5 Harsh Lessons Learned in Prison That Made Me a Better Entrepreneur Business success and prison survival both require managing relationships, accepting consequences and maintaining the right balance of humilty and confidence.
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The full body tattoos, obnoxious screaming, and violent conflict resolution were foreign to me as a nerdy, upper-middle class kid with thin wire-frame glasses. Keeping my head down and ears open was the only thing I could do to prevent myself from getting caught in the wrong situation.
From age 17 to 20 I stole historical documents and sold them to fund my college education abroad. In an ill-fated attempt to follow a woman, my insecurities led me to a prison cell. I was arrested and spent three-and-ahalf years free until my conviction.
My six months in the Texas state penitentiary taught me much about living righteously. Minding my own business left me ample time for reflection. Lessons I learned from prison have changed my perception on life and what it means to be a successful entrepreneur.
1. Let go of control.
It's impossible to control things from prison. The guards controlled the daily schedule, the food I ate, everything down to the people with whom I associated. Even gangsters, who felt powerful, still had to wait in line for egregious-tasting prison food.
Power and control are illusions that prison made evident. Likewise in life, and especially in entrepreneurship, there are few things in our control. We can't control competitors, market forces, or the economy, but all of those things can ruin a business.
I am far more successful when I relinquish control in my business. When I launched my recent ecommerce store, I tried to control an affiliate's ad-copy. It failed miserably and I realized I had to let him try his own way. My desire for control is usually driven by insecurities. When I am too afraid to let go or detach myself from something, I invariably try so hard to make it work to my advantage that I precipitate the very event I'm trying to avoid.
Related: How to Stop Being A Control Freak
2. Consequences for every action.
One consequence for my crime was prison. Inside prison this point was driven home further. I said "excuse me" every time I walked in the personal space of another inmate. I offered my food with others out of respect. The consequence for disrespecting others can be death.
Those experiences made me more mindful of actions I take in my new business. I'm conscious of the possible repercussions when I choose the formulation, the label design, and every other detail of my product.
Laziness and egotistical thinking prevent productive decisions. By seriously considering every action with presence and care, you will avoid many negative repercussions that make your life inconvenient, or even drag down your business.
3. Self acceptance and confidence.
I stole historical documents and I acknowledge the harm I caused, but I have to accept myself and my motivations. My insecurities and lack of confidence with women motivated me to commit the crime. I now realize confidence is less about tangible assets I have or things I've accomplished, but being comfortable with what I lack.
Deep down, everybody wants to feel loved and accepted. Each individual is doing the best that they can with what they have been given. Whether it was abusive parents, bad genetics, they are doing their best in this moment.
Love and acceptance motivates you as well. Accept who you are and what you lack. Grow comfortable with your flaws and seek love from yourself as opposed to others. When you accept and love yourself, confidence will grow and so will your business. Suddenly you'll stop acting strange around investors and journalists, you will take decisive action, and you will stop wasting your time and energy chasing validation.
Related: 6 Tips For Accepting Failure and Moving On
4. Vulnerable and emotionally open.
It may sound odd that an entrepreneur can benefit from being vulnerable and emotionally open, but I connect with people more deeply now. This level of connection makes people want to help me succeed, so they make more introductions, edit poorly written Entrepreneur.com articles and provide moral support.
I hate how asking for help makes me feel diminished and vulnerable. Nobody likes asking for help, but the more comfortable I have become with being vulnerable, the easier it is to ask for help in an authentic and humble way.
Being vulnerable and emotionally open should not be a means to an end. It will certainly help you to grow meaningful business relationships and achieve more with your venture, but it will be more important to have support during the emotional roller coaster of a small business.
Related: From Prison to Silicon Valley: How One Entrepreneur Spun a Jail Sentence Into a Y-Combinator Backed Startup
5. Make the best out of every situation.
Prison sucks. There is nothing good about it, but I made the best of the situation and found some positives. I had a library where I could read classics and philosophical books. I had free time to workout to stay physically fit. I had a phone to call my manager or business partner to organize my business.
Sometimes I feel like everything is wrong with my business. I invested too heavily, I didn't test the market enough, the formula is terrible and people hate it. These are pretty typical thoughts for entrepreneurs, but they aren't helpful.
Each failed marketing campaign is a lesson, every customer emergency is an opportunity, and you can make the best out of any situation in your business.
I'm blatantly taking advantage of my experience in prison. I'm okay with that. If my violent, awkward, and somewhat traumatic experiences can help you learn more about entrepreneurship, then I don't mind spilling my guts. Naturally, going to prison has had a profound impact on how I view the world and, as an entrepreneur, how I do business. Sometimes negative experiences and pain are the easiest ways to grow and mature.
Remember, accept there are things you can't control and let go. Take every action seriously, as there are repercussions for each. Accept and love yourself to build your confidence. Be vulnerable and emotionally open to connect deeper with everyone. Make the best out of every situation, no matter how negative.
I hope my experience resonates with you.
Related: How My Life as an Entrepreneur Shaped My Time in Prison