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

Andrew’s Experience With Anxiety (0s)

• Andrew Wilkinson, a successful entrepreneur, shares his experience with anxiety and how it has impacted his life. He describes himself as a "walking anxiety disorder harnessed for productivity," constantly striving to achieve and solve problems. This drive, while beneficial for his entrepreneurial endeavors, has made him miserable at times.
• Wilkinson explains that he realized he needed to find a balance between his high-pressure lifestyle and his mental well-being. He acknowledges that he had achieved his financial goals and could afford to reduce the intensity of his work. He also emphasizes the importance of delegation and leveraging other people's skills to achieve success.
• Wilkinson discusses his decision to start taking an SSRI (selective serotonin reuptake inhibitor) to manage his anxiety. He initially hesitated due to the stigma surrounding mental health medication and the mixed experiences reported online. However, after careful research and understanding his own genetic predisposition, he found a medication that worked well for him. He acknowledges the potential downsides of SSRIs, including nausea, but emphasizes the positive impact it has had on his overall well-being.

Are Most Successful People Driven By Anxiety? (7m27s)

• Many successful people are driven by anxiety and a desire to prove themselves. This is often rooted in past experiences, such as a difficult childhood or a feeling of inadequacy. Andrew Wilkinson uses the term "trauma" to describe this, both in its larger and smaller forms. He believes that many successful people are driven by a need to overcome past challenges and achieve success.
• There are two main types of successful people: those who are grandiose and those who are humble. Grandiose individuals often display their wealth and success through extravagant displays, while humble individuals may choose to live more modestly. However, even those who appear humble may still be driven by a desire to be seen as successful.
• Highly successful individuals often have a singular obsession that drives their success. Warren Buffett, for example, is deeply focused on business and investing, spending most of his time reading annual reports and making deals. Charlie Munger, on the other hand, is driven by a desire to learn and build things that work. Both men have achieved extraordinary success through their unwavering dedication to their passions.

The Downside of Taking Advice (13m21s)

• Taking advice from others can be detrimental to achieving your own goals. The speaker argues that blindly following advice, especially from those in different industries or time periods, can lead to poor decisions. He uses the analogy of lottery numbers to illustrate this point, emphasizing that what works for one person may not work for another.
• Personal growth requires making your own mistakes and learning from them. The speaker believes that individuals need to experience setbacks and failures firsthand to truly learn and grow. He uses his own experience with trust as an example, highlighting how he had to be personally defrauded to understand the importance of caution.
• People should focus on identifying what makes them unhappy rather than trying to predict what will make them happy. The speaker suggests that instead of seeking blueprints for success, individuals should identify their least favorite activities and use those as a guide to choose a fulfilling career path. He argues that humans are better at recognizing what makes them miserable than what makes them happy.

Stop Doing What You Hate (17m54s)

• Focus on stopping what you hate rather than solely pursuing what you love. Andrew Wilkinson and his business partner Chris realized they were unhappy despite their success. They decided to focus on eliminating things that made them miserable, like constant travel and packed schedules, rather than solely pursuing their goals. This shift in focus led to greater happiness.
• Invert your thinking to identify and eliminate pain points. Charlie, a mentor of Andrew's, advocates for "inversion." Instead of focusing on what you want to achieve, consider what is preventing you from achieving it. By eliminating these obstacles, you can create a more positive and productive environment.
• Embrace laziness and build a machine. Entrepreneurship is not about constant hard work and self-鞭策. It's about identifying problems and building systems to solve them. The goal is to create a machine that runs efficiently without requiring your constant input. This allows you to focus on your strengths and passions, ultimately leading to greater success and happiness.

