Three Lessons on Overcoming Obstacles From John Dillinger

Obstacles: we all face them, but entrepreneurs have them in spades. While there’s plenty of inspirational content that might help entrepreneurs face challenges, we’ve turned to a slightly more sinister source: organized crime. As you’ll soon find, if you’re an entrepreneur you have more in common with a crime boss than you think. A mobster always has the odds stacked against their success- and they have their fair share of problems to solve.  Sit tight for some lessons on overcoming obstacles straight from John Dillinger himself.


John Dillinger

John Dillinger mugshot

Long considered “The Original Public Enemy #1”, John Dillinger rose to fame in the 1930’s, in the midst of the Great Depression.  Dillinger was the people’s criminal. While other American gangsters inspired fear and thrived on intimidation, Dillinger was lauded for his quick wit, sense of humor, and his ability to remain calm under pressure. Dillinger’s main gig was robbing big banks, hold-up style. We join his story right after he was caught for the second time, on his way to Crown Point Prison.

Indiana’s Crown Point Prison was the strongest maximum security jail in the US, and Dillinger was its celebrity prisoner. With more armed guards per offender than any penitentiary he had ever been in, it seemed to be the last of Dillinger and his exploits. Yet even Crown Point couldn’t keep Dillinger, who broke free in 1934, within three months of landing in the joint.  Not only did he make his escape without shooting a single bullet, but he walked out the front door of the jail in front of his guards. His weapon? Wood.

Dillinger knew the value of the small things, even something as insignificant as a scrap piece of wood. He used his sanctioned razor to carve the wood carefully into the shape of a gun (it’s worth noting- some historians claim that the gun was made of a potato).  With his convincing sculpture in hand, Dillinger performed his classic hold-up on the prison, threatening the guards as he walked right out the front door to his freedom. Here are the three lessons we can learn from this story:


Improve Your Mindset

Crown Point Jail

Before Dillinger landed in Crown Point, the security of the prison was boasted about to no end. He was constantly being told that the jail was “escape proof”, that it would be impossible to break through the state-of-the-art facility. Instead of accepting these statements as facts, Dillinger blatantly ignored the hype, and instead shifted his mindset to figuring out how he could manipulate his situation to liberate himself. He created tools, investigated systems, and pushed his way through until he succeeded.

As an entrepreneur It can be easy to accept obstacles as “facts”, when in most situations, our challenges can be faced, skirted around, or avoided altogether. Instead of “can it be done?”, ask “how can it be done?” Move forward with confidence, and think outside of the box.


Plan to Overcome

Dillinger wood gun carving

We admit: it’s not all sunshine and wood carving. Just because you know what you can leverage to be successful, doesn’t mean you know how. Had Dillinger attempted to bolt out the prison door the second he realized his plan, there’s a good chance his Wikipedia page would be a lot shorter. Instead he planned.

When you have a big objective, breaking big goals into smaller, easily achievable tasks will help you reach the end game faster. Little targets that build up to the big target. Dillinger began his planning by breaking up an almost insurmountable task of breaking out of the country’s most heavily guarded prison into small achievable steps. Find the wood. Hide the razor. Carve the gun. Get moving.

As an entrepreneur you must do the same. You need to crawl, then walk, then run- in that order. The next time you are faced with a huge obstacle, break up your game plan into small tasks and watch your brick wall crumble before your eyes.


Do More with Less

We’re not here to say holding up prisons, or threatening violence, is the way to get things done in the business world. But we all know there are those days in the life of an entrepreneur that can feel like our obstacles are as impenetrable as a max-security prison. However, we’re willing to bet that you have a piece of wood lying around.

Startups and small businesses will always have to do more with less. It’s the reality of being a small shop, and it can be an advantage. How can you achieve your desired result with less money? Less people? Less time?

Survey your life for resources you have available, whether that’s extra time to work, a connection to a potential first client that you can leverage, or even an interest in writing that you want to explore. That one small thing, could turn into your next big achievement: your first product sale, client, or published book.

dillinger mugshot

Dillinger’s Steps to Overcoming Obstacles

  • Improved mindset- Not if but how. Confidence can’t be replaced.
  • Plan to overcome- Break up a big goal into small achievable tasks. Maintain your cool
  • Do more with less- You will never have all the resources you need. What can you leverage?

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The Business of Crime was created by a bunch of crime-obsessed startup junkies. We don’t condone the bad guys, but we do think we can learn something from them. What criminal mastermind’s strategies would you like to hear about next?

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