David “DHH” Heinemeier Hansson: The Entrepreneurial and Unstoppable Stoic

In our interview with Daniele Bolelli we said how there is a certain class of people who can’t be placed in a single category. Their interests and accomplishments span multiple industries and fields and are often at complete odds with one another. David “DHH” Heinemeier Hansson is one of them. He is the creator of the widely popular programming framework Ruby on Rails, he is the founder & CTO at Basecamp, he is a New York Times best-selling author, a Le Mans class-winning racing driver, as well as a talented photographer. David has also been an outspoken critic of many so called “best practices” in Silicon Valley—from the growth at all costs mentality to the cult of workaholism. It turns out, he is also a deep admirer and student of the Stoics. We’ve seen references to Stoicism in his writing online but it was only after his interview on the Tim Ferriss podcast that we understood how deeply DHH has studied Stoic philosophy and how big of a part it played in his life.

In the interview below DHH shares some of the most important techniques from Stoicism that help him cope with success, achieve tranquility, key book recommendations and much more.

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Can you tell us how you first encountered Stoicism? Was it a specific book or author? Do you remember your reaction?

The first book on Stoicism I picked up was William Irvine’s A Guide to the Good Life back in 2014. I’ve heard references to Stoicism before that, but it was Irvine’s book that really gave me the full tour of the philosophy, and it instantly resonated with me.

Partially because I had already independently been practicing many of the Stoic principles, like negative visualization and detachment. So I was already running the partial, home-grown version of Stoicism as my personal operating system. Thus upgrading to the full-fledged philosophy through the writings of Aurelius, Seneca, and others was both easy and enlightening.

It’s funny, because this trajectory, to have independently arrived at a set of conclusions about life and the world, then finding them validated in a grander sense, is the same one that readers of my books REWORK and REMOTE often write me about. That you think you’re the only one in the world with these thoughts, and therefore less willing to commit fully, or even acknowledge them. Then you discover a crystallized version of these thoughts and it fills you with confidence and vigor.

It also serves as an important way to define who you are and what you believe to yourself. That feeling when something is just right for you, that it just clicks, is rare and valuable. The only other time I can really say that I’ve found that at a grand scale like this is with the programming language Ruby.

 

In your Quora session earlier this year, you mention that in Stoicism you found a “kindred thought for mental coping mechanisms I had employed since childhood.” Can you tell us what you mean by that? Is there a specific coping mechanism you might recommend to our readers that you’ve taken from Stoicism?

The key mechanisms from Stoicism that I had been practicing since childhood were negative visualization, detachment, and deliberate comfort-zone expansion. All three of these techniques helped fortify my drive and my tranquility. I’ve had all sorts of ups and downs in my life, as has most anyone. But I think having this bag of tricks has helped me weather the challenges better than most.

In some ways, I think the Danish mentality is a very easy fit for the Stoic philosophy. There’s this broad sense that whatever hits you, “it could always be worse”. We said that many times in my family. It helps put negative events into a broader perspective. Whatever I’m going through as a kid or young adult in one of the richest, happiest, equal countries in the world, well, it’s probably not that bad compared to whatever just about anyone else outside of the 1st world or our time had to endure. That doesn’t mean that your own problems aren’t real or that they don’t suck, just that they’re pretty far from the worst that could happen, and thus easier to cope with.

 

In one of your popular pieces, “Try harder to be someone else,” you mention envying the tranquility of Seneca and Marcus Aurelius. What does that tranquility represent to you? How have you been working to get closer to it?

“Trying harder to be someone else” is another technique I’ve used since childhood. Picking role models and emulating their thoughts and actions until they become part of yourself. I find that to fit right in with the Stoic ideal of mental self-improvement and strengthening. So naturally upon discovering the writings of the great Stoic masters, like Aurelius and Seneca, I instantly employed the same technique to become more like them, and thus get closer to their fortitude.

