When (Not) to Follow Your Heart

When it comes to your career, always follow your heart. Do what you’re passionate about. Easy, right? It turns out, not always.

For much of my life, I kept hearing this piece of advice over and over again—from my parents, university counselors and mentors. The smartest people I knew told me the same thing: do what you love, and the rest will follow.

But what I discovered, through a lot of twists and turns in my career, is that it’s not always that simplistic. Sure, aligning your passions with your career makes sense. But the real challenge—especially for future entrepreneurs—is first figuring out exactly what you’re passionate about, then finding a way to keep that flame alive while the rest of life happens all around you. Here are some ways to help make that happen for you:

Explore a little and let 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.

I majored in business in college, but it all felt too abstract for me. I ended up dropping out to open a pizza joint back in my hometown. 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.

The takeaway here for entrepreneurs is that 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.

Engineer some serendipity. Around this time, I noticed people were making a lot more money working with the Internet than I was making 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.

So, 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 ‘90s was so hot that I managed to land a job at a dotcom - with almost no experience.

Yes, 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.

Keep the flame burning. By now, I knew I wanted a startup of my own. But my timing was terrible. In 2000, months after I struck out to start my own business, the dotcom boom went bust. Tech became a dirty word and investors shied away from new ventures.

But I plugged away, piecing together enough work to pay the bills and slowly grow my own web development firm, designing websites for companies and building marketing apps. It wasn’t always thrilling—but it was at least in my wheelhouse … and it paid the bills.

My point for entrepreneurs is I didn’t abandon my passions completely. I found ways, sometimes just small ones, to build them into my work life. The startup experience can look from the outside like a rocketship ride. It rarely is. Steven Boal of Coupons.com, which recently IPO’d for more than $1 billion, has said, “I get a lot of amusement out of people who call us an overnight success. [It was a] 12-year night.” Finding ways to stay inspired during that time—when the work itself may not be all that inspiring—is a key to success.

Double down on passion—when the time is right. Eventually, however, you have to take the plunge. In 2008, my team hacked together a tool to help companies manage multiple social media accounts from one website and called it Hootsuite. Hundreds of thousands of people signed up in the first few months. I decided to pour everything I had into it, at the expense of other projects bringing in good revenue.

Nearly every successful entrepreneur has this decisive moment. It will normally come at the middle of a long, difficult journey, not the beginning. Over the years, real passions grow clearer and mere distractions fade away. At the same time, critical skills have time to develop—the essence of Malcolm Gladwell’s 10,000-hour rule. Then, if you’re lucky, you get a shot to double down on your dream.

But it rarely comes without risk. Doing what you love will never be easy or convenient. Managing risk is something entrepreneurs need to get very good at—personal passion turns out to be one of those risks.

Accept the grey area between love and reason. Today, my social media management tool is used by 11 million people, including most of the Fortune 100 companies.

But here’s the thing: I wouldn’t be here if I had just blindly listened to all of those counselors and mentors years ago. If so, I probably would have ended up studying computer science in college (since my biggest passion at the time was playing video games). Sure, I might have loved it and gotten a great job. But I’m glad I didn’t go down that path.

Instead, I waded into that grey area most of us live in—where the desire for career fulfillment clashes with the need to make money, ego and simple indecision. Almost every entrepreneur I know has spent hard years in this limbo, figuring out exactly what they love and ways to act on it.

This isn’t as romantic or inspiring as just saying, “Do what you love,” but it’s an important piece of advice for entrepreneurs on the frontlines: You can’t always follow your heart, but don’t give up on it. Where passion and pragmatism meet, great things happen.

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