The first step is to find out what you love–and don’t be practical about it. The second is to start doing what you love immediately, in any small way possible.

– Barbara Sher

There have been three key moments in my life so far that have, more than anything else, shaped who I am today. In every case, I gave up something significant. In every case, I had people telling me I was crazy, stupid, or otherwise trying to talk me out of it. Sometimes those “people” included myself.

The first moment was in June 2002. I was working at one of my first programming jobs out of school. I’d gone from working for $6.50/hour in a restaurant kitchen, to making $25/hour working at a job from which it was impossible to get fired: I was a Systems Developer for the Department of Justice. I’d just bought a brand new car. At 23 years old, I was already making more money than my parents. I’d even gone from being a virgin loser with women to effortlessly meeting and dating hot girls, using online dating.

My comfort zone was complete. Or so I thought.

The Intellectual Cemetery

It turned out that what other people called a “dream job” was no dream to me. The office I worked in was more like an intellectual cemetery. I had some extremely smart colleagues, but the work-is-optional vibe of a government job drained me of my will to live. My motivation to produce, in an environment that rewarded seniority rather than productivity and ingenuity, was gone. And while I really enjoyed the car, I hated the city I lived in, and I knew how much paying off my wheels was tying me down.

So what did I do? I quit the job, sold the brand new car–losing a few grand in the process–packed my bags, and ran away to Europe. My Dad didn’t believe I’d do it. And it took the actual sale of the car for my Mom to realize that I was serious.

The first week I arrived in London, I met a girl. We ended up going out for most of the 7.5 months that I was travelling. I slept in trains and airports as I moved from place to place, had sex in the bushes in Hyde Park, went to a squat party in Berlin, thwarted a pickpocket in Paris, worked as a telemarketer in a little town in the North of England, briefly took an off-the-grid programming gig in Eastern Europe, and even got pulled off a bus at 2:00 AM one morning, travelling between Lithuania and Poland, for not having the right entry visa. Hilarity did not ensue.

It was wonderful and terrifying. But fuck me if life is meant to be lived any other way.

Throwing Out a Growing Business

My second defining moment was September 2004. Six months earlier, I’d left a day job as a web programmer to immediately quadruple my income as a consultant. Since then, I’d grown my company to seven clients, including a few high-profile names in the Plone community. I began interviewing other Plone consultants to help me handle the workload. Things were going well, and only seemed to be getting better.

But then a friend of mine, who I’d met while travelling a couple years earlier, contacted me. He was working for Canonical, the company that created Ubuntu Linux, and made me an offer I couldn’t refuse.

So I made calls to Vancouver, Toronto, Los Angeles, Rotterdam, Cambridge (MA), and a few other cities, and “fired” all my clients. It was a pretty big risk to throw away a great client base for what was only guaranteed to be a three month contract to work with some guys on some up-and-coming Linux distro, but hey, why not? As a computer geek, it was a chance to work with rock stars and to develop with the web framework that most interested me at the time: Zope 3. My first assignment was to show up in Mark’s flat in London to hack on something they called Launchpad. It sounded like fun.

And it was. I was getting paid good money to work on things that interested me. Every couple months, they flew us off to some exotic location like Spain, South Africa, Brazil, or Australia, to participate in development sprints. I learned a lot from the people I worked with. And I was always amazed by Mark’s dedication to Ubuntu. He was usually the first one to show up and the last one to leave. He exemplified the maniacal determination I’ve written about previously.

Money and Happiness

But, for various reasons, I became increasingly unhappy with the job. Even a healthy six-figure salary and jet set travel schedule was nowhere near enough to keep me interested. I already knew intellectually that money couldn’t buy happiness, but now I’d learned that lesson by living it. My heart just wasn’t into it anymore. However crazy it sounded to other people, I had to leave.

Which brings me to the third time in my life that I started over. In September 2006, I gave one month’s notice to my employer and left what was, to that point, by far the coolest and highest-paying job I’d ever had. I had no other job lined up. There was no specific incident that set me off. But when you work at a job you don’t like, you throw away eight hours of every day.

For the third time in a row, my intuition was right. I decided to spend the next six months focussing on building my social life, specifically on practicing the art of talking to strangers. It was a life-changing experience. I had no idea how easy it was to meet girls by just talking to them anywhere, anytime.

All those social experiences, and the other things I’d studied and applied in the realm of personal development during the same period, eventually led to the creation of 30 sleeps.

Fast forward to now, and life is pretty interesting. These days, I’m getting emails from people all over the world about how this site has helped changed their life. Articles like How to Quit Drinking Alcohol seem to have inspired a lot of long-time drinkers to sober up. Guys write in telling me how something I wrote inspired them to finally break out of their bubble and take the risk of getting blown out. People are realizing that vulnerability pays off. A female expat living in Saudi Arabia wrote in to tell me how she’s used my advice to meet an “extremely hot” younger man. I even had someone write to me the other day wanting to translate some of my articles into Russian.

The Benefits of Being Unreasonable

Why am I telling you all this?

In each of the above situations, I gave up everything–jobs, cars, big salaries, security, even my own businesses–and started over. Every time, it was never the right time. I never knew how it was going to turn out. Every major change I’ve made has presented me with plenty of obstacles of its own.

And every time, it was the best damn thing I’ve ever done.

This, to me, is what it means to be alive: passion, vulnerability, uncertainty, and a healthy disregard for what other people think. The only way to live is dangerously. Life minus risk equals death.

When you give up everything, you really aren’t giving up anything. If you’re terrified of change, then change is your only option.