I remember standing in the middle of the airport, totally screwed. I had missed my flight, and not by 10 minutes but by three hours. I hadn't been paying attention. I had been at a conference, networking and living it up: buying some pairs of shoes, making some new connections, getting potential clients for my company. I didn't think about my travel, because I was a Sexy Young Entrepreneur. Or at least I was trying to be.
Every flight to D.C. for the next three days on the airline I was supposed to be flying on was booked. Standing there, blindsided as people hurried to check in, some looking various degrees of despondent, as you do while traveling, I did a not Sexy Young Entrepreneur thing. I sat in the middle of the floor and cried. Snot-laden, I walked up to a ticket counter and bought the first ticket available to the East Coast. It wasn't even Washington. It was New York City, where I would then find out I had missed the last train to D.C. It was a comedy of errors, or just an expensive, expensive pain in the ass.
Here's the thing they don't tell you about running your own business. Well, there are many, many things they don't tell you: how your stomach will feel when you're afraid you can't pay your rent, or how you'll feel when a client tells you you're bad at your job and you have to hold the phone away from your face because he's yelling. (Or that he would then try to hit on you three years later at a party.) Another thing they don't tell you--that I bought into and struggle with--is what it's like to try to keep up with what I've dubbed the "Startup Joneses." You know who I'm talking about: the ones on a private plane; the ones Instagramming, with bright light filters, beautiful apartments or hotel rooms; the ones smiling from rooftops with their teams, or on the runway--the exact image comes to mind--with the trio of passport, a book (related to running their business), and coffee. Who wouldn't want this? Or try to portray it?
Sobbing on the floor of an airport in 2013 was not when I realized how badly I wanted to keep up with the Startup Joneses. But now I know that taking a bunch of trips, to be seen in the startup scene, coalesced into rotten finances. The missed flight was after attending a conference I probably shouldn't have, spending a bunch of money I couldn't really, not paying attention to the ins and outs of my self-funded company to be in circles that I thought would get me farther. Don't get me wrong, I've worked hard to get to the point I have, be a part of the communities I'm in. I'd consider myself pretty successful. But I fell hard for a lifestyle. My company does not have investors. I didn't start with a nest egg. But at one point, I was convinced I had to keep up in a way that was based mostly on appearances.
When I started my company in 2010, there were only inklings of running your own business as the new normal. Now it's the constant calling card. Everyone is some sort of entrepreneur, and he or she definitely has an app. You can't turn away from this. Plot lines in movies now involve sexy startups (five years ago, the plot of The Intern, in which a young women runs an e-commerce startup in Brooklyn, wouldn't have made any sense). Not to mention, our lives are now consumed by this strange work-as-play and play-as-work line blurring. Tons of writing, entire verticals even, glorify failure, glorify success, mock the startup world, or provide "entrepreneur porn"--listicles about productivity.
There's another, less overt, danger. It's the constant pressure when you work for yourself, or have pulled something out of the sky to avoid working for someone else (my own situation), to be "killing it." In one sense, this has been covered extensively: whether to convey your vulnerability outside of a system, outside of an infrastructure. It's lonely as hell, and we know about that too. But what I'm talking about is the kind of "killing it" in which you are "everywhere": attending all the conferences and dinners and trips. It's about looking and seeming and portraying that you are successful, that you have already succeeded. Panel shots, conference tags, dinner place settings, exclusive gatherings.
You're forced to keep the lights on, sure, but that wasn't my concern. I wanted to be in the right places, wearing the right clothes, at the right conferences. It's expensive to be a fancy feminist. It's time-consuming. It can be all-consuming. And I felt like everyone was doing it better than I was. At every turn, someone I knew was on a plane or a train or a jet, Instagramming his or her way through yet another entrepreneurial victory. It's not enough to be successful now--there's the pressure to look sexy doing it. It's hard to watch, and even harder to turn away from. With glimpses into worlds like those on Snapchat, it can feel like there is even more to keep up with. I admit to editing my photos and to calculated sharing to put me in the best light, literally.
A few years ago, I wrote a piece about comparing yourself with others, and it is one of the most popular things I've ever written. But there's an addendum to that, which is: You (I) need to stop comparing yourself with the Sexy Entrepreneur. I tried to be her. The thing is, she's a figment of everyone's imagination. She's a figment of mine. There will always be someone doing it better than you, in cooler shoes, in a more exotic locale. There will always be someone with more money than you to spend or invest, and that is a hard thing to accept. If you don't attend a certain conference or go on a trip you can't afford, that's OK. I thought by being in certain rooms, I would finally be the woman I wanted to be. To get where I'm going, it doesn't require a sun-soaked picture of my passport. It doesn't require any money, either. I have to build her myself.