The Career Dilemma of When to Move On


It’s not like I was looking for change.

I had started Invoke—a small company that built web pages and Internet apps—in my apartment when I was 26. As the months turned into years, I hired one employee, then another and another and finally brought on partners.

We struggled (a lot) but stuck with it. By the time our eighth Christmas party rolled around, there were 21 of us, and we needed a new office.

Then, during a rainy stretch of days in late 2008, one of our teams hacked together a nifty little tool for managing multiple social media accounts. Instead of signing into Facebook and Twitter and LinkedIn separately, you could do it all from one dashboard. It was rudimentary, but — before long — the app had hundreds of thousands of users. And, suddenly, I had a decision to make.

At the time, Facebook was adding tens of millions of users a year. Something called Twitter was just taking off. Social media was still looked at as a dorm-room toy back then, and nobody knew how to monetize it, but some kind of cultural sea change was definitely happening.

So, I jumped in. I spun off our social media tool into a brand new company called HootSuite. I handed over the reins at Invoke to my partners, and I took the helm of an untested, unprofitable business with no paying customers and no investors.

It was among the best decisions I ever made. Five years later, HootSuite has seven million users, including 237 of the Fortune 500 companies, more than 300 employees and offices in North America and Europe. We just finished a series B investment round at $165 million and are looking to expand globally.

The decision to leave a company and move on to a new project is never an easy one. You leave behind years of work and often a stable, promising business for a world of unknowns. For me, opportunity knocked. Given the choice between plugging away at a sure thing and hitching a ride on a rocketship, I climbed aboard.

Passion, of course, also comes into play. This is a cliche in many ways, but if going to the office every day no longer excites you, then there’s a problem. I believe successful people, by disposition, are built to think big. When a role no longer affords those opportunities, it might be best to leave it in capable hands and move on, whether you’re moving to a new role in the same company, or exiting to pursue a whole new path. Inertia is one of my worst fears.

And the longer you’re stuck in a position that doesn’t truly challenge you, the less likely you’ll be able to leave it.

*****

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Photo Credit: Martin Barraud / Getty Images

A good read. Thanks.

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Deidre Rosenberg

Co-Founder, CEO and Film Skills Trainer at Reel Partners NPC / Producer, Screenwriter, Director at Beyond Reel Entertainment

10y

I'm busy launching my new project Reel Swift. Thank you for your inspirational words of wisdom. South African Film Industry... here we come!

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Amy Zuchowski

Columnist at Feminine Collective

10y

Great post. Fear keeps us from becoming our best selves. It's always fear. Interpersonally, professionally, and so on - it's always fear.

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Tara Feeley

MC-DJ-Entertainer-Singer, Tara Feeley Entertainment. Real Couples, Real Love, Real Celebrations!

10y

Great post Ryan Holmes!!! Resonates for sure and was a wonderful reminder! Thanks so much for sharing! :-)

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