I didn’t find my career path right away. I ricocheted from business major to pizza maker (yup) to software developer to entrepreneur, with lots of stops in between. I learned pretty quickly that there’s no point in sticking with an unfulfilling role, but that you’ve still got to learn something from the roles you leave behind. If knowing what you dislike is half the battle, the other half is tuning into the subtler signals that it’s worth sticking things out.
This is harder than it sounds. Whenever there’s something irritating about your job (and there always is), it can cloud out everything else. Sometimes it takes real effort to pay attention to what’s rewarding. But when you do, it can offer a kind of ballast, helping you weather rough times and avoid making hasty career changes or giving up on a dream prematurely. After all, even the best jobs will have their tough spots, hellish weeks, and disappointing quarters.
In hindsight, I overlooked some key clues along my own career path that could’ve saved me a lot of trouble had I spotted them earlier. Here are five not-so-obvious signs that you’re on on the right track, even if it may not feel that way right now.
1. Your 10-Year-Old Self Would Be Having A Blast
When I was in Grade 5, I wrote a fan letter to Richard Garriott, the video-game developer behind the classic Ultima series, saying I wanted to make computer games when I grew up, just like him. (I never got a response, but that’s not the point.) Eventually, I gave this up as a childish fantasy and, many years later, ended up pursuing a degree in business. It would take me nearly a decade to find my way back to tech and computers and the things that I loved as a boy.
I think we all carry with us an instinctive knowledge, present from a very early age, of what we’re meant to do. These “childish” aspirations rarely take money into account–they’re born of pure passion and joy. Honor these early dreams, rather than dismiss them out of hand. I’m not saying that you should literally become a ninja or a pop diva or a dinosaur. But there’s probably a map to your future in those 10-year-old fantasies, if you’re willing to read it.
2. People Always Said You’d Be Great At It (Even If You Didn’t Listen)
I remember the computer science prerequisite for my business program I took in my first year of college. I spent countless hours just coding–at the expense of my other classes. My instructor noticed my enthusiasm and suggested I consider changing majors. I didn’t listen. To me, a business degree was the ticket to a “real” career.
Looking back, there were lots of moments like these–teachers, family, and friends trying to point out the obvious to me. These days, I’m much more inclined to trust the wisdom of the crowd. The people around you often see aspirations and potential (and flaws) that, for whatever reason, you may be unwilling or unable to see in yourself. Back then, all the arrows pointed toward a tech future for me except the ones in my own head. So I slogged my way through a business degree, until I couldn’t stand it anymore and dropped out before my final year.
3. It’s The Middle Of Your Venn Diagram
It’s tempting to say we all have one true passion or calling, and that if you find it–whether it’s writing novels or driving race cars or starting companies–you’re set for life. But the older I get, the less I buy that. Most people have pretty multifaceted personalities, meaning there are multiple things that can leave them feeling satisfied.
This is a good thing. Personally, I get my kicks out of entrepreneurship, tech, and that little adrenaline rush that comes from pushing personal limits. I think the best jobs represent the sweet spot where all those passions overlap, the center of a Venn diagram.
After dropping out of university, I moved back to my hometown, maxed out my credit card, and opened a pizza joint. Despite the long hours, it was a true startup bootcamp and felt thrilling to work for myself, at least for a while. Eventually, I realized there was one big problem: I wasn’t passionate about the restaurant business–it was somewhere in an outer field of my Venn diagram. After a couple years, I got bored and sold the place. I used the proceeds to buy a fancy new iMac and move to the city.
4. It’s Ultimately Not About The Money
In my late 20s, I threw myself into learning PHP and MySQL and got a job with a dotcom company. Six months later, the tech bubble burst, putting me out of work. But I loved what I was doing, so I stuck with it. I ended up opening my own agency out of my apartment–just keeping my head above water.
But real passion is infectious. It attracts customers. It attracts employees. It attracts believers and investors. After a few years, my agency had grown to more than 20 employees. That’s when we developed Hootsuite to monitor multiple social networks at once. Suddenly we had thousands of users, then millions. Within a few years the company had grown to hundreds of employees.
I don’t want to oversimplify that experience, but my point is this: Work that you truly love has a way of creating its own momentum. Rewards–monetary or otherwise–generally will come, if your heart’s in it from the outset, rather than just chasing a paycheck.
5. You Feel In Over Your Head But Never Drown
No, I don’t mean you’re just hovering on the edge of burnout–which probably is a sign that you’re on the wrong career path. It’s the opposite: You feel regularly challenged, and sometimes downright daunted, by the work you’re doing, but it doesn’t get the best of you.
I remember the first time I convinced major investors to visit Hootsuite. After a day of presentations, we all went out to dinner. I watched as they ordered the most expensive things on the menu like it was nothing. At the end of the night, to my horror, they left me holding the bill. I kind of laugh looking back, thinking how little I knew then about business. From the moment my company entered hypergrowth, adding dozens of employees a month, I was in way over my head. From courting investors and scaling a global sales team to recruiting senior leaders and negotiating million-dollar contracts, it was all new to me. But as hard as that was (and is), it was also thrilling. I should have drowned, but amazingly, I didn’t.
I think this is the most important characteristic of any dream job. The challenges don’t let up. You’re constantly scrambling and being tested. But because there’s a real underlying passion, this all feels less like a grind than an adventure. You’re always learning and growing, and you eventually realize what a privilege it is to be in that position, and how important it is to stick with it–even if it’s not always easy.