Vol. 5, Issue 5: What If Work Wasn’t the Point?

The Creativity Paradox And How We Can Take Back The Interesting Things

This one is going to be a little serious, so let’s put on our big boy pants for a minute.

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.

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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.