Harley Finkelstein: You Must Requalify for Your Role, Every Year
Harley Finkelstein, President of Shopify, discusses maintaining unreasonably high standards in career and relationships. He shares insights on intentionality, the power of storytelling, finding complementary partners, and leveraging AI for entrepreneurial success.
Deep Dive Analysis
20 Topic Outline
Living with Unreasonably High Standards and Generational Trauma
Harley's Childhood: Immigration, Financial Struggles, and Father's Arrest
Developing Ambition and Entrepreneurial Spirit from Adversity
Prioritizing What to Be World-Class At: Storytelling, Father, and Husband
The Family Motto: How You Do Anything Is How You Do Everything
Shopify's Culture of 'Spiky Objects' and Annual Requalification
The Importance of Finding Complementary Business Partners
Transitioning from COO to President/Chief Storyteller at Shopify
Impact of Storytelling on Shopify and Setting Industry Standards
Strategies for Developing World-Class Storytelling Skills
The Evolution of Commerce: Passion-Based vs. Forced Entrepreneurship
Leveraging Specialized Mentorship and Personal Boards of Directors
Overcoming Fear of Rejection and Failure for Long-Term Success
The Superpower of 'Out Caring' in Entrepreneurship
Parenting Philosophy: Teaching Hard Work and Gratitude Post-Success
The Concept of High Agency and Taking Responsibility
Harley's Calendar Management System for Prioritization and Audit
AI's Transformative Impact on Shopify and Small Businesses
The Golden Age of Entrepreneurship Driven by AI
Defining Success: Harmonizing Joie de Vivre and Life's Work
14 Key Concepts
Scarcity Mindset
A belief system where one constantly feels they don't have enough, aren't doing enough, or aren't enough, often stemming from past financial struggles or generational trauma. This can manifest as high standards for achievement and relationships.
Multi-generational Trauma
The idea that the psychological and emotional impacts of traumatic experiences, such as the Holocaust or financial hardship, can be carried and manifested across generations within a family, influencing mindsets and behaviors.
How you do anything is how you do everything
A family motto emphasizing intentionality and high standards in all aspects of life, from professional work to personal relationships and daily tasks. It suggests a deliberate approach to every action.
Spiky Objects
A philosophy at Shopify where team members are encouraged to be world-class experts in one specific area rather than generalists. The company values individuals who are exceptionally good at their specialized craft.
Requalifying for your job
The concept that past achievements are not sufficient for continued success, especially in a rapidly growing company. It implies a continuous drive to improve, find new gears, and exceed previous standards each year.
Local Maxima vs. Global Maxima
Local maxima refers to being the best within an existing framework or industry standard, while global maxima means completely redefining or creating a new, higher standard that is fundamentally different from what others are doing.
Type Two Fun
Activities or experiences that are not enjoyable or 'fun' during the process itself, often involving struggle or challenge, but are realized to have been fun and rewarding only after their completion.
Energy Vampires and Energy Catalysts
A categorization of people or even geographic locations based on their impact on one's energy levels. Energy vampires drain energy, while energy catalysts boost and invigorate it.
Go Direct Manifesto
A communication strategy, particularly in business, that advocates for direct engagement with the audience (e.g., customers, investors, media) rather than relying on traditional intermediaries or gatekeepers. It emphasizes authenticity and direct storytelling.
Forced Entrepreneurship vs. Passion-Based Entrepreneurship
Forced entrepreneurship is starting a business out of necessity or lack of other options, often with little personal interest in the product. Passion-based entrepreneurship is driven by a deep personal connection, mission, or love for the product or industry.
Personal Board of Directors
A strategy for mentorship where an individual seeks out multiple mentors, each specializing in a narrow category (e.g., relationships, philanthropy, a specific skill) rather than relying on one general mentor for all aspects of life.
High Agency
A quality where an individual takes deep personal responsibility for problems and proactively works to fix them, rather than saying 'that's not my job.' They act as a single-threaded owner, willing to accept both wins and losses.
Techno Optimist
An individual who believes that technology is continuously improving at a rapid pace and remains optimistic about its potential, even when encountering initial flaws like AI hallucinations. They focus on future capabilities rather than past limitations.
AI by Default / Reflexively
The expectation at Shopify that employees should automatically and instinctively consider using AI tools for any problem, challenge, or project they encounter. It's about integrating AI into daily workflow as a first thought, not an afterthought.
15 Questions Answered
Harley's father's struggles as an immigrant, being a child of Holocaust survivors, and his arrest for white-collar crimes when Harley was 17, forced Harley to grow up overnight. This experience, combined with realizing his family's financial situation was 'below average' in South Florida, instilled in him a deep ambition, competitiveness, and a constant drive to do more.
It's crucial to prioritize because you cannot be world-class at everything. Life requires picking your battles, deciding what you want to be truly excellent at, and making peace with not excelling in other areas. Trying to do everything well often leads to mediocrity.
At Shopify, 'requalifying for your job' means that stasis is unacceptable; what earned praise last year is not good enough for the current year. Due to the company's massive growth, leaders are expected to continuously push themselves to find another 'gear' and reset industry expectations for their role.
The best business partnerships often consist of people who are completely different from each other, bringing complementary skill sets to the table. For example, someone from drama club might partner with someone from AV club or coding club to build something remarkable.
This transition allowed Harley to move from a role that didn't feel natural to one that aligned with his 'ground state' and passion for storytelling. It re-energized him, reconnected him with Shopify's mission, and allowed him to focus on being world-class in a role that adds significant value to the company by communicating its message globally.
To improve storytelling, one should practice extensively, watch themselves to identify and correct habits (like connector words), develop an authentic personal style rather than emulating others, learn from great mentors like Seth Godin, and always start stories with personal experiences to speak with conviction.
