so, you make space for something surprising: connection. You start to recognize grief in other people’s eyes. You learn to sit with them in their pain without rushing to fix it.

Loss will never feel fair. It will never feel neat. But when you stop trying to outthink it and start allowing yourself to feel it, something shifts. The loss doesn’t get smaller, but you get larger.

I don’t have much of a clever ending here today, but part of the inspiration for this today was the passing of my Uncle Al. My aunt Jackie (my mom’s sister) is a regular reader and a staunch supporter of everything that I do. So let it be known that loss is difficult, things can be challenging, but there’s always light in the support of friends and family. Zikrono L’vracha - May his memory be a blessing.

That’s all for this week, friends. Until next time.

And when the NFL season comes, the sports wagering season starts in earnest. Don’t get me wrong — we all mess around with silly prop bets throughout the year. “Will Aaron Judge hit a home run tonight?” “Will Anthony Volpe trip over his own feet on the way to shortstop?”* But the real action doesn’t start until the football players take the field, and Sunday mornings are filled with parlays, teasers, and same-game specials designed to make us believe we’ve found an edge that Vegas somehow missed.

*Probably and probably

There’s an old quote: “The race is not always to the swift, nor the battle to the strong.* Generally speaking, that’s not a bad way to live when your money is on the line. It’s the primary reason I bet against the New York Jets** most of the time — even though, as a fan, I desperately want them to win.

*Attributed to Ring Lardner, Jr.

**There’s another quote, “A fool and his money are soon to part.” That’s the other reason I bet against the Jets.

That quote captures a healthy pragmatism. It reminds you not to fall in love with the favorite, not to assume the fastest horse will win just because it should. It’s a reminder to bet with your head, not your heart. And that’s excellent advice: for DraftKings, for FanDuel, for your buddy’s office pool.

But if you’re trying to build something: a business, a team, a community, even a family - that mindset is dangerously incomplete. Because building is not about hedging against risk in the short-term. Building is about creating something resilient enough to withstand the long term.

Let’s stick with the horse race metaphor for a moment. In a race, all that matters is who crosses the finish line first. Everything else is irrelevant. Second place pays less, third place pays almost nothing, and if you’re the horse who finishes last … let’s just say you don’t want to be the horse that finishes last

That works fine when the objective is a singular outcome. You pick the winner, cash the ticket and walk away.* But in a society, a company, or a team, strength doesn’t come from one winner. It comes from the web of contributions that make the whole system function.

*And come home a hero with armloads of gifts for your adoring family, which treat you like a king when you walk through the door in a dream that you had about 1956

That makes the village metaphor is a better fit. A village doesn’t just need one fast runner; it needs all kinds of functions that provide objective value: farmers, teachers, nurses, caregivers, the people who keep the water clean and the power running. These aren’t glamorous roles, and they rarely make the highlight reel, but they are the difference between a functioning community and chaos.*

*I’m not gonna get political here, but I am going to say that too much of perceived value of how well society is doing is based on corporate shareholder value, which is antithetical to the village mentality and incentivizes things like rent seeking

You see this dynamic in sports too. Sure, the stars fill the highlight reels and sell the jerseys, but championships are usually won by the supporting cast: the reliable utility infielder who plays three positions, the bullpen arms who keep games close, the backup quarterback who keeps the season alive when the starter goes down.*

*I’m generally exhausted by the still remaining 1972 Dolphins celebrating their undefeated Super Bowl-winning season every year, but they’re a perfect example. Their star QB Bob Griese went down early in the season and didn’t come back until the AFC Championship game. Backup (and very old by 1970s football standards) Earl Morrell won the majority of the Dolphins games that season at QB

When organizations only “bet” on their stars, whether it’s a company overindexing on its top sellers or a sports team mortgaging its future for one superstar, they create fragility and leave themselves exposed to all kinds of common issues. What happens when that star gets hurt? Leaves for another team? Burns out?

I’ve seen this in our business over and over again. Teams that only reward the top performers often struggle with morale, retention, and culture. They churn through talent. They become brittle. The “glue people,”* the ones who keep the trains running, mentor new hires, and quietly solve problems, leave because they feel invisible, underappreciated or lost. And then leadership is shocked when results crater, because the very people who made success sustainable have been neglected.

*I’ve spoken before about how much I value people who “brown bag” it to whatever it is they do. These are the people worth focusing your time and energy in.

Compare that to organizations that celebrate contributions at all levels. Not just the sales leaderboard or the quarterly revenue hero, but the SDR who books the meeting and fosters the day to day relationships, the ops person who gets the campaign live and makes the optimization that changes the trajectory of the campaign, the account manager who keeps the customer happy. Those teams weather downturns, transitions, and even market shocks far more effectively.

The difference comes down to mindset. Betting is about optimizing for the short-term. You double down on the players or reps who have the best odds right now. You lean hard on the obvious markers of success: closed deals, touchdowns, home runs.

