How To Stop Feeling Like Your Success Is Never Enough - Andrew Wilkinson

Added: Jul 30, 2024

Views on Entrepreneurship and Success

Wilkinson believes that entrepreneurship is fundamentally about laziness - finding easier ways to solve problems and build systems. He contrasts the "craftsman" approach of someone like Jiro Ono, the legendary sushi chef who obsesses over every detail, with the "systems builder" approach of someone like Steve Ells of Chipotle who creates scalable business models. Wilkinson advocates for the latter, arguing that great entrepreneurs build machines that can run without their constant involvement.

He's skeptical of the glorification of hard work for its own sake, noting that many people conflate busyness with productivity. Instead, he recommends focusing on high-leverage activities and delegating or eliminating low-value tasks. Wilkinson aims to be "Teflon for tasks", letting go of anything he doesn't enjoy or isn't the best person to handle.

Mental Health and Anxiety

Wilkinson describes himself as having an anxious disposition and being hyper-aware of potential problems. While this makes him a good entrepreneur, he acknowledges it can make him miserable. He's found that chemical intervention through SSRIs has helped reduce his anxiety, though he was initially hesitant to try medication.

He emphasizes the importance of setting boundaries around technology use and information consumption. Wilkinson uses apps to limit his social media usage and avoids consuming news, recognizing that being aware of every global problem is psychologically overwhelming. He treats himself "like a drug addict" when it comes to managing his information diet and work habits.

Wealth and Happiness

A central theme of the conversation is the relationship between wealth and happiness. Wilkinson argues that most successful people are "walking anxiety disorders harnessed for productivity." He's observed that even billionaires often feel unsatisfied and continue striving for more. This ties into his book titled "Never Enough", which explores why accumulating wealth often fails to bring lasting contentment.

Wilkinson shares personal anecdotes about how achieving great financial success didn't fundamentally change how he felt day-to-day. He recounts the moment he realized he had become a billionaire while reading to his kids, noting that he felt exactly the same. This illustrates the hedonic treadmill effect, where people quickly adapt to improved circumstances and return to a baseline level of happiness.

He's critical of the common assumption that more money will solve all problems, noting that extreme wealth often comes with its own set of challenges. These can include the burden of managing vast sums, the distortion of relationships, and feeling increased responsibility to solve global problems. Wilkinson advocates for finding a "enough" point financially and focusing on other aspects of life.

Philanthropy and Effective Altruism

The conversation touches on the challenges of effective philanthropy. Wilkinson expresses interest in exploring how to give away wealth in ways that maximize positive impact. He mentions signing the Giving Pledge and committing to not leaving large inheritances to his children.

There's discussion of the Effective Altruism movement and how it's been impacted by the Sam Bankman-Fried/FTX scandal. While acknowledging the damage done to Effective Altruism's reputation, Wilkinson defends the core idea of trying to maximize the impact of charitable giving. He argues that isolated bad actors shouldn't discredit an entire approach to philanthropy that has demonstrably saved many lives.

Business Lessons and Hiring Practices

Wilkinson shares several key business lessons he's learned over the years. One is the importance of "fishing where the fish are" - finding markets with less competition rather than trying to compete head-on with well-funded rivals. He recounts losing $10 million on a project management software startup that tried to compete with Asana, realizing in hindsight that it was like "Fiji trying to invade the United States."

When it comes to hiring, especially for CEO roles, Wilkinson emphasizes finding people whose natural instincts align with the direction he wants the business to go. He looks for candidates who have successfully run similar businesses at a slightly larger scale. He is wary of trying to change people's fundamental approach, likening it to being a "rider on an elephant" - you can guide somewhat, but ultimately the elephant (the person's core tendencies) will go where it wants to go.

He advocates for aligning incentives by giving executives meaningful equity stakes or profit-sharing arrangements. Wilkinson also employs extensive background checks, including using former CIA operatives to deeply vet candidates' histories and references.

Personal Growth and Future Aspirations

Reflecting on his own journey, Wilkinson expresses a desire to reach a point where he's not constantly asking himself "what's next?" He acknowledges the difficulty of deprogramming the drive that led to his success but hopes to find more contentment in the present moment.

Writing his book "Never Enough" was partly an exercise in holding himself accountable to the realizations he's had about wealth and happiness. By publicly committing to giving away his fortune and exploring effective philanthropy, he hopes to align his actions with his evolving values.

The Limits of Learning from Others' Mistakes

A recurring theme in the conversation is the difficulty of truly internalizing lessons from others' experiences. Wilkinson believes that many important realizations, especially around the limitations of wealth to provide happiness, can only be truly understood through personal experience. He likens it to the challenge of teaching math without explaining its real-world applications - without feeling the pain or seeing the relevance firsthand, the lessons often don't stick.

This ties into his skepticism about changing other people. Wilkinson has found that trying to change employees or partners is often futile. Instead, he advocates for finding people whose natural tendencies align with what you need and letting them operate in their own style.

Fame and Public Recognition

The conversation touches on the challenges that come with increasing public recognition. Wilkinson shares an unsettling experience of having a stranger show up at his home wanting to pitch a business idea, illustrating the downsides of even modest fame. He and the host discuss how being well-known within a niche while maintaining general anonymity might be the ideal balance.

There's acknowledgment that both extreme wealth and fame come with unique difficulties that are often dismissed by those who haven't experienced them. While these may be "luxury problems," they are nonetheless real challenges that can significantly impact quality of life.

Reflections on Capitalism and Human Nature

Wilkinson offers an interesting perspective on capitalism, describing it as a system that "takes crazy people and greed and builds benefit for all of us." He notes how many highly successful entrepreneurs have difficult backgrounds or personality quirks that drive them to achieve at extreme levels. While this can lead to personal unhappiness, it often results in innovations that benefit society broadly.

This ties into a broader discussion about the relationship between trauma, anxiety, and success. Wilkinson suggests that many highly accomplished people are driven by some form of "chip on their shoulder" - whether from childhood experiences, perceived slights, or innate personality traits. While this drive can lead to impressive achievements, it often comes at a personal cost.

Conclusion

The conversation with Andrew Wilkinson offers a nuanced look at the realities of entrepreneurial success, the challenges of extreme wealth, and the ongoing quest for personal fulfillment. His reflections on anxiety, the limitations of money to provide happiness, and the importance of setting personal boundaries provide valuable insights for anyone navigating success in business or life more broadly. Wilkinson's evolving focus on effective philanthropy and finding contentment beyond achievement reflects a mature perspective on what truly matters beyond financial metrics.