David Heinemeier Hansson

October 31, 2022

The best teacher is a bad boss

It takes a lot longer to learn how to run a good business, if your lessons are derived solely from the confines of calm, comfortable companies operated by kind and caring bosses. Of course you can pickup on the subtleties of a well-run organization, but it's far more memorable to deal with the chaos and aggravation that comes from working in a mad house.

I was very fortunate to have plenty of bad bosses early on in my career. Bosses who instilled in me an urge to operate differently. These were often people who had themselves been deprived of experience working for other bad bosses in the same industry. And thus couldn't relate to how their decisions would manifest for the people they were responsible for.

One of those early, defining experiences involved the seating arrangement at a company in Copenhagen back in the dot-com heydays. One day, the boss decided we should change how we were sitting, so as to create a more "dynamic" office aesthetic (especially to visiting investors). That meant round tables in open rooms where some would sit with their back to people passing by. Thus creating a fishbowl experience where anyone walking behind them could see whatever was on their screen at the time. I hated it.

It left me with a revulsion to dictating the physical working environment of others on the basis of vanity, especially if the boss wasn't willing to abide themselves. And if I ever got to call the shots somewhere, I'd make damn sure that people were free to work where and how they saw fit.

Now I'm sure I've made decisions over the years as a boss that those working for me would characterize as bad. It's inevitable that different people will perceive the work environment differently. So I hope that perception at least serves as a spark for some of them to start their own businesses from chiseled principles that were carved in opposition.

Everyone deserves at least a few bad bosses in their career to teach them what not to do, illuminate what really matters to them, and hopefully endow them with a perspective on how they'd operate themselves if they ever got the chance.

About David Heinemeier Hansson

Creator of Ruby on Rails, co-owner & CTO of 37signals (Basecamp & HEY), best-selling author (REWORK, It Doesn't Have to Be Crazy at Work, REMOTE), Le Mans class-winning racing driver, antitrust advocate, investor in Danish startups, frequent podcast guest, and family man.