Why Good Business Leaders Are Miserable People

🌈 Abstract

The article discusses why many successful business leaders are "difficult to deal with" and explores the reasons behind their misery and unhappiness, despite their wealth and success.

🙋 Q&A

[01] The Reason Why Successful Business Leaders are "Difficult to Deal With"

1. What is the key insight the author shares about why successful business leaders are often miserable people?

• The author shares a story about a very rich and successful friend who attended an event with other ridiculously rich and successful people. At the event, each person complained that they would only be truly happy if they could achieve just a little bit more, revealing the "more money, more problems" phenomenon.
• The author concludes that there is a "sweet spot" between being rich and poor, and that constantly chasing more success and happiness is actually detrimental to finding true fulfillment.

2. What does the author suggest successful business leaders should do instead of chasing money, success, and happiness?

• The author advises successful business leaders to:
  • Stop chasing money, success, and happiness
  • Just go do the impossible thing and quit complaining about the effort required
  • Put on a "stupidly happy face" when facing failure, frustration, or pressure, as that is what being a successful business leader means

3. What personal experience does the author draw from to understand the mindset of successful business leaders?

• The author states that they have been on both sides of the table, as both a leader and a follower. They have had the privilege of working with many great leaders, but have also had coffee and drinks with successful business leaders who are miserable people.

[02] The Author's Perspective on Chasing Success

1. What key insight did the author have about chasing success, similar to the insight about chasing happiness?

• The author had a revelatory experience in realizing that constantly and doggedly chasing success is detrimental, similar to the idea that chasing happiness is actually counterproductive.
• The author used the example of successful athletes practicing mundane things repeatedly, so they don't have to think about it under pressure, to illustrate this point.

2. How does the author's own experience as a writer and creator inform their perspective on chasing success?

• The author shares that they used to be someone who was constantly chasing success, driven by a desire to create something they didn't know how to build based on a murky vision.
• They found that the best advice they could get to unblock the challenges they faced was often just a shrug and "you're on your own", but that they love the process of unblocking those challenges.
• This personal experience helps the author understand why successful business leaders are often so miserable, as they face similar mental costs and frustrations in pursuit of their goals.