How I escaped my Alcatraz

A story about a recovering attorney now working in the tech startup scene, with no coding skills.

It was 18 months ago when I escaped my Alcatraz for the bright and shiny dream of charting my own path.

After almost eight years working as a lobbyist/public affairs officer and corporate lawyer, I finally pulled the trigger and set sail to my new life.
My career started in September 2010. I had just graduated from law school and had only one certainty in life: I didn’t want a career in law.

I’d always dreamt of becoming a diplomat or having a political career. However, the road to reaching any of those destinations seemed impossible. The last exams for a career as a diplomat took place in 2008 and the government wasn’t planning any more exams for 2011–2012.

So, after thinking about how to kick-start my career, I began working as a lobbyist/public affairs intern in Brussels. Within two years, I had been promoted twice and I had an offer to move up the ladder.

Despite excelling at work, I missed my country, my friends, and my family. It was time to pull the plug and go home. I had hoped that this political experience would help me pursue my political career in Portugal, but that wasn’t the case.

So, for the first time in my adult life, I realized that I would need to put my diploma to good use. My nemesis was at my door.

Overnight I joined an international oil & gas company as an entry-level lawyer. Within 5 years I was promoted four times, and I was told I was one of the rising young talents there. People respected my work and I grew fond of what I was doing. But despite all this, I started to resent going to work. It wasn’t a lack of motivation to wake up and go. It was that I really and truly resented working in law.

Time Travel

Let’s travel back to September 2011. I was in my second year working as a lobbyist/public affairs officer in Brussels. While waiting for the Vietnamese Ambassador to the European Union, my boss, in his funny-sounding French accent, asked me to tell him something intriguing about myself. I promptly replied “Christophe, I wish someone would invent a time travel machine.”

I had been dreaming about this for as long as I can remember. Traveling back in time and (re)living iconic moments or incredible periods of history. Stephen Hawking once claimed that backward time travel isn’t necessarily physically impossible, so there’s hope!

But in the meantime, I use reading to travel back and forth in time.
I believe it was somewhere in 2015 or 2016 that I embarked on a 4,000-year journey to ancient Babylon that changed my life.

I accidentally stumbled upon the Richest Man in Babylon, by George S. Clason. Filled with valuable information, one of the things that had an immediate impact in my life was how Arkad told his students that, no matter what business they were in, they had the power to increase their ability to earn.

“Thus the seventh and last remedy for a lean purse is to cultivate thy own powers, to study and to become wiser, to become more skillful, to act as respect thyself.”

I had just realized that, contrary to popular belief, my greatest asset wasn’t money but my time.

Mundus Novus

Arkad had piqued my interest. And overnight something changed. I wanted — strike that — I needed to discover this ‘New World’, this promised land, where my time, the one thing I control, is my biggest asset.

I had just found the motivation I needed to turn things around. So, I started spending my lunch breaks daydreaming about reclaiming my life. A life where I was truly in control of my time.

I often spent hours thinking about what kind of work would make me happy. Could I find something that would (a) motivate me enough for the rest of my life and (b) where I could make enough money to keep living the life I became used to?

I read hundreds of “9 life lessons”, “7 ways to” or “3 reasons why” blog posts glorifying self-validated ‘entrepreneurs’ and ‘hustlers.’ But we are all unique. We have different skillsets, we live in different countries, and we come from different backgrounds. It wasn’t possible to find a ‘one-size-fits-all’ solution. I had to forge my own path.

This is easier said than done. I made hundreds of plans in my head and at some point, I always let self-doubt win: What if all goes wrong and this doesn’t work? The ‘Impostor Syndrome’ hit me hard.

I anticipated failure. I anticipated what my SO, my friends and my family would think of me if I didn’t succeed. I discredited all my plans, thinking that this life would only work for developers, designers, or marketers. I couldn’t code if my life depended on it.

How could I walk away from something that had taken years and thousands of dollars for me to achieve? I was plagued with self-doubt and it took me over 12 months to leave my career and start a new life.

I realized that one of the scariest things was to drop a cushy, stable high-income job for a vision.

I had been reading extensively about personal finance and most specifically about financial independence, and I quickly understood that I needed to see the numbers.

I started tracking my expenses. I noticed immediately that I wasn’t saving as much as I could, whilst maintaining my lifestyle. That was a grand improvement, which was fundamental to regain confidence and to tell myself I knew what I was doing.

I started crunching the numbers. I have read about six-month emergency funds or 12 months of covered expenses. It all sounded good, but I still wasn’t comfortable.

So, I ran some simulations. 12 months, 18 months, and eventually 24 months. I understood that I needed to have a 24-month cushion. I started feeling less anxious. I was ready to jump ship.

New beginnings

During its 29-year history, there is no evidence of any successful escape attempt from Alcatraz. The only exception might be in 1962, when the Anglin brothers and Frank Morris may have escaped by carving their way out using spoons.

The constant weight that used to exist at the back of my mind has now dissipated. I have since founded a tech startup, worked with some of the biggest and most respected soccer clubs, and I am looking into new projects.

I escaped my Alcatraz and you can keep following my adventure on Twitter