“Trading” Your 20’s For Your 30’s

David Heinemeier Hansson recently wrote a post about trickle-down workaholism in startups that got me thinking.

I don’t have many career regrets, but if I do have one it’s that I spent most of my twenties working with the mentality that I was overworking myself now so that I wouldn’t have to overwork myself later. I thought I could “trade” my twenties for a more enjoyable thirties (and forties and fifties and so on). I worked 7 days a week, typically very long and very intense days. I only avoided burning myself out because I had a reasonably good foundation of healthy diet, sleep, and exercise habits, as well as some good friends, family members, and my partners to keep me sane.

There are a few problems with this approach. First and foremost, I didn’t understand that in business effort doesn’t equate directly to success. You can work on something for years and make $0. You can come up with a brilliantly simple idea in a weekend and generate revenue immediately. I see it all the time with the entrepreneurship students I work with: invariably someone figures something out that enables them to profit thousands of dollars in a month or two while putting in very little time.

This “hard work = success” mentality is almost all we’re exposed to from our parents, in our school, and in most jobs. If you work hard, you’ll almost always get good grades or good performance reviews. Coming up with a product or service that has good market fit and then executing on that idea certainly involves hard work, but it also involves creativity, intelligence, and a variety of other traits.

Overworking also instilled a set of bad habits, where I placed work above all else. I didn’t understand that it doesn’t necessarily get easier as businesses grow, the challenges just change. As one problem – not making any money – goes away, new problems arise with technology, human resources, vendors, customers, partners, etc. It’s not too hard to see how someone can start a business with a “plan” to dial it back once they reach a certain point, and then never do so.

Lucky for me it worked out and I now have a pretty balanced life. I didn’t miss out on having a family or burn any bridges with friends or compromise my health, but a lot of that was good fortune rather than anything that I intentionally did. And I still have that nagging feeling of “I should be working” in the back of my head, even when I know that things are running smooth and that I definitely should not be working. I know that my partners have the same feeling because it’s something we discuss from time to time. It’s now a mentality that we have to work on letting go of, when it probably could have been prevented in the first place.