"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: Continue reading Working For Yourself: One Year








































































