Your Turn

Gunslinger, Castaway: The Life of a Freelance Writer

By John Cantwell '05

I am a freelance writer, and I am going to tell you what that is like.


Maybe there's a new graduate thinking about writing for a living. Or maybe there are readers who find stories about the Writing Life inherently fascinating.

This is the hope, at least.

The first thing to know, and probably the most important, is: What is a freelancer?

A freelancer is a contract worker. You have clients. These clients might be magazines, or design firms, or dentists or other enterprises. You are not a member of anyone's staff. You are paid by the hour or by the project, and when you are done, you are gone, like a ghost. The only traces of your existence? Your work, and an invoice.

Some people say a freelance writer is a kind of hired gun. That's true. We are a lot like hired guns. We are solitary creatures. We live by a code few people understand. Imagine Clint Eastwood when you think of us. Not octogenarian Clint Eastwood, with his pants pulled up past his belly button. Young Clint Eastwood, in a poncho, smoking a loosely rolled cigarette.

Now, there is a fine line between being a hired gun and simply wandering around shooting people. The former is a kind of unofficial title, bestowed through experience and training; the latter implies you're possibly a lunatic.

A similar distinction applies to freelance writing. Freelancers are made, not born. One must gain experience before going solo. But how do you gain experience without having experience? It is the Zen-like paradox each of us must navigate. "The path is no path," said Guidance Counselor Buddha.

It was my former roommate, Eric, who introduced me to freelancing. I would come home from my day job in market research to find him at the desk in his bedroom eating a hamburger off a Styrofoam plate. He would tell me how he woke up at noon and how he hadn't showered. This, he said, was "work." "Teach me your ways," I said one day.

Eric led me to my first client, a large Internet company that needed someone to edit listings on one of its websites. I did the work on weekends. The pay was good; money went straight into a PayPal account every week. Very hush-hush.

After that first gig I found another. Then another, and another. I quit my day job. Burned all my khakis. I was a freelancer, and there was no going back.

Being a freelance writer is different from other jobs. But it is not entirely different.

Sometimes my job looks like a traditional office job. I sit at a desk, type things on a computer, watch some YouTube videos, take a lunch break, then sit and type some more, then maybe go to dinner with my girlfriend or watch a movie. Office jobs are like this, too. It looks like you're not working, but you're actually kind of working.

Sometimes I work very hard, or work long hours. Email is a very important aspect of my life, just as it is for many other people. I own an iPhone, and I check my email on that regularly. Admit it: You do this too.

Beyond these basics, I'm afraid that's where the similarities end.

One big difference is that I work from my apartment. Another difference is that I am my own boss. As such, it is important that I do not hate the boss.

You may have heard that freelancers work in their bathrobes or their underwear, and it's true, we do that. But sometimes we must leave the house to go other places, like coffee shops, where we are forced to wear outside clothes, so we choose flannel, which is like street-legal pajamas, and all we talk about is how we can't wait to get back home and into our intimates.

It can get lonely working at home. Sometimes it starts to feel like the movie Castaway. You are Tom Hanks, and your cat is Wilson the volleyball. You grow a long beard. The only difference between your life and Castaway is you have shelter, food, Internet and TV where you are, and are free to leave whenever you like. And instead of becoming sinewy and very tan, you grow soft and impossibly pale. Yes, freelance writing is almost exactly the same as Castaway.

Freelance writing is not for everyone. People who desire stability, human interaction or sunlight may find it a bad career and/or lifestyle choice. But if you enjoy personal freedom and not always wearing pants and, of course, writing, I strongly recommend it.


John Cantwell '05 ( is a writer living in Brooklyn. He teaches at Rutgers University and the School of Visual Arts, and is currently working on a book about immortality.