Sure, you wouldn’t orchestrate a prison break, but can you leave your awful job?

What do a prison break and leaving an awful job have in common?

It takes a desperate person to decide to instrument a prison break. If you’re desperate to leave your job, find a way to leave it, but move wisely. Use that desperation to fuel your intensity. Learn how to break out of the prison of your awful job just like the two prisoners in the story below by reading on.

In 2015, two men convicted of murder escaped from Clinton Correctional Facility. The community and authorities alike were shocked by this daring escape. When authorities investigated how the two inmates, David Sweat and Richard Matt, had broken free from the confines of incarceration, they discovered they had employed an advanced level of planning and forethought.

If you feel like it’s time to leave your job, you should strive for the same level of careful planning as these men. Plus, you want to never get caught unlike these two. Matt lost his life, and Sweat was taken back to prison.  Since they had both been convicted of murder, this is where their story probably differs from yours. But you are going to use similar qualities to institute change and get yourself a brand new job.

Below, we’ll go through the steps the two prisoners took, and what your list of actionable items should be when trying to escape a trying day job.


Sweat and Matt believed in their cause. They wanted out and they were willing to reap the repercussions if they were caught. How bad is your job really? Weigh the pros and cons of your current work situation. Is it fulfilling? Is it paying for everything you need, and allowing you to save? Are you still learning? If the answer to these questions is a resounding no, it’s probably time to make a change, despite how scary it can be.


It’s a pretty big motivator to be contemplating the rest of your life in prison. A bad job could never make you feel that stuck, but sometimes the way out feels uncertain. The two prisoners in this story dared to dream and decided their reality was untenable. They put a plan in place and enacted the necessary steps to make it happen.

Create a detailed escape plan. Are there any reasons to stay at your job longer―higher 401K contributions from your employer after a certain amount of time, more pension, a training you’ve been wanting to attend? Create a timeline for action.

What type of job are you looking for? Where are the best places to search for it? How long will it take you to find?

break out of the prison of your awful job

Police search for the inmates. (Photo by Krisoffer Grogan)


The escapees created dummies from sweatshirts and put them in their beds so guards would not catch on that they were missing. Although it’s funny to imagine a blow-up doll sitting in your cubicle, what’s more important in your case, is showing up for your job. Be careful not to make outward comments about your dissatisfaction, or about how you’d like to be elsewhere. Use that energy to propel your job search. Get out of work when the day is over. Tout suite. Move toward your dream of getting the F out of there for good. Do not get talked into extra hours. Don’t spend time waiting for coworkers after work. Do not pass go. Just go home, or wherever it is you like to search for new positions.

Accept Help

Sweat and Matt curried favor with a prison worker, Joyce Mitchell, who brought them hacksaw blades (among other tools) to saw through their walls. Another prison worker named Gene Palmer took them tools disguised in meat. Although one might argue both prison workers were manipulated, they must have considered the inmates friends at the time.

The two prisoners also became accomplished artists in lock-up. They would give their impressive pieces to other inmates and guards, and expect favors in return. Palmer was one of their biggest collectors; he had about 10 paintings and the men received favors from him in return. This is how the men were able to get the tools they needed to orchestrate their escape.

Reach out to your own friends. Finding a job is always easier when you use your own channels to find connections. Instead of sending a job application off into the outer space that is online jobs, ask every friend you know about possible firms, positions, and people who might know more. They’ve got your back, and luckily you don’t even have to ask them to smuggle you a pickax. This ask is much smaller and they’ll want to help.

Just don’t ask your work friends. That could get you in hot water. It’s better to keep your job search totally separate from the current work realm.

break out of the prison of your awful job

Attention to detail

Sweat said he didn’t fear being caught on his nightly explorations because guards often slept on their shifts. It was part of  “culture of complacency” at Clinton Correctional Facility. Like the prisoners, keep your eyes open for your employer’s weaknesses. Not because you are a wicked person, but because once in a while, an employer will act petty if they find out their employees plan to leave. If you find yourself in a tight spot or being treated unfairly after your employer finds out about your plans to leave, you can protect yourself by having information about problematic practices in the workplace, either those that are aimed at you or others.


An OAM Air Interdiction Agent searches for Richard Matt and David Sweat on June 16, 2015. (Photo by Krisoffer Grogan)


After Sweat sawed a hole in the back of his cell, he spent time after lights out, exploring the complicated tunnels of the prison walls for five hours a night. He believed in his end goal enough to stick with this, despite the danger of being caught, and his escape plan being foiled. A job search can be just as much of a convoluted maze, where patience and followthrough are two powerful skills.

When you hate your day job, it could feel slightly reminiscent of a prison sentence (Prison is worse. Duh. Desperation could tempt you to make rash decisions. But don’t jump from one bad situation to the next. Rationally explore your options, and don’t rush. Put thought into any possible jobs that arise. Evaluate them honestly. Take off your desperate, rose-colored glasses. No, you haven’t really wanted to be a cake-icer your whole life, it just sounds better than the current doldrums that is your work existence.

break out of the prison of your awful job

Harness your desperation like David Sweat. A job change is much less life-threatening than attempting to escape from law enforcement, after all.

Being Open to Uncertainty

David Sweat’s prison worker friend, Joyce Mitchell, had promised to pick the men up, after they made their way out of the prison pipes. However, she did not show up and they had to figure out another way to get out of the vicinity of the prison. They dashed into the forest.

The best-laid plans can go awry. Have a Plan B lined up, so you don’t feel stuck. You have a job lined up? Great. You have two jobs lined up? Even better.

Read more about the escapees’ stories here. 

Do you hope to leave your awful job? Or maybe you love your job and have a friend who’s suffering. Why don’t you share this escape plan with them, so they can work out their daring plan?