Vol. 4, Issue 18: If You Don’t Believe in What I’m Building, Do You Still Believe in Me?
On self-worth, external validation, and the quiet fear beneath every creative pursuit
Editor’s note: I will have a piece related to this up at Cognitive Frames, focused largely around the movie You Hurt My Feelings, this week as well.
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.


