When I founded my first company I was in my late 20s, single, childless, and renting a room in a group house. When I left my 4th tech start up, I was almost 40, married to a career woman, and had 2 young children, a dog, and a mortgage. I expected having a family to change a lot of things. But I didn’t expect it to figure into my job search.
Tech start-ups are notoriously risky. Even when investors are on board, most tech start-ups have only 6-12 months to prove themselves, and 95% of them fail. So around-the-clock work is the norm. Before kids, all I had to think about was “can I survive doing this start-up for a few more months?” The pay was low, but doable for a single guy, especially with the potential for a huge payday if the company took off. The work was fascinating and challenging, and I was constantly learning new skills. I always figured that if one start-up didn’t go well I’d just found – or join – another one. So 18 months ago, I was surprised to find myself daydreaming about getting out of the start-up business.
How to pay the bills, be a day-to-day dad and co-primary parent, build a meaningful career, and have time for personal passions like community service, playing violin, and golfing were front and center on my mind. I found myself yearning for job stability of the sort that no pre-revenue start-up can provide. The kind that comes from knowing your company will still exist 6 months from now.
Which brings me back to my job search last year. For the first time in years, I found myself wanting to work for bigger companies for the more stable paycheck. I was burnt out from the craziness. I realized that in our 14 years together my wife and I have never both held traditional stable jobs at the same time.
We value passion in our professional endeavors above almost anything else. So years ago we together decided that my wife would leave a lucrative legal career to found a nonprofit. I’ve never for a second doubted that it was the right decision, but it meant that we’ve always juggled back and forth who earns money and who pursues a risky start-up or a short-term can’t-pass-up professional opportunity. Occasionally we’ve even leapt feet-first at the same time. The craziest stretch was in 2008 when my wife was bootstrapping her nonprofit, our first daughter was born, and the nuclear explosion of the Great Recession hit my 3rd tech start-up. We’ve managed to keep our heads above water, but only by being very calculated and strategic in managing our finances. No wonder I was exhausted and my hair had turned gray.
Still, as crazy as it’s all been, I wouldn’t do it any other way. Our family north star is the “20 year rule”: Faced with any significant decision we ask ourselves, “20 years from now will we regret NOT having done that?” If yes, then we find a way to make it work, even though it almost always requires both of us to re-balance a zillion other things. It’s definitely not the easy way, but it’s the only way that makes sense for us.
This blog post originally appeared on April 28, 2014 as part of the Religious Action Center’s blog series “Double Booked: A Conversation about Working Families in the 21st Century.” Double Booked deals with the many issues that affect working families, and features everything from personal stories to policy analysis. Visit the Double Booked portal to read more posts and subscribe for updates, or join the conversation on Twitter and Facebook with the hashtag #doublebooked.