It works if all you care about is the immediate outcome.

Building, by contrast, is about designing for resilience. It’s not as sexy. It requires patience. It requires investing in depth, redundancy, and interdependence. And to finally beat this baseball analogy to death, it requires recognizing that the boring, unglamorous work of the farm system, the bench players, the infrastructure is what keeps you competitive year after year.

The San Antonio Spurs are a perfect case study in this philosophy. They weren’t just a “bet” on Tim Duncan — they were a system. A culture. They built around teamwork, player development, and selflessness. The result? A dynasty that lasted nearly two decades.

The same logic applies in business. The betting mindset says: “The top 10% of reps bring in 80% of the revenue, so let’s just back them and hope for the best.” The building mindset says: “Let’s support the SDRs, the operations team, the account managers, because they’re the ones who make that 80% possible in the first place.”

The key insight is this: the betting mentality is extractive. It asks, “How can I maximize what I get right now?” The building mentality is regenerative. It asks, “How can I create a system that keeps delivering value tomorrow, and the day after that?”

Because winning isn’t just about this quarter or this game. It’s about whether your team can sustain performance across seasons, market shifts, even generational transitions. And that requires investment in the less visible roles, the ones that don’t get the headlines but make the machine work.

So here’s the challenge: are you thinking like a bettor, always putting your chips on the fastest horse and hoping today’s edge pays off? Or are you thinking like a builder: investing in depth, cultivating resilience, designing for the long term?

Perhaps if we all started thinking a little more like builders, we’d create teams, companies, and communities that scale and last longer than the average NFL quarterback’s career.

Because while the race may go to the swift and the battle to the strong, the future belongs to those who build together.

OK, folks, we’ve got news this week:

The teaser for “Leadership In” featuring Greg MacDonald and me is live and can be found here - you can catch episode 1 with Ronan Shields of Digiday on Tuesday Sept. 16.

Additionally, I’m thrilled to announce that Stacy Bohrer and I will be going into production on “Beta Tested” - a podcast diving deep on the realities of being a woman in technology: the victories, the pivots, the invisible labor, the leadership leaps, and everything in between - very shortly. A 10-episode season will be coming later this fall.

If you’ve got thoughts about who might be a great guest for either of these, please reach out here for Leadership In and here for Beta Tested.

Finally, I’m looking to continue to scale OK, So … Media as a venture. Part of what I’m trying to do OK, So … is bring airtime to underserved or under heard voices, so if you’ve got an idea that you’ve been struggling to bring to life, let’s at least talk. I can’t promise that it’ll have a home here, but I can promise that I’ll listen.

That’s all for this week. Until next time, friends.

*Man’s Best Friend out on all major music platforms today

People ask me pretty frequently why I like Sabrina Carpenter and her music so much as a 48-year old dad. And that’s a reasonable question to ask, I suppose. I think a lot of people assume it has less to do with her music and more to do with the fact that she’s young and pretty and blonde. And again, I suppose that reasonable. But here’s the thing:

Those things may be true. But that’s not what draws me to her. Her music, I think, is good - I don’t think there’s any specific debate there.* I really enjoy listening to it. She’s got a lot of real bops. She’s an extraordinarily talented woman who can play more than one instrument and has an absolutely beautiful voice. But really, that’s not entirely what draws me to Sabrina Carpenter either.

*Here’s a very hot take: I think “Please, Please, Please” is the best pop song of the last 2 years

No, what draws me to Sabrina Carpenter can be pretty easily summed up in one word: joy. She is a woman who exudes joy and I am manically drawn to people who demonstrate that level of joy: in their life, in what they do, in how they present themselves. I love joyful people and it makes me want to engage with them in whatever way I can. In the case of Sabrina Carpenter, that means listening to her music, it means watching her on Instagram and it means paying an exorbitant amount of money to go see her in concert at the Crypto.com Arena* in November.

*How much longer do we give this name as a real thing? A year? Two?

There’s a certain magic that happens when someone genuinely loves what they do. You can feel it in their energy, the way they show up, and how their work resonates with others. It’s not at all manufactured. It’s authentic joy, and it’s contagious.

Beyond the success of her music, what really stands out is the joy she brings to her craft. You can see it when she’s performing live, whether she’s belting out “Juno” or leaning into “Espresso”, she’s not just going through the motions. She’s having fun. And the audience feels that.

It’s not just on stage. In interviews, in her interactions on social media, even in off-the-cuff moments, Sabrina shows up as her authentic self*. That consistency, her joy, wit, and passion being the same across every medium builds a kind of trust with her audience. It’s why so many people are rooting for her: because she’s doing what she loves, and we can see it.

*There’s an interview she did with Colbert where she was talking about how they told her backstage to not worry about cursing, and she told him that usually people are telling her not to curse, and when she came out ready to say whatever came to her lips, she looked around and said the Ed Sullivan Theater looked a little like a church, so she was uneasy about cursing because “Jesus is here” - and that’s one of those silly interactions where you can’t help but like her

There’s a lesson in that for all of us.

