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July 29, 2024 • 1hr 52min
#818 - Andrew Wilkinson - How To Stop Feeling Like Your Success Is Never Enough
Modern Wisdom
Andrew Wilkinson is an entrepreneur, co-founder of Tiny, and an investor. In this wide-ranging conversation, he discusses the psychology of successful people, the pitfalls of extreme wealth, lessons from building businesses, hiring strategies, and finding contentment. Drawing on his own experiences becoming a billionaire, Wilkinson offers a candid look at the realities of entrepreneurship and wealth accumulation.
#818 - Andrew Wilkinson - How To Stop Feeling Like Your Success Is Never Enough
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Key Takeaways
- Most successful people are driven by anxiety and trauma - Andrew describes successful people as "walking anxiety disorders harnessed for productivity". Many have childhood traumas or chips on their shoulders that drive them to achieve.
- Money and success don't necessarily lead to happiness - Even billionaires often feel unfulfilled and keep striving for more. The hedonic treadmill continues no matter how much wealth one accumulates.
- Entrepreneurship is about building systems and leverage - The goal should be to build a machine that runs without you, not to work harder yourself. Delegate and build systems to scale.
- Hiring well is critical - Look for people who have done similar work at 2x the scale. Ensure alignment on vision and strategy. Do thorough background checks.
- People rarely change fundamentally - It's very difficult to change someone's core traits or behaviors. Hire for fit rather than trying to mold people.
- Awareness and boundaries are key for mental health - Limit exposure to news/social media. Set boundaries around technology use. Be selective about information intake.
- Find your "enough" point - Determine how much is truly enough for you financially and stop moving the goalposts. Contentment comes from within.
- Give back effectively - Think carefully about how to do the most good with wealth. Effective philanthropy requires strategy.
Introduction
Andrew Wilkinson is an entrepreneur, co-founder of Tiny, and an investor. In this wide-ranging conversation, he discusses the psychology of successful people, the pitfalls of extreme wealth, lessons from building businesses, hiring strategies, and finding contentment. Drawing on his own experiences becoming a billionaire, Wilkinson offers a candid look at the realities of entrepreneurship and wealth accumulation.
Topics Discussed
The Psychology of Successful People (02:07)
Wilkinson argues that most highly successful people are driven by anxiety and a constant need to achieve. He describes himself as "constantly whipping myself" and feeling like "if I don't achieve, I'm a piece of s**t." This anxious, hyper-vigilant mindset can be beneficial for entrepreneurship but detrimental to happiness.
He notes that many successful people have some form of childhood trauma or "chip on their shoulder" that drives them. As investor Josh Wolfe says, "Chips on shoulders put chips in pockets." However, this often leads to a never-ending treadmill of achievement without contentment.
- Successful people are often driven by anxiety, trauma, or a need to prove themselves
- This mindset is beneficial for business but can be detrimental to happiness
- Even extreme success rarely resolves the underlying psychological issues
The Realities of Extreme Wealth (42:10)
Wilkinson shares his experience of becoming a billionaire, noting that it felt anticlimactic: "I felt exactly the same, and I went on reading the book with my kids." He argues that money doesn't fundamentally change your day-to-day experience of life.
In fact, extreme wealth often comes with new burdens and challenges:
- Greater awareness of global problems you feel responsible for solving
- Complexities of managing large sums of money
- Distorted relationships and social dynamics
- Family conflicts over inheritance
Wilkinson emphasizes: "At the end of the day, the money doesn't actually do anything. In fact, it magnifies the misery in many ways."
Entrepreneurship and Building Businesses (26:11)
Wilkinson argues that great entrepreneurship is ultimately about building systems and machines, not working harder yourself. He states: "Your job is to fire yourself as an entrepreneur."
Key points on entrepreneurship:
- Delegate and build systems - The goal is to create a business that can run without you
- Be "Teflon for tasks" - Let go of everything you don't enjoy or aren't best at
- Leverage other people - Hire great people and empower them to run things
- Buy existing businesses - Often easier than starting from scratch
He uses the analogy of sailing to Hawaii: Most entrepreneurs try to build a raft from scratch, while buying a business is like boarding an existing cruise ship.
Hiring and Managing People (30:58)
Wilkinson emphasizes the critical importance of hiring well, stating "hiring a new CEO is like a brain transplant for a company." His key strategies:
- Hire people who have done similar work at 2x the scale
- Ensure alignment on vision and strategy - "Are they rowing in the same direction?"
- Create proper incentives - Ensure they have skin in the game
- Do thorough background checks - He uses former CIA agents to dig deep
- Throw them in the deep end - No hand-holding, see if they can swim
He notes: "I want to hire people who are fully formed...When it comes to CEOs, it really is just, let's get us aligned...and then here's what we care about. Let's go."
The Difficulty of Changing People (1:23:35)
Wilkinson argues that people rarely change fundamentally. He uses the analogy of being "the rider on an elephant" - you can guide slightly, but the elephant (a person's core traits) will ultimately go where it wants.
Key points:
- Don't try to change people - hire for fit instead
- People usually need to experience failure themselves to learn
- Even after failure, people rarely blame themselves
- We all build charitable narratives about ourselves
He states: "The path to misery is trying to change those around you."
Mental Health and Technology (1:02:21)
Wilkinson discusses his own struggles with anxiety and the strategies he uses to manage his mental health:
- Medication - He takes an SSRI which has helped reduce his anxiety
- Limiting information intake - Avoiding news and limiting social media
- Setting technology boundaries - Using apps like Opal to restrict phone use
- Treating himself "like a drug addict" - Being very cautious about information consumption
He emphasizes the importance of awareness and boundaries: "By drawing those boundary boxes around myself, I find that my mental health is better and that I'm less stressed."
Finding Contentment and "Enough" (1:17:15)
Wilkinson discusses the challenge of finding contentment and determining when you have "enough." He shares the example of Derek Sivers, who sold his company for $20 million and put it in a trust that pays him a set amount annually.
Key points on finding "enough":
- Determine a specific income number that is truly enough for you
- Consider "burning the boats" - putting wealth in a trust or giving it away
- Focus on relationships and experiences rather than accumulation
- Recognize that the hedonic treadmill never stops on its own
Wilkinson notes his own ongoing struggle: "I would love to get to a point where I do not ask myself 'what's next,' and I don't know if that's possible."
Effective Philanthropy (1:44:04)
Wilkinson discusses his commitment to giving away his wealth and the challenges of effective philanthropy. He sees money as a "byproduct" of his business success and is focused on how to do the most good with it.
Key points on philanthropy:
- Public commitment can create accountability (e.g. signing the Giving Pledge)
- Effective Altruism offers promising frameworks despite recent controversies
- Need to balance judiciousness with action - can't let perfect be the enemy of good
- Exploring how to give effectively is a key focus for Wilkinson going forward
Conclusion
Andrew Wilkinson offers a candid and insightful look at the realities of entrepreneurship and extreme wealth. While achieving business success and accumulating vast wealth, he has come to recognize that these external achievements do not necessarily lead to happiness or fulfillment. His experiences highlight the importance of self-awareness, setting boundaries, determining one's "enough" point, and finding ways to give back effectively. Wilkinson's journey demonstrates that the pursuit of success and wealth is often driven by underlying psychological factors, and true contentment requires addressing these root causes rather than simply achieving external markers of success.