Featured clips
Living With Unreasonably High Standards
Generational Trauma and Family Relationships
Prioritizing In Life And Becoming World-Class
Requalifying For Your Job
Mindset for Professional Growth and Success
What does it mean to live – and lead – with intention?
Shopify President Harley Finkelstein explores what happens when you treat every role in your life—father, husband, leader—as something you have to requalify for, every single year.
It’s a candid look at ambition, identity, and the challenge of holding yourself to a higher standard—everywhere it counts.
Available Now: YouTube | Apple Podcasts | Spotify | Transcript
Key Takeaways
1. Outcome Over Ego: Harley managed thousands of people as COO at Shopify. “There was a little bit of ego in there,” he admits. “I felt very important.” But it wasn’t natural. In 2021, he stepped down to become president with a significantly smaller team. To outsiders, it seemed like a demotion. Within weeks, his energy exploded. The company started growing even faster. He went from managing many things adequately to doing one thing exceptionally. The best never choose titles over impact.
2. Don’t Care What They Think: “I can’t be everything to everyone,” Harley says. “I kind of made peace with it years ago.” He’s particular about who he spends time with. Some people are energy vampires. Others are energy catalysts. He only makes time for catalysts. While others bend over backwards to organize their lives around pleasing everyone, he organizes his life around his priorities. The cost of trying to please everyone is disappointing yourself.
3. Find a Good Co-Pilot: “Most people need someone else to help them pull up to the next level,” Harley says about his partnership with Tobi Lütke. For 16 years, Tobi has seen a better version of Harley than he saw in himself. When Harley thinks he’s peaked, Tobi shows him another gear. No coasting. They’re opposites. Tobi builds products. Harley tells stories. Together, they built a company worth over $100 billion. While some people can push themselves to greatness alone, most need a partner who won’t let them settle. The right partner unlocks everything. The wrong one kills everything.
4. Find a Model to Emulate: Before getting married, Harley and Lindsay identified couples with great marriages. Then they scheduled double dates. They observed. How did these couples argue? How did they repair? “We ended up developing these relationship mentors,” he says. They never told them. They just watched and learned. Most people learn by failing. Smart people learn by watching.
5. Embarrassment is the Entry Fee: Harley’s first interview was painful. His eight-year-old daughter has it memorized. She’s also seen his recent ones where he commands the conversation. “Getting really, really comfortable with being uncomfortable is magic,” he says. He watches every single one back, obsessing over improvements. As Charlie Munger said, “You have to rub your nose in your mistakes.” Most people hide their mistakes. Harley analyzes his. Guess who improves faster.
6. Obsession Beats Talent: “(the best) entrepreneurs just simply out-care other people,” Harley says. You can’t beat someone who cares more than you. They work harder. They work longer. They work smarter. Most people reach “good enough” and stop. The obsessed never stop. That’s why they win.
7. High Agency: “High agency is someone who sees a problem and says, ‘I’m going to fix it’ and then fixes it themselves,” he says. No committees. No permission. Just solutions. Life happens to most people. High-agency people happen to life.
8. Calendar Your Priorities: Harley meditates eight minutes daily. It’s calendared. So are walks with his wife Lindsay, family time, and thinking blocks. Everything is color-coded. Purple means social dinners. One per week maximum. As I like to say, show me your calendar and I’ll show you your priorities. Most people say one thing and do another. The system or record is how you spend your time, not what you say.
9. Adapt or Die: “If you’re not using AI reflexively, you’re in trouble,” Tobi wrote to all of Shopify. Every year, the bar rises. What qualified you last year won’t qualify you this year. A lot of people dabble in AI. Harley jumps in. He uses it for health tracking, speech analysis, and detailed research. Environments change. You either change faster or get replaced by someone who does. At Shopify, everyone must requalify for their job annually. The standard keeps rising. Keep up or get out.