Work can sometimes (read: a lot of the time) feel like obligation or duty. But when we have the space to seek out and to find joy in what we do, when we connect with the parts of our job that energize us, we show up differently. People notice. Clients, colleagues, and teams can feel the difference.

As I go through the continued work of trying to find my footing in building a business or investing the work I do with non-profits or the content that I create in podcasts or these rambling, sometimes incoherent newsletters, I take a moment to remind myself that my mere existence is a gift. That what we get to do every day when we sit down at our desks or whatever can be joyful sometimes or interesting or fun or whatever. And that it also enables us to go out and seek joy in other facets of our lives.

I’m not gonna sit here and pretend that this is something that you can snap your fingers and make happen. It certainly doesn’t mean every day is easy or that the challenges magically disappear. But what I will say is that like anything else, it’s a practice. It’s about building new muscle memory. It’s about taking a moment to remember that small actions can create large outcomes.

And it does mean that when your work is fueled even in a small way by genuine passion and love, it’s far more sustainable. It’s far more inspiring. And it has a huge ripple effect that goes well beyond you.

So when I sit and think about how to put this into practice, what the action is that gets all this started. Maybe the question to ask is this: Where can I bring more joy into what I do?

Because if Sabrina Carpenter has taught us anything, it’s that when you love what you do, it shows and it makes all the difference.

Labor Day is, unbelievably, upon us. I hope you all have a beautiful, safe and amazing holiday weekend.

I’m gonna tease a little news here, since I’ve got several things in the works, but the podcast is very much coming, we’ll be launching in a couple of weeks, so stay tuned to this space and LinkedIn for more. Additionally, I’ll be announcing two other ventures that I’m extremely excited about.

That’s all for this week. Until next time, friends.

If you think about it, there’s something particularly unfair about getting sick in the summer. It’s strangely more demoralizing than getting the flu in the winter, because all you want to do is be outside during the summer doing stuff that you specifically can’t do in the winter.*. In the winter, blankets, soup and the literal worst TV you can think of. In the summer, sweat, discomfort and inconvenience.

*Unless you live in LA like I do, then you can do those things in the winter too, but the offset is that you have to sit in unimaginable traffic and consider driving off of a bridge literally all the time

Because here’s the thing about a summer cold: it’s not debilitating; just annoying. So you wind up just pressing on through whatever your day is: video calls, coffee meetings, that one email that you’ve been sitting on for two weeks because it’s in the not urgent, not important bucket but you do need to respond because if you don’t soon, it’s going to shift into the urgent bucket pretty quickly (while remaining unimportant) and someone is going to really be up your ass about it and it’s like guys there has to be something bigger for you to focus on than this specific thing. No? Just me?

The summer cold is demotivating*. It got me asking the question: What do you do when you’re supposed to be productive but you just don’t have it in you? What do you do when you simply have to get something done, but you had a poor night’s sleep? Or your kids have been particular jerks? Or, and I cannot stress this enough as a viable thing, you just don’t have it today?

*That was the cold open. Please hold your applause until the end for that world class pun. And also you're welcome for that world class pun

Here’s the problem with motivation: it’s the least reliable partner you have*. It’s fickle, striking at unpredictable and sometimes inconvenient times. It’s fleeting, coming and going as it pleases. And frankly, it tends to abandon you just when you need it most or at the worst possible moment.

*Even more unreliable than that one friend - you know who I’m talking about

But I’m gonna let motivation off the hook a bit here: motivation may be fickle, but it almost always follows quickly when you take action. To state that slightly differently, we often wait for motivation to take action, but the reality is that it’s action that precedes motivation.

The way that I like to think about this is a story I often tell about my kids. When my kids were little and friends and family would come over to visit, the visitors would often say to my kids “do you want to play with me?”* And my kids would basically tell them to fuck off and do their own thing. My advice was always to just sit on the floor and pick up one of their toys and play with it. The kids will come over. And sure enough, when they sat and started playing, the kids would come over and play with them.

*My kids today would call this “pick me” behavior

So let’s say it again for the people in the back: action precedes motivation. But that begs another important question: how to take action when you don’t want to?

I think there’s a few things there, because when you’re not motivated to do something it all feels heavier. Think about how when someone calls you and you miss the call or can’t take it. The longer you wait to call them back, the more difficult it becomes to call them back* - you start to think about them giving you guilt for taking so long to call back or that they’ll be upset with you, so you keep putting it off.

*Reminder to call someone. They miss you

When I’m in this state, I like to think about reframing the effort. No one is perfect. No one is constantly motivated. So lower the bar a little temporarily to keep some forward momentum. Don’t answer every email; answer the really important ones. Don’t write 1000 words; write 100. And to use the call example, don’t hop on the phone thinking you need a 30 minute phone call; a quick call to say “hey, I’ve been thinking about you, but I’m not feeling 100%, so I wanted to say hi and let you know that I’ll call again soon and I love you.” Turn the tables and create short term goals that are attainable.

