letters

I asked ChatGPT to be brutally honest with me + Retreats, Retreats, Retreats

June 3, 2026 / Original Kit letter

I asked ChatGPT to be brutally honest with me.

Not about my business, AI or strategy.

About me.

I asked:

"What am I still holding on to that's keeping me from moving into my next season?"

The answer wasn't what I expected.

It wasn't a missing funnel, or a missing offer, or a better content strategy.

It was the belief that if I could just explain myself clearly enough, people would finally understand.

Understand my intentions.

Understand my vision.

Understand how much I've carried.

Understand why I see things the way I do.

The problem is that understanding isn't something you can force.

Some people will understand you.

Some won't.

Some will only understand the version of you that fits the story they've already decided is true.

And that's where I've spent more energy than I'd like to admit.

Trying to get people to see what I see.

Trying to get people to acknowledge what feels obvious to me.

Trying to create resolution through explanation.

Lately I've been wondering if the next season requires something different.

Not better communication.

Maybe it requires releasing the need to be understood.

And putting that energy back into building.

Back into creating + becoming.

Because at some point the question stops being:

"Why don't they see it?"

And becomes:

"What could I build if I stopped waiting for them to?"

Curious:

What's something you've had to release before you could move into your next chapter?

What I'm Focused on This Week

Retreats, Retreats, Retreats

This has easily been the biggest thing on my mind this week.

Over the past few weeks, I've received what I can only describe as a flood of downloads around what building retreats here in Roatán, Honduras could look like.

For a long time, I've thought about retreats as events.

Lately, I've been seeing them more as containers.

A place where people can step away from the noise of everyday life long enough to hear themselves again.

I've been sketching out different retreat concepts, thinking through locations, experiences, conversations, and what makes a gathering transformational instead of just another trip.

Some of the ideas are focused on founders. Others are centered around men, relationships, family, purpose, and the questions we don't often make space to ask.

It's still early, but this is the project that's asking for more of my attention.

Content Creation

The other thing I've been working through is my relationship with content.

I've realized that some of my favorite content has always been the kind that simply documents what I'm thinking about, building, wrestling with, and learning in real time.

Somewhere along the way, I started creating content based on what I thought I was supposed to publish instead of how I naturally like to communicate.

So lately, I've been experimenting with a return to a more personal style.

In many ways, it feels less like creating a new style and more like returning to an old one.

Substack

And finally, I'm preparing to make the move to Substack.

Partly because I want a better home for longer-form writing.

Partly because I want a place where ideas can breathe a little more than they can on social media.