Three years ago, I left my job to devote myself full-time to building One Tiny Problem.
I had a plan. And to be clear, it wasn't a bad plan. I had decades of experience behind me. I knew how to produce and edit video. I knew how to teach people how to do it themselves. So the business seemed like it could be divided pretty cleanly into two things:
Done for you.
Done with you.
Simple enough.
Then the plan made first contact with reality.
Three years later, I don't look back at that original plan and think, Man, I didn't know shit.
I knew a lot.
What I didn't have yet was access to the kind of knowledge you can only get by participating.
I was missing nuance.
Some things you can't know from the starting line
There are things I understand about this business today that no amount of planning in 2023 could have given me.
I had to meet people. Try things. Get things wrong. Listen. Change my mind. Build something, live with it for a while, and discover that the people I could be most useful to didn't fit neatly into the categories I'd created for them. That distinction matters to me.
Because there's a version of entrepreneurship where every change in direction gets turned into some inspirational lesson about how your original idea was wrong and failure made you smarter.
I don't think that's what happened here. The original idea got me moving. Movement gave me information. Information gave me nuance. And nuance changed what I was able to see. One of the biggest changes has been in how I think about visibility.
Being visible isn't the same as being seen
I have spent a lot of time over these three years thinking about what it means for a person or a business to become visible. Because visibility matters. People can't engage with something they don't know exists.
But I've also come to understand that visibility doesn't equal engagement. And engagement doesn't necessarily equal action. You can be visible as hell and still not create much of a relationship with the people looking at you.
Here's what I've started noticing instead:
People engage differently when they see you seeing them.
When I sit down for a discovery conversation with someone, I'm not trying to discover how to sell them something. I'm trying to discover them. I'm listening for what they've been trying to say. I'm listening for the thing they understand intuitively but haven't quite found language for yet. I'm listening for the gap between who they are, what they care about, and how they're currently describing their work.
And then I try to reflect back what I've heard.
If I understand you correctly, here's what I think you're telling me…
Sometimes that conversation reveals a clear way that One Tiny Problem can help. Sometimes I know somebody else who would be a better fit and I make an introduction. Sometimes the answer is simply: I don't think I'm the person for this, and unfortunately I don't know who is. From a traditional sales perspective, that last conversation might look like it didn't produce anything. I'm no longer sure that's true. Because somebody can still leave that conversation having had an experience that is surprisingly rare:
They were witnessed.
For all the complexity that comes with being a human being trying to build something meaningful, they were at least moderately understood.
That has changed something fundamental about how I think about storytelling.
Storytelling isn't just transmission
I've believed for a long time that storytelling is some of the most powerful magic human beings possess.
I still believe that.
What I didn't fully appreciate three years ago was just how deeply story is woven into the way we understand ourselves and each other. Story isn't only what you publish. It isn't just the video on your website or the LinkedIn post or the beautifully produced brand film. It is also what happens between two people when one person is paying close enough attention to help the other recognize something they've been carrying.
That's relationship.
And increasingly, I think relationship is where the interesting stuff happens. Which creates a funny problem for a business. Because relationships don't always move efficiently. Understanding people takes time. Listening takes time. Figuring out what you're actually seeing takes time. And sometimes the most useful thing you can do in a conversation has absolutely nothing to do with making a sale. That isn't particularly convenient. But three years into building this company, I'm less interested in forcing the work into somebody else's definition of what a business is supposed to look like. I'm much more interested in paying attention to what the work itself is teaching me.
If your business isn't learning, it's dying
There's a phrase I've heard a thousand times:
If your business isn't growing, it's dying.
I'm starting to think about that differently.
If your business isn't learning, it's dying.
One Tiny Problem knows considerably more today than it did three years ago. It also has considerably more infrastructure. There are systems now. Support. Relationships. Processes. Tools. Things I couldn't see from where I stood in September 2023.
And somehow, having more knowledge has made me more aware of how much remains unresolved. There are things about the future of this company I genuinely don't know. There are things I'm testing. Things I'm questioning. Things that are taking shape but don't have names yet. Three years ago, that kind of uncertainty probably would have bothered me a lot more. I would have wondered why I hadn't figured this shit out already.
Today, I think uncertainty can mean something else.
It can mean you're still paying attention.
The sidewalk doesn't tell you where you're going
During the walk where I recorded the reflection that eventually became this essay, I crossed an invisible boundary between El Sobrante and Richmond. If you didn't know the boundary was there, you'd probably miss it. But something changed. There were sidewalks. Infrastructure. Later, while talking about uncertainty, I found myself walking alongside the busiest road on the route. And somewhere in the middle of talking about how much a business can learn, a squirrel appeared.
Hi, squirrel.
None of these things is a grand metaphor for entrepreneurship. Sometimes a sidewalk is a sidewalk and a squirrel is a squirrel. But I think there's something useful in noticing them anyway. Because that's increasingly the posture I'm trying to bring into this work.
Not constantly asking:
How do I make the world confirm the plan I already created?
But:
What's actually happening here?
What am I learning?
What am I available to notice now that I couldn't have noticed before?
Three years isn't an especially long time. But it has been long enough to learn that experience and certainty aren't the same thing. Long enough to understand that visibility without recognition can be pretty hollow. Long enough to discover that helping someone feel seen may sometimes matter more than explaining myself perfectly. Long enough to build some real infrastructure. And long enough to see more clearly how much I still don't know.
So I'm entering Year Four with known unknowns and unknown unknowns.
There is no dramatic reveal coming at the end of this essay.
No seven-step roadmap for what happens next.
I don't know exactly what happens next.
What I know is that One Tiny Problem needs to keep learning.
I need to keep listening.
And my job, as far as I can tell, is to keep making myself available to notice.
Three years in, that feels like a pretty good place to begin.
