I Made a Positioning Mistake
What happens when your own strategy backfires.
I Made a Mistake
Not in what I created – but in how I positioned it.
(Which, let’s be honest, is a little embarrassing… considering brand positioning is literally what I do.)
Last year, things got quiet.
Client inquiries slowed.
A major opportunity blew up after months of time, energy, and effort (a story for another day).
A few projects veered off track or fell apart.
And I kept asking myself: What happened?
I had just doubled down on a niche I deeply believed in: helping founders clarify both their business and personal brand so they could confidently exit and step into what’s next. It was bold. It was needed. And I heard again and again how brilliant the idea was! How unique, how timely, how everyone was talking about exits.
There were plenty of things I could have blamed: the economy, Trump, tariffs, AI… and maybe all of that played a part. But here’s the uncomfortable truth: They didn’t want it. Not yet, anyway.
I was selling what they needed…not what they wanted
I’ve been doing this long enough to know the difference.
But somehow I forgot.
Founders absolutely need brand clarity. They need a strong narrative that separates them from their business. They need positioning that makes them exitable.
But that’s not what they were buying.
Because people don’t buy what they need.
They buy what they want.
And what they want (especially pre-exit) is this:
Growth.
Leverage.
Recognition.
A brand that attracts buyers and partners.
A way to increase the value of their business and their leadership in the market.
They want to feel like the obvious choice.
They want credibility, status, and ideally… a killer payday.
I wasn’t wrong about what they needed.
But I was too early. And maybe a little too righteous about it.
After the Exit, Everything Changes
The business is sold. The papers are signed. The champagne’s popped. Everyone says, “Congratulations.”
But instead of feeling freedom, many founders feel fog. Suddenly, they’re trying to figure out who they are now.
The business is gone.
The team is gone.
The inbox is (blissfully) quiet.
And they’re left wondering: What’s next? What matters now? Who am I without the business I built?
When I talk to post-exit founders on the Legacy Branding Podcast, I hear it over and over:
“I built this amazing business… and now that it’s gone, I have no idea how to talk about myself.”
“I’ve never felt more free (and more lost) at the same time.”
That’s what they want now.
A new sense of purpose. A renewed identity. And a brand that actually fits this chapter of life.
Maybe They Needed the Crisis First
I think I was trying to spare them the existential crisis.
But that crisis? It’s kind of necessary.
I say this in my keynote A Life Worth Dying For – we grow through challenges.
We need pressure to evolve.
So maybe that’s where I went wrong. Not in the offering or the methodology. But in assuming I could shortcut their journey.
So Where Do We Go From Here?
If you’re a founder who’s already exited – and you’re staring down the blank page of your next chapter – let’s talk.
We’re here to help you rediscover who you are.
What you stand for.
And what you’re here to do next.
Because legacy isn’t what you leave behind.
It’s what you choose to build now.
Ready? → Book a call with me here.