For me, tranquility is the ultimate in personal control and perspective. Control over your emotions, your reactions, and the perspective to let all the little (and big) things in daily life flow by without putting you off course. That’s not an easy state of mind to obtain when you’re also passionate about being the best human you can be, doing the best work you can do, and pushing society forward. But it’s an ideal I keep returning to. Whether it’s in some technical discussion, sporting situation, or dealing with a 4-year old’s tantrums. Being deliberate about this pursuit has raised my baseline of happiness and given me more time to appreciate more of life.

 

You are a creator of the popular programming language Ruby on Rails, the founder of Basecamp, a best-selling author and a Le Mans class-winning racing driver. Instead of asking whether you credit Stoicism to help you achieve any of that, what about: How has Stoicism helped you enjoy and appreciate success? Clearly you live a good live, you’ve made quite a bit of money, you have nice things (nice cars especially)–people see the Stoics as being austere and joyless, but it’s more than that. How do Stoicism and a rich life overlap in your eyes?

Stoicism has been instrumental in coping with success. Yes, I say coping, even though I’m sure that’ll get an eye roll from plenty of people. The old adage of “I’ve never seen an unhappy person in a Lamborghini” is something plenty of people truly believe, but boy are they wrong. I’ve known miserable people with hundreds of millions to their net worth and carefree, happy people living paycheck to paycheck.

Now, don’t get me wrong: Wealth and success absolutely can help to raise your baseline. Not having to worry about money for groceries, health care, education, and other basics is a real benefit. But there’s a large underbelly of new and largely unexplored problems and challenges that come with that. Seneca and Aurelius were both fantastically wealthy and successful people, and they show that such trappings do not absolve the mind from the burden of learning to live a good life.

I explored this theme in my Medium post on “The day I became a millionaire”, so I won’t repeat all the points here. But I’ll say that Stoic philosophy has been absolutely key to being able to deal with the situation without being trapped. I used negative visualization every week to imagine what life would look like if it all went POOF!, as it frequently does for wealthy people. I actively search to tie my happiness to something more durable than fame or accomplishments or material things. One of the worst things that can happen to people who seem to have it all is that they start fearing losing it all. I mentally embrace losing it all, such that if it does happen, I’ll be able to cope just fine.

 

One of our favorite posts from you is your article RECONSIDER. You basically say: Stop copying what everyone else is doing. Opt out of the endless competition and workaholism. Find your own path. Stick do it. This echoes Seneca in many ways. How do you think Stoicism can help ambitious young people (particularly in Silicon Valley) who are trying to figure out their path in life?

I think Stoicism can help anyone, and certainly also the extremely ambitious. It help puts the pursuit in a broader perspective. Nobody is going to care or remember whether you flipped some startup for $100M in 50 years. Your time in the limelight is short, and, in my opinion, ultimately unrewarding. Trading the best decades of your life to compress work into it so you can live in retired leisure afterwards is a mistaken pursuit. Life isn’t meant to be conquered.

I’ve made all the money in the world, and the vast majority of my favorite things don’t require any of it. Programming Ruby. Reading. Learning. Playing video games. Taking photos. Playing with my kids and talking with my wife. Yes, I get to enjoy some activities at the edges, like motor racing, that wealth made possible, but they’re a small sliver of the pie of happiness, and I’d be just fine without it (I know this because I was).

It’s both scary and liberating to arrive at a point where you basically could buy anything. Or retire and do nothing. It forces you to confront the fact that happiness and a good life isn’t correlated very well with neither of those things. No matter how hard people strive to get them.

 

You are an avid learner and reader and you had a lot of book recommendations in your interview with Tim. What are some books that you think the Daily Stoic audience will enjoy and learn from?

I’d start with A Guide to the Good Life, then On the Shortness of Life by Seneca, then Meditations by Marcus Aurelius, then The Daily Stoic. In that order. And my wife recently picked up How to Be a Stoic, which she’s been enjoying a lot too. It’s not like you need to read 100 books on Stoicism to get it. The basics are pretty simple, but living them consistently is hard. So returning to the same key texts will serve you well.

 

Last question: Favorite Stoic quote?

Life is long enough, and a sufficiently generous amount has been given to us for the highest achievements if it were all well invested.” — Seneca

Follow DHH on Twitter, Instagram and Medium. His official website is david.heinemeierhansson.com.