From Chapter 11: I'm a Sophomore

Comcate and homework weren't the only things on my mind that busy sophomore year.

I also faced the monster that cripples the self-esteem of many girls and layers a thick coat of cynicism on guys: high school social life. In other words, what happens when you stew hormonal adolescents in a big city. As an experiment, it's fascinating. For this reason, I often tried to play armchair sociologist when I could, but in the end I couldn't avoid the reality that I was just another roasted carrot in a feast of Corona, condoms, and confusion.

To succeed socially in high school I had to adjust my habits. I couldn't be "me" all the time. Even though friendships with teens preceded my splash into the adult world, adults and their style of living had become the dominant force in my life. Over the summers and during freshman year, while founding Comcate, I found inside of me an approach to living that was shared by my adult friends: serious, intellectual engagement with the world counterweighted by not taking myself or my experiences too seriously. But even in an intellectual and prestigious high school like the one I attended, this “me” did not always grease strong relationships with my school peers.

I endeavored to try to adapt myself to the traditional high school social scene so I could form stronger friendships—after all, I found most of my peers smart and funny. How could I strike a balance between my natural, more traditionally adult inclinations and those of my teenage friends?

To figure this out I followed my own advice as stated in the earlier sidebar on finding your passion (see Chapter Two): I explored the unknown. I went to some high school house parties, where alcohol and marijuana run the show, girl-on-girl hookups entertain, and, at the amusement of my African-American friends, ghetto chivalry turns white boys into Sean John–toting G’s from the hood. Serious conversation is shunned in the pursuit of the hookup—hedonism and intellectual masturbation rarely make good bed partners, I learned. I went to school dances, where we all start with a common vision of an MTV music video but then splinter in a million directions, our lack of athleticism and beauty shredding any synchronized movement. It was an enlightening, if somewhat depressing, experience

I never dated anyone in high school, nor did most of my classmates. The one-off hookup—think microwavable TV dinners—is the new trend. My business activities didn't seem to help my romantic life; if anything, I think they contributed to a sense of intimidation (or as one female friend put it, "Ben's impenetrable outer shell").

I focused instead on building strong relationships with my guy friends by being clear in my own mind about how I would agree or disagree with them on issues such as drinking and drugs, two common activities in high school. Instead of denying a drinking-and-drugs reality that I found a little unpleasant, I staked out new ground on which we could base our relationships. Most of my close friends played with me on the basketball team, a commitment that forced us to spend a lot of time together, revealing common intellectual interests, shared humor, and a general spirit of happiness about the world—and even some lightweight partying on the weekends. Whereas during freshman year my Comcate schedule raged uncontrollably, by sophomore year I owned more hours and tried to redirect them to building friendships with my age-similar peers at school. I wasn't totally successful. Maybe this is a good thing, since, as you may have already guessed, I found high school social life “broke” on several levels and, as Indian spiritualist Jiddu Krishnamurti once said, "It is no measure of good health to be well-adjusted to a profoundly sick society.". This doesn't mean I did not form wonderful friendships – I did, and I thrive off our fellowship.

My sojourn into adolescent social life also taught me what my "personal life" needs are. And this, in my experience, is an important realization that all work-driven entrepreneur types need to have: instead of simply defaulting to bars and drinking buddies on one extreme, or the socialite life of the opera on the other extreme, figure out what activities and people allow you to recharge and enjoy yourself.

In his landmark book The Presentation of Self in Everyday Life, University of Chicago sociologist Erving Goffman uses the metaphor of a theatrical performance to argue that each person in everyday social interactions presents himself or herself in a calculated fashion, working to control the impressions of others like an actor who presents a character to an audience. We employ different "masks" depending on the situation; indeed, our behavior in social situations, Goffman argues, is largely dependent on who's around.

Throughout my sophomore year I experimented with different masks. In business with adults, the appropriate mask seemed close to my instinctual self. I would layer my vocabulary and appearance with professionalism, politeness, and intensity. In school with teenagers, the appropriate mask—if I wanted to be engaged, friendly, social—was different. Not professionalism, slickness. Not "I look forward to picking you up tomorrow morning," but "I'll swoop you tomorrow A.M." Being "chill" trumped all. The prop change wasn't a simple swap. The teen setting required the same category of skills, only of different gradations. Pick the wrong shade and your voice cracked. You're supposed to be polite to teachers and peers, yet too polite and you're side-brushed as a suck-up, a pushover, a brown-noser. You're supposed to be funny, except when you become too obnoxious. You're supposed to be academic and get straight A's but also be “ghetto” and loose. You're supposed to treat girls as equals and not objectify them as sex objects, but also confirm your own heterosexuality through silent catcalls at someone who just walked by. There's even another teen mask for those weekend drinking parties, where you're supposed to morph into a wild-and-crazy drunk dude after just a few sips.

Every high schooler wades through these unforgiving waters, kicking fervently to find a balance among all this sociological nuance. But most high schoolers are also placed in the right sea at the outset; they just need to figure out how to swim north. For me, though, it took effort to even find the sea. How do I reimmerse myself in the highly self-conscious environment of a high school cafeteria after finishing a conference call with a client on the cell phone outside? On the conference call, or in any business meeting, professional and personal aren't mixed. It's a one-dimensional interaction predicated first and foremost on the exchange of ideas rather than personal appearance, social plans, or dating history.

What resulted from my hourly negotiations between these two very different realities? Well, I wrestled on the right mask for school about half the time. When I screwed up—when my nomenclature didn't match the social situation, when someone would spot me on a cell phone, when I would try to at once indulge and analyze weekend hedonism, when I would be pecking away at my BlackBerry in a class—my school friends just ignored me. They never asked about any business meetings. I liked it this way. They liked it this way. I'm lucky. Because until I could pull off the balancing act fluidly and successfully in each dimension, it was nice for us all—me, my school friends, and adult business colleagues—to believe in the illusion that I was just one of them. Looking back, I’m not entirely sure which one of them I really was.