Prison Advice That Works Outside of Prison For Your Own Life

Craig Stanland
2 min readJan 7, 2022

I’m a member of a white-collar support group that meets every Monday night on Zoom.

The group has been instrumental in my journey, and I’m grateful to be a part of it.

We have people on the call at pretty much every point in their justice journey.

From just indicted to being out of the system for over 20 years.

This is just one aspect of the group that makes it so powerful.

Multiple perspectives.

When one of our members is set to report to prison, we’ll dedicate the call to them and share our collective wisdom so we can prepare them as much as possible.

There is one piece of advice that stands out amongst the rest:

For the first couple of weeks in prison, be an observer.

Nothing more.

If a group of inmates is sitting next to you trying to come up with the name of the movie starring Russell Crowe set in ancient Rome, do not, as badly as you want to, interject with the answer.

Sit and observe.

Observe the inmates, decipher who’s a trouble maker and who’s not.

Observe the CO’s, decipher who seems to treat the inmates with a modicum of respect, and who to steer clear of.

Observe the unwritten rules of prison life so you can navigate your time as smoothly as possible.


It took going to prison and being a part of the support group to understand that this piece of advice is not just for prison.

It’s for each and every one of us and the lives we’re living.

It’s too easy for our lives to be set on autopilot, to get so wrapped up with egotistical things, careers, money, cars.

The millions of little acts we do every day/week/month/year to keep our lives moving forward.

We don’t get into the habit of standing back and observing our lives and inquiring,

“Am I fulfilled?”

“Is something missing?”

“Is what I’m doing serving me?”

In order to create the lives we want to create, we need to understand the lives we’re living.

We do this by stepping out of the rushing river and observing the river.

Try to be an observer in your own life; you might surprise yourself.


My new book, “Blank Canvas, How I Reinvented My Life After Prison” is now available on Amazon.

I wrote this book from my heart, and I gave it everything I had.

My dream, my goal for this book is that it helps one person — the one person who feels right now how I once felt.

I’d be honored if you checked it out.

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.