Founder Lost and Self Found

Sometimes, the best way to find yourself is to get a little lost.

We can choose to let go of what’s comfortable, leave the map of expectations behind, and walk into the darkness—trusting that we can handle this.

I’ve recently returned from such a trip. Traveling alone across six cities in two weeks, I found parts of me that had been hiding for 50 years. Among many revelations, I gained insights into what really, really drove me to become an entrepreneur, and why selling my startup hit me so hard.

It took joining the company of strangers in a strange land, ego naked and afraid, to uncover and encounter fears that were holding me back.

This post is going beyond my usual business stories. I’m taking a leap of faith that, by sharing who I am and how I’ve changed, I might inspire a few of you to uncover something new about yourself, too.

Relevant links:

Meghan French Dunbar on Joy Trips: https://meghanfrenchdunbar.substack.com/p/i-just-want-to-remember-what-it-feels

Douglas Rushkoff’s Retreat: https://rushkoff.substack.com/p/just-die

Heather Havrilesky on Attuning to Social Cues: https://www.ask-polly.com/p/attuning-to-social-cues-can-be-empowering

Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours

Fleet: https://fleetholdingco.com/