First Day of the Rest of My Life
I am a 23 year-old corporate dropout. During university I did what I saw everyone else around me doing – internships with major corporations. When the company I interned at offered me a full-time job at the end of my summer after 2nd year, I jumped at the chance. Why wouldn’t I? Definite salary and the ability to travel for the two summers I had remaining before my entry into the real world. Little did I know the entrepreneurial adventures that lay ahead of me between that internship and the end of my degree. After that internship I ran Canada’s largest undergraduate international business plan competition as Co-Chair. I traveled to Australia on exchange, where I shaved my head for charity, created a concept for a wireless internet business, and tried every extreme sport I could get my hands on. I had been bit by the entrepreneurial bug – permanently. When I returned home I began competing in international business plan competitions and doing fairly well – I even managed to convince my school to pay to send me to a graduate business plan competition in Brazil, and placed second. As early as my first few days on exchange in Australia, I began to doubt my decision to go to the corporate world after graduation – I was witnessing this whole new world, full of people following completely non-corporate lifestyles. Yet despite my better intuitions and instincts, I followed the advice of friends, family, peers and career advisors, and decided to maintain my commitment to the corporate world.
So there I landed, in the heart of one of the biggest corporations in the world, after two years of relentless traveling like it was going out of style to “make it count” before I was limited to three weeks of vacation a year. I certainly enjoyed the first few weeks of work, but sure enough, within a few months, I was miserable. This is not to say that this was a bad company or job – in fact, I have the utmost respect for this company and consider myself extremely fortunate to have been able to work there. But I’d changed a lot between my internship and my full-time position, and it wasn’t the right fit for me any longer. I wasn’t passionate about the work, and knew enough about my strengths and weaknesses to understand that it was not focused on building on my strengths, but rather on fixing my weaknesses. And I am a big believer in leveraging my strengths, knowing that the most successful people have identified their strengths and found positions where they can utilize them. I also know that great people who have major strengths also have major weaknesses, and people who say they have no weaknesses are generally mediocre. I began to wake up in the morning and dread what I was about to go do, often choosing to languish in bed for half an hour more and then another. Before long, I was routinely showing up late to work. And when I got home from work, I was so drained from a day of doing what I didn’t like that I had no energy to do the activities that I love, like salsa dancing, DJing and entrepreneurship. I usually fell asleep right after getting home. It was a sad existence – one that I’d never experienced before. One that I hope never to experience again.
After a few months of this I decided to take a trip to Silicon Valley in California to see what all of the fuss was about – to check out Stanford, Google, and the entrepreneurial scene. The trip left me forever changed. As soon as I touched down, I began to have serendipitous experiences. But not just one or two – one after another after another. I have a list of about 20 of them in my journal. I was showing up to trains, buses and boats at the perfect moment to catch the last one, without any planning on my part. I was meeting people who could give me the right message I needed at that exact time. For example, I was signed up to do a MBA infosesion at Stanford and realized on my way there that I had completely forgotten to bring the address information and also didn’t have internet on my phone to figure it out. Then, lo and behold, the guy next to me on the bus was speaking and I realized he was going to the same infosession, so I found out the address info from him. Countless other things like this happened. In addition, I began to meet all these cool young entrepreneurs that were absolutely loving life and had their time as their own. I had such a great time that I seriously contemplated just not taking my plane ride home – I found a place to stay, found someone to rent out my apartment back home, etc. But as I was still in a bit of student debt and it would mean leaving my company without saying goodbye, I realized it probably wasn’t the right decision. A few months later, I went on a kiteboarding vacation, and once again, I didn’t want to go home. This time I was finally out of student debt (after scrimping and saving for months), and to my friends’ and brother’s disbelief, I actually unloaded all my stuff from the car after we’d just packed it up to go home and contemplated staying there. That was when I knew things had to change.
