Read If You’re Thinking, “I Want to Go Freelance, But Who the Hell is Going to Pay Me?!”

The first time I ever thought about striking it out on my own as a professional freelance writer, you know what held me back?

Not “fear.” <–Gaaaaad, the overuse of this word can eat my armpit.
Not a lack of conviction in my abilities.
Not imposter syndrome.
Not the fact that I had no fucking idea what a “copy deck” was, or how to make one.

You know what it was?

The Winner's Circle Sports Bar in Exton, Pennsylvania.


At first glance, it was nothing special: it was just an everyday sports bar at the end of a mediocre strip mall in suburban Philadelphia, next to a Cheeseburger in Paradise, across the street from TGI Friday's. All the families sat at the little square tables and all of the overworked corporate professionals sat up in the booths by the bar, and nobody knew how to eat wings with white collared shirts on, so they ate buffalo chicken flatbreads, instead, because this was The Winner's Circle, after all, and they were a crafty bunch.

I would go there, not because I care about watching some guy named Rog score a homerun—HAHAHAHAHAHAHAH baseball's only worth it in person for the hot dog man—but because the shopping center was adjacent to my apartment complex, and I could walk. Walking + Miller Lite (what the ancients drank back then) = Good Life Decisions™️.

^Holy shit, could I go for a Miller Lite.

ANYWAY. I'd walk over there and I'd throw open the door, as if I were very late to a very important meeting, and I'd look all around the bar as if I was meeting someone there, all the while knowing I was not meeting anyone there, because that is what you do when you are in a new city and DON'T HAVE ANY FRIENDS.

So I'd rush all professional-like up to the end of the bar —there were only three seats on that side and it felt like my own private little slab—and I'd order myself a beer, or maybe a rum and diet, if I were feeling outrageous (I was 22, after all). And then, I'd wait.

Groups of young professionals would come in, planting themselves at the long part of the bar.

Guys, with their white collared shirts, would remove their ties.

Two or three would of them walk past me to go play darts, or maybe some pool.

And then I would get up and walk past them, on my way to the restroom, just hoping….hoping….that one of them would ask me to play.

Geniuses never did.

And so I'd sit there at my slab of bar, pretending to be perfectly happy being there by myself, while all the while, the real reason I was there? Was because I desperately missed having friends. I had said goodbye to them in high school, in college, and in every other place along the road that had taken me there. I was always saying goodbye, but I didn't yet know how to say hello.

And so I'd sit there, and I'd wait. Paaaatiently, and with a higher bar tab than was appropriate for my $32,000 salary. I thought that eventually, someone would approach—preferably someone with dimples, because I like dimples, you know—and we'd banter and we'd laugh and we'd order another round of beers, and maybe they'd tell me that their mom died, too, and then maybe my eyes would get wide and I'd tell them that the same thing happened to me—but secretly I'd be thinking that I wouldn't get a tattoo of her face, like he had done, because I'd think that was creepy—but it didn't matter, because I'd be so happy to have made a new connection. I wouldn't even mind if he liked mushrooms.

But that guy never approached. (I really would have forgiven him for the mushrooms.)

Honestly, neither did anyone else.

In the 12-month period that I lived in Chaddwell Apartments, I never met a single other soul at that fucking bar.

And it now occurs to me: this is what starting a business feels like.

You have an inkling to strike it out on your own, start your own photography business, start your freelance writing career, start doing whatever it is you think you might actually like. I had already started feeling that way, shortly after starting my corporate career, but I didn't dare pursue it, then, because you know why?

If I didn't even know how to find friends, how the hell was I going to find clients?


The thought was on repeat in my head: I could try it, but…who the hell was going to pay me?

I didn't know that there were PLENTY of people who would have happily paid me, just like there were plenty of people who would have happily talked to me…had I taken the initiative to find out.

But I was too worried about looking stupid, desperate, and weird to try. So I sat back and passively waited. And waited. And waited. For my life to get better at the hands of other people.

Just like you might be waiting right now.

Waiting for the guy with the dimples to come up to you and tell you that you were BORN to be a model. (HAHA, FANTASIES.) Waiting for your spouse to encourage you. Waiting for your friends to take an interest in your dream. Waiting for your family to not think you ridiculous. Waiting for the world to give you a sign.

Waiting for other people to validate your ideas.

But if we know anything from that RIVETING story about a sports bar in suburbia, we know that other people aren't going to do jack. But they don't have to, because YOU will.

You will start this.
You will find clients.
You will make money.
And you will take the initiative to make things happen for you, instead of waiting for them to happen to you.

And you will never look back.

Because the people in the real Winner's Circle?

Aren't waiting for shit, my love.

They're too busy winning.



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