Business Lessons

Here's How Prison Taught Me How to 'Lead From the Front'

The lessons I learned during my 17,520 hours of incarceration may help you, too. Just don't learn them in their native environment.
Contributor
Serial Entrepreneur, Digital Strategist, Web Designer, Author, Volunteer
7 min read
Opinions expressed by Entrepreneur contributors are their own.

In an earlier part of my life, I went to prison for two years. My incarceration began two months before my 28th birthday, and I was released two months before my 30th. I went to prison due to previous convictions and a fight I was in when I was 22 (six years earlier).

Related: The 10 Biggest Business Lessons We Learned In 2017

I was a much different person going into prison in my late 20s than I had been when I got into that fight at 22. So, prison was a crushing blow to my life, considering that I'd already changed my life around.

That's how, going in, I found myself confronting two choices about how I'd spend my time:

Choice 1: Be a part of the "yard society," playing cards all day, shucking and jiving with the fellas, talking about past and future crimes I had committed or planned to commit . . . or

Choice 2: Figure out how to use every waking second of my upcoming prison time to be as productive as possible.

I chose the latter option (which I've previously written about). Specifically, I chose to stay open to learning in prison, which I did, in terms of the specific subjects I studied and the stuff I learned about myself that I'd never known.

One more thing I learned about was leadership lessons. I used those lessons and my prison experience as the launch pad for my current success. I'm a firm believer that any situation can create an opportunity to learn if you have the right mindset. That's how I came to the leadership insights I gained as an inmate.

What kind of leader are you?

Before I expound on those lessons, it's important to review the various leadership styles, as there are many out there to choose from. There's a leadership tactic, for instance, called shepherd leadership, which is fashioned after a shepherd taking care of a flock.

Related: 5 Important Business Lessons You Can Learn From Billionaire Oprah Winfrey

A shepherd leads from the front versus a leader who "facilitates" and "guides." I believe that the latter leadership style is important at times -- for example, for empowering employees or teams to handle objectives while you work on the business versus in the business.

I also believe that there are times when a strong leader knows when to follow (and here I've been inspired by an article I read in 2012 in the publication Executive Education, from The Wharton School). A strong leader puts aside her or his ego and steps aside in order to focus on what's best for the group. An example would be a medical emergency when a doctor -- with the technical skills to deal with the scenario at hand -- is best equipped to handle it.

I believe a true leader knows when to flex his or her leadership capabilities, and knows to be ready for that exigency, with a massive arsenal of leadership weaponry he or she can choose from.

I also believe that taking charge and leading from the front (as Napolean did and as I explain below) is a powerful skill and equally needed when the time is right.

As cultural icon 50 Cent and his co-author Robert Greene explained in their book The 50th Law: "The greatest generals in history . . . are invariably those who lead from the front and by themselves. They can be seen by the troops at the head of the army, exposing themselves to the same fate as any foot soldier.

"The Duke of Wellington said that the mere appearance of Napoleon Bonaparte at the head of his army translated into the equivalent of an additional forty thousand men," the book continues. "A kind of electrical charge passes through the troops -- he is sharing in their sacrifices, leading by example. It has almost religious connotations."

This is the type of leadership I admire. In prison, I quickly learned that taking charge and being a frontward-facing leader was the most effective approach for that environment, where respect is demanded and aggression is the norm. However, my frontward-facing leadership wasn't planned, and was a lesson I accidentally stumbled upon.

Here's how that happened:

1. Mindset is everything.

As I already wrote, in prison, I made the conscious decision to make the waking portion of those 17,520 hours productive. Overall, I was relentlessly focused on bettering my mind, body and spirit. I learned conversational Korean, studied everything from string theory physics to ancient Greek and even taught myself the basics of computer programming without the internet, using textbooks.

I had all sorts of business publications sent to me, from Entrepreneur, Forbes, Fast Company and Wired, to the Wall Street Journal and San Jose Mercury (for tech related news).

And I trained my body religiously, performing hundreds of burpees a day. No matter what yard I was sent to, I diligently focused on my program. That left me little time or room to get mixed up in prison politics or yard dramas. Mindset was the only thing I had any control over, and it empowered me to be the person I needed to be for myself, my future, my family and even the people around me in prison.

2. How I became an agent of change.

By having the right mindset, I saw an interesting thing happen. No matter where I went, and whoever was around -- from my cellmate to other prisoners in my housing unit, to even the correctional officers who delivered my mail, people gravitated toward me, asking questions about what I was focused on.

Even though I wasn't leading groups or recruiting people to better themselves, my actions made me an agent of change, no matter where I was in prison. I began to positively influence the people around me. The people in my housing unit started reading my books, joined my workouts and focused on their emotional and spiritual states.

3. My responsibility increased.

Carrying myself the way I did, resulted in an overall respect for my character during my incarceration. As counterintuitive as it may seem, in prison, character and respect are two very important traits to possess. There are prison politics that are put in place to make sure people treat one other with respect and don't steal, and to weed out the people causing problems on the prison yards.

I found myself in leadership positions in prison, where I helped make sure the yard ran smoothly and ensured there was continued peace throughout. This increase in responsibility helped me improve my leadership ability even more and allowed me to focus on being the best version of myself.

If you're looking to improve your leadership capabilities, the best way to do that is just start leading. Be bold in your requests to take on new positions, seek ways to be an agent of change and experiment with the various types of leadership. In those ways, you'll improve your leadership experience.

Also, take a page from my upcoming book on my convict period: When leading teams and people, recognize that it's critical that you understand how you show up. It's critical that you become conscious of the actions you represent, versus the words you speak, and how you treat your teams. Learn various leadership styles, and adopt the ones that will empower you and your teams.

As I look back, I see how prison taught me more about myself than almost any other experience I've faced. It made me mentally stronger and helped me establish habits I still use today (like my insatiable hunger for knowledge and self-education).

Related: 7 Business Lessons From the Gridiron

Eager to learn more? How about we agree that you just take my word for it (or read my book), rather than try to learn these prison leadership lessons in their natural setting?

My Queue

There are no Videos in your queue.

Click on the Add to next to any video to save to your queue.

There are no Articles in your queue.

Click on the Add to next to any article to save to your queue.

There are no Podcasts in your queue.

Click on the Add to next to any podcast episode to save to your queue.

You're not following any authors.

Click the Follow button on any author page to keep up with the latest content from your favorite authors.

The 10 Biggest Business Lessons We Learned In 2017