Marlon Brando, freelance writer.

IMAGE VIA: Gatopoder

I had an interesting experience two nights ago that I’ve been debating telling you guys about. I’ve started this blog post many times in my head, but each time it’s stalled out, which very well may happen here. I guess we’ll just see.

So, I’m about two weeks into freelancing, right? And it’s COOL. But SCARY. For someone like me, I mean. Someone used to deadlines and structure and all that. I don’t want to make the 9-to-5ers jealous here by saying I wake up in my jammies, pad around the house with coffee until 8 or 9, and then eventually think about firing up the computer, but I do wake up in my jammies, pad around the house with coffee until 8 or 9, and then eventually think about firing up the computer.

As any freelancer can tell you, there’s an extremely fine line between feeling triumphantly independent and lumpishly unemployed, and I think the key is not wearing sweatpants. I’m serious.

But when I wrote that post a month ago, the one about quitting my job, a kind woman named Gabi Garcia got in touch with me. Would I like some life coaching? She asked. Yes. Yes, I think I would, I said. (And see this is why I’ve been debating about writing this, because “life coach” just has so many self-helpy trappings that I feel silly writing it.)

Anyway, if there was ever a time for a life coach, I figured now would be it: I am stumbling into new career ventures, and need…goals. Structure! Someone to dress up for so I don’t stay in sweatpants. “Gabi, you’re the girl for me,” I wrote. And it’s true, she was. But I didn’t realize how much so just yet.

So I showed up to Gabi’s late for my appointment on Tuesday, in a tizzy because I hadn’t finished the day’s writing deadlines. “HI!!” I cried when she answered the door. “Oh my gosh, WHAT a cute PLACE!! Seriously! This is like Dwell Magazine! Would I like tea? YES I WOULD LIKE TEA! Tea is my favorite! Peppermint? Sure!!!”

This is what happens whenever I meet a new person, and especially a new person under the pretense of me being late for a meeting. I tap dance for them, trying very hard to win them over in a matter of seconds. Maybe it comes off as charming, but more likely, slightly manic.

“So, Tolly,” said Gabi, calmly. “One of the things we’re going to talk about in your coaching is the concept of the Inner Critic. Do you know what that is?”

This is where things got interesting.

Gabi is a trained psychotherapist, you see, and while that’s not necessarily a part of her coaching practice, I could tell that she saw through my bullshit — the “like me! Like me!” dance I did at the front door — and the Inner Critic thing got to me. I started crying because, subconsciously, I guess things were not going according to plan. I had intended on meeting Gabi, becoming momentary BFF’s, setting some career goals, and swooping out.

“What is that bringing up?” she asked, offering me some tissues.

I didn’t have an answer, really. She asked where I felt the emotion in my body.

“My…throat?” I said.

 “Mhmm,” said Gabi, “and how about your energy? Has anything…shifted?”

As my friend Sarah would say, I’ve got a whole roster of witch doctors, and “energy shifts” — as opposed to Western doctory jargon like “symptoms” — is my kinda language. Maybe I’ve just been living in Austin too long. Or maybe that stuff actually does make more sense to me. At any rate, I told her that I did feel calmer, like a dam had broken or something.

We talked for a while, and I told her honestly how I felt about freelancing. That I’ve got these two distinct entrepreneurial dreams in my head for my future, but for the time being, I’m just so nervous and scared and paranoid about money that it’s hard to remember my dreams sometimes. “Even though money is fine!” I told her. “I’ve got plenty of clients so I don’t know why I freak out constantly!”

Gabi reminded me that our human brains are wired to keep us safe, and safety usually means status quo. Upheaval — particularly upheaval of our own design — is cause for alarm, because our brains are like, “what the f-k? Why? Why are you changing?” In other words, growth is scary.

So I left Gabi’s house, a little mascara runny, but intact enough to go to a cocktail tasting with Amy. Then, I proceeded to get very drunk.

Have you ever had one of those times where you’re sipping a cocktail, and you’re feeling classy, and at some point a small, quiet chorus of brain cells says, “based on our calculations, the amount of sips you’ve had equals a 100% chance of insobriety!” Which you ignore. And you keep on sipping because, after all, you feel great! Your brain doesn’t know what it’s talking about.