Moving From Operator to Executive (27m24s)

• The transition from operator to executive is a common challenge for entrepreneurs. This shift often occurs when a business grows beyond a small team, requiring the founder to delegate tasks and responsibilities.
• The author describes three phases of delegation: 1) Basic Delegation: Hiring someone to do tasks you don't want to do or can't do yourself. 2) Higher One to Higher 10: Hiring a manager to build and manage a team. 3) Firing Yourself: Delegating your own role as CEO, recognizing that someone else may be better suited for the position.
• The author emphasizes that the transition from operator to executive can be difficult. It requires letting go of control and embracing a different way of working. He acknowledges that some people are better suited to being individual contributors, while others thrive in leadership roles. He also highlights the importance of understanding your own personality and preferences when making this transition.

Books That Helped Andrew (34m4s)

• Andrew Wilkinson emphasizes that many important life and business lessons are learned through personal experience and pain. However, he acknowledges that books can provide valuable insights and perspectives.
• He highlights "The E-Myth Revisited" by Michael Gerber as a book that significantly impacted his understanding of business.
• Wilkinson emphasizes the importance of psychology in understanding human behavior, particularly in business contexts. He recommends "Influence" by Robert Cialdini, which explores common causes of human misjudgment and how psychology is used in sales and marketing.
• He considers "How to Get Rich" by Felix Dennis to be a particularly impactful book for entrepreneurs. Despite its seemingly boastful title and cover, the book offers a unique perspective on wealth and its potential downsides. Dennis, a successful magazine publisher, argues that true wealth doesn't necessarily equate to happiness and that pursuing excessive riches can lead to unforeseen consequences.

What Does ‘Never Enough’ Mean? (37m56s)

• The "Never Enough" Phenomenon: The speaker observes that regardless of wealth, people always seem to desire more. He shares anecdotes of individuals with varying levels of wealth, all expressing a desire for even greater financial success. This phenomenon is attributed to human nature's tendency for comparison, leading to a constant striving for more, even when already possessing significant wealth.
• The Burden of Wealth: The speaker argues that wealth can become a burden, particularly for those who are empathetic and aware of global issues. They may feel a responsibility to address these problems, leading to a sense of overwhelm and inadequacy. Additionally, managing large sums of money can be demanding, attracting unwanted attention and manipulation.
• The Perverting Influence of Wealth: The speaker highlights how wealth can distort relationships and create social awkwardness. He describes the challenges of navigating social situations where generosity can be misconstrued as showing off or being condescending. He also points out the societal pressure to engage in philanthropy, leading to a sense of obligation and judgment regardless of one's actions.
• The Impact of Wealth on Family Dynamics: The speaker emphasizes how wealth can create tension and conflict within families. He suggests that children of wealthy families may struggle to develop their own identities, becoming entangled in the dynamics of inheritance and power struggles. He also notes how wealth can lead to disputes over family assets, even seemingly simple things like vacation homes.
• The Misinterpretation of Wealth and Happiness: The speaker criticizes the tendency to dismiss the struggles of wealthy individuals, often met with responses like "look at all the things you have" or "there are people starving." He argues that wealth does not guarantee happiness and that external validation cannot fill an internal void. He draws a parallel to fame, where positive experiences can be overshadowed by unwanted attention and intrusions.

The Perils of Being Rich & Famous (48m23s)

• The perils of fame and wealth: Andrew Wilkinson discusses the challenges of becoming famous and wealthy, particularly the distorted reality that comes with it. He notes that while most people desire more wealth and fame, those who achieve it often find themselves with limited avenues for sympathy or advice.
• The reality distortion field: Wilkinson highlights the phenomenon of people behaving differently towards those who are wealthy or famous. He shares a personal anecdote about a man who became obsessed with his business idea after learning of Wilkinson's success, illustrating the potential for unwanted attention and even harassment.
• The importance of anonymity: Wilkinson emphasizes the value of anonymity, citing Morgan Howell's idea that true success lies in being wealthy and anonymous. He also mentions Jennifer Lawrence's experience with fame, where she felt like a "freak" despite being a princess to many, highlighting the disconnect between public perception and personal reality.

