How I Started Freelancing

And a few things I've learned along the way

My coworker, Kona

Hi friends.

This February is my 2-year freelance anniversary. I quit my full-time editing job at Outside Business Journal (formerly SNEWS) in January 2020, took a few weeks off, and then dove into signing contracts and pitching new publications in February 2020. A lot has happened in those two years. I’ve landed stories in dream publications. I’ve worked with amazing editors. I’ve increased my salary on my own terms. There have been hard times too. At this moment though, I can’t imagine working any other way.

I’ve been freelance writing since I was 18 years old after my unpaid internship at a local newspaper ended. My editor there, Jessica Lipsky, featured in Vol. 3, continued to assign me stories on topics like city council meetings, a ride along with police, and business openings. I can’t remember what my rates were back then, but probably no more than $100 per story. I was already working two other jobs. The next summer, when my internship at a regional magazine ended, the editors again asked me to keep working. I was paid $10 an hour for fact-checking work. And as I made my way through college and my first real jobs, I was always freelancing on the side.

But I never really believed I could make it my full-time job, even though I knew people, including friends, doing it. My doubt was completely rooted in fear and self doubt. Would I be able to make enough money? Would I get any assignments? Could I keep up with all the assignments? What if I ran out of ideas? Would I be able to stay motivated?

When I grew frustrated at my full-time jobs—more work for the same, meager pay—a few friends encouraged me to seriously consider freelancing. I realized that the years of sitting in coffee shops on weekends to finish up freelance assignments really prepared me for the moment I turned in my notice. I had been building my network, skills, portfolio, and money smarts all those years. I was ready to at least try it out.

Below, I put together a little list of advice that I’ve absorbed over the last decade and especially over the last two years.

1/ Access your network

Who do you already know who is either an editor or a freelance writer? Are you close enough to them that you could ask for a few tips? If not, reconnect on LinkedIn or Twitter or through their website. Asking to “pick their brain” isn’t the best approach anymore. Instead, offer to buy them coffee/send them a Venmo/do some other type of trade in exchange for their time. Whatever they share, take their advice to heart. And down the road, maybe you can return the favor and/or work with them.

2/ Bookmark pitch resources

I have a huuuuge list of pitch guides bookmarked in a folder that I reference whenever I’m thinking about reaching out to a new publication or feeling a little lost developing a story. It’s always helpful to review these handy guides to get a sense for what different publications expect in a pitch and finished piece. There’s also this incredibly helpful page where you can read successful pitches and the story’s details.

3/ Read where you want to write

This is crucial. Editors can tell when you don’t read their publication. Before pitching, get a sense of the outlet’s voice, types of stories, etc. Make sure you could see yourself writing for them, too. Basically, study up. And don’t just breeze over the homepage or a single issue in an afternoon. Read it for months, even years. Get to know the different sections and the editors who shape them. Pitch guides will also help here.

4/ Hire a coach

If you don’t even know where to begin, it’s worth hiring someone who does. You basically pay them to give you their freelance secrets. In some cases, they can even help you land published pieces. Coaches are also helpful for freelancers who have been at it for a while, but have a certain goal in mind or feel like they’re plateauing. My friend, Kassondra Cloos, is accepting clients. She recommends her coaches Natasha Khullar Relph and Ellen Donnelly. There are tons of other freelancers who offer coaching services, so look out for those hybrid professionals.

5/ Keep an ideas/pitch notebook

I’m a sucker for notebooks. I have ones dedicated to all sorts of things—sewing, doodles, quote-worthy advice, even my passwords. But the one I reference most is my idea notebook. It’s where I jot down the seeds of stories, sometimes even just one word. Cartographers. Slippers. Hostels. When I’m lacking assignments or inspiration, or when someone shares something interesting, I turn to my pocket-sized treasure trove. Maybe your notes app is sufficient. Maybe you need a physical notebook like me. Whatever the form, start writing stuff down and return to your list often.

6/ Start freelancing on the side

If you’re not ready to leave your job, or you don’t want to, try freelancing on the side. Only by actually doing it will you start to pick up your own lessons. How to work with editors. How to advocate for higher rates. I started freelancing because I wanted an outlet for stories that didn’t fit into the publications employing me. The newspaper was not going to run a deep dive into the rock shoe resoling industry (one of my first pieces in an outdoor publication). So it was worth it to me to spend a few evenings interviewing people and weekends writing up the stories in coffee shops.

These are just a few tips I’ve found helpful both for getting started and continuing my craft. I hope some of them resonate with you, and I’d love to hear in the comments what other ideas I missed or what topics I can expand upon. I’ll also dedicate a future journal entry to an exhaustive list of my favorite freelance resources, so you can look forward to that.

Be back in your inbox in two weeks with another longform interview!

With love,

Amelia

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Monthly Favorites

• Making: Lap duvets and the Morning Glory Top

• Using: This Slow North neck wrap is saving me from headaches

• Baking: Peanut butter dog treats because I’m that dog mom

• Reading: This feature on skier Jessie Diggins by Ariella Gintzler

• Writing: A featurette about my favorite bookstore, the Raven

• Wearing: A soft, supple quilted jacket that keeps me cozy

• Listening: Spotify’s Music for Plants playlist

• Collecting: Silly stickers in my bullet journal