Brett Trainor
Corporate quit on me at 45. Six years later I've made money fifteen different ways, and I'm still figuring it out in public alongside a few thousand other Gen Xers.
Corporate is ending earlier. We're living longer. Nobody wrote a playbook for this part, so I'm building one out loud. Testing what works, sharing what doesn't. In corporate or out.
Publications that came looking for my point of view
“Top career coach warns Gen X…” Fortune
Work with me
Every Gen Xer I talk to hits the same wall. You can picture the life you want. You just can't see how to pay for it without a job somebody else controls. That's the stone everybody has to get over, and it's the one thing you shouldn't try to figure out alone.
Two ways to do that with me, depending on where you are.
You're planning your way out, or you just got pushed out, and you want somebody in your corner while you figure out what's next. Not a course. Not a group. Just us, working on your actual situation.
Where the money comes from. What you're building. What to do first, and what to ignore entirely. I've done this with hundreds of people and it's still the part of the week I like best.
You're out, or you've got something going on the side, and mostly what you need is somebody to ask. Pricing, proposals, a stalled deal, whatever's got you stuck this week.
Unlimited answers from me and our experts, 1-on-1 calls when a thread isn't enough, and a few hundred other solo owners running a business exactly your size. This is where The Collective lives now.
The Podcast
A Gen X quest to build the life we've earned.
No script, no production, no guru voice. I'm figuring this out and I bring in people who can help me, and us. Money, work, health, what the next forty years actually look like. I ask them all if they'd go back. Nobody says yes.
A few steps down the trail, turning around to tell you what I see. Wins and flops, honestly, as I go.
What I Believe
Six years in and hundreds of conversations later, the people living the way I want to live all look kind of the same. Not rich, not perfect. Just clear. Here's the pattern.
They stopped overcomplicating. Fewer goals, fewer moving parts, fewer things demanding their attention. Simple is a competitive advantage most people are afraid to use.
They stopped giving it away by default. They know what their hours are worth and they spend them on purpose, on the people and things that actually matter.
Not their life around work. The job stopped being the center that everything else scheduled around. That one shift changes everything.
About
I spent more than 25 years in corporate go-to-market roles. Good jobs, work I mostly liked, paid well. On paper nothing was wrong. But something was off and I couldn't name it. I was high-functioning and quietly miserable. The commute, the endless calls I was done with but kept taking, the grind of looking busy.
Then they made the decision for me. What I decided was that I wasn't going back.
Getting out didn't fix it. I thought the hard part would be replacing my income. It wasn't. When I first went solo I filled every hour, optimized everything, and felt guilty the second I wasn't busy. I'd escaped the grind and rebuilt it in my own house.
The answer turned out to be less, not more. Simpler. More intentional. I got lazy on purpose about everything that didn't matter and ended up happier, healthier, and more effective than I ever was grinding. Six years later I'm still on the quest, and still learning.
We overcomplicate everything, we give away too much of our time, and we keep asking for permission we don't need. I learned that the hard way. You don't have to.
Also
For events, associations, and companies navigating the Gen X moment. Direct, practical, and built for people who've heard enough motivational speeches.
Coaching if you're making the move. The Hotline if you're already building.
See both