The Proxy

For a long time, my audience was freelancers.

Not by accident. I was one. I came from corporate, took the leap, taught myself Squarespace, built a plugin business around it, then started teaching other designers how to do the same.

The work felt natural because I was talking to a version of myself that was a few steps behind. I knew the questions because I’d asked them. I knew the fears because I’d had them. The authority came built in.

That worked for a long time.

It is not working anymore.

Here’s the part I’ve been slow to admit: my work has been organized around survival for most of my career. So when I served freelancers, I was solving my own problem through theirs. The proxy was efficient. They paid me to figure things out I needed to figure out anyway.

Two birds.

But proxies only work while the equation is the same shape on both sides.

Survival is no longer the level I’m organizing the work around. The plugin business is past me. The asset base is real. The work I’m trying to do now is about something else — about what you build when you have already proven you can survive. About what comes after the question of whether you can do it has been answered.

That is not a freelancer question.

That is a founder question.

And here’s the harder thing to say: serving who I once was had a hidden function. As long as I was speaking from a stage I had already crossed, I could stay safely ahead of the room. I could be the authority because I had structured the room so I always was. Growth was optional. The audience would always be a step behind me, no matter where I stood.

Most coaches never break that pattern. The audience that knew you early is the audience that pays the bills, and the gravity of that is enormous. You stay there. You become the person who still talks about the leap from corporate even though it was ten years ago. You become professional about your own past.

I am not doing that.

The reframe took me longer than it should have, but here it is: the best way to serve who I once was is to reorient to a higher level. The freelancer version of me does not need another peer talking to him. He needs to see someone who came from where he is operating at a level he has not seen yet. The proof that it is possible is more useful to him than my companionship at the same level.

Staying down to keep him company is the abandonment.

Going up is the service.

So this site is moving. The audience I’m writing for now is the founder in transition — the person running something real, who has solved enough of survival and is sitting with the bigger question of what to do with the room they have built.

The questions about money are still on the table, but they are no longer the table.

The table is identity, structure, and the governance of what comes next.

Some of you who have been reading me for years will recognize yourselves in that and come along. Some of you will not, and that is fine. The work has to move where the work is going. Forcing it to stay where it was already serves no one.

I’ll be writing here on a regular cadence from here on.

Less broadcast. More public thinking.

If that is the room you are in now, this is where I’ll be writing.