Forced entrepreneurship arises from necessity or lack of choice, often seen in past generations where people started businesses (like selling eggs or garments) for survival. Passion-based entrepreneurship, a more modern concept, stems from a deep personal connection, love, or mission related to the product or industry.
Mentorship should be specialized, focusing on specific narrow categories where a mentor excels, rather than trying to emulate everything about one person. Mentors are often spiky objects, great in one area but potentially lacking in others. Also, mentorship is timely; you may outgrow a coach's toolbox and need to move on to new perspectives.
The largest blocker is the 'cringe factor' or fear of rejection. Most people are unwilling to send numerous texts or emails, or look 'stupid' in the short term by asking for help, which prevents them from seeking out and building a diverse network of specialized mentors.
Harley believes that 'out caring' (sheer innate, deep-rooted ambition and desire to succeed) is a superpower. While skills can be taught and improved, the fundamental level of ambition and care is harder to change and ultimately drives individuals to work harder and achieve more than those with higher innate capacity but less drive.
Parents should focus on what they 'do' rather than just what they 'say,' as children emulate observed behavior. This includes showing respect, working hard, and involving children in small projects or chores to experience the journey of building and earning, rather than creating artificial scarcity.
High agency means taking deep responsibility for problems, seeing them, and proactively fixing them oneself, rather than saying 'that's not my job.' It involves stepping into the role of a single-threaded owner, maneuvering levers, and accepting the consequences of those actions.
'AI by default' means that when facing any problem or project, Shopify employees are expected to reflexively consider and utilize AI tools as a first step. It signifies a fundamental paradigm shift in how work is done, with AI embedded across all functions rather than being a separate product.
AI acts as a great equalizer by providing small businesses with resources that historically only large companies with massive headcounts could afford. It allows small teams to achieve high-quality product descriptions, photography, and other tasks, enabling them to compete more effectively and grow faster than ever before.
For Harley, success is the harmonization of 'joie de vivre' (joy of life) and 'life's work.' He aims to have more of both in his life without sacrificing either, finding deep satisfaction in his professional contributions and personal enjoyment.
59 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.
8 Key Quotes
How you do anything is how you do everything.
Harley Finkelstein
You cannot be good at jumping, defense, offense, kicking, punching, in sort of the you know in the the metaphor of Street Fighter. I think you have to pick.
Harley Finkelstein
The thing you did last year may have got you a high five and an attaboy and a pat on the back and whatever all the great stuff that comes along with that, that is not good enough anymore.
Harley Finkelstein
Most people don't want to prioritize because I mean they do in a way but they don't want to say no to anything.
Harley Finkelstein
I will take someone... I think entrepreneurs the right entrepreneurs the best entrepreneurs they just simply out care other people.
Harley Finkelstein
I think that stress like comes from like when like fundamentally your mind and like your body like are just not aligned very well.
Harley Finkelstein
It is what it is. What does it even mean? It is what it is. It means that like somehow you were just this thing happened you're accepting it you can change your own fate you can change your own life you can change everything about everything around you.
Harley Finkelstein
It's like having a best friend in your pocket.
Aldo Bensadun
5 Protocols
Developing Storytelling Skills
Harley Finkelstein- Practice extensively, starting with smaller audiences and working up to larger ones.
- Watch recordings of yourself to identify and eliminate filler words or other areas for improvement.
- Develop your own authentic style rather than trying to emulate other speakers.
- Seek out and learn from great mentors in storytelling, observing their techniques.
- Always start stories with your personal experience, as it allows you to speak with conviction and passion.
Creating a Personal Board of Directors (Mentorship Strategy)
Harley Finkelstein- Identify specific, narrow categories in your life or career where you want to improve (e.g., entrepreneurship, parenting, philanthropy).
- Seek out individuals who are exceptionally good at those specific things, rather than looking for one general mentor.
- Ask them specifically for help or advice within that narrow category, understanding they may not be perfect in other areas.
- Be prepared to send many messages and face rejection; develop a high 'cringe pain tolerance' and don't worry about looking foolish.
- Recognize the timeliness of mentors; you may outgrow a mentor's toolbox and need to move on to new coaches or perspectives.
Calendar Management for Prioritization and Auditing
Harley Finkelstein- Calendar everything, including personal activities like walks, meditation, and social dinners, not just professional meetings.
- Color-code all calendar entries to visually distinguish different types of activities (e.g., social, work, personal).
- Bundle similar tasks, such as scheduling meeting days on certain days (e.g., Monday, Wednesday, Friday) and reserving other days for 'maker time' or deep work.
- Conduct a quarterly audit of your calendar to review how your time is being spent and ensure it aligns with your stated priorities.
- Use a large, visual calendar (like Jesse Itzler's 'Big Ass Calendar') to map out important dates and commitments for the entire year, allowing for a step-back perspective.
Philanthropy Strategy (David Rubenstein's Rules)
David Rubenstein (described by Harley Finkelstein)- Only write a significant check for an organization or project that wouldn't start without your investment.
- Invest in projects that wouldn't end without your continued support.
- Ensure you can see the efficacy or impact of your investment within a 10-year period.
- Choose projects that are deeply personal and meaningful to you.
Teaching Kids Responsibility and Work Ethic
Shane Parrish and Harley Finkelstein- Assign age-appropriate chores and tasks around the house.
- If a child refuses, explain that it is now their responsibility (e.g., by temporarily removing paid help).
- Set clear consequences for not completing tasks (e.g., no screen time).
- Show, don't just tell; children will emulate the hard work and intentionality they see from their parents.
- Inspire them by showing how much you enjoy your own projects and passions, rather than just 'throwing' things at them.