The Biggest Danger of Running Your Own Business That They Don’t Tell You:

The Biggest Danger of Running Your Own Business That They Don’t Tell You:

Keeping Up With the Startup Crowd

Trying to run with the in-crowd in a new economy.

IMAGE: Getty Images

By Meredith Fineman / Founder, FinePoint


I remember standing in the middle of the airport, totally screwed. I missed my flight, and not even by ten minutes. I missed it by three hours. I wasn’t paying attention, I was at a conference, networking and “living it up”. I had bought some pairs of shoes, made some new connections, had promising 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 DC for the next three days on the airline I was supposed to be flying on was booked. I had checked out of my hotel. I was already at the airport, standing there, blindsided as people hurried to check in or looking varying degrees of despondent, as one does 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, where I would then find out I missed the last train to DC. 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 about to drop out when you’re afraid to 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, loudly. (Or that he would then try to hit on you three years later at a party, not making the connection.) The thing they don’t tell you – or that I bought into and struggle with – was trying to keep up with what I’ve dubbed the “Startup Joneses”. You know who I’m talking about too – 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 – the trio of passport, a book (related to running your business), and coffee. Who wouldn’t want that? 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 now, a bunch of trips, wanting to be seen in the startup scene, coalesced into rotten finances. The missed flight was after attending 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 is entirely self-funded. I don’t have investors, I didn’t start with a nest egg. But I was convinced I wanted to keep up in the way that I felt I had to. And it was mostly based on appearance.

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 it. Major plotlines in movies now involve sexy startups (five years ago the plot of The Intern, with a young women running an e-commerce startup in Brooklyn, for example, wouldn’t make any sense). Not to mention, our lives are now consumed by this strange work as play and play as work line-blurring. There is also tons of writing, entire verticals even, to glorifying failure, glorifying success, mocking the startup world, or “entrepreneur porn” – endless listicles about productivity.

There’s another less overt danger. It’s the constant pressure when you work for yourself or have created something that you pulled out of the sky to avoid getting another job (my own situation) to be “killing it”. That has been covered extensively — whether or not to convey your own 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 a very specific kind of “killing it” which is being “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’s not what I was concerned about. 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 turn someone I knew was on a plane or a train or a jet, instagramming their way through yet another entrepreneurial victory. It’s not enough to be successful now, but 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 calculated sharing to put me in the best light, literally.

I wrote a few years ago about comparing yourself to others, and it is one of the most popular things I’ve ever written. But there’s an addendum to that, which is that you (I) need to stop comparing yourself to the Sexy Entrepreneur, specifically. 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 go to a certain conference or attend a trip you can’t afford, that’s okay. I thought by being in certain rooms I would finally be the woman I wanted to be. To get to 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.


March 28, 2016 / by / in , , , ,

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