If you haven’t read the book Atomic Habits*, I would highly recommend the book. There’s a lot of incredible insight in there, but the way he frames this habit is through the construct of “Reduce the Scope, Keep the Streak” - sometimes doing anything is something. Momentum > Intensity.

*There are very few books in the genre of Atomic Habits (meaning non-fiction books that have a thesis and then 9,000 examples of the same exact type) that I read all the way through. Usually by the 3rd example, I’m like “OK, I get it,” but this was a rare exception where I read the whole thing. FWIW. YMMV. OMG, right?

And in case it wasn’t abundantly clear, this isn’t just about being sick. This applies to all human emotion where we just need to give ourselves a bit of grace because we can’t possibly be firing on all cylinders all the time. It applies to grief, burnout, stress, self-doubt. You can’t live your life and be your best self through these things, while also punishing yourself for not being as productive as you think you should be. Motivation is the luxury; discipline and grace are the infrastructure, so even when you don’t have full power, showing up in a small way is a signal to yourself that you’re still in the game.

The reality is you don’t have to be operating at 100% all the time to be effective. Doing something - anything - even poorly, slowly, whatever is always better than doing nothing while waiting to feel lightning strike.

The trick isn’t staying motivated.

The trick is reminding yourself that it’s OK to be less than perfect.

OK, folks. We’ve been busy at JPEG HQ, so a few interesting notes:

Leadership In is locked in and Greg and I are finalizing those launch plans this week. Which is extremely exciting. That’s OK, So Media in conjunction with Greg’s truly fantastic consultancy Chelsea Strategies.

I’ve written a couple of things for and will continue to do so as inspiration strikes, but I’m also thrilled to announce that I’ve joined their board and that I’ll be exploring options through the autumn to bring CFS to the west coast. Extremely exciting. If you’re in the LA area and want to collab on that, reach out to me!

Last thing, I cannot thank everyone enough for the support on everything that I’m doing. I’m pursuing a bunch of passion projects and the response from our community has been overwhelming.

*I go back and forth on this. On the one hand, these are artful movies with deep storylines, intelligent writing and enjoyable songs. On the other hand, they’re cartoons made for children. Not to yuck anyone’s yum

That’s likely not a surprise to anyone reading this, but there’s a few reasons for this. First, over time I’ve developed pretty bad motion sickness, so when I’m in the parks, I basically can’t go on any rides anymore - unless they’re like the cruise through the jungle or whatever that goes 2 miles per hour - and let’s not forget that it’s like $1000 to take a family of 4 there.

Second, I watched so many Disney movies so many times with my kids when they were little that I have very little appetite to do it now. Third, I’ve worked in media and advertising for so long that I’ve gone the other way completely on content consumption (in that I consume very little). My attention span has shortened so significantly that any movie over 90 minutes takes me at least 2 sittings to get through.

And finally, I tend to index away from anything that people get super obsessed with.*

*The lone exception to this is, apparently, Sabrina Carpenter, who I can watch over and over on Instagram and might pass out if I ever met her in person

However, because I’m a good father (translation: I’m soft and fold to my kids too often), I have taken them to the parks in the past. We went a few times when they were smaller. We were at the Animal Kingdom* in Orlando back in December. These are long days that almost always result in a meltdown (by me) or a giant fight of some kind. It’s like walking through an IKEA on Valentine’s Day. You’re just begging for something confrontational to happen.

*I wish I were joking, but we went to get on the line for the Avatar ride and the wait was 280 minutes. ALMOST 5 HOURS to get on a 90 second ride. I’ll be honest: I aspire to that level of patience for literally anything

Here’s the thing about being a kid, even in today’s world: you’re never really in charge of anything.* You go to school and teachers tell you what to do and where to go and then you go home and your parents do the same - eat your vegetables, do your homework, go to dance/soccer/gymnastics/art/music class, go to bed, etc.

It used to be that kids were at least in charge of their free time, but there isn’t much free time to be had these days.

*I constantly tell my children that I do not negotiate with terrorists

And as I was going through the research to book my Animal Kingdom excursion, I stumbled on a rule that Disney has their costumed characters follow. If a child hugs a costumed character, the characters are trained not to let go of the hug until the child does. At first, it struck me as strange. Something about it felt… off. I couldn’t put my finger on why. I couldn’t put my finger on why, though. But the more I thought about it, the more I realized: it’s not wrong at all. In fact, it’s extraordinarily right. It’s quietly profound. That simple rule puts the emotional pacing in the hands of the child. Not the adult, not the performer, not the park schedule, not the line of guests behind them. The child.

Let’s talk about emotional intelligence. Because that hug rule? That’s EQ in action.

