The other day a colleague called me out of the blue wanting some career guidance.
“You’ve got the kind of job I’d love to have,” he said. “I’m wondering if you could give me some advice on how you got started.”
It made me think. I am pretty damn lucky. As the editor of HackSurfer, I spend my days getting paid to write. I get to coach and teach new writers. I get to try new things. Basically, I get to do whatever the hell I want.
When football season started, we created our own game called Fantasy Cybercrime. Every week our staff faces off against each other and we post the results. I’m currently in second place. The winner gets a bobble head trophy. I want it.
I host webinars using Google Hangouts. I get to interview experts in the field. I mess around on social media. I create graphics and videos and papers and ebooks. Most of all, I get to write and come up with new ideas. Every day. Soon, we may start a podcast.
I have an amazing boss like that. “Tell me when I’m shitting the bed, otherwise, I’ll just run with this,” I told him. I had no idea what I was supposed to do, so I started running.
It’s awesome and I love it. Occasionally, I forget how lucky I am. Everyone does. Like anyone who gets to live their dream, I’m constantly waiting for the rug to get pulled out from under me. So far, it hasn’t.
It’s been a long and strange journey to writing full-time.
My First Paycheck for Writing
It was 2001. I was 16. I wanted to write, but had no clue how to go about it. Truthfully, I had no clue what to even write about.
I bought that ancient tomb, the Writer’s Market, and would pour through the submission listings, circling anything that sounded like it might let a hack like me slip through. I bought writing magazines, there were a handful at the local bookstore, and read them cover to cover. One in particular had a short story writing prompt each month. I used them to pen some truly horrific short fiction, including a version of this short story. A few years later, with a bit of editing, it’s not that bad.
I had no idea what it meant to be a writer. I’d just watched Almost Famous. I imagined myself penning in-depth features for Rolling Stone that sprawled across a half dozen glossy pages.
But even at 16, the math of it all didn’t add up. How could a person survive? There were listings at the big magazines that paid big — maybe $2 a word — but damn, that would mean I’d need to land a feature at a brand name magazine every single month to keep putting food in my mouth.
And I hadn’t published anything, or submitted anything other than some terrible short stories that wouldn’t even pay if they were published. It was a daunting hill to climb.
But I kept looking and reading, and I found a few sections in writing magazines where they accepted stories from writers about writing. I wrote a short piece, “Another Day, Another Rejection Letter,” about walking to the mailbox and the excitement, and fear, of seeing that envelope with your own writing on it — the joke of it all being that evil editors would not only make you wait months to reject you, but also make you pay for your own rejection with those damn self-addressed-stamped envelopes.
The one line I remember: “There is some kind of sick, self-inflicted torture that I find in paying for my own rejection.”
It was funny and interesting, and I knew it.
It got rejected one or two places with encouraging comments before being published in FellowScript, a quarterly Canadian newsletter.
I was paid $15 — in Canadian money, which at the time was actually like $13.75.
Phase 2: Being a Broke Writer in College
Truth be told, I may not be the most inspiring case. I was never the plucky young writer who wouldn’t give up until he reached his dream, bashing down barriers one heartfelt story at a time.
I stopped writing. I changed course. I gave up — many times.
I was going to be an engineer. I kicked ass at Advanced Calculus. I kicked ass at Advanced Physics. But throughout my high school and college years, I loved writing assignments.
Every moment where a teacher wrote, “You’re a great writer!” or “I loved it!” on a paper stayed with me. I remember my Food Journalism professor reading out loud an essay I wrote in college, and I could sense the classes disappointment — it was pretty damn good, even moreso the way she read it. She encouraged me to write for the school paper, and if it wasn’t for her, I wouldn’t be where I am today.
But writing some bullshit personal essay is cheap. That kind of stuff didn’t count. It’s not going to get you paid, I told myself. I still believe that’s true. I blog here, and it’s fun, but I don’t expect to make any money off of it.
I decided to not work for a year, snagged some private loans to pay my expenses, and tried writing again, eventually for the student newspaper.
I’ve said it before and I’ll say it again, interviewing was the most important thing I learned. For years, I had no idea how to write something that would actually lead to getting paid — other than some abstract idea like writing a book and praying it sells — but with interviews, I could write about anything.
I interviewed professors. I interviewed students. I even got to interview Patrick Rothfuss, who taught at my college, about a book he was releasing. This was before he was the badass international bestseller he’s now become, though the epic beard has never changed.
