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Harley Finkelstein: You Must Requalify for Your Role, Every Year

Jul 8, 2025 1h 47m 59 insights
Shopify’s Harley Finkelstein reveals the one standard that actually scales your career and your family. Harley shares why stepping down as COO was his hardest choice, the family motto that guides his daughters, and what makes someone good at storytelling. They discuss AI's real advantage, the calendar system that keeps him accountable, and how he maintains high standards. If this gives you one standard to raise your team—or your family—share it with a friend who needs to hear it today. ------------ About Harley: Harley Finkelstein is the President of Shopify. He leads storytelling, external relations, and company energy—translating world-class product into world-class adoption. Approximate timestamps:
Actionable Insights

1. Adopt “How You Do Anything…” Motto

Embrace the family motto “how you do anything is how you do everything” to bring intentionality to every aspect of your life, making life fun and interesting.

2. Cultivate High Agency (Problem Solving)

Take deep responsibility for problems, proactively fixing them yourself and embracing the role of a “single-threaded owner” rather than deferring.

3. Reject “It Is What It Is” Mindset

Actively reject the passive “it is what it is” mindset, believing you can change your own fate and everything around you through intentional action.

4. Prioritize and Specialize Your Skills

Consciously pick what you want to be world-class at, focusing your efforts and accepting that you must close doors to other pursuits.

5. Cultivate Courage to Close Doors

Develop the courage to say no and close doors to things, even those that bring some joy, as intentionality and doing everything well require selectivity.

6. Choose Energy Catalysts (People & Places)

Be deliberate about who you spend your time with and where you spend your time, seeking out “energy catalysts” that uplift you and avoiding “energy vampires.”

7. Align Role with Core Strengths

Realign your professional role to match what you are naturally good at and passionate about, as this can dramatically re-energize you and lead to recommitment to your mission.

8. Embrace Your World-Class Niche

Accept that being world-class in one specific, deeply valuable area is “totally enough” and can have a profound impact, rather than trying to be good at many things.

9. Find Your Ikigai (Purpose)

Seek to align your professional role with your “Ikigai” – the intersection of what you love, what you’re good at, what the world needs, and what you can be paid for – to reignite passion.

10. Align Personal Mission with Work

Seek work where your personal mission is deeply tied to the company’s mission or product, as this deep connection fosters passion, commitment, and greater success.

11. Pursue Passion-Based Entrepreneurship

Differentiate between “forced entrepreneurship” and “passion-based entrepreneurship,” striving to pursue your life’s work in an area you are deeply passionate about for greater fulfillment.

12. Requalify for Your Role Annually

Commit to being the very best in your area of responsibility, and annually “requalify” by continuously striving for improvement and pushing beyond last year’s achievements.

13. Aim for Global Maxima in Your Field

Strive to perform your job so exceptionally and differently that you could keynote an industry conference, demonstrating a “global maxima” approach rather than just being the best on the current path.

14. Seek Mentors Who See Your “Next Gear”

Find mentors or partners who consistently see a better version of you than you see for yourself, pushing you to find “another gear” and inspiring continuous improvement.

15. Partner with High-Standard Individuals

Seek out partners who hold themselves and you to extremely high standards, as this mutual commitment and drive can elevate performance and lead to remarkable achievements.

16. Form Diverse Co-Founder Teams

When starting a company, seek co-founders with diverse and complementary skill sets from different backgrounds to bring varied perspectives and capabilities to the table.

17. Overcome Fear of Admitting Misfit

Overcome the fear of admitting when a role or responsibility is not a natural fit, even if it means stepping back from a “bigger” job, to pursue what truly aligns with your strengths.

18. Practice Deliberate Saying No

Be very selective about what you take on and say no to many things, as this intentionality allows you to focus on what you truly want to be world-class at.

19. Ask “Solve or Listen?” in Relationships

When a partner shares a problem, ask if they want you to solve it or just listen, as the default problem-solving reflex is often not what they need.

20. Maintain High Relationship Standards

Hold your friendships and relationships to a very high caliber of quality because you hold them dearly, understanding this may sometimes lead to disappointment but ensures meaningful connections.

21. Encourage Ideas with Tangible Support

When someone shares a business idea, provide simple, tangible support (like making business cards) to physically manifest their idea and convey unequivocal belief in their capacity.

22. Share Struggle Stories with Kids

Share stories of your early struggles, grit, and willpower with your children to instill an understanding that success comes from hard work, not just fate or luck.

23. Model Desired Behavior for Kids

Understand that children emulate what they see; model respectful and hard-working behavior yourself, as this is more impactful than simply telling them what to do.

24. Foster Gratitude, Hard Work, Resilience

Actively foster gratitude, hard work, conviction, and resilience in children by encouraging projects, allowing them to experience failure, and celebrating their efforts.

25. Teach Responsibility Through Direct Experience

To teach children responsibility, create direct experiences where they must complete tasks normally done by others, linking privileges to their completion.

26. Avoid Artificial Lifestyle Imposition

Do not artificially impose a different lifestyle on your children than you are genuinely living, as this can create resentment and is not a real or sustainable way to teach values.

27. Inspire Kids Through Your Passions

Inspire your children by visibly demonstrating your own passions and the joy you derive from them, rather than simply providing them with equipment or opportunities.

28. Calendar Everything (Personal & Professional)

Calendar every aspect of your life, both professional and personal, to clearly visualize your priorities and ensure you allocate time to what truly matters.

