How to Plan Your Next Great Escape

Yesterday while re-listening to Kanye West’s College Dropout I started reminiscing on the situations in which I felt trapped in my life (or parts of my life) and the actions that led me out of them. The album chronicles many of Kanye’s frustrations with the flawed institutions in his world and life before he achieved the creative success and autonomy he strived for, as well as his not so straightforward journey toward actualizing his dreams. He finishes the album with a story of his career, ending at the moment he decided to sign as an artist for Rock-A-Fella, letting the potential success of the album and his future life as a creative speak for itself. While I may have not gone from endless summers of working late nights, wasting my money on diamonds and other unfulfilling material goods, getting evicted from my apartment, to signing a contract to release my Opus with the artists I looked up to as a child, I think the feelings and the message that Kanye communicates in this album are universal.

There have been so many times in my life when the institutions in my world felt like a personal prison. When I was working 40+ hours week at a restaurant to pay rent and coming home to what felt like just enough time and money to survive, but not enough to enjoy my life or better it in any way. When I was burning myself out and destroying my relationships because it’s what I thought I had to do to meet my demanding academic expectations, studying a field I had yet to see support the lifestyle I wanted. When I had to go to school everyday where I knew I’d be bullied and have to pretend to ignore it, and not understand why. When I’ve felt stuck and dissatisfied in many recurring situations in my life, big and small, and realized I wanted something different. Even when things are good (as they are for me right now) and as they continue to get better, there will always be ways in which I want my lifestyle to be more closely aligned with my values and the institutions that lock me out from the life I desire always present themselves as a challenge.

While reflecting on these memories I identified how I escaped these institutional prisons and lifestyle plateaus. I made an escape plan. The more I investigate this pattern, it seems an escape plan is the your best bet at living a better future. In The Four Hour Work Week Tim Ferruss tells the story of building a sports supplement company to escape his unfulfilling job technical sales job, then building an escape plan to get away from the prison of his own creating, running a company 80 hours a week so that he could Escape the 9 – 5, Live Anywhere, and Join the New Rich. How did Tim escape? He built the plan that is detailed in the Four Hour Work Week and carried it out as a series of experiments with no assurance of success (in fact he was almost certain he would fail, but figured that most failures are reversible). When he grew tired of the pressures writing gigantic technical self help books alone he made a few more escape plans. First a Vimeo talk show with his best friend. Then a television show that ended up never airing. Finally a podcast, which grew into another life altering success. What I always loved about Tim Ferris was the way he encouraged his readers to challenge their assumptions, find and demolish the walls that construct their personal prisons, and to view life as a series of experiments, or in this context, escape attempts.

How should you go about developing your escape plan?

  • You should be able to start right away
  • You should be able to fully execute it with only a few hours of effort a week for six months
  • Failures should be either reversible, or wins in a different direction
  • You should be able to see yourself progressing biweekly
  • The act of working on it should be its own reward
  • You should walk away with something to show for it
  • It should have the potential to change your life in a huge way if you’re lucky, and in a noticeable way if you’re unlucky
  • It should be a step towards a life you want to explore

For some commentary on the above points, I’ll walk through an example of an escape plan I built and executed for myself. I wanted to work on things that would give me more personal satisfaction and creative fulfillment. So I decided to start a website. At the time I knew next to nothing about web development. I decided to take an online course that walked students through the process of building multiple websites so I could start right away. After the course I planned to build on the sites I’d already made to create a site that was useful for me. I continued to do good work at my job and keep my ambition private. As I learned a new skill or built a new site in the course every two weeks or so, I added them to my resume and portfolio so I could see and show my progress, even before I was sharing it with anyone. I set up my environment so that when I’d make progress on my site in the morning before work I would feel like I’d already won the day before it started. I focused on the valuable and important skills I was developing in the process and the products of my work more than the potential success of my new website. I ended up building, which certainly could have been the next Yelp and turned me into an overnight billionaire, but instead became a fun tool for myself and others to review the skateparks they visit. I redesigned my resume around my new site and used it to leave the workplaces where I felt a cultural divide between myself and my coworkers. I used my improved resume to find a much more ideal job, working with bright web developers, building cool applications and learning new useful skills everyday. Put simply, the plan was to make a website, a very achievable stretch goal within my control, and I went through the bullets above when designing the process to optimize my upside and minimize my downside. In a few hours a week for six months I reinvented my career and built something I’m proud of.

With my recent experiences with these escape plans, and the experiences of my peers, I’ve decided the most surefire path to a better life next year than last year is to build an execute two ~6 month escape plans. I’m excited to see the surprising places my new plans will take me in 2018.

So where do you find yourself now? You’re Andy Dufresne at the Shawshank prison. Your life has good parts and bad parts, and you’ve figured out how to make it work for you so that you can survive and possibly even thrive in the position you find yourself. Since you are neither reckless nor obtuse you are not going to throw out the good parts of your life for a chance at something better. Instead you are going to develop a plan, a plan that will evolve as you learn more about yourself, your surroundings, and the way out. You are going to spend the waking hours of your days maintaining your position in life and acting as if nothing has changed. At night while others fantasize about the other side you will slowly carve your tunnel to freedom one etch at time. Every night you’ll save your work so you can build on it the next day. You will notice an improvement in your demeanor as you realize you feel less trapped when you see your tunnel growing closer to freedom every night. You understand that it might not work, but you will stick to your plan until either it does or you realize the ways in which it is flawed and start developing a new escape plan. One day, while doing your daily carving, you will notice the wall you are scratching at sounds hollow. Eventually a crack will develop. Soon light will shine through and when you least expect it you will be able to fit through. Once you’re free you’ll remember the patience and persistence it took to achieve your goals and you’ll understand you can apply it to accomplishing anything you want. You’ll remember how a little bit every day started to add up after a few months, and after a few years you’d developed the skills to sculpt part of your life in your image. Then, before you get too settled with the status quo, you’ll find the unfavorable walls of the world you escaped to and start carving again.