What I Got Wrong After Selling My Company: Chasing Titles, Not Alignment.
July 24, 2025
I thought selling my company would be the hard part. Turns out, what came next was harder — figuring out what I actually wanted. Its a struggle.
After I sold my company, I thought the next chapter would be easy. I'd put in the hard years, built the product, raised the money, survived the chaos, and gotten to an exit. Now it was time for the reward: a “real” job with a fancy title, stability, and maybe even a stocked snack bar.
I took two of those jobs.
And I got it wrong — twice.
Not because the companies were bad. Not because the people weren’t smart or the work wasn’t interesting. I got it wrong because I made the same mistake both times: I chased the title when I should have chased the alignment.
Job #1 — The Safe, Impressive Role
The first role came with all the things a post-exit founder thinks they want:
- Senior title
- Established company
- Predictable hours
- Big team
- Big budget
On paper, it was perfect. The kind of job people nod approvingly at. But within a few months, I felt it — the drag. Meetings with no decisions. Layers of approval for simple actions. A culture more focused on maintaining than building. I wasn’t solving problems; I was managing process.
What I got wrong: I thought stepping into a big organization would give me room to lead. What I found was a system that wanted me to fit in, not drive change. The work needed stability. I’m built for momentum.
Job #2 — The Overcorrection
After that, I swung hard in the other direction. A smaller company. Looser structure. More ambiguity. I told myself this was my chance to jump back into the arena.
And I did.Product, ops, growth, systems — I took it all on.
But I rushed in without asking the most important question: Do they actually want what I’m about to build?
They didn’t.Not because it was wrong — but because it was misaligned with their pace, vision, and appetite for change.
What I got wrong: I assumed a startup needed a fixer. What they needed was stability and incremental growth. I came in trying to reinvent the engine. They just wanted a tune-up.
The Realization: Alignment > Title
It took two missteps for this to finally land:I’m not looking for a title. I’m looking for alignment.
Alignment with vision.With how decisions get made.With how fast the team wants to move.With a culture that values action over optics.
That’s what drives me.
Whether I’m consulting, launching something new, or embedding inside a team — the title doesn’t matter. The vibe does (the term the kids use these days). The mission does. The fit matters more than the frame.
If you’ve ever taken a job that felt right on paper but off in your gut — you’re not alone. The biggest leaps in my career came when I chased alignment first, and figured the title out later.
Am I the only one who has made this mistake?