29. Color-Code Your Calendar for Balance

Color-code all calendar entries to visually audit your time allocation, allowing you to quickly identify imbalances and adjust your schedule to preserve energy.

30. Pre-Populate Calendar with Key Priorities

At the start of the year, populate your calendar with all major personal and professional priorities to visually confirm if your schedule aligns with your stated goals.

31. Align Calendar with Stated Priorities

Reduce stress by aligning your calendar with your stated priorities; if an activity you claim to value isn’t reflected in your schedule, acknowledge that you might be lying to yourself.

32. Be Honest About Your Calendar Style

Be honest with yourself about your preferred calendar management style and create guardrails that align with what genuinely brings you joy and reduces anxiety.

33. Schedule Tasks by Energy Levels

Schedule less enjoyable or lower-energy tasks for times of day when your energy is naturally lower, reserving your peak energy times for high-impact activities.

34. Use AI Reflexively for Problem Solving

When facing a problem, challenge, or project, reflexively consider what AI tool can be used to do your job better, making it a default part of your problem-solving process.

35. Create AI Projects for Personal Data

Create dedicated AI projects for personal data like health records or speaking transcripts, using them to analyze information, check tone, or identify patterns.

36. Prioritize AI Tools Over New Hires

Before hiring a new person, evaluate whether an AI tool can perform the task better or more efficiently, prioritizing AI solutions to maximize productivity and resource allocation.

37. Be a Techno-Optimist with AI

Adopt a “techno-optimist” mindset, believing in the rapid improvement of AI and not letting initial “hallucinations” create scar tissue; continuously engage with evolving AI tools.

38. Cultivate Cross-Generational Friendships

Actively cultivate friendships across different age groups to gain diverse perspectives, stay updated on new technologies, and continuously learn outside your immediate peer group.

39. Observe How People Use Technology

Pay close attention to how people, especially younger generations, are actually using technology in unexpected ways, as this observation can reveal new insights and opportunities.

40. Harmonize Life’s Work and Joie de Vivre

Define success as the harmonization of your “life’s work” (meaningful professional pursuits) and “joie de vivre” (joy of life), striving to maximize both without sacrifice.

41. Practice and Self-Critique for Skill Development

To develop a skill, start small, practice extensively, and engage in rigorous self-critique (e.g., watching recordings of yourself) to identify and fix specific issues.

42. Develop Your Authentic Style

Instead of emulating others, focus on developing your own authentic style in your craft, embracing your unique traits and ensuring it’s genuinely “the version of you.”

43. Learn from Great Mentors

Seek out and learn from great mentors in your specific area of desired improvement, observing their techniques and insights to accelerate your own development.

44. Prioritize Consistent Repetition (Reps)

Understand that mastery comes from consistent repetition (“reps”); dedicate yourself to putting in the necessary hours and practice, similar to how top athletes train.

45. Start Stories with Personal Experience

When telling a story, always start with your personal experience, as this approach ensures authenticity, cannot be factually wrong, and allows you to speak with genuine conviction.

46. “Go Direct” with Storytelling

Adopt a “go direct” approach to communication, transforming traditional corporate events into genuine storytelling opportunities to differentiate yourself and set new industry standards.

47. Seek “Spiky” Mentors for Specific Areas

Instead of trying to emulate a mentor’s entire life, identify mentors who are exceptionally good (“spiky objects”) in specific, narrow categories where you want to improve.

48. Rotate Mentors/Coaches as Needed

Recognize that mentors and coaches have a “timeliness”; once you’ve learned their core lessons, it’s a good time to move on to a new one for fresh perspectives.

49. Proactively Identify Relationship Mentors

Before significant life events, proactively identify and observe couples or parents with relationships you admire, then subtly spend time with them to learn and emulate their successful dynamics.

50. Apply Rubrics to Philanthropy

When engaging in philanthropy, establish a clear rubric for giving, focusing on projects that wouldn’t start or end without your involvement, and where you can see the investment’s efficacy.

51. Practice Precise, Entrepreneurial Philanthropy

Adopt an entrepreneurial approach to philanthropy by being highly precise: identify a specific problem, determine exact resources needed, and fundraise for that precise solution.

52. Seek Specific Advice from Experts

When learning a new skill or hobby, actively seek out experts in that field (even local ones) and ask them precise, technical questions about their methods and tools.

53. Overcome “Cringe Factor” for Mentorship

Develop a high tolerance for the “cringe factor” and rejection; proactively reach out to potential mentors without hesitation or fear of looking foolish.

54. Embrace Looking Foolish for Long-Term Gain

Be willing to look foolish or “stupid” in the short term when learning new skills or pursuing ambitious goals, as this high tolerance for discomfort is essential for long-term growth.

55. Assess Cost of Failure for Ventures

Before embarking on any venture, assess the “cost of failure” and weigh it against the potential benefit of success; if the cost is low, be willing to try and iterate quickly.

56. Cultivate Comfort with Discomfort

Actively learn to become comfortable with being uncomfortable, as this cultivated resilience is a “magic” skill essential for success and personal growth.

57. Out-Care Others for Success

Cultivate a “superpower” of simply “out-caring” other people in your endeavors, as this deep-rooted ambition and desire to succeed can supersede IQ, EQ, or raw talent.

58. Follow What You Do for Fun

When seeking career direction, identify what you genuinely do for fun, as deep care and passion for an activity often indicate where you will naturally develop skills and excel.

59. Embrace the “What About the Other 2%?” Mindset

Adopt a mindset of continuous improvement, questioning what could be better even after achieving high success, to avoid complacency and strive for global maxima.