When you shouldn’t follow your heart

I’m 17 and sitting in my high school guidance counsellor’s office. She’s asking me what I want to do with my life and I have no idea.

“What are you really passionate about,” she asks. Awkward silence. What I want to say is playing computer games. Ever since 5th grade I’ve been hooked. But I’m not sure that’s a career. Then she says this: “The most important thing is to follow your heart.”

It’s something I would hear over and over again through the years — from my parents, university counselors and mentors. The smartest people I knew offered that same piece of advice: do what you love.

Aligning your passions with your career makes sense. But, let’s be honest, it’s not always that easy. The real challenge — especially for future entrepreneurs — can be uncovering exactly what you’re passionate about and why, then finding a way to keep that flame alive while the rest of life happens all around you.

Letting your calling come to you

Some people were born knowing they want to teach, or dance, or design cars. For many budding entrepreneurs, however, interests run in lots of directions, all at once, or sometimes in no clear direction at all. Steve Jobs, for instance, wandered India, experimented with psychedelics and even dabbled in calligraphy before starting Apple.

Ultimately, I majored in business in college, but it all felt too abstract for me. So, I ended up dropping out to open a pizza joint back in my hometown in rural western Canada. It took me a few years to realize what I really liked about the pizza business wasn’t pizza at all. It was marketing — getting into people’s heads and figuring out exactly which promotions would boost sales.

Passions won’t always jump out at you and that’s fine. Sometimes you have to do a little living first to figure things out. It just so happened that I discovered a passion for marketing via a pepperoni detour.

Engineering serendipity

Around this time, I noticed people were making a lot more money working with the Internet than I was working with pizza. I didn’t know exactly how to break into tech, but I knew it wasn’t going to happen in my little hometown.

I sold my restaurant and moved to the big city, Vancouver. For a newbie, the easiest way into tech was web design. I home-schooled myself on the basics and scraped together a portfolio. The tech space in the late 1990s was so hot that I managed to land a job at a dotcom with almost no experience.

I got lucky. But being in the right place at the right time was not just an accident. So many entrepreneurial success stories seem to begin with a twist of fate — from Zuckerberg meeting the Winklevoss twins to Henry Ford landing his first job at Edison Illuminating Company. What’s important to recognize is that successful entrepreneurs put themselves in a position to get lucky. They engineer their own serendipity.

Keeping the flame burning