I think generally a lot of people mistake EQ for being something that’s supposed to be soft or warm or fuzzy. That’s really not it at all. EQ is about reading the emotional cues of others, understanding their unspoken needs and honoring their energy in that moment. And what I came to realize as I thought about it is that the Disney rule is a masterclass in EQ. It’s about attunement (staying with someone until they feel complete), empathy (not pulling away because you’re feeling done) and permission (letting others decide when it’s time to move on).

Think about it: how often do you let go too soon? How often do you cut short real connection for whatever reason? Perhaps by changing the subject because the emotion got too heavy. Perhaps by not being attuned to the energy of the other person who is still reaching out. Sometimes we do this to others and sometimes we do it to ourselves, but leaving the moment before it’s fully landed does a disservice to all parties.

I think of EQ as the tool that helps calibrate all of this. EQ is knowing how to show up differently for different people. Reading and understanding their energy and meeting people where they’re at, which in turn allows them to meet you where you’re at. In the same way that the Disney Hug Rule is designed to read a child’s energy and respond to them in kind, the development of your EQ allows you to read the room or the person, to feel when someone needs more time to process or that they’re forcing an emotion. The best leaders are emotionally intelligent enough to read energy, sense unspoken cues, and stay present until the team, the moment, or the person is ready to move forward.

Good leaders know when to act. Great leaders know when to pause. And the real skill, the real importance of that pause is being able to sit in the emotion - the discomfort, the joy, the feeling of loss, whatever - until it’s done. It’s staying with your kid when they’re melting down, or with a friend who can’t quite name what they’re feeling but needs to know that someone is with them. It’s hanging with your employee while they process. In nearly every case, it's not fixing. It's not pushing forward. It’s simply not letting go too soon.

Sometimes, the most human thing we can do is just stay: in the hug, in the silence or in the story.

The Disney hug rule gets this right.

Because that rule says: I’ll stay with you. You decide when it’s time to let go.

And honestly? That’s the kind of presence we all need more of - in leadership, in parenting, in friendship, in life.

OK, friends, I’m back with some exciting news. We’re in the process of recording two new podcasts:

“Leadership In …” will feature Greg MacDonald (of Chelsea Strategies and I in conversation with leaders in the advertising, media and technology space about what it means to lead - both as part of a company that leads in its space and personal leadership narratives

“Beta-Tested” will feature dear friend and host Stacy Bohrer in conversation with women in technology around various topics - motherhood in the workplace, entrepreneurship, being a woman in the boardroom.

I’m extremely excited for both. Both launching in the fall post-Labor Day. More to come on both of these.

That’s all for this week, friends. Until next time.

*Lite-FM was (is?) the most listened to radio station in the entire country for a long time. And if you like Michael Bolton, you’re not gonna believe this …

There were other radio stations - if you were lucky and you leaned out your window far enough in my neck of the woods, you could get 92.3 WLIW, which played edgier stuff from New Wave to bands from the UK to “alternative” music*. There was 97.1, which was like WPLJ and Z100, until it became the home of hip hop in the late 80s.

*This was the radio station where I heard Bad Brains for the first time. I’m not a Henry Rollins fan, per se, but boy can he scream.

There were other stations too, but there was only one other one that really mattered:

101.1 - CBS-FM

CBS-FM played oldies, unapologetically. And they recruited all manner of DJs from radio’s heyday in the 1950s and 1960s who worked in the New York market - guys whose names you’d either have to be really old or have listened to CBS-FM to recognize: Ron Lundy, Dan Ingram, Harry Harrison, Bill Brown*. And for a long time, their station refused to play anything released after like 1972.

*True story: Bill Brown used to solicit submissions for a playlist format that he aired during the lunch hour called “The Brown Bag” - and back in 2003 or 2004, he used my submission called the “Pleasant Conversation” Brown Bag, which was Hello It’s Me (by Todd Rundgren), How Do You Do (by Mouth and MacNeal), and I’m Doing Fine Now (by The New York City Queens). I won tickets to a Broadway show called “Anna in the Topics” that starred Jimmy Smits.

Anyway, this is all prelude for me to tell you that I was listening to an oldie today called “Concrete and Clay”, of which the chorus goes “the sidewalks and the streets, the concrete and the clay beneath my feet begin to crumble.” And as I think through some work I’m doing now, it seemed an apt metaphor for data and data fidelity and the importance of knowing and being able to identify your audience

In the world of data, we build with both concrete and clay. One gives us strength and certainty. The other gives us scale and adaptability. But only one can bear real weight.

• Concrete = deterministic data (solid, foundational, fixed: email addresses, logins, telco IDs)

• Clay = probabilistic data (flexible, shaped by inference, but unstable: modeled behavior, lookalikes, device graphs)

And as I said on LinkedIn a couple of weeks ago, in a world full of signal and noise, fidelity matters*. Which brings me to my thesis: More data isn’t better. Better data is better. When your source is unstable, everything downstream becomes noise.

