Message in Milan

In which I find myself in Milan

Recently, I was in Milan doing some workshops (because that’s the kind of glamorous thing that I do) on networking (it turns out that all the world is interested in networking) for the Bocconi School of Management’s MBA program. I had been quite nervous before going, because this was a new client and there’s always a question of how well things I do here adapt to international audiences, even though most U.S. audiences are themselves quite international.

I have traveled overseas on business before a few times, but mostly under the name and protection of big institutions – the foreign service, Davis Polk, etc. Mostly I’ve just traveled for pleasure. This time, it was me qua entrepreneur, trying to make money and deliver a service, as opposed to me qua tourist, just spending my dollars and being friendly. Going overseas in an entrepreneurial capacity is simultaneously thrilling and scary. I felt exposed. What if the carbinieri locked me up for some unknown tax code violation? What if the PowerPoints didn't work? What if I felt unattractive next to all those skinny Italian guys on Vespas?

My story, heard two different ways

As it turned out, the workshops were really fun and successful. Later, some of the Italian MBA students took me out to lunch. One of them asked me to explain my career progression, which had been hinted at in the bio attached to their handouts.

I briefly went over the story – foreign service, more school, law firm, internet start-up, unemployment, coaching. I actually left out several pieces – the first post-college internship I had in investment banking, my year in consulting, the stupid hedge fund, attempts to make it as a screenwriter, philanthropy consulting projects, my SAT prep business, temp jobs. As I jogged through my past (both what I told them and what I edited out), I felt that awkwardness you sometimes feels when questioning judgment in telling people things that might give them a negative opinion about you—like when they ask you how you are and you start going on too long about a bad relationship or a skin disorder.

The students listened very intently. A student named Tommaso said, “I wish I had that freedom. We can’t do that in Italy. Here it’s very hard to do anything besides the one thing you are trained for. People don’t accept your changing fields so most people don’t even try. I would like to be able to try a lot of different things, as you have.”

Well. That made me think.

The part I forget to think about

You see, I don’t often think about the freedom inherent in my choices. On several things I have not made it to the finish line (like being a rich entrepreneur, or a successful screenwriter) but no one has stopped me from taking the first step. Or the second, or the third. I can look back and see the cost of trying new things. But I never really ask myself, “how much would I pay for the ability to make changes, if I didn’t have it?”

Here in competitive New York City, it’s easy to focus on the outcome of everything. We always think, “what result did I get?” I don’t think we ponder as often the value of the process. Do I want a life in which I get a particular result? Or do I want a life in which I’m able to live fully—which means being able to sample a lot of what life makes available?