I spent years dreaming of full-time freelance life as I sat behind a desk at my day job.
When I hopped on to what I thought was a regular all-hands Zoom meeting in May 2020, I had no idea that day was going to be my last as a nine-to-fiver.
I, along with thousands of other employees from every industry around the world, found myself unemployed in the middle of a global pandemic, wondering what I was going to do.
I had a few freelance gigs on the side then, mostly to fund after-work drinks and dinners — nothing fancy, nothing extravagant. I didn’t know how I could possibly make enough money if I didn’t have a full-time job, especially in Boston, one of the most expensive cities in the United States.
Imagine my surprise when after one month of full-time freelancing, I raked in $10,000. And when I rang the bell at the end of my first year, I crossed the six-figure threshold for the first time in my career.
Here’s exactly how I did it — and what I learned along the way.
“What are you going to do after graduation?”
I always loved to write as a kid, but when I got to college, I wanted to do something “more serious.” I majored in Government and Global Studies at a small liberal arts college in Maine, thinking maybe I’d try to change the world, and if that didn’t work out, I could always become a lawyer.
Then came the dreaded question my senior year: “What are you going to do after graduation?”
I realized way too late after a study abroad semester on international law that I had no interest whatsoever. I wandered around my liberal arts campus counting down the days to graduation with a deep fear of what came next, rushing from class to track practice to my campus job in the communications department and tried not to think about it too much.
I spent a lot of time shepherding prospective students and parents around campus as a tour guide, but this question (always from parents) consistently stumped me.
I went on disastrous consulting interviews (I still do not know how many tennis balls would fit in a 747 jet), went to financial services workshops, talked with professors about graduate degrees, left Peace Corps and fellowship applications unfinished, desperately messaged alumni for advice.
It wasn’t until Thanksgiving that my aunt mentioned that working in the admissions and communications departments kind of seemed like working in sales and marketing that I had any direction at all.
It sounds obvious now, but I had no idea walking backwards or writing the occasional blog post about my college experience was an actual thing I could do in the real world.
I got the call from a big tech company’s marketing development program two days before Christmas covered in flour, baking cookies with my grandmother. A job! And so began my first fledgling steps into becoming a professional writer… though I didn’t know what that meant yet.
From full-time marketer to freelance writer
The very first thing I learned about working in marketing at a big tech company was that I hated working in marketing at a big tech company.
Working in an office stifled everything about me. I wore my big girl heels and Hillary Clinton pantsuits and remembered to circle back and update the spreadsheets, but not much else.
While I got a front row seat to some incredible marketing programs (and very talented marketers!) I didn’t appreciate it at all in the chaotic transition between college and post-grad life. I didn’t know who I was or what I wanted, but I knew it wasn’t this.
I started freelancing as a side hustle (this was back in the peak #girlboss days, mind you, where everyone had a side hustle to match their rose gold desk signs) in 2016.
My first gig wasn’t paid at all, but a monthly assignment for Her Campus, a popular lifestyle website for the millennial “collegiette.” I wrote on their post-graduate beat on topics like feminism in the workplace and post-graduation anxiety after work on a twice-hand-me-down couch in my first apartment, and I loved it.
It quickly snowballed into a few small business-related assignments until I got my first big pitch accepted at The Kitchn for $200. I couldn’t believe my luck.
I kept writing, generally for less than $100 a post, but occasionally for $200, at food and lifestyle publications like Fodor’s, Paste Magazine, and Tasting Table.
Assignments came few and far between.
I generally averaged around $2,000 a year in freelance income, almost 100% of which went toward dinners out so I could keep writing about food.
I hopped around to several tech companies for full-time positions between 2016 and 2018, but never once did I give myself a chance to try out my side hustle for real. I never fully admitted to myself how afraid I was to give it a go — I already felt like a failure for job hopping (not always by choice) and wanted to build a life as financial equals with my boyfriend-turned-husband.
It wasn’t until 2020 that I became a full-time freelance writer, and then only because of a big gigantic shove: A pandemic layoff during a time when no one was hiring.
My first year as a full-time freelancer
Talk about terrifying.
I sat down with my husband and nervously looked at our budget. While I didn’t intentionally find myself a full-time freelancer, I’m very lucky to have a supportive partner who believed in me — and more importantly, maintained his full-time position that could fit our major expenses, like our mortgage, utilities, and groceries, and cover my health insurance.
Based on our calculations, I had to make $200 a month for us to get by, and $5,000 a month to get back to what I was making in my full-time job.
I gave myself six months and decided that if I couldn’t hit at least one $5,000 month, I would start job searching for another full-time marketing role in the Boston area…an idea that filled me with dread.