People At the Top Still Don’t Feel Enough (59m28s)

• Even those at the top of their fields can still feel like they haven't achieved enough. This feeling is often driven by a constant desire for more, even after achieving significant success. The speaker, Andrew Wilkinson, shares his own experience with this feeling, even though he has written a book on the subject and understands the principles involved. He describes this feeling as a "homeric treadmill" that keeps running, even when you reach the top.
• This feeling of inadequacy can manifest in different ways, often leading to obsessive behaviors. Wilkinson suggests that when one area of life is "solved," like financial security, the mind often shifts to another area, like health, politics, or other anxieties. He emphasizes the importance of awareness in recognizing these patterns and actively managing them.
• Wilkinson advocates for limiting exposure to negative information and creating boundaries around information consumption. He compares this to managing an addiction, suggesting that excessive exposure to news, social media, and other sources of negativity can exacerbate anxiety and stress. He shares his own strategies for managing this, including limiting screen time, using apps to control access to certain platforms, and being mindful of the information he consumes. He believes that focusing on the present moment and limiting exposure to "tickers" (things that fluctuate and can trigger anxiety) is crucial for mental well-being.

How Childhood Impacts Views on Wealth (1h6m17s)

• Andrew Wilkinson shares his personal experience with money and how his childhood shaped his views on wealth. He grew up in a household where money was a constant source of tension, with his father being an optimistic entrepreneur and his mother a strict budgeter. This created a sense of money being the solution to problems, which he still carries with him today.
• He believes that childhood experiences can be "hard-coded" into our personalities, and that his upbringing instilled in him a desire to use money as a shield against potential problems and a safety net for emergencies. He acknowledges that his parents' struggles were not as severe as some others, and that his perspective on wealth could have been different if he had experienced more traumatic childhood events.
• Wilkinson finds it fascinating that capitalism can turn individual greed and suffering into benefits for society. He uses the examples of Jeff Bezos and Elon Musk, both of whom had difficult childhoods, to illustrate how their personal struggles have led to innovations that benefit many people. He argues that even though these individuals may be disliked by some, their contributions to society are undeniable.

The People Andrew Admires (1h12m19s)

• Andrew Wilkinson admires people who have achieved success but have also found a sense of contentment and presence in their lives. He uses the example of Derek, a successful entrepreneur who sold his company for $20 million and chose to live a post-economic life. Derek put his money in a trust and only receives 5% of the earnings annually, allowing him to focus on writing, tinkering with new businesses, and enjoying life without the pressure of wealth.
• Wilkinson believes that many people, including himself, are caught in a cycle of chasing success and constantly moving the goalposts. He questions the value of constantly striving for more and suggests that focusing on relationships and personal fulfillment might be a more fulfilling path.
• Wilkinson acknowledges that while some people may need to work harder to achieve success, many others are already working hard but lack the leverage or perspective to find contentment. He wonders if new technologies, like GLP-1 agonists, could help people break free from obsessive behaviors and find a sense of "enough."
• Wilkinson believes that many people are unaware of what will truly make them happy and instead chase material possessions and external validation. He suggests that people should work backward from a desired income level and prioritize experiences and relationships over accumulating wealth.
• Wilkinson concludes by suggesting that the pursuit of extraordinary success often comes at a cost, and that the most successful people may be driven by a pathology or an internal drive that makes them prioritize achievement over well-being. He uses the examples of artists like Amy Winehouse and Kanye West to illustrate this point.

Can People Actually Change? (1h21m37s)

• People are resistant to change: Andrew Wilkinson argues that it's incredibly difficult to change people's behavior, even when they are presented with evidence that their current approach is not working. He uses the analogy of a rider on an elephant, where the rider (the person trying to influence change) has limited control over the elephant's (the person's own ingrained habits and beliefs) direction.
• Failure is a necessary catalyst for change: Wilkinson believes that people often need to experience failure firsthand before they are willing to change. He suggests that trying to force change on someone can backfire, as it can make them double down on their beliefs. Instead, he advocates for allowing people to learn from their own mistakes, even if it means a temporary setback.
• Self-reflection is crucial for growth: Wilkinson acknowledges that he himself struggles with taking responsibility for his failures, often attributing them to external factors. He recognizes that this is a common human tendency, as it's easier to protect our ego by blaming others. However, he emphasizes the importance of challenging this self-protective narrative and engaging in self-reflection to identify areas for improvement.