* You guys of course remember Family Matters, the TGIF show and of course Urkel** (and his suave counterpart Stephon Urquell). But do you remember that the show started out with 3 kids? And the younger daughter got Chuck Cunninghammed right out of the show with zero explanation. And we caught up with her and here’s what she had to say! JK, but that would be pretty wild if I did that. Maybe another time.

**Also never forget Urkel and Bea Arthur “doing the Urkel” at the 1991 American Comedy Awards

Let’s start with this: what do we even mean when we talk about “data fidelity”? For me, I think of four things: accuracy, integrity of the source, consumer consent to use the data, cross-channel resilience of the data. Like anything else, the recipe and mix of those things may be different for each source, but in the same way that you need flour, sugar, eggs and milk to make a cake, you need some combination of those four things to make a data, er, cake.

Let’s set the table here quickly by being super clear on what we mean:

Deterministic = logged-in user IDs, telco IDs, email-based graphs

Probabilistic = modeled identities, cross-device guesses, cookie stitching

The pervasiveness of “data” as a thing has created this sense that the more data you have, the better off you are. But the obvious problem with that is that not all data is created equally, most data is guesswork and some data isn’t even 1:1. And while it’s true that the modeling around probabilistic data allows it to scale faster (I’m talking about volume here, not actual scalability), the reality is that deterministic data performs better.

And, just because I’m a psycho for closure, here’s a case study for you. Published in 2023, it appeared in a German publication from the Axel Springer network called Springer Professional. And in true German style, it’s not only extremely clinical, it’s extraordinarily detailed. The extraordinary thing about this study isn’t even that deterministic data outperformed probabilistic data. Generally, that’s not a terribly surprising outcome. The surprising outcome here in this specific study is that random approaches outperformed probabilistic data. I’m not saying that one exhaustively researched and peer reviewed study is the one ring to rule them all, but as we say where I come from, it doesn’t hurt.

And all of this matters now more than ever. Third-party cookies are staying for now but are highly questionable (both from an efficacy and a privacy perspective) - and a viable replacement hasn’t emerged. We’ve already got some signal loss from Apple and Firefox and from privacy regulations around the globe. And given all of the constraints on margin, there’s increased scrutiny on ROI, incrementality, and trust. And as Billy Joel would say, it’s always been a matter of trust.

The cost of low fidelity data may simply be too much to pay in the long run - without real high quality data fidelity, we’re wasting impressions, have poor frequency management and measurement is completely misaligned. There’s also the potential for brand safety issues and ultimately, the further erosion of consumer trust.

This is the pivot*. Advertisers, publishers, platforms all have to choose: Do we keep modeling our way out of a broken system? Or do we start rebuilding on something solid?

*When you hear the word “pivot”, you scream PI-VOT in your head, right? That’s not just me?

You don’t have to ask me twice.* The future is consent-based identity. The future are high grade signals from telcos or other deterministic sources. The future is fewer intermediaries and more transparency. The future is data that traverses channels and devices while maintaining its integrity.

*Or I guess I don’t have to ask me twice, but you get it.

Fidelity isn’t a luxury - it’s the foundation. And if we want the industry to stand up to what’s coming, we better start pouring ourselves some concrete.

The time has come - we’ve arrived at Issue #10 and the summer is upon us. It’s time for a little brain break over here. I’ll be honest: this is the most fun that I’ve had writing in years, so I’m going to keep after it. But I’m going to keep after it after the July 4th holiday, so expect Issue #11 sometime during that week following Independence Day.

Let me take a moment to earnestly thank those of you who read this thing. I don’t quite know what it is but I know it brings me joy - and if it brings you something too, that means the world. Thank you.

That’s all for this week. Until next time, friends.

But regular readers of this newsletter* know that I’m semi-obsessed with my physical fitness and my health - what I put into my body. As of late, that’s manifested itself as a deep dive into longevity. I’ve read more than a few things about this, including a super interesting book called Outlive: The Science and Art of Longevity. It’s pretty likely that the first person who will live to 150 has already been born. We can argue whether that’s good or bad or whatever, but given that in the US a hundred years ago, life expectancy was 57 for men and 60 for women, that’s an astonishing possibility.

*Thanks again to both of you

In my obsessive drive to consume everything I could on the subject, I came across a limited documentary series on Netflix* about Blue Zones. Blue Zones, in short, are areas in the world where people live substantially longer than the average person in the country in which they live by an order of 4, sometimes 5x. As an example, Okinawa has 80 centenarians per 100,000 residents. The average for the whole of Japan is 20 per 100,000.

*The rule of thumb for Netflix documentaries is as follows: if it’s 90 minutes, it should be a half an hour; if it’s 3 episodes, it should be 90 minutes; if it’s 8 episodes or more, it should be 3 episodes

The guy who made the docuseries, Dan Buettner, has been studying these Blue Zones for 25 years and the series itself seeks to understand why these folks outlive their fellow countrypeople by so much. It’ll come as no surprise that there are shared values across these societies like exercise, community, local food sourcing, etc. and also some things unique to the places themselves. The last episode deals with whether Buettner can create his own Blue Zone where one doesn’t currently exist. It’s fascinating, at least it was for me, so give it a watch if you’re so inclined.

