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Working For Yourself: One Year

“He hadn’t pushed through that one last barrier, his fear of succeeding, beyond which the world lay totally open to him.” —Chad Harbach, The Art of Fielding

This year has been hard. There. I said it. As I’ve been trying to wrap my head around the fact that I’ve been working for myself all year, as I’ve gone back and read each monthly post I’ve written about self-employment, the only honest thing I can say is that this year has been staggeringly difficult. It’s also been by turns magnificent, surprising, and joyful. It’s clearly been life-changing. It has been actually awesome, full of awe.

But I think the two defining words for this year are success and terror.

I went through large parts of my twenties consumed with worry that I wouldn’t make something of myself, that I wouldn’t live up to my own internal standard of success. I have something inside me, wound up like a spring, that won’t let me stop until I’m creating something and putting it out into the world. In my early twenties, when I was one of three partners in a theatre company, I had that moment of feeling like everything clicked. I was running a creative business, producing shows, doing something that I thought mattered. The only problem was that running a small theatre company in New York City is virtually financially unsustainable. So when that project ended, I spent years feeling around in the dark, trying to figure out what else would work for me, scared out of my mind that I wouldn’t find something and that my time would run out. And the simple reason I got to where I am now is that I could not rest until I’d gotten to that place where things clicked again. I’m profoundly lucky that for me, unlike so many creatives, that drive was constructive not destructive. For me, that drive was paired with an entrepreneurial drive, the skills to hustle, the desire to create a business structure that could support and sell my work. So I’m running a business, not drinking myself to death in a corner somewhere, and I’m acutely aware of what a blessing that is.

After that period, I thought things could not get more scary than the constant gnawing fear that I was not doing what I was made to do. Sadly, this assumption was false. I was absent the day that the “nothing is more terrifying than success” memo got passed out. Or maybe that memo never got distributed because no one wanted to be the asshole that said, “I got what I wanted, and it’s scary as shit.” So, f*ck it. I’m going to come out and say it because I would have felt a hell of a lot less alone this year, had I known.

Let’s start here: It turns out that success looks totally different than it feels. Success looks like everything magically coming together for another human, who (when it’s happening to anyone other than me) I immediately imbue with slight magical powers. This is happening for them and not for me because they are half-human half-magic. Duh! Logic! The thing is this is not, strictly speaking, true. From the inside, success feels like being in the center of a hurricane that you are both in charge of and is threatening to pull you apart.

This year at least, I found that things did not happen to me, as much as I made things happen. And then managed the things happening. And then followed up on the things happening. Success didn’t happen to me, nor did my year feel like it was about success, except in retrospect. Instead, I woke up almost every morning feeling terrified because I was going to push myself as hard as I could and as far as I could. I was going to push myself to the point where I felt comfortable, and then push myself way beyond that point. I was going to do that over and over and over, all year long.

By the end of the year, I was going to learn a lot about my own personal terror cycle:

  • Set a really ambitious seeming goal
  • Say, “Oh yeah, I can totally do that.”
  • Start working on it
  • Panic
  • Have something go wrong
  • Possibly have an actual panic attack
  • Keep working
  • Have the thing happen imperfectly but wonderfully
  • Slowly feel panic recede
  • Surf a wave of joy

…Over and over and over. By the end of the year, this cycle would start playing out in hyperspeed. Because the strange thing about success is that it pushes you up against your own limits faster than you thought humanly possible. I spent this year worrying about turnout for each individual event that APW threw. And now I’m facing down a whole book tour worth of events. And interviews. And new experiences. In very rapid succession. And I’ve learned that the only way through… is through. So I just push through work, panic, work, more panic, event, joy, as fast as I can. Over and over again.

Success is some of the most terrifying shit I’ve ever experienced. And I never saw it coming.

When I look back at my writing in entrepreneurship this year, some themes emerge: Showing up every day no matter how you feel. Doing the work without worrying if it’s good or bad. The importance of building my work life around the core of my creative craft. Pushing through the fear over and over again. The fact that it’s been hard (surprisingly hard). Letting Go. Joy. Here are some of the best bits:

From month oneI’m glad that I was trained with the idea that you show up Every Single Day (we were only allowed three absences in studio per semester), no matter how sh*tty or uncreative you were feeling, and you do the work. You do the work when what you’re doing sucks, you do the work when what you are doing seems brilliant, you do the work when you’d rather be in bed. And thank God, because that takes some serious pressure off. You just have to show up and work, not show up and do brilliant work. So every day these days, I show up.

On finishing the bookAfter I finished the first half, people would ask what I thought about the book, and I’d look into the middle distance and wave my arm around and say, “It’s not shitty.” And then I’d pause and say, “I really don’t have any perspective.”

From month sixFor years, when I got a piece of disappointing business news, I allowed myself to feel crushed. “Can APW make it?” I’d ask David, “Is it all falling apart?” And erm, I don’t claim to have totally retired those questions from my repertoire. But I have learned that when you build a business, it has a whole lot of moving pieces. If you spend too much energy on the one part that isn’t working well, you end up wasting your time (and feeling sad for no reason). Better to focus on what is going well and realize that the train is going to keep on moving, so you might as well be on it.

From month sevenI felt like I was failing, over and over again. My mantra on those days was “Fail forward.” And I kept reminding myself that the only way I know to be successful is to fail, over and over again, and learn from it. On a particularly rough morning, Lisa of Privilege reassured me, “If you aren’t failing here and there you are certainly leaving money on the table somewhere else.” And I realized, yes. We fail when we want to test the boundaries of what we know how to do well, and that’s how we grow.

From month eight: I spent all of last year focused on building APW so I could quit my job. Every single morning, I would hop over the cable car tracks in my high heels, running to my job as a (fancy) secretary—a job I’d taken just so I could fully get APW off the ground. And every single morning as I did that, I’d say a little prayer, “Please, let me sell the book. Please, let me work for myself. Please, let this be worth it.” And then it happened. But this year has been such a whirl of adjustment that it’s been hard to focus on the fact that I finally got what I wanted. I figured out how to write a book… and wrote a book; I got an office, I gave up an office; I figured out accounting, I fell behind on accounting; I got a staff, I realized I had to learn how to be a boss. It’s been really complicated. And in the midst of that complication, I kept looking back on myself last year and saying, “I got it. Now I’m going to try really hard to enjoy it fully.” But it’s been hard. Complicated.

From month elevenYou can’t succeed without being willing to fail with full force. You can’t figure out how far you can go, until you push yourself so far that you risk completely falling on your face. And seriously? This never stops sucking, don’t kid yourself.

So now year one is over, and I’m on to year number two. A year ago I was full of questions: Would it work out? Would I thrive working for myself, or would there not be enough structure? Now, most of those questions are gone (though of course there are new questions in their place). I don’t spend a lot of my time worrying about what-ifs these days. Instead I focus on trying to do the best job I can for the company I built, day by day.

Which brings be back to the idea of working for myself. It’s perfect that this series is winding to a close, because I no longer feel like I’m self-employed. These days, I feel like I’m running a small company. Which, technically, I am. We incorporated last fall, and I’m now CEO of Practical Media, Inc., with a staff that I’m overwhelmingly grateful for every single day.

Which is how it should be. We keep changing, and we keep pushing through the fear. Beyond that barrier, the world is totally open to us.

Life gets better, but it sure as hell doesn’t get easier. Which is how it should be.

Photos: At home on New Years Day, Personal for A Practical Wedding

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