Photo by Carl Cerstrand on Unsplash
Seven years ago this week, I was snowed in, stir crazy, and fighting off the certainty that I’d just made a huge mistake.
And now — sans snow — I’m struggling with that fear again.
(But more on the changes afoot here in a minute.)
That snowy January seven years ago, my husband and I had just moved to Portland, OR. I’d worked my last shift at the Elysian Brewing Company, said goodbye to all our friends, and hung my shingle as a full time freelance copywriter.
I was terrified.
One year earlier, I’d worked my way out of my full time catalog copywriting gig by freelancing on the side until I was too busy to do both.
I’d gone down to part time at the catalog company, then picked up shifts at the Elysian and a local Mexican restaurant (the excellent Fonda La Catrina in Georgetown) to bolster my shaky freelance income.
Working three jobs on top of being a freelance writer was exhausting — and, more critically, it was hindering my ability to grow my freelance business.
But letting go of that steady income?
I couldn’t do it.
Not on my own, at least — not until my husband got a job in Portland, and I had to cut my safety net loose and trust my writing business to support me.
I remember checking my dwindling business bank account, wondering if I’d made a mistake.
“If this doesn’t work, you can always go back to waiting tables,” I’d said to myself.
And I got to work cold-calling potential clients.
A new transition point for this freelance writer
“You can always go back to waiting tables” was my mantra for years.
Every time I lost a client, every time a dream gig fell through, every time I found myself checking a near-empty bank account.
And in seven years, I never did.
My hustle in those early years paid off. As I slowly gathered portfolio clips and confidence, I grew from charging $50 for a blog post to charging $500. I gathered a stable of reliable, well-paying clients I loved to work with. I said no to projects that weren’t a good fit for my goals, or a good use of my time.
In the back of my mind, I’d always known that as long as I kept relying on my waitress shifts for cash, I wouldn’t take the risks and pour enough energy into the freelancing.
And now?
Now I’m in a similar period of transition with my fiction business.

A focus on fiction
I’ve been diligently working to write and publish books while still keeping up with the freelance writer hustle, terrified that if I pull the plug on that regular income, my fiction income won’t sustain me.
It can’t — not now, anyway.
But what if I gave it the same full-time energy that nurtured my freelance writer career in those early years?
What if I trusted myself to work the fiction hustle as well as I worked the freelance one?
After all. I can always go back to copywriting.
Learning to say no
Of course, there’s a key difference between quitting waiting tables and quitting copywriting: I like copywriting. I find most of the work I do incredibly fulfilling, and love my clients.
Waiting tables, on the other hand? For all that I loved my coworkers, that job gave me stress nightmares almost every night.
In 2020, I started learning to say no to the work that no longer fit my goals, and opening space both for writing fiction, and for more of the work I do want to take on.
Going into 2021, I’ve set myself clear guidelines around the type of work I can say yes to as a freelance writer — and those guidelines are incredibly narrowly defined.
It’s terrifying to say no to money when you don’t have a big project on the horizon.
It’s terrifying to invest weeks and months into writing books on spec, rather than putting those hours under contract to a paying client.
But after seven years of watching my income ebb and flow, after watching myself build a business out of scratch, to succeed past every setback, I know I can do it again.
What I learned in my seventh year as a freelance writer
All that to say, welcome to my seventh annual reflection post. Changes are obviously afoot in Kwakland, and I’d like to talk a bit about how I got through 2020, what I learned along the way, and what I’m taking into 2021.
As always, my goal is to be transparent about my business and my struggles to help out freelancer writers who are earlier on their journeys than I am.
(And if that’s you, I’d love to hear from you! Drop me a line: jessie at jessiekwak.com).
Read about Year 6 (2019), Year 5 (2018), Year 4 (2017), Year 3 (2016), Year 2 (2015) and Year 1 (2014).
So…. 2020.