Anyway, one of the Blue Zones is in Costa Rica up near the Nicaraguan border and while they’re going through the culture and what they do to stay healthy and fit well into their 80s and 90s, Buetter (who is conversational in Spanish) asks one of the centenarians how he gets up every day to do his work at his age. And the guy responds pretty simply “es mi plan de vida” - it’s my life’s plan - and then says “¿cual es su plan de vida?” - what’s your life’s plan?

So … ¿cual es su plan de vida?

Before you think of an answer, let me take a moment to clarify what I *don’t* mean here. I don’t mean what are the discrete things that you’re planning to accomplish with your life.*

*My daughter is in high school and it sounds like when kids apply and commit to colleges, they’re going into specific schools within the school (business, liberal arts, whatever) and also effectively declaring a major (!). Which seems right. I assume every 16-year old dreams of being a CPA for a mid-size firm and retiring to Boca after a stable 50 year career

What I mean is “what’s your purpose?”

Do you even think about that? Does anyone?

Honestly, I’m not sure I have, at least not with real depth. I’ve set goals and intentions - sometimes I’ve met them and sometimes I haven’t. I’ve built things, helped move businesses, given my clients direction. I’ve trained for races. But does that qualify as purpose? Or is that just positive inertia or momentum?

I’ve actually been sitting over this newsletter for days trying to figure out where to go and what to think through - and sitting here right now on Thursday June 5th, 2025 at 8:21pm in the City of Angels* - Not just “What am I doing?” but “What’s the point of it all?”, which I recognize is an out there thing to think about between meetings or while making one of the last bag lunches of the school year**. But it’s been hanging over me. In a culture obsessed with performance - physical, professional, personal - asking about purpose feels like the epitome of privilege. Like a luxury we can’t be afforded in the face of our overwhelming and insane Outlook calendars. But what if that’s backwards? What if purpose is the thing we’re supposed to start with?

*Shoutout to Vin Scully

**This is the time of year that I’m so done with making lunches for my kids that I’m pretty sure they go to school with a half made sandwich and fruit that’s just on the good side of the fresh-rotten continuum

I’ve spent a lot of time focused on the what. What is my purpose? What gets me out of bed in the morning? What is my own personal North Star? Those are important questions to ask. I don’t think a lot of people are asking those questions of themselves, so I’ve actually shifted my thinking to “why” - why don’t people ask themselves these questions.

I’ve got a few guesses:

• The hyper-productivity culture we live in

• The pressure to define identity by career/title/output

• The lack of stillness or reflection in American life at all and/or the passive judgment someone feels or puts on themselves when they stop to smell the roses

And when you’re cranking along in your day without a minute to eat or use the bathroom or even rest your brain, it’s impossible to even realize that the net gain of increasing the load from 75% to 125%* that you’re putting on yourself (or is being put on you) barely moves the needle positively while having the negative effect of pushing you past the point of exhaustion.

*When I started working, my day was 8:30am-5:30pm. 9 hours and one of them was allocated for lunch, where we would frequently pull together a small group of people, walk somewhere and sit down for 30 minutes and eat and talk. And as I’m writing that, it sounds like I’m describing a scene from before the war or something

What’s the secret to a long, productive life? The secret to finding yourself in a personal Blue Zone? Maybe the secret isn’t in the mitochondria or the collagen peptides or the wearables. Maybe it’s in having a reason to get up every morning that isn’t simply optimized for efficiency. When I’ve thought about longevity in the past, I’ve thought about simply living longer. But is that it? Or is it something bigger? Perhaps longevity isn’t about the time, but what you fill it with.

So one more time for the people in the back … ¿cual es su plan de vida?

OK, team - I’ve got one more of these coming (Issue 10 - pub date June 17), before I take a small break to refresh and recharge. We’ll be back after the Independence Day break.

Let’s take a moment to recognize two phenomenally talented sitcom actors who passed recently. If you know me, you know how formative 1980s sitcoms were for me, and even though M*A*S*H* is mostly a 1970s sitcom, it was ubiquitous in syndication when I was young. So RIP to Loretta Swit - acid-tongued, intelligent, unsympathetic turned super interesting Hot Lips Houlihan.

And RIP George Wendt - there were a ton of great entrances by a superbly talented comic actor, but none better than when Frederick Crane - yet to utter his first word - shouts “Norm!” when Wendt greets everyone with his customary “Afternoon, everybody”

Legends never die.

That’s all for this week. Until next time, friends.

Good afternoon graduates, faculty, families, friends and to the guy in the back who’s so hungover that he can barely hold it together and is almost certainly wearing shorts and a t-shirt under that gown, thank you for being here.