Back at home, I found out that I had been selected as one of the top 6 finalists from over 300 applicants to job shadow Dave McClure, who runs 500 Startups and is a very famous entrepreneur and supporter of entrepreneurs, and that I had an interview with him in a few weeks. This was a huge deal for me, and it reminded me that I didn’t need to be beat down at work everyday because I had the entrepreneurial skills and experiences to place in prestigious competitions like this and the international business plan competitions in Canada and Brazil that I came 2nd in. I also did a training at work (which was the best training I’d ever attended) that had us reflect deeply on our purpose in life. Although I’d done a lot of this kind of reflection over the months of unhappiness in my job, this training took it even further. It involved getting feedback from friends, family and coworkers, and my scores showed that they rated me as “disengaged” in the areas of “passionate about work” and “finds work personally fulfilling”. I’d rated myself as “seriously disengaged” across all dimensions in the survey, which it said could lead to serious problems with health and happiness. The part where we wrote about our purpose in life brought me back to what I’d figured out while traveling solo and reflecting deeply during the months prior to starting work full-time – that my purpose and passion in life is helping other people follow their passions, and specifically, supporting young entrepreneurs (since this is a great illustration of following passion and because I really believe in the power of young people). I realized that I had no excuses for not to be following my passion and purpose in life. I didn’t have kids, a marriage, a mortgage, or any debt, and I had external validation of my entrepreneurial abilities. In the part of the training where they asked us to write a letter to ourselves that they’d send to our desks in 21 days to help us follow our commitments, I found myself writing “you’d better not be here to receive this”. I’d written a similar contract with myself while in California, where I wrote that I’d quit and move there in September 2011. I also knew I wanted to go to there to do the interview with Dave McClure in person and would need to quit on Monday in order to give my 2 weeks notice to make it on time (I offered to come back after and stay longer if needed). Over the weekend I plotted out my life in Excel and determined how long I could last with the amount of money that I had before needing to start making money. I realized that the worst-case scenario for me was that I would have to take a job at another consumer packaged goods company, and considering that that was the worst-case scenario, that I definitely needed to leave. I spent most of Monday gathering up my courage and finally pulled all the right people into a room and told them. I thought it would be such a big deal, probably since this was my first big career move – I know a few decades from now my friends and I will have all made many career moves and it won’t be an issue – but they were actually quite receptive and supportive, which I really appreciate. I packed up my apartment, rented it out, and flew down here to San Francisco for at least 3.5 weeks (encompassing the interview and job shadow), perhaps longer.
We’ll see where it goes, I mean I could end up penniless and have to spend some time living at my parents’ place, but at least I will have tried doing what I love. As a very good friend put it, there are two options in life that can lead to three paths. First, you can take the safe and mediocre route and continue down that path forever. OR you can take a big risk that can lead to two different paths – one, you become incredibly successful and famous. Or two, you fail and end up dying in a flaming fireball. We both agreed that we’d rather die in a fireball than have never tried at all. Better to have loved and lost than to have never loved at all.
After making my decision a lot of people from work told me that they’d known the job wasn’t for me but were just waiting for me to figure it out and go be an entrepreneur. A few people said it was the first time they’d seen me happy. My relationships with my coworkers vastly improved during my last 2 weeks at work because they became so much more authentic – I finally felt like I could be myself, could dress the way I wanted to, and could tell everyone about my love for entrepreneurship. Since quitting to follow my passions, a lot of awesome things have been happening. I see it as the universe rallying around you to help you when you are trying to do what you love. I went to Startup Weekend Toronto last weekend, and after vocalizing an idea for the first time (OneCal.Me), I formed a team, had investor interest, won a prize, and was mentioned in the Globe and Mail and Techvibes within a few days. I was loaned an apartment in San Francisco to stay in for free for three weeks (with a rooftop patio and hammocks!), from another entrepreneur who’d moved into another place but was still paying rent on his old place while it sat empty. I found someone to take my place back home at the very last minute, for the exact time period I’d be away. I got entry to two major entrepreneurship conferences for free (one is today – I am volunteering at it). And I had my interview with Dave McClure and it went pretty well. Even if I don’t get the job shadow position, I am happy with my decisions and will meet with investors and founders while I am here to try and propel my business forward. Last night I came 2nd at Startup Poker and got $180 – my first seed investment for OneCal.Me!