What Does Success Even Mean?

Robert Holden once asked me a question that stopped me cold:

How do you define success?

I was completely caught off guard.

Had I ever actually slowed down long enough to answer that for myself? It felt like one of those questions that should be easy—like Who are you?—and yet somehow it’s the hardest one in the room.

He said something that has stayed with me ever since:

“Your definition of success will inform every other decision you make.”

Well…shit.

This is my steering wheel?
And I don’t even know how to use it?

No wonder I’ve felt a little lost. A little seasick. Like I’ve been driving without a steering wheel and wondering why I keep drifting.

So I asked him his definition. I needed somewhere to start.

He said, “I define success as knowing who I am.”

Dang.

That felt right. Solid. Grounded. I borrowed it. Held onto it for a long time. And honestly—I still do.

But recently, here I am in Costa Rica on a yoga retreat with my wife, and someone asks me again:

How do you define success when it comes to your writing?

Bam.

Right across the face.

Because if I’m honest, my default answer has been:
publication, readers, money.

And by that definition?

I haven’t been very successful.

Maybe that’s why my energy for something I love has been so low.

So I sat with it.

What does success actually mean to me when it comes to writing?

Not the version I was handed.
Not the version that gets applauded.
But mine.

And what came up surprised me a little:

Engagement.
Connection.
Learning.
Curiosity.
Exploration.

Can I sit with a question and share that process honestly?
Can I write something that invites someone else into the conversation?

I was talking to the counselor at Leo’s school the other day, and she told me she shared one of my Substack pieces with a student.

And I had this immediate, full-body reaction:

That’s fucking success.

Not small success. Not “that’s nice.”

Gold medal success.

To write something that might help a high schooler feel even a little less alone?

That’s it. That’s the thing.

And here’s the part that stings a little:

I stopped writing.

Because I was told that if I publish on Substack, I might not be able to publish that piece somewhere else.

Which, according to the old definition, meant I couldn’t be “successful.”

So I didn’t publish.

And now I’m sitting here realizing I haven’t been feeling very successful in any realm.

Funny how that works.

So I’m coming back.

Back to writing.
Back to Substack.
Back to myself.

I’m not chasing publication right now.
I’m not optimizing for money or reach.

I’m looking for community.

People who want to sit in the conversation of transformation, learning, growth, and being human in real time.

I want to share the way I see the world. The way I process things. The questions I can’t quite answer but keep circling.

If something I write makes one person—one kid, one adult, one human—feel less alone?

That’s success.

Full stop.

So now I’m curious:

What does success mean to you?

Not the version you were handed.

Yours.

In your art.
Your music.
Your writing.
Your life.

What’s your steering wheel?