Today’s a big day. You’re stepping out of classrooms and group chats and into the real world - whatever the hell that means. It’s a world with fewer course notifications and more Slack notifications. Fewer office hours, more meeting hours. More spreadsheets, fewer naps. But before we get started here, I’m gonna tell you something right out of the gate: the real world isn’t a place where you magically become an adult the moment you walk across that stage and take your diploma from a guy in a slightly fancier robe than the one you’re wearing. It’s just a different kind of classroom. The lessons are definitely messier, much louder, and way less predictable, but it’s full of opportunity to learn.

I run a business that helps companies grow. That’s the sanitized version. What we actually do is help organizations figure out why their sales strategies are stuck, why their teams aren’t scaling, and why they keep hiring people who leave within 18 months. And I’ve learned a few things while I’ve been doing it. This is what I want to leave you with today:

Success isn’t about doing more. It’s about doing the right things, at the right time, with the right people.

What does that mean practically?

1. Doing More Is Not the Same as Scaling

In the world you're about to enter - especially the tech, media, or advertising worlds - there’s this illusion that moving fast equals success. We glorify speed. “Fail fast.” “Move fast and break things.” “Scale or die.” But there’s a dirty secret there: speed without direction is just chaos in fancy clothing.

Companies don’t grow because they add more tools, more people, more pitch decks. They grow when they understand who they are, who they serve, and how they show up consistently. That’s scale. Scale isn’t just big—it’s repeatable, it lasts and it’s rooted in something real.

Don’t fall into the trap of equating moving forward with advancing.

2. Authenticity > Hype, All Day Long

You’re graduating into an era that’s fueled on attention. Everyone wants to be viral. My 15-year old daughter poses for Instagram photos like she’s being photographed by Annie Leibovitz (ask your parents who that is). Everyone’s curating their social persona like they’re the big get at Met Gala. And let’s be fair: there’s value in learning to tell your story well. But there’s a fine line between branding and bullshit. Most people are terrible at knowing the difference.

I’ve worked with so many companies that look great on paper. Big logos, fancy offices, high-growth potential. But under the covers? A culture built on fear, confusion, and burnout. A sales team that can’t tell you what makes their product actually matter. A leadership team chasing trends instead of building a vision. That’s the result of performance as a substitute for purpose.

Here’s what I believe at my very core: Authenticity scales. Hype doesn’t.

So whatever you do - be it in a boardroom, on a set, writing code, or leading a team - do it with your full voice. Your real voice. The one that asks hard questions, admits what it doesn’t know, and builds trust by showing up earnestly.

3. Trust: The Only Metric That Compounds

A lot of what we measure today - clicks, impressions, email open rate - is just noise. The only metric that compounds over time, in business and in life, is trust.

Trust is what keeps customers coming back. It’s what makes a client say yes when your price is higher. It’s what makes a team stick together during rough quarters. And it’s what turns talent into leaders.

Trust isn’t about being perfect. It’s about being clear. It’s about keeping your word. It’s about saying “I don’t know, but I’ll find out.” It’s about owning your mistakes faster than anyone else in the room.

And that’s not just a professional skill - it’s a life skill. It was Thoreau who said “it’s a fine thing to build your castles in the air, as long as your foundations are on the ground.” Build your reputation on trust and everything else will have a foundation worth standing on.

What No One Tells You About What’s Next

I know graduation speeches are supposed to be uplifting, and I promise I’ll bring this ship in for a landing in a minute. But I wanted to say one more thing first: The next few years are probably going to feel a little weird.

You might take a job that doesn’t look like what you imagined it would. You might feel imposter syndrome so strong you start Googling “how to not look dumb in meetings so that my boss thinks I know what I’m doing.” You might realize that what you studied isn’t exactly what you want to do - and that’s totally OK and very normal. Take it from a history major.

The truth is that progress is rarely a straight line. It zigs and zags and gets interrupted by pandemics or pivots or podcast ideas you couldn’t see coming even if you were looking. What matters isn’t how fast you figure it out. It’s that you keep figuring it out. With intention. With honesty. With faith in yourself that you will figure it out.

You’re not falling behind. You’re building something that takes time.

My Final Ask: Build Things That Make Other People Better

Whatever you choose to do next, whether you’re launching a start-up or joining an agency or freelancing while figuring out your life, my genuine hope is that you build things that make other people better. That make teams stronger. That challenge the default. That leave a place more human than you found it.

Because the real work doesn’t start when you get your business card or your first promotion. It starts when the cameras are off. When no one’s watching. When you decide to lead not because you have to but because you can.

Congratulations, Class of 2025. You’ve got the world at your fingertips. Let’s go build something real. Together.

Well, it’s morning in America and we just wrapped our Memorial Day weekend. Summer is unofficially here. If you’re going to Cannes next month and have some room in your calendar, I’ve got people for you to meet. Reach out and let me know and I’ll make some connections.

I won’t be there, but I will be in NYC for the summer. If you want to catch up, give me a holler. I’d love to see you.

That’s all for this week. Until next time, friends