I’m writing this from San Francisco!!!

A few times a year, my full time job brings me to one of my favorite cities in the world. This trip happened to overlap with something I never could have planned: two of my closest friends from completely different chapters of my childhood were also in town.

So between after long days at the office: I had the best dinners. We walked up hills that felt personally aggressive, I literally ripped my pants (that’s a different story) and laughed until I cried.

At both of the separate dinners, my friends insisted on paying.

Which sounds small, but my brain immediately started doing the math of how to make it even. Letting old friends take care of me for a night felt strangely tender. Not because I needed the dinner. Because I realized how rarely I let myself simply receive help without turning it into a debt.

I didn’t have language for why that felt connected to everything else I was thinking about this week until later, when my IT team called me.

Earlier this month, I started building my first external AI project for work. For the first time, I could describe features, generate code, iterate on designs, and watch ideas come to life in hours instead of weeks.

Then I hit security.

Authentication, permissions, infrastructure, deployment, and all the invisible pieces that make software safe.

That’s where everything came to a screeching halt: I had reached the part of the project that simply wasn’t mine to love.

For weeks, I assumed I just needed to try harder. Read more docs. Ask better prompts. Push through the discomfort. Become the kind of person who could figure it out alone.

Then my IT team called me.

My first thought was, Uh oh. What did I break?

Instead, they spent the call explaining why they actually needed a favor from me and I was able to help them out quickly. During that call, they also explained that they have been working on my project in the background. They had researched solutions and even offered to upgrade my GitHub account so I’d have access to the infrastructure I actually needed.

The problem wasn’t that I lacked motivation.

It wasn’t that I wasn’t smart enough.

I had simply reached the edge of my expertise. And I was honest about it.

Both of these experiences reminded me of one of my favorite quotes - Scott Galloway said: “Greatness is in the agency of others.” I think this means that the best things we build are rarely the result of our own capability alone.

Which is an interesting thing to believe right now because technology is moving in the opposite direction. AI makes it easier than ever to do things alone. You can write code, research a market, draft a plan, learn a skill, and build something real without asking another person for help.

Capability and success are not the same thing.

There is a difference between a skill gap and an ownership gap.

A skill gap sounds like: I don’t know how to do this yet, but learning it would make me better at the work I actually want to do.

An ownership gap sounds like: I don’t know how to do this, the downside of getting it wrong is high, and even if I mastered it, the project would not be meaningfully better because I personally owned it.

Those should be treated completely differently.

If the gap is core to your judgment, taste, or ability to serve the person on the other side: learn it.

If the gap is high-risk, highly specialized, or mostly invisible when done well: ask for help.

The mistake I made was assuming every gap was a personal challenge. Sometimes the mature move is not pushing harder (which is very hard as an enneagram 3). It’s knowing which part of the work deserves your effort and which part deserves someone else’s expertise.

That is where AI can get slippery.

When a tool makes you feel capable of almost anything, it becomes very easy to confuse access with mastery.

There’s a name for a version of this in psychology: the illusion of explanatory depth. It’s our tendency to believe we understand complex systems better than we actually do. Then someone asks us to explain how it works, build it, defend it, or make it real, and suddenly the edges appear.

I used to think those edges were embarrassing, but they are actually super duper useful. They show us where the next question lives. They remind us that self-sufficiency is not the same thing as wisdom.

Maybe help is underrated because we treat it like proof that we’ve failed.

But this week made me wonder if help is actually one of the clearest signs that something is growing. A real project eventually needs more than your own taste. A real career eventually needs people who see what you can’t. A real life eventually asks you to receive care without immediately trying to pay it back.

I still think being a generalist is an incredible advantage.

But I’m also learning that the best generalists are not the people who pretend they can do everything.

They’re the people who know when to invite a specialist into the room.

AI is making independence cheaper than it has ever been. That is exciting. But it has not made relationships less valuable. If anything, it has made them more valuable.

When everyone has access to the same tools, our biggest advantage becomes the people who challenge our assumptions, fill our blind spots, and make our ideas better than they would have been alone.

Two questions I’m leaving myself with this week:

Am I avoiding this because it’s hard, or because it’s not actually mine to own?

And where could asking for help unlock the next level of this work?