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Shopify’s Harley Finkelstein With Some Advice to His 19-Year-Old Self

Shopify’s Harley Finkelstein With Some Advice to His 19-Year-Old Self

The Ottawa Citizen recently sat down with Harley Finkelstein, the Chief Operating Officer at Shopify, to ask what wisdom he’d share with his 19-year-old self if he could travel back in time to that age, as they call it, of “potential, idealism, and, oh yes, insecurity.”

Named “Newsmaker of the Year” in 2013 and made a “Dragon” for CBC’s Next Gen Den in 2015, here’s Harley’s advice to his younger self, read the original article here.

When I was 19, I was earning my economics degree at McGill and running a T-shirt business, but I was struggling.

I was full of insecurities, which I counteracted with ego. I lacked any self-awareness.

Looking back, it’s hard not to dislike that version of myself. If I could give my 19-year-old self advice, there’s no guarantee I would even listen, but here’s what I’d say:

Harley, your ego is your enemy. Learn to speak less and listen more.

It’s not actually a good thing to be the smartest one in the room. Surround yourself with people smarter than you. Find mentors who have a trait you want to emulate, and work hard on developing those relationships. Seek out more people like Philip Rimer, Ken Ages, Dan Goldberg, Roger Greenberg and John Ruddy — they will become your mentors.

Don’t give up when times get tough. The things in life that challenge you most are the very things that will give you the greatest strength. They build character, and character can’t be bought, rushed or faked. Only earned. So take those challenges as they come, and use them as a catalyst to become a better version of yourself.

Learn self-awareness. It’s the key to a better life. Your anxiety won’t go away, but meditation is the greatest life hack you’ll find to manage it. Mindfulness can become your superpower.

Discover what you love doing as soon as you can, and do that thing.

Find a life partner who makes you want to be a better human; who will allow you to grow in ways you couldn’t alone. (In a couple of years, you’ll meet her. Her name is Lindsay, and she’s the girl of your dreams.)

Oh, and get ready for the ride of your life, because it’s coming — in the form of a rocketship called Shopify.

Harley Finkelstein started from the ground up. To put himself through law school, he sold t-shirts using Shopify — an e-commerce platform that was relatively unknown at the time. That decision in 2005 ultimately led him to become Shopify’s Chief Operating Officer, where he helped transform the company into a global industry leader.

Harley lives by his personal entrepreneurial philosophy of “the hustle”: go hard, go fast, build the best, and execute. Interested in learning more and Harley and what he can bring to your next event? Email us at [email protected].