Four Lessons I Learned In Prison

What Do You Think It Is REALLY Like Behind Bars?


It’s been said that a good friend is one who would come get you out of prison, but a great friend will be sitting next to you.  Recently, I had an experience finding me in prison with a whole bunch of new friends. And, in only one day, I learned some valuable lessons — many of which are easily overlooked by the majority of us on the “outside”.

Prison Entrepreneurship Program 2013
Prison Entrepreneurship Program 2013

Several months ago, a colleague of mine had to decline a meeting we were attempting to schedule because he “had to go to prison that day”.  I stopped in my tracks. “What?”, I replied. He confirmed that, indeed, he was going to prison the next day…and he smiled. Yesterday, I volunteered to attend (and help judge) a business plan competition carried out by the Prison Entrepreneurship Program (PEP)  at the Cleveland Correctional Facility in Cleveland, TX. It was a moving experience.  Here are a few of the lessons I learned in prison:

  1. Everyone craves connection.

    When the volunteers walked into the room, we were immediately met with a huge cheer from the PEP participants immediately melting away any scenes I had previously recalled from Shawshank Redemption or an episode of Sons of Anarchy. Early in the day, I asked one of the long-time volunteers what kept him coming back. “Just wait until the end of the day. You’ll understand” was his reply.  In just one day, after hearing pitches for 14 legitimate businesses and observing the interactions between the PEP participants and executive volunteers, the only differences I saw between the two sides were the clothes.  Everyone in the room wanted to be successful. Almost all of them also mentioned their families.  Nobody focused on the differences.

  2. Mentors can learn from you, too.

    The focus for our day was to select four finalists (from a pool of 75+ business plans) in a “Shark Tank” style contest ahead of the finals, which would be judged the following day.  What I found amazing was the type of conversations that occurred by the judges AFTER the pitches were over.  Rarely did anyone seem to care that the presenter was a convicted criminal, rather the conversations were absolutely centered on the business attributes of the presented plans.  Many of the mentors even considered the fictional “investment dollars” as if it truly was their own actual dollars to invest, wrestling back-and-forth with how to allocate the money.


  3. Skills are transferable, even across very different disciplines. 

    No doubt, some of the men whose pitches were delivered yesterday once ran their own criminal enterprises.  But when you pull back the curtain, allow for time and healing to occur, create distance from bad situations and influences, underneath it all are many of the same skills someone would need to create a successful business.  Skills like marketing, business development, strategic planning, customer service, and, yes, even a little bit of “hustle”.  I don’t know of a single, successful entrepreneur who made it without a little bit of hustle.


  4. When telling someone your story, remember…it is your story to tell!

    Each plan I reviewed yesterday included some information about how that individual found himself in jail.  In many cases, I’d venture to guess what happened to them would not be much different from some of the decisions you or I might have made in a similar situation. These men, however, over the course of a six month program, learned that their story was just that.  Theirs.  Every one of them owned their story.  Most are heartbreaking to read or hear. Each of them knows that a leader is not defined by what has happened to them, but how they react, learn, and grow from that experience.

A few years ago,  following some setbacks in my own life, I wrote a book called Powerful People Overcome Powerful Failures. It is a success journal in which the reader invests 5-7 minutes a day to help get their thoughts and actions headed back in a positive direction.  In retrospect, my challenges were not near as steep  nor did they come with the consequences found by the men I met behind bars, however, the journey back to a blessed, fulfilled life was still a process.  As you consider the setbacks, failures and obstacles you may strive to overcome, just remember these four lessons I learned in prison and chart a course forward.  Abundance awaits, no matter what you have come through!

Click here to pick up your copy of Powerful People Overcome Powerful Failures (also available as an eBook).

2 Replies to “Four Lessons I Learned In Prison”

  1. Really appreciate your blog about the Prison Entrepreneurship Program. Volunteers and Executives are what help spread the word of this beautiful program. Very glad you were able to experience PEP. I’m sure the guys in the program are appreciative.

  2. Thank you, Robert, for stopping by to read the article. As you may have heard, I’m looking forward to becoming a “repeat attender” in 2014! See you in prison!

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