At my job, we are sporadically required to attend these fancy, high-end functions. Do not get me wrong. We are not suits. (No! Really!) On a daily basis, I throw on my headphones, crank Faith No More, drink Diet Coke straight out of the bottle and, when the feeling strikes me, occasionally wear a shirt. We have a small staff, and even though we don’t drink in the office like my old Web startup, it’s a fairly informal place. But we do sometimes host these functions, and since our target audience is rather upscale, we are obligated to dress up for them.

The other day, we had this breakfast at the storied Harvard Club in midtown Manhattan. Now, I’ll forsake any jokes about what a University of Illinois club would be like — OK, I’ll make a couple; there’d be a keg in the middle of the banquet hall with half-empty Dixie cups scattered about, we’d all be wearing cutoff jean shorts and inevitably one of our members would be in the corner embracing a nitrous tank — and simply point out that this place is nice. Paintings of storied alumni surrounding the table, waiters and busboys wearing tuxes and a coat-check room that’s both the size of my parents’ home and has a better kitchen. We all had to be there at 7:30 decked out in our finest suits and ready to promote our startup magazine to an audience that, when it’s freezing outside, tosses a couple logs of hundred-dollar bills on the fire to keep warm.

I sat down at an end table, looking as sharp as a guy in a suit that his uncles were going to throw away anyway possibly can, and delicately placed a cloth napkin — a napkin that’s made of cloth! Seriously! No joke! — over my lap. To my left was one of those middle-aged white men whose toupee probably cost more than my winter wardrobe, and he started asking me about our magazine. He looked me dead in the eye, like he respected me, like he thought I belonged.

I won’t lie; it was awesome. After months of unemployment and scraping together pennies just so I could catch a subway downtown, here I was, in the freaking Harvard Club, wearing a suit, talking about the venture capital industry, and the storage infrastructure sector, and business plans, and the future of our long-term fiscal securities. I made a pithy little Inside Venture Capital joke, we shared a hearty chuckle and he patted me on the back with a mixture of respect and knowingness. All I was missing was a copy of Crain’s Business Journal in my leather briefcase, a tasteful handkerchief positioned strategically in my breast pocket and a cigar dipped in Cognac. Dammit … I did belong!

I then felt a tap on my shoulder. It was my boss. “Hey, listen Will … I think we overbooked this thing. We don’t have enough chairs. We, uh, need you to give up your seat.” Some other middle-aged white guy loomed behind him ominously. I sighed, buttoned my jacket, excused myself and went out to the hallway, hands in pockets, swaying aimlessly, looking around, whistling silently to myself.

The transition from devil-may-care free spirit to proud, upstanding member of the capitalist community our culture revolves around, with 401k plans, two-car garages and matching linens is not something that is coming all that easily to me, and I think maybe I should stop trying. My idea of a schnazzy wardrobe, in the past, has been a pair of khakis with no visible stains and a T-shirt without a sports team logo on it. With the assistance of a now-ex-girlfriend — like you hadn’t figured that out already — I tried to look nicer, even spending a solid two hours in this H&M store that’s apparently popular. I would try on clothes, I would see if this matched this, I even started putting this goopy crap in my hair. I tried. For a while there, I was even starting to look kind of nice, like one of those people who knows where all the sample sales are and can tell you whether or not it’s acceptable to wear light green turtlenecks with dark black pants. I even attempted putting on cologne, no small feat for a guy with no sense of smell.

But I was only fooling myself, striving to be something I wasn’t. When I visited St. Louis for an old friend’s wedding, she remarked that I looked downright sharp in my tight-skin Banana Republic shirt and DKNY jeans. Then she paused. “You look like you’re dressed up like somebody else.”

Looking and acting and feeling like a grownup is such a difficult endeavor, requiring focus, discipline and restraint that would test the patience of monks, that it’s a wonder anyone even bothers. We all sit in meetings with colleagues, and we go to parties where there are people we don’t know, and we make polite small talk with various acquaintances in order to put across a positive, secure, wholly sane image … and I’m not sure any of us believe a moment of it. We’re all crazy and insecure and happy and sad and laughing and crying, and we spend most of our time trying to hide those very things, the parts that make us human. It seems that there’s rarely a moment where we simply be; we’re too busy trying to impress everyone all the time.

I’m reminded of when I was laid off from Brill’s Content. It hadn’t been announced by the higher-ups, but everybody knew it was going to happen, including me. Half the staff was out at a bar, and I happened into a conversation with my boss. She knew it. I knew it. So I just told her. I said it was OK, that she was going to have to cut me loose, that I knew it wasn’t her fault, that we were just simple human beings thrust into these managerial/employee roles by society and circumstance, that we should merely talk to each other as people, that I didn’t hold it against her, how could I? She looked at me like I’d beamed in from Neptune. The frank discussion had upset her notions of middle management and proper employee relations, and as far as I was concerned, I was this crazed Guevera-esque revolutionary who didn’t know his proper place in the capitalist food chain.

After all this employment strife and a girlfriend who would rather not date a guy who wore shoes with holes in them, I decided it was time to change. I tried to become a grownup. I studied Esquire pages about How a Man Should Dress, I learned how to tie a tie and I started talking about the weather and other banal, boring topics that always go over in non-threatening, conventional way in crowds. Working in public relations or studying the stock market started seeming like legitimate, honorable ways to live my life. Shit, I even stopped hitting on women I worked with, because that’s wrong, that’s not the way it works, bad bad bad. I wanted to play ball. There is a point where you’re just too old to be the wacky, goofy, let’s-PLAY-everybody! guy. I thought I’d reached that point.

And, I’m realizing, that point is a delusion. I think I might, for once, actually be right. I yam who I yam. I think we’re all just stupid people who have absolutely no idea what we’re doing, scrambling around, trying to move from one point to another while causing as little damage to ourselves or others as possible, hoping our illusion earns the respect and affection we all desperately need. Some of us are better at hiding this than others. Some, like me, aren’t. When you start believing you have to put up this facade to people, that there’s this act you have to put across, well, in my experience, you end up sitting alone in the hallway while someone bigger, and smarter, and richer, and better at playing the game than you are … they’re sitting in your chair.

I’m beginning to realize my place in this world, which is to say, I don’t really have one. When I go to parties, I will continue to make a spectacle of myself, calling people “sir” and “ma’am,” bowing incessantly, making silly jokes for a cheap laugh, ignoring the regular protocol of such matters, doing what I do. That is who I am. I am not a guy who wears snappy suits, or tasteful turtlenecks, or appropriately tucked scarves. I’m just a dude out there, trying to be happy, hoping others are happy, crossing my fingers that I don’t step on anybody’s toes while I’m shambling about with no real guiding force by myself. Dammit, I am not a venture capitalist, and I never will be, and that’s just fine with me. No need to pretend anymore.

Unless of course you’re a hot girl I run into at a party. In that case, I’m whatever you want me to be, baby.

*BT*

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