How to Hire the Right Candidates (1h28m50s)

• Andrew Wilkinson emphasizes the importance of hiring the right people, especially for CEO positions, as it significantly impacts a business's success. He believes that finding someone who has successfully scaled a similar business is crucial. He looks for individuals who have a clear vision and strategy for the company, aligning with his own.
• He prioritizes alignment in terms of vision and values, ensuring that the potential CEO shares his goals and approach. He emphasizes that misalignment can lead to sabotage, even if the candidate is highly competent. He also believes in incentivizing employees, particularly CEOs, by giving them a stake in the company's success through profit sharing or ownership. This ensures that their interests are aligned with the company's growth.
• Wilkinson conducts thorough background checks, going beyond standard references to ensure the candidate's integrity and past performance align with their claims. He also utilizes recruiters as a leverage point, allowing them to conduct initial interviews and record them for his review. This helps him quickly assess candidates and avoid wasting time on unsuitable individuals. He believes in hiring fully formed CEOs who can hit the ground running, rather than mentoring or training them. He compares hiring a CEO to a brain transplant, emphasizing the importance of a good "DNA match" to ensure the new leader is accepted by the company.

Making Gut Decisions (1h37m54s)

• Gut decisions are based on experience: Andrew Wilkinson argues that your entrepreneurial gut is only as good as the experiences you've had. He uses the example of a lunch business idea, which he would have pursued years ago but now knows is too complex and low-margin due to his experience in the food service industry.
• Reading is important, but experience is crucial: While reading about entrepreneurship is helpful, it's not a substitute for firsthand experience. Wilkinson emphasizes that even after reading about common mistakes, he still had to learn from making them himself.
• Pain is a powerful motivator: Wilkinson believes that pain is essential for learning and growth. He connects his own experience with the book "E-Myth" and how reading about the struggles of a bakery owner resonated with him because he was experiencing similar challenges. He argues that pain, combined with reading and learning, can lead to success.
• Passion and excitement are key: Wilkinson uses the example of his son's guitar lessons to illustrate the importance of finding passion and excitement in learning. He suggests that the most successful learning often comes from a place of pain or a strong desire to overcome a challenge.
• Learning needs context: He criticizes the way math is often taught, arguing that it lacks context and motivation. He believes that learning should be connected to real-world applications and experiences, just like learning guitar should be tied to the desire to play music or impress someone.

Andrew’s Future After Writing the Book (1h41m42s)

• Andrew discusses the psychological effects of consistency and commitment bias, explaining how publicly declaring his intention to give away all his money through the Giving Pledge creates a commitment to follow through. He also acknowledges the byproduct of his wealth and the need to find ways to maximize its positive impact.
• Andrew expresses his desire to deprogram himself from the constant pressure to be productive and achieve more, aiming to appreciate the present moment. He recognizes that this might be a difficult goal, but he feels content with his current situation.
• Andrew explores the concept of effective philanthropy and its potential to be a more efficient way to distribute wealth. He discusses the controversy surrounding Sam Bankman-Fried and the FTX scandal, acknowledging the potential for bad actors to damage the reputation of even well-intentioned initiatives. He believes that effective altruism, despite the setback, remains a valuable philosophy and that the focus should be on maximizing the impact of every dollar donated.

Where to Find Andrew (1h50m18s)

• Andrew Wilkinson encourages viewers to follow him on X (formerly Twitter) at @Wilkinson to stay updated on his activities.
• He also suggests checking out his book, which is available at it'sneverenough.com.
• Wilkinson expresses his enthusiasm for hearing feedback from his audience and thanks them for watching.