2020, amirite?
This past year turned me (and many others) from a homebody into hermit. I forgot to leave the house for days. Honestly, I barely left my office.
It was a year of extremes. Some times I was so busy with freelance work I could barely breath. Other times it was crickets, and I used the lull to work on fiction. Some days I was laser focused on my work and goals — other days I could barely manage to find the energy to scroll Twitter and try not to scream.
I was used to working from home as a freelance writer, but I wasn’t used to my husband being constantly at home with me, and our forced co-captivity surfaced some issues we needed to work through. (As well as making our relationship even stronger.)
We all have our 2020 story, and I’m grateful to be in a place where I could weather last year’s storm relatively painlessly.
But, wow. I’m looking forward to the coming vaccine.
As for how COVID-19 impacted my freelance business, it’s hard to say. At the beginning of the pandemic, I took on a couple of COVID-related projects, such as an ebook about pivoting your business during the pandemic for Microsoft.
But as the uncertainty stretched out, marketing budgets froze and projects for Jessie dried up. I still had a few regular clients, but new work just didn’t seem to be coming in.
I used the time to finish the last book in the Bulari Saga and begin planning my next series, the Nanshe Chronicles — but as I watched my bank account drain, I started to worry.
Fortunately, I landed a few big projects at the end of the year that brought my income back up to par with what it had been in 2019. But October and November were probably two of the busiest months of my career, and I was perilously close to burnout by the time December rolled around.
But that’s a freelancer’s life, right?

Income analysis: How I made my living as a freelance writer in 2020
I had some shifts this year, but overall the makeup of my freelance income stayed on par with 2019. As I’ve mentioned in past posts, it’s a bit hard to break down by project since I sometimes do different types of writing for the same client.
The big change is that I had fewer clients overall. Whereas I did work for 16 separate clients in 2019, last year I only billed 10 clients — and two of those were for single projects that took less than a few days to complete.
I spent 2020 slowly shedding clients in an attempt to free up more time to focus on writing fiction. Going into 2021 I have only one monthly blogging client, and an ongoing relationship with one main client that feeds me regular content marketing work.
I’m still open to new work — particularly ghostwriting — but I’m in a position where I can be very choosy about who I work with and how it fits with my goals.
Here’s my income breakdown for 2020:
- Content marketing (ebooks and such): 60%
- Business blogging – 18%
- Ghostwriting – 8.5%
- Copywriting (website copy) – 8%
- Fiction – 5%
- Knitting product copy – 0.5%
Content marketing and ghostwriting are my favorite types of work, so I’m glad to see them making up a good chunk of my income for 2020. I’m also excited that my fiction income held strong at 5% — especially since I had planned to do several big in-person book events that got canceled.
Growing a fiction writing business

I mentioned that I’m paring down my client list to free up time to write fiction. The hope being that by pouring energy into writing and marketing that side of my business this coming year, that income will grow to a level that actually is sustainable.
Currently, my plan for that is to launch a new series (probably in fall of 2021), and re-launch the Bulari Saga with new covers (sometime next month).
My goal is to get these books in front of new fans, but also to double down on my core fans. To that end, I’ve started a Patreon, where I’m documenting my journey of writing the new series (the Nanshe Chronicles), sharing behind-the-scenes information, and posting sneak previews.
I also had a chance to go on the No Shelf Control podcast and talk about the Bulari Saga with authors Lindsey Fairleigh and Lindsey Pogue. It was an incredible amount of fun! (Listen to the interview here.)
A year of Chaos and Creativity

As well as fiction, I’ve been growing the nonfiction book side of my business. From Chaos to Creativity came out at the end of 2019, and I spent part of the summer of 2020 writing a followup book about the writing process.
While I couldn’t travel to do events like I did in 2019, I did have a few fun virtual opportunities come up to talk with people about creativity.
The first one was in May (remember May?) when I got a chance to chat with Lydia Rogue from Microcosm Publishing about pandemic productivity, and how to be gentle with yourself. (You can watch it here.)
The second amazing opportunity was with Joanna Penn of The Creative Penn podcast. (Listen here.) I’ve been a longtime fan of Joanna’s podcast, so it was a complete thrill to get to come on the show!
Finally, I was invited to give a presentation on productivity for writers at the virtual Willamette Writer’s Conference in