What The Shawshank Redemption Can Teach You About Entrepreneurship


It was a disappointment at the box office, but grew to popularity on cable television to the point that almost everyone I know considers it one of the top movies of all time. I'm talking about The Shawshank Redemption. It's a deep movie, and while talking with a friend the other day, I came to realize how well some of the lessons in the movie carry over to life as an entrepreneur.

Lesson 1 – The Discontinuity of Success (Why Overnight Successes Are Really Long Battles)
Overnight successes aren't really overnight successes. They only seem that way. I touched on this in my post about Elton John and How To Make Millions in 30 Minutes or Less. In The Shawshank Redemption, Andy Dufresne spends 19 years digging a tunnel to escape prison. The result is binary. He's either in prison, or he isn't. For 19 years, he's making progress, but he's still in prison. Then one day he is free. It seems like a huge jump, but it wasn't.

This happens a lot to entrepreneurs. They go years without reaching the level of success they seek, and when they find it, it often comes in the form of a discontinuity. You go through each day, working hard, not knowing if you will ever see the payoff you hope for, but taking satisfaction in the process of building something. Then one day you are acquired, or go public, or get to the point that you don't have to be involved every day. All of the sudden it's different.

Many people in Andy's position would have tried to break out of Shawshank like this:

1. Get a rock hammer and start digging.
2. Realize it's going to take a long time.
3. Give up. Or possibly…
4. Get a bigger hammer that gets you caught, and lose any hope of breaking out because the guards keep a better eye on your activities.
5. Start trying again, every time the place really gets to you, but always give up after a few weeks because it's hard and progress is slow.

The result is that you would spend your life in Shawshank. So the lesson of Andy Dufresne is to keep plugging away. Do whatever you can. It's all about forward progress. Overnight successes tend to happen to people that have put in years of paying their dues.

Lesson 2 – Institutionalization (Get Busy Living, or Get Busy Dying)

Entrepreneurship isn't for everyone. I'm not one of these bloggers that will chastize people who work for corporations. There is nothing wrong with that. It fits some people very well, and is a surer path to success. But it can kill the spirit of an entrepreneur to spend too much time in a big company.

Here is what Red (Morgan Freeman in the movie) says about Brooks, a long time inmate who threatens to kill another inmate because he's afraid to leave Shawshank.

He's just institutionalized…The man's been in here fifty years, Heywood, fifty years. This is all he knows. In here, he's an important man, he's an educated man. Outside he's nothin' – just a used-up con with arthritis in both hands. Probably couldn't get a library card if he tried.

Spend a long time at a company, and you get some nice perks. You get seniority. You get an expense account. Leave for a startup and all of the sudden you are building desks out of old doors and staying at Motel 6 instead of the Hyatt. It's not a jump everybody can make easily.

The other point that is relevant is that if you have an entrepreneurial spirit, too much time inside a slow bureaucratic company can kill it off. Here is the rest of Red's quote about Brooks.

..these walls are funny. First you hate 'em, then you get used to 'em. Enough time passes, it gets so you depend on 'em. That's 'institutionalized'…They send you here for life and that's exactly what they take, the part that counts anyway.

Like I said. Corporate life is a perfect match for the skills and interests of many people, and that's fine. But for entrepreneurs, anything more than a year or two could kill off that urge to build something. It's hard to leave the comfort of a steady paycheck and the 8-5 life, but it's like Red says in the movie – "get busy living or get busy dying."

For those of you struggling in the trenches of your own business each day, take a night off and watch Shawshank. It's entertaining, inspiring, and it will help you remember why you march to the beat of your own drum.

  • What a great lesson to draw from that movie. It is a favorite of mine, though I had to be forced to watch it. I didn’t want to see another prison movie. It is a great inspriration for the human spirit, I have just never thought of it in terms of the entreprenurial spirit. Great job Rob.

  • DJM

    I agree. I didn’t see the green mile b/c shawshank was so good. i didn’t like oz b/c it was so dark compared to shawshank. rethinking on it about lessons for entrepreneurship, think i have to watch it again, could delve into the black market (where he got the hammer and poster).. also, the work for the warden (danger of entrepreneur losing control — warden to andy)… just off the top of my head…

  • Creative thinking, Rob. A great article. The prison/corporation symbolism chills my spine though. Maybe it’s time to escape…before it’s too late. ;-)

  • This is a great article. Persistence is what counts. Keep plugging away.

  • Excellent stuff!

    I am an entrepreneur myself and it is quite like the story of the guy taking 100 swings at the big boulder and it not showing a crack, then splitting in two on the 101st blow. It gets difficult sometimes, but it is that big picture that keeps you going.

  • Danielle Forenze

    I read this post only because you pointed in out in your Top Ten (http://www.businesspundit.com/50226711/the_top_10_businesspundit_posts_of_2007.php) and I now agree with you. It is one of the better posts you’ve written, and all the more so because it reflects the power of the simple, profound life lessons that The Shawshank Redemption gives to us. I’m going to give Stephen King a few more dollars now as a token of my appreciation.

  • ConcernedFellowBlogger