Why Anxiety Can Be Your Superpower with Shopify’s Harley Finkelstein

The Anxious Achiever

Morra Aarons-Mele

Careers, Management, Mental Health, Business, Health & Fitness

4.7 • 600 Ratings

🗓️ 11 September 2025

⏱️ 32 minutes

🔗️ Recording | iTunes | RSS

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Summary

Behind every bold move is often a quiet fear. In this episode, I sit down with Shopify President Harley Finkelstein to talk about how anxiety has shaped his path from navigating family financial loss as a teenager to leading one of the world’s most influential platforms for entrepreneurs. Harley explains how to view anxiety not as a flaw, but as a tool that sharpens foresight, fuels ambition, and prepares you for what others can’t see. He also shares how to build your team that balances your energy and why vulnerability in leadership is your strength. Get ready to turn anxiety into your advantage! In this Episode, You Will Learn 00:00 Meet Harley Finkelstein, President of Shopify. 05:45 How Harley turned survival-driven anxiety at 17 into his first business. 11:45 Tools Harley uses to manage anxiety. 16:15 How to use anxiety as a checklist for risk and anticipation. 21:00 How do you handle anxiety when it affects your leadership? 24:30 Why extroverts and introverts recharge differently. 27:00 The #1 skill every anxious achiever needs. Resources + Links Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam Follow Harley: on LinkedIn @harleyf + Instagram @harley

Transcript

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0:00.0	Talk to enough really successful entrepreneurs, and you'll get the sense that they are driven by a vision for the future, but often a sense of not wanting to repeat a past, of wanting to create an outcome in adulthood
0:25.3	that maybe was difficult for them to create in childhood. Today, Shopify president,
0:32.5	Harley Finkelstein, on the roots of his entrepreneurial soul, he started his first business when he was 17 and his
0:41.5	lifelong relationship with anxiety, driving him towards creating big things and allowing him to
0:51.1	explore what really makes him tick.
1:00.1	I'm Maura Aaron's Mealy, and this is the anxious achiever, the show that looks at the intersection of mental health and work and asks, how can we do it all better?
1:06.2	I'm going to be bringing the show to you twice a week. On Tuesdays, you'll get a brand new episode
1:13.1	of the show. And on Thursdays, I'll be sharing my favorite classic episodes from the archives as well
1:20.6	as some sort of fun, informal conversations and experiments as they come. But I wanted to share this conversation with
1:28.9	Harley, who offers, I think, a really rare insight into the role that anxiety naturally plays for
1:38.9	most entrepreneurs who are taking big risks and creating big things.
1:45.2	I hope you enjoy it.
1:48.2	So we were kind of joking on Twitter before,
1:51.0	but you call yourself, or I guess Tim Ferriss called you a power extrovert,
1:57.0	and I'm a pretty outspoken introvert.
2:00.6	So are we mortal enemies?
2:02.6	Can we get along?
2:03.6	I actually think we would be best of friends.
2:06.9	I mean that.
2:09.0	I think that the whole extrovert versus introvert thing first of all, I think, has
2:11.8	completely been, it's gone too far.
2:15.4	I think that what it really means is where people derive energy from.
	...

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