How Getting Stuck on the “How” Almost Stopped Me From The Extraordinary

Craig Stanland
3 min readMay 25, 2023

3 experiences I’ve created that seemed utterly impossible when I was incarcerated.

  • Delivering a TEDx
  • Publishing an Amazon Best-Seller
  • Traveling the world for speaking (booking into 2024 already)

I’m wickedly grateful for the 3 experiences above; they’ve changed my life.

All 3 ideas were born in federal prison, they were goals I wanted to pursue, but I had no idea “how” they would happen.

My desire and need to understand “how” undermined my ability to move forward effectively.

My past thinking (and I still succumb to it today) was,

“When I understand “how” it will happen, then I can move forward. And until I understand that, I can’t move forward.”

Because if I don’t know “how” it will happen, how can I make it happen?

So I racked my brain thinking about the “how” and tricked myself into thinking I was making meaningful progress.

I was emptying the ocean a thimble at a time.

Lots and lots of work, no results.

I don’t know when the tumblers fell into place for me, but I understood I was on a fool’s errand and needed a more…



Craig Stanland

I write about my journey from corporate success to federal prison and finding joy, mission, meaning, and fulfillment beyond professional and financial success.