I learned a ton. For one, I learned what it’s like to be a real writer. I remember one story I wrote about student debt and all of the pieces that I had to assemble. I must have interviewed a half-dozen people for it. I read studies. I quoted statistics.
It started with a student. “I’m scared to go to school,” he said about the mountain of debt he faced. “I’m contemplating if I want to continue.”
It was my first every true feature-style story.
Another story I wrote began:
As semesters draw to an end at the University of Wisconsin-Stevens Point, Anthony Ellertson usually can be found standing in front of his class quoting T.S. Eliot’s “Four Quartets” and telling his students that, if Einstein’s right about time, each moment is eternal, and they will always be sitting in that room together.
As semesters begin he often tells his students they’re going to change the world.
It’s not quite the expected subjects for a group of students learning about Web design.
I quote those to illustrate a key point, one that I will make again and again. People want stories. In order to tell those stories, you have to go out into the world, or at least pick up the phone. It seems obvious now, but for years I couldn’t make the connection.
Yes, it was terrifying at first, especially for us introverts. I made a fool of myself on more than one occasion. But once you begin to collect those stories and statistics and ideas and play around with them and shape them, it’s exhilarating. That’s the fun part.
Interviewing is now, hands down, the favorite part of my job.
I should point out that throughout this short period I didn’t get paid. And a lot of what I wrote was crap. But some of it was good, at least a couple of articles, and it gave me a variety of stories that I could showcase when people asked for clips. You need them.
My professor put me in touch with a local paper, and I wrote an occasional story for them. Sometimes I’d rework a story for the college paper for their weekend edition. A few times they asked me to cover something in the community: a new charity in town, or a man who put a camera on huge kites and took beautiful aerial photos of the city.
Each story paid $40. I was moving up in the world.
Then I graduated. I moved. I had to start over. I gave up writing.
Phase 3: Quitting My Job
Writing, I thought, can always be a part-time thing, a hobby. So I looked for a real job. I went through a few different ones. I worked hard. I became a manager. For the first time in my life, I made decent money.
Then I quit.
After years of not writing, I realized I wanted to try again, and rather than dust off that old Writer’s Market, I went online.
I found a few sites where I could make money: content mills like TextBroker and Content Authority. Writing for them certainly wasn’t fun (get paid $5 to write 300 words on how to stain a deck!), but they gave me confidence that I could slave away and live off ramen noodles while waiting for something better to come along.
They’re mostly shitty, soul-sucking places that pay less than minimum wage, but they are an easy way to make something if you can quickly produce error-free articles.
I quickly moved to Elance, a site where you can bid on articles. A lot of the stuff on there is similarly shitty work at slave wages, but I actually found decent success there and some good opportunities.
The challenge was to stand out, and not undersell yourself. When I saw a job I really wanted to land, I put some effort into my bid. I’d make sure I had a few quality, relevant clips to send along as PDFs, and I made sure to provide several ideas or options to give them less of a chance to write me off.
That short bid is all they have to choose who to hire. Finished clips show them what you can produce. Ideas show them you understand what they want and can provide it to them several different ways. A realistic price shows them that you’re a professional and understand what you’re worth.
Yes, I did undersell myself a few times to get those initial jobs and ratings, but I was always looking for a big fish.
That’s where I found HackSurfer.
Phase 4: Becoming a Full-Time Editor
This post is becoming long, but it’s for a reason. When people ask how I got started writing, I tell them I quit my job and four months later I was the editor at a new startup and managing its cybercrime website.
Yes, I got lucky, but luck plays a part in everything. Mostly though, I knew I wanted the job, and I made damn sure I got it.
The point I want to make is that it wasn’t as easy as I quit, I found Elance, I landed a job at a cool company.
I wasn’t the only person on Elance writing stories for HackSurfer, and I knew that they’d be hiring someone full time soon.
I took it for what it was: a test. May the best man win.
Problem was, I knew absolutely nothing about cybercrime. Years ago this would have terrified me. It would have been a show stopper.
But I knew I could write about anything if I found the right people to talk to. So I found a few experts each week to interrogate for new stories. I built up a roster of contacts. I leaned on them heavily, perhaps too heavily at first.
And a few months later, I got the job. I knew I would. Because I stood out.
That’s it. That’s the long answer to how I got started and how I became a full-time writer.
Now I’ll keep working and improving — and hoping the rug doesn’t get pulled out from under me.
Want more tips on freelance writing? I’ll collect them all on my Freelance Writing Guide Page for future reference.