Why Familiar Pain Feels Safer Than Freedom
The prison we refuse to leave
A friend of mine, Corissa Saint Laurent, texted me today:
I wrote some articles from the most salient episodes I’ve done over the years. Yours was one of them.
It’s called The Prison of Familiarity, and it explores something I see constantly in leaders, creatives, and coaches: the quiet ways we stay loyal to identities that once kept us safe, but now keep us small.
The piece weaves together leadership, ego, nervous system patterns, frequency, and the strange comfort of suffering. It includes a story from my work that gets right to the heart of it: how freedom often feels more threatening than pain, simply because it’s unfamiliar.
If you’ve ever felt like you know you’re meant for more ease, more impact, more alignment, but keep hitting an invisible ceiling, this is worth your time.
Read the article here:
The Prison of Familiarity: Choosing Freedom Over the Safety of Suffering (Featuring insights from Zack Bodenweber)
And if you want to go deeper, just about a year ago Corissa and I recorded a full conversation unpacking these ideas and what it actually takes to exit the “survival-based” version of success.
It’s called Shattering the Upper Limit
This is one of those pieces that doesn’t give you tactics. It gives you a mirror.
And sometimes, that mirror shows you the key that’s been in your hands all along.