I started the only way I know how, which is to learn. I signed up for Rebecca Weber’s Freelance Writer Bootcamp, which gave me an anchor to build my days around as each quarantine day melted into the sticky summer heat.
I messaged a few editors I had long-standing relationships with and got a few more assignments.
I called up my local paper and got assigned the DPW beat at $50 a story and called it my first full-time client.
Then I signed my first contract with an hourly client for 10 hours a week.
I did more than 20 assignments that first month running myself ragged, but came out of it with $10,000 — and all of the sudden, full-time freelancing went from, “maybe this will work” to “holy shit, I can do this.”
I finished Freelance Writing Bootcamp and pitched every single day, landing assignments in Conde Nast Traveler, Eater, Apartment Therapy, and Food and Wine.
But the real business-building began when I found repeat B2B tech clients, people who remembered me from working together in years past. I gained more confidence, posting on LinkedIn and using all of the marketing techniques I learned over years of crafting emails, copywriting, and building campaigns for other companies for myself.
I cried when I got my first assignment for $1,000. Half of what I made in freelancing just a few years before, from less than one week’s worth of work. It meant I could start exhaling again instead of constantly writing at all hours to keep myself afloat.
By the end of the year I blew by my financial goals, took a week’s vacation, and made well over six figures. (Many, many) mistakes were made, and I learned a lot:
1. Relationships matter more than anything else
Everyone says this, but I promise it’s true.
When I posted on LinkedIn to announce my new freelance business, I didn’t think I’d get any comments — but instead, my network showed up.
Several past coworkers immediately hired me and several others referred me to friends looking for writers. I wouldn’t have been able to scale up so quickly without the relationships I’d cultivated in my years as a full-time marketer.
2. Diversify your income streams
There isn’t one way to be a freelance writer.
Whenever I started feeling stuck or bored with one type of writing, I jumped to another. I tried web journalism, listicles, newsletters, long-form content marketing, blog posts, website copywriting, book copyediting, print newspaper journalism, consulting, and blogging before settling down on my key offers.
Now, I only write blog posts, ebooks, and web journalism — and I launched my own content marketing course for freelancers looking to break into a new type of writing.
Similarly, I’m all about niching down, but sometimes, it’s nice to try new things and build up a new niche.
In my first year as a full-time freelancer, I wrote articles about fruit salad, how to create your own fonts, citizen science, Christmas cookies, AI-driven wine subscriptions, translation memory software, u-pick apple farms, virtual reality, and ‘00s movies.
I love getting to talk to so many different kinds of people from so many different walks of life. It’s the best part about freelancing, and I’m not going to give that up.
3. Focus on repeat clients to drive income
That being said, part of why I can try all kinds of different types of writing and topics is that I have five anchor clients that I love working with that assign a certain number of pieces a month in advance.
I’ve worked with them for over a year now, and so I understand their business model, content strategy, and process in a way that isn’t possible with one-off assignments. This makes every subsequent assignment a little easier and a little faster — and gives me predictable income every month.
It’s also what allowed me to start taking more time off in my second year of full-time freelancing — 10 glorious weeks of vacation! — because I could plan more easily and charge appropriately rather than chase those $100 articles.
4. Don’t be afraid to fire clients
Every time I’ve fired a client, I’ve had to hold my hands under the table to keep them from shaking.
It’s so scary to say goodbye to income, especially with repeat clients, but if they’re not a fit anymore, you have to let them go.
It took me time to be able to do this. At the beginning, I said yes to everyone, which resulted in total disaster. But after a few months of understanding what makes an ideal client and what are my red flags, I no longer work with anyone who:
- Won’t pay me on time (which eliminates a lot of consumer publications, unfortunately) because predictable, repeatable income is important to me, and reveals deeper issues about their business longevity.
- Companies without a set marketing strategy in place, or at least a few goals about what they hope to accomplish by hiring a freelancer. It never ends well.
- Make the editing process hellish with multiple rounds of nitpick-y edits and/or rewrite the majority of the pieces. If that happens for more than one article, it means I just don’t “get” their style, or they have control issues, and it’s best to part ways.
5. Find something fun once a quarter
Six-figure freelancing gets a reputation for being all hustle. And while it definitely takes hard work to get there, it doesn’t have to be all boring!
There’s only so many times I can write about digital transformation (something that tech companies have been talking about since my first job in marketing years ago) before I need a break.
Each quarter, I plan to take one article that’s purely fun — for me, usually about food or travel and pays less than $200. I’ve written about Mickey-shaped foods at Disney, microbakeries, beginner camping tips, and more this way.
They’re some of my favorite pieces despite contributing very little to my overall income goals. And that’s ok! I don’t want my career to be all grind the way it was as a full-time employee, and since I’m the boss, I get to decide what I work on and when.
There’s not much better than that kind of freedom.