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…



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.