YOU: Mmmmm rum. So gooooood.

YOUR BRAIN: Hey, stop! You’re getting sloppy!

YOU: Shh. No more talky.

YOUR BRAIN: No, really! C’mon help me out here! You’re being a moron!

YOU: YER the…moron..

YOUR BRAIN: Ok ok, I know usually I’m the crazy one, and you’re the sensible one, but right now we are reversing roles and I am asking you to get it together! Drink some water!

YOU: You jus need to settle down.

YOUR BRAIN: I am settled! I am your voice of reason!

YOU: But u talk too LOUD. Here I know.

YOUR BRAIN: Wait, what? Are you —

YOU: Drinkie time!

YOUR BRAIN: NOooo! (drowning gurgled sounds)

It was like that.

I really don’t drink that often, but I think I was still kind of processing everything from Gabi’s house. When I got home that night, I fell asleep for a little while, then woke up at 3am. Does alcohol do that to you, too? I find this is almost impossible to fight, alcohol insomnia. So I got up, went to the kitchen, nibbled on some crackers, then journaled for two hours with the absolute clearest mind I have ever had. (Take that, brain.)

Here are three things I wrote down that may be helpful for any of you who have recently gone freelance, or are considering it:

A) FIGHT THE URGE TO FIT IN. One of the things Gabi and I talked about during our session was a Brene Brown concept, of “fitting in” versus “belonging.” As I journaled, I thought about that — how much I am constantly trying to fit in, in whatever job or social situation I encounter, and how it really does work in the short term. If you can assess what a group or community’s behavior rules are in a matter of moments, and tweak your own behavior accordingly, then bam — acceptance.

But you screw yourself in the long run, because eventually you get tired of being everything other people want you to be, and it’s a lot less work just to be yourself. In freelance work, you’re constantly encountering new clients and new companies — but don’t feel like you have to instantly integrate into their culture. You’re you. They’re them. Maybe one day those two things will meld. But they don’t have to instantly, and this is really hard for people-pleasers. If you keep on trying to fit in though, your core gets all mushy and you don’t know who you are anymore.

B) PRESENCE = BELONGING. For anyone trying to build a “brand,” be it a food trailer or a blog or a yoga business or whatever, your goal isn’t to fit seamlessly into a larger professional culture. It’s to stand out. To belong, because you contribute something unique and different to the culture. You’re not like every other food trailer. You sell beer popsicles. Or whatever.

How do you belong? By cultivating presence. By being present, you’re aware of all the weird little ideas that pop into your mind, and you can catch them as they bubble up to the surface. Those are what make your brand unique. But if you’re worrying about your competition all the time, or worse, worrying about playing it cool and fitting right in, you can’t be present. You’re preoccupied.

C) BELONGING INVOLVES SCREWING UP. SOMETIMES PUBLICLY. Because the willingness to fail in front of your community also means that you trust your community. And people respond to trust.

I’m not saying you have to contrive situations where you fall on your face, just to endear yourself to people. But when I look back on my life and think about the two areas where I felt most at home, most like myself, they were both places where I wasn’t a perfect, shining star all the time: Aerial silks, and working at a magazine in California. I have horrified people on silks before. I got chewed out working at that magazine. But I don’t think any activity has ever fulfilled me as much or made my heart burst.

When you’re a freelancer, or entrepreneur, or just thinking about leaving your full-time job, it’s a cliche that failure breeds success. But more and more, I’m finding that the cliche is true. I can think of places where I fit in — grad school, for example. I got great grades. But I didn’t feel like “me.” I was just acting the part, and I didn’t belong. I know folks who did belong though, because they took risks, and wrote weird papers, and taught truly questionable material in their undergraduate classes, and now they are successful professors.


I don’t know how many of you work for yourself, or if you’re even thinking about it. Some folks work for a company and that is GREAT. They believe in that company, they have benefits, their work days are fulfilling, and life is good.

But. If you do make the leap. I’m here to tell you that I think this fear is normal.

(And cheers to that.)