I took my legal practice full-time in April. Almost every day since, somebody has asked me how I like running my own business. My usual response is a very enthusiastic, “Great! I love it and wish I’d been able to do it sooner.”

This is a true response. I have a very healthy number of clients, I love and am excited about the work I’m doing, and I have more ideas for projects I want to tackle than there are hours in the day to tackle them with.

But there is another true answer, one I don’t share. That answer is: “It is flipping terrifying.”

By Jennifer Gergen via Flickr.com

We’ve gone through more of our savings than I thought we would have by this point. There are projects I can’t seem to finish, either out of lack of time, or fear. And I screw up—not getting things back to clients as quickly as I had planned, accidentally double-booking myself, snapping at a peer. Screwing up, even the little things, makes me feel awful and spend a lot of time fretting over how to make sure it never happens again. Or as close to never as I can get.

It was with all of that buzzing in my head that I attended the XOXO fest this past weekend.

I felt stupidly lucky to attend, having heard about it previously from friends and folks I admire. I was prepared for an inspirational weekend getting to talk about creativity and independence. With cool people! And goats!

I was not prepared for my mind to be blown quite the way it was, though.

A number of the speakers articulated points about the fear factors of being a freelancer that I’ve been grasping at (or avoiding) for a long while, but hadn’t managed to make complete sense of. My vague ideas about success and the fear of failure were uncomfortable and made me feel vulnerable, which is likely why I found them so slippery on my own.

Hank Green being helpful.
Photo by me.

And then there it was. On a huge screen, in a charming font, were messages compelling me to ask difficult, intimate questions about my hopes, dreams, anxieties and bad habits.

It could have been an overwhelming experience to be confronted like this. But it wasn’t. I was relieved. Relieved that someone finally said, out loud, in front of a room full of peers and strangers, “This is hard. I’m not always sure of what I’m doing. I work really hard and sometimes I screw up really big. I’m still proud of my work. Some of the things that I make and love are successes; some of the things that I make and love are failures. How I feel about it and how hard I work on it don’t dictate how successful it becomes. Sometimes what I thought was right was wrong, wrong, wrong.”

Earnestness is not enough. – Rachel Binx

On the way home from the closing party, my favorite public radio show, On Being, was broadcasting a conversation with Professor Imani Perry about identity. Someone in the audience asked Professor Perry, with an earnestness that nearly broke my heart, “If you could do something that would magically transform people’s consciousnesses and would help white people be better allies to the African-American community, what would that thing be?”

The Professor gracefully demurred. She reminded the young woman that it is in the process, through the act of doing, that people are transformed. There is no magic wand for such things.

Whether in work or life or spirit, we are all searching for easy-to-follow answers to help us avoid the uncomfortable, difficult parts of living a human life.

Darius Kazemi saying the thing no one likes to hear (but needs to be said).
Photo by me.

We want there to be exact steps we can follow when we ask questions like:

“How can I make money doing what I love?”

“What do I need to do to be an ally to others when I’m a member of the privileged class?”

“What is the secret to success?”

There are no answers to these questions, at least no real apply-them-for-immediate-results answers. There are listicles and self-help books and tweets galore that try to make you feel as if there are answers to these difficult, uncomfortable, I’d-rather-not questions, but those “solutions” are cons that pull you farther from, rather than closer to, your goals.

I think it’s normal to want answers to these questions. I don’t think it is weak or foolish to genuinely, fervently hope that someone, somewhere, can help untangle these wicked knots in an easy decipherable way.

The only way out is through. — Erin McKean

But here’s the thing: To deal with the difficult ugly side of life, you have to engage. You have to do.

And that is terrifying. Doing means that you might screw up. You might not know what you’re doing and make mistakes. Those mistakes might be embarrassing or hurtful.

But without doing, without being willing to try a thing you aren’t quite sure of, you will never uncover the beautiful and great parts of life.

Jonathan Mann has been writing and recording a song a day for the last 2,084 days. He told us his theory about making stuff:

70% of what you’ll do will be OK, 20% of it will suck and 10% of it will be really frickin great. Want more great stuff? Do more.

By Duncan Rawlinson via Flickr.com

The more you do, the more experience you have. And the more experience you have, the greater the likelihood is that you’ll be transformed. That the old inchoate ideas will come together in a useful thesis; that the hard-to-find answers are revealed; that the questions you didn’t know to ask show up and start pushing you on to new things.

People ask me what my goal is for this. The goal is “to work on it.” — Paul Ford

When you start doing, don’t make the goal success or perfection; make the goal doing. And I say this as someone who struggles with perfectionism. (For instance, I’ve reworded that sentence three times because I don’t want to imply that I’m perfect because I know I’m not because just today I messed up at least three different….you get the idea.)

I know how hard it can be to be comfortable with “well, I did it.” Turns out though, that you can’t get anywhere close to success or perfection without “well, I did it.”

Listening to all of these talks over this weekend I realized what it is I’m very specifically scared of. As a person who advises people on how to run their freelance businesses, I’m freaked out by what it would mean about me and my abilities if I struggle to run my own freelance business. I feel like I’m in a position where I’m not allowed to fail; too much is at stake.

And what I also realized is this: if I don’t give myself the room to fail, I most certainly will. I’ll only be able to succeed if I make it OK to screw-up.

If you’re reading this blog, there a few specific things you’re probably trying to do, things that I’m probably trying to help you with. I cannot give you the magic wand to make what you’re attempting easy, but I can give you small things to help you gain experience and push yourself to try more.

So here’s a message to get you started, and then to hopefully keep you going:

You will not negotiate your first contract perfectly. But you’ll do it and you’ll learn something and that will be good.

You will not deal with every client conflict brilliantly. But you’ll do it and you’ll learn something and that will be good.

You will not create the most perfect, beautiful, wonderful thing in the world the first time you try. But you’ll do it and you’ll learn something and that will be good.

Go forth and do.

xoxo,
Katie