Two years ago, from a couch in Brooklyn, things seemed to be simultaneously going horribly awry and working out just splendidly. I was a year into the dream of supporting myself by freelance writing. I had just returned stateside from Kenya, where I covered their 2013 elections as a freelance journalist. But that trip, and my previous six months living in New York had led to a zero balance of my savings account and brought my credit card debt to an even five grand. I had a 50 dollar bill in my pocket. I had no writing assignments pending. Only $100 was coming in from an previously written article. My website was not profitable (and well, still isn’t[But don’t worry amigos, we’ll get there!]).

The friend who had picked me up from the airport in New York told me I could crash on her couch for a week. A year since I’d left my previous job, my eight grand in savings had slithered away and returned as the growing five grand credit card debt. I was still alive, had that going for me, but the only thing saving me from the streets was the kindness of a friend.

My three months in Kenya had been nothing short of spectacular, but the financial gains I’d hoped to earn by writing about it had not materialized. It was a moment when self doubt danced wildly about the room.

Financially speaking, this was the lowest bottom I reached as a freelance writer. Nowadays I’m not just alive, but can pay for a place to live, I eat as much as I want, and never worry about how I will pay for my next drink. I still have a long ways to go as a writer and author. I dream of a day when I have health insurance again. But I don’t really have doubts about what I am doing anymore. Just a lot of work do. These are some things that I learned from my three-year freelance journey from broke ass to just broke.

We Are Programmed To Purchase Things That Are As Essential To Our Survival As Moldy Cheese Bread Dipped In Day Old Salsa Made With Rotten Onions

When I was earning a regular salary, I bought a lot of things for the same reason George Mallory summited Mount Everest–simply because they were there. It’s called a consumer economy for a reason—though another name for it could be an economy fueled by recurring dissatisfaction.

When you start as a freelance writer, many of those initial months your earnings are comparable to a Kia car payment. Some months, you will basically earn nothing. So it becomes important at some point to get out a paper and pen and go through saved receipts to find out where all your money is going to—rent, food, airline tickets, and bar tabs (the four essential elements) are likely to top many a list.

While Hemingway would not agree, there will be many months where (gasps) you may have to work more and go to the bar less. Even if you became a writer so that you could hang out in bars all day without arousing suspicion, that first year is about spending days, weeks and months figuring out the wild world of freelance writing.

In the beginning, you will likely have little money to date anyone but gypsies. But this will just give you more time to work, and remember, that’s priority numbero uno. 

Being location independent also tends to make one thrifty. Living out of luggage and between geographical bases, if I buy something new, I have to get rid of something old.

But everything I own is like a child, so how could I just cast it to the wayside like expired feta? I may want a new bear mask, but if I buy one, it will mean I will have to throw out an existing bear mask—and I love them all. Each pair of underwear I own is dear to my heart and near to my secrets. I could not cast a single pair into the garbage without being jealous of its new life with the garbage man.

The Yoda Was A Freelance Jedi

“Do or do not, there is not try.” Basically, things started getting much better for my peace of mind when I just decided writing is what I wanted to do and writing was what I was going to do. For that first year freelancing, watching my savings account dwindle and my credit card debt rise, I dismissed doubt with the thought, “If things don’t work out, I can always get a ‘normal’ job.” My parent’s constant mantra was, “Go to the oil fields! Make tons of money!”

If you are going to write, then do it. Go into debt if you have to. But keep on writing and writing and writing. Live off whatever you can bring in. If you can only pull in $400, then live off that and try better next month. “There’s always someone who will pay you for your writing,” a travel writer I met seven years ago in Colombia once told me.

In order to support yourself off your writing, it may mean you have to live in an palm tree’d expat paradise somewhere in the developing world half the year like I do. The problem with thinking, Well, if this doesn’t work out I’ll do this instead, is (at least in my case), you need that proverbial gun to your head to compel you to make it happen. If you have the compulsion to write and the personality that demands freedom, then I’d bet you’d be uncentered and dissatisfied doing something else.

Going into writing for money is the same as going to Vegas to quit gambling. What my experience has been is that there are some people that are destined or cursed or gleefully endowed or all three with the compulsion to write and if that sounds like you, you can either find a way to make it work, or have it haunt you relentlessly.

It’s Worth It

There’s that part in the Tao te Ching that goes something like, “When the rabbit climbs atop the trees and uses his bunny binoculars to peer upon the garden, he will climb down the tree and will not stop to talk to the squirrels until he has secured himself a place in the carrot patch.” Ditto freelancing. When it starts to work out, you’ll have nothing but gratitude that the past version of yourself stuck it out on that Brooklyn couch with nothing but fifty dollars in his pocket and a vague notion of how to make his dream work.

The world has never been bursting with so many ways to earn your living on your own terms, outside of the strange structure of 8-5pm. Some weren’t built for that. Some don’t understand sitting in an office when they body tells them to go to the beach. Some want to whistle and be naked while they work. If that’s you, then I’d say go for it. Unless there are mouths relying on you to feed them, the most many of us risk is having to turn up at our parents house with our head down having to chill with them until we try something else. So things might not be guaranteed to workout, but the chance of having them is worth risking just about everything but your life.