Quitting

This year has seen a number of endings. Bill Gates is retiring from his day job at Microsoft to focus on his foundation. Justine Hénin, the best woman tennis player in the world, retired at the age of 25 while still ranked #1 to focus on the rest of her life. Euromad is moving back to the U.S. after two years in Europe and slowly winding down his blog. And, after eleven years, three jobs, and several hundred plane flights, I am retiring from the business world.

I have been planning to retire for a long time, but didn't want to discuss it here until the announcement to my company, which happened two weeks ago. I will be going to Yale Law School starting in September, with the eventual goal of becoming a public interest lawyer - probably working as a public defender, in legal aid, or for a civil rights organization. I've wanted to make this change for several years now, ever since listening to an episode of This American Life entitled "Perfect Evidence," about four teenagers who were framed by the police for a rape and murder and spent fourteen years in prison before being exonerated by DNA evidence. It's an old cliché, but I want to help people. Of course, there are many ways to help people, many of them more obvious than spending $130,000 in tuition and three years of your life to go to law school, in order to become a member of one of the most despised professions in this country. But my hope - or fantasy - is that as a lawyer you can help people in a very concrete way, one person at a time, when they need help the most. In any case, we shall see.

Of course, the hard part of opening one door is closing the other one behind you. One problem is that we grow up expecting our lives to be a linear progression onward and upward in which we monotonically accumulate skills, work experience, titles, money, and prestige. On paper, I should be staying at my company until we go public, or I should become a vice president at a bigger company, or I should start another company, or I should use my glittering resume to get a job in venture capital or private equity, or, if I have a philanthropic bent, I should get into the burgeoning field of social entrepreneurship.

But there's an opposite perspective, which I heard best summarized in an episode of This American Life called "Quitting." (Yes, I think that virtually every significant life experience can be illustrated by one or more episodes of TAL.) In one segment, a woman who wrote a zine about quitting (this was the mid-'90s - today it would no doubt be a blog funded by AdWords) talks about the central importance of "the quit" to ... well, to everything. Before you can ever do anything new, you have to quit whatever you were doing before. This is most obvious in the case of jobs, but it applies to many other things. Before you can have a child, you have to quit that simpler, easier state of not having children. Before you can be a vegetarian, you have to quit eating animals (and yes, I like eating animals - especially In-N-Out hamburgers, and New York City hot dogs, and roast chicken, and on and on). In many cases, in order to do something new that is good, you have to give up something that is also good. Quitting is empowering. Quitting is door-opening. Without it, your life would be the same thing, over and over.

And so I'm quitting career #3 (business) to start career #4 (law). When I was younger I regretted careers 1 and 2 because they seemed in retrospect like a waste of time and energy. In college I wanted to be come a professional musician, and auditioned for the conducting program at the Curtis Institute of Music (at the time, I was the music director of one of my college's orchestras). I was going to conduct Mozart Symphony #40 at the audition, but when I stepped up to the podium the parts weren't on the musicians' stands, so my slot was delayed until they could get the music. However, my friend Ben was also auditioning that day, conducting Mozart Symphony #39, and I knew that equally well because my orchestra was performing both of them that same night. One of my few regrets about my life is not volunteering to do #39 instead on the spot. But in any case I didn't get into Curtis, and after a couple more years of indecision I gave that up. Instead I got a Ph.D. in history at Berkeley, but by the time I finished I had neither the scholarly track record necessary to get a good job, nor the real interest in and dedication to the field necessary to stick with it. So I became a management consultant at McKinsey, for no particularly good reason other than that they gave me a job, and it was prestigious and well paid. I had no ambition to make a lot of money or start a company or anything, really.

Now, though, I look back and I feel lucky to have spent my college years playing cello and conducting, and I feel lucky to have spent most of my twenties learning about history and living in Berkeley and traveling around Europe. And while I have very mixed feelings about the business world, I feel extraordinarily lucky to have spent seven years at a company that I founded with five friends and that has provided a great working environment to hundreds of people and great products to thousands.

As a result, for the first time that I can remember, I'm back at home with absolutely no business trips planned and, besides a trip to Yellowstone with my father in August, no plane trips of any kind scheduled or even anticipated. I already earned elite status on United and Delta this year, but that will expire in February 2010 and then I'll have to wait in the long line with everyone else - a trade-off I'm more than happy to make. I won't have to get a new passport because there is no room left to stamp mine, like the cool kids. My last international trip was the three-day trip to, appropriately enough, Paris in mid-April, cut short because I wanted to get back to Yale for an admitted student program, and my last business trip of any sort, although I didn't know it at the time, was to our headquarters in late May for my last management team meeting.

I will miss the travel a little, and I will miss my company and my friends there a lot, but that's the price you have to pay to open a new chapter. And I'm grateful that the last chapter was one I will look back on fondly.