As Long As I’ve Got My Suit and Tie, I’m Going to Leave It Out On The Floor Tonight

I’ve never been very good at dressing up. My roots are in technical tinkering and the creative arts, with a healthy dose of New England punk rock (and think New Hampshire, not New York), so maintaining appearances was never interesting or natural to me. As a kid, I agonized over even basic, semi-formal requirements for things like school dances, performances, or graduations — never mind things like weddings.

This remained fine as I grew up, primarily because I went into tech instead of my other potential destination, journalism (or, God forbid, law). I interned as a clueless D.C. journalist in the fall of 2002 and enjoyed a lot of what I got to do, but still found myself jealous of the CSPAN cameramen who got to play with cooler equipment and dress like AV guys while I poked at the itchy collar on my shirt and my uncomfortable shoes. So when I started my career at a mid-stage Boston tech startup in 2004 and discovered that they cared a lot more about how fast I could format press releases and assuage customer concerns over the phone than whether I could tie a tie, I knew I had a path.

From then on, nothing brought me any closer to formalwear. Support, technical writing, product management, and eventually product marketing required me to be increasingly strategic, but not sartorially impressive, especially since I worked for bosses who understood my value and trusted my ideas and execution skills, but usually handled dealing with customers and company brass themselves.

As a result of all this, when I found myself running FiscalNote’s marketing team this fall, I suddenly found myself in the unexpected position of representing our company and our function at an executive level — even if somewhat by default. While in the past I had never felt any real internal pressure to figure out how to fit in with the suit and tie crowd, this seemed different. My company had given me a chance to step up into a role even I wouldn’t have thought myself capable of just a few years ago; why shouldn’t I at least try to meet those expectations on every possible front? Customer events, board meetings, etc. — these were important things I was being given an opportunity to attend, influence, and make as successful as possible.

Basically, while I still loved the idea of not wearing a suit (or anything other than Boston sports-franchise related t-shirt, to be honest), actively refusing to didn’t resonate with me the way it used to. That kind of line in the sand just didn’t feel like a part of my identity anymore, and I felt worse about the idea of letting my colleagues down (even just a little) than I did about wearing silly clothes.

Man, did that ever make me feel old.

this suit is black not

So I bought a suit. It wasn’t fancy, but it wasn’t cheap, either — the nice people at the nice store in the nice mall I usually don’t go to tailored it and told me it looked great and had me try on different jackets and stuff. My wife was very helpful, and didn’t laugh at me too much.

I went home, put on my suit, and went to work. Here’s what I learned about the dressed-up version of myself.

  • Clothes aren’t magic. Instead of feeling like a badass captain of industry, I felt self-conscious and stupid most of the day. Worst of all, I felt inauthentic, which I think is an even bigger hang-up for me than it is for most people.
  • I thought about my clothes a lot, which is not a great frame of mind to be in when you need to get work done. There are just a lot of things you can do wrong with formal clothes that people who wear them all the time naturally avoid, and I probably did them all several times.
  • Eating, drinking, sitting, leaning against things, bathroom breaks — pretty much everything is risky behavior when you’re walking around in what are basically pajamas made out of money, and that didn’t make me any more comfortable with my environment.
  • If you’re the kind of person who doesn’t wear formal clothing, and you’re suddenly thrust into an environment where everyone there is dressed up, there’s really no way to succeed when your goal is to fit in and not be a distraction. If you don’t dress up, you’ll make a scene. If you do, people will notice, and you’ll make a scene. (“Whoaaaa, look at this guy!!!”) Hopefully this gets better with time.
  • I’m pretty sure that my problem with most real-time interactions is my preference for honesty and candor. I’m certainly not rude, or inappropriate — I just have trouble naturally interacting with other folks with the right professional safeties on, so rather than say something stupid, I prefer not to say much at all. I don’t hate small talk so much as I’m actively bad at it. I’m not disinterested in you as a person, I’m disinterested in the stupid, safe topic we’re inexplicably discussing, but since many people are uncomfortable having honest conversations with people they’ve just met (myself included), that’s what we’re going to talk about.

In short, my trouble with suits doesn’t really have anything to do with work, or business — I’m actually pretty good at that stuff. The trouble I have is with many of our oldest, most irrational social traditions, and that’s been a problem that’s dogged me since I was a little kid. I literally just don’t understand ties, just like I literally don’t understand how to feign more interest in another person’s story than I actually have, or how to impress a girl in front of a keg in a frat house where I can barely hear what anyone is saying.

(That last one hasn’t been important in about 15 years, so at least I’m making progress.)

“That’s just how things work” has always been the exasperated response from my well-intentioned, more socially flexible friends and colleagues, and I’ve always grudgingly accepted it and never insisted or expected that anyone else think the way I do. The funny thing, though, is that when I am actually praised for my thinking, it’s almost always for clearly and accurately modeling a complex situation into something real and approachable. And yet many people are often surprised by the fact that this same person would struggle to integrate irrational, distracting bullshit into their natural behavior.

Suits and ties don’t make any more sense than skinny jeans, or those crazy things that make you have giant earlobes, or the safety pins on leather jackets kids at our shows used to wear. And while I understand that our society uses them to convey a complex series of social indicators (suits indicate business acumen and wisdom, or at least the possibility of wisdom, now hoodies sort of mean tech, etc., etc.), I’d be lying if I didn’t admit that I still think it’d be a lot more efficient if everyone was just honest with each other and evaluated what we all said and did on the merits.

The fact that I’m old and realistic enough at 35 to realize people aren’t going to do this doesn’t make it any less true, or any less the way my brain works. But I’d like to think being able to work around that is just another thing I’ve been able to improve about myself.