The more successful CEOs and founders I work with, the less I envy them

And the more I’ve started to admire and respect them instead. 

A line by a founder caught me deeply off guard recently. He said: “Leo, I’m set for life, but I don’t feel that I can talk to anyone that understands the difficulty I’m going through.” 

I’ve coached some of the most successful people that I know by the hundreds over the last years. I believe that this has helped me gain some unique insights into the challenges and dreams of these people. What my line of work helped me do most importantly is to break down the stereotype of “success” that tends to include lots of money, big companies, big houses, and fancy things. And to break down into individual stories, led by individual humans that all experience deep hardship, failure, excitement, warmth, and sad moments, just like the rest of us. 

Personally I’m in the same position that I’ve previously called “envious”. By age 26 I had made enough money to never work another day and comfortably live off the interest rates of the money that I made without ever actually spending said money. Yay capitalism! 

Now, this article is not a pity-fest for the rich and successful. But instead, it is a reality check on what it means to be human, no matter what it is that we’ve accomplished. And how to unfold more deeply into our humanity and wishes for ourselves. 

Successful vs. successful & happy

The more people I speak to in 2020, the less interesting the conventional idea of “successful” has become and the more exciting version of “successful & happy” has emerged. What exactly is the difference between those two? My definition of successful as the word already contains is a series of accomplishments that succeed each other. And most of us set out to make life about having the longest-lasting streak of accomplishments possible.

Even if there are some failures and setbacks along the way, those that eventually become “successful” were able to somehow find enough strength and courage and favorable circumstances to have accumulated wealth or built large companies or written best-selling books from their streaks of accomplishments. 

I’ve personally had a similar run and here’s a very (very!) simplified version of it: 

• Accomplishment – 18 years old: Enlist in the military for a year to save up enough money for a year of College
• Accomplishment – 19 years old: Enter college and work hard to get a paid internship over the summer to keep paying for college 
• Failure – 20 years old: Fail to get any internships, drop out of College and instead bet on working on a Tweet scheduling app with a friend from College
• Failure – 21 years old: Fail to get funding or a visa to stay in the US. 
• Accomplishment – 22 years old: Eventually manage to raise $500k for the business, grow it to $1m in revenues, hire a team and manage to get a Visa to stay in the US.
• Failure – 23 years old: Get 500,000 of our user accounts hacked, risk of losing the whole business
• Accomplishment – 24 years old: Recover from the hack and raise more money, where I can personally sell some stock to become a millionaire 

And so on and so forth, you get the idea. 

And as admirable and at times enjoyable succeeding is, i.e. having a streak of accomplishments, inherently it doesn’t make us happy. Anyone who has ever played a video game all the way through to the end would barely after succeeding to beat the game state that they have now become an inherently happier person, even though they might have enjoyed playing it. 

What is “happy” anyway?

After leaving the tech world for a number of years, I spent almost 2 years living in a Buddhist monastery. From living with the monks and nuns every day, I enjoyed a deeply simple life. The whole idea of accomplishments and success was turned upside down. As was the idea of happiness. 

Conventionally, I’d learned to associate happiness with a state. A sense of warm, fuzzy, giddy, loving way to look at the world. That state would be assisted by as much money as possible, partners and relationship, fame, doing what I love and so on. Through whatever means possible, the goal of life became to somehow accomplish that state and then live in that state permanently or as often and as much as possible. 

What the monastics taught me however is that what I had was inherently a recipe for success, but not for happiness. What was underlying my setup was the idea of accomplishing a certain state. Since the accomplishing of any one state, even that of the elusive “happiness” state, is never permanently possible, it is always doomed to become a race. And one that I was forever doomed to run after and lose again even after I had caught it for a while. 

Instead, they taught me that true happiness is not a state, but our relationship to our states, be it sadness, anger, irritation, warmth, or relaxation. This might sound like your regular Instagram mindfulness quote along the lines of “accept who you are” and in a way that is true. But it doesn’t capture what a fundamentally different approach to life that is. And that it takes training and dedication to shift into that mindset compared to the conventional one that I was raised within the Western world. 

Since I left the tech world as a software entrepreneur a number of years ago, I’ve made that idea that I learned at the monastery the heart of my approach to life. And my life as I’m writing this is most definitely the happiest it’s ever been following the above definition. I have no proof for this, it’s not reflected in my bank balance or anywhere else, but in the experience of the world in my own heart. Relying on that alone without any external markers is part of what makes the path of happiness difficult and scary.

The path to successful and happy

Most of us don’t want to give up all striving for success. And me neither! I decided against becoming a monk full-time, in part because I enjoy certain conventional things in the world. In some way, most founders or CEOs come to me with the hope to find a path that brings them both deep happiness and fulfillment AND continued success in their life and business. 

Along-side the above-described mindset change, what the path towards happiness includes is a commitment to learning and being with all states of our human experience. Most of us are deeply averse to that. Yet, once we learn how to enjoy being scared, being angry, being ashamed that is the only place in my experience where our outlook on life can truly shift. That is when we can deeply find peace, because no matter what experience we wake up to in the morning, we’ll have a way to enjoy the state we’re in, without needing to change it or run after something else. 

When I was living in the Korean mountains to study with a Korean Zen monk and friend of mine, I woke up one more morning and said to him “I am so angry today!”. He looked at me and asked “In the body or in the mind?”. What he showed me with that question was that anger in the body is not a problem, it is simply an experience. But anger in the mind, when there is no space between us and the experience of anger is when we’re caught up in the race to get away from it.

How to best practice “being with our states to become deeply fulfilled and happy” has a lot of answers – coaching, meditation, therapy, time in nature are among my own favorite tools. But it most importantly begins with our intention and ability to see happiness and success as distinctly different things.