How Will You Measure Your Life?

It's easy to get wrapped up in your startup and life as an entrepreneur, but sometimes you must step back and reflect on your greater life journey. Bruce Upbin has an excellent profile on The Innovator's Dilemma author Clay Christensen's new book called How Will You Measure Your Life? I haven't read the book but plan to do a full review after it releases next week.

Much of the book's subject seems to come from a Christensen address to Havard Business School 2010 graduating class. It's a lecture that I highly recommend and have personally read many times over the past several years. To quote from it:

"On the last day of class, I ask my students to turn those theoretical lenses on themselves, to find cogent answers to three questions: First, how can I be sure that I’ll be happy in my career? Second, how can I be sure that my relationships with my spouse and my family become an enduring source of happiness? Third, how can I be sure I’ll stay out of jail? Though the last question sounds lighthearted, it’s not. Two of the 32 people in my Rhodes scholar class spent time in jail. Jeff Skilling of Enron fame was a classmate of mine at HBS. These were good guys—but something in their lives sent them off in the wrong direction."


He goes on to describe that no one ever plans to get divorced, or plans to go to jail. But something along the way changes that.

I’ve seen more and more of them come to reunions unhappy, divorced, and alienated from their children. I can guarantee you that not a single one of them graduated with the deliberate strategy of getting divorced and raising children who would become estranged from them. And yet a shocking number of them implemented that strategy. The reason? They didn’t keep the purpose of their lives front and center as they decided how to spend their time, talents, and energy.

This comes from a man who has seen his fair share of trials. Two years ago he had a stroke that made this 30-year esteemed Harvard professor unable to speak. He's also had a heart attack and fought through cancer. "Can you learn something from somebody that has gone from success to success to success about how to be successful? I don't think so. It has to be somebody who has failed and failed and succeeded and succeeded."


Generally speaking, our Silicon Valley and technology culture doesn't address these concerns or ideas. We're taught to win whatever the cost. We're taught to hack our way through things, to act and beg for forgiveness later. There was a story yesterday in Pando Daily called The Greatest Hack of Them All: Family Planning that personifies this thinking. I believe it's misguided. The last thing in the work I want to be known for is "hacking" my family. This thought makes my stomach sick.



I often tell fellow entrepreneurs when we part ways to "not give up." Most entrepreneurs do give up at some point, but I firmly believe that being successful with your startup is as much not giving up as it is having the right idea, building the right team, going after the right market, or all three combined. The only way that I personally believe I will ever give up is if my family is in jeopardy. No startup dream has even a fraction of the value that my relation with my family has. Easy to say of course, harder to live.



There is an article from earlier this year entitled Top 5 Regrets of the Dying. It's no scientific study, but the #2 biggest regret was "I wish I hadn't worked so hard." I'm not advocating anyone stop working hard, but just think about the cost of your work. I worked until 1am last night, you probably did too. I was also able to have dinner with my family, put my boys to bed, and hang with my wife. In doing so I felt like I met all my personal relationship goals, and pushed forward on my professional ones. Nothing meaningful was ever created without sacrifice, just make sure you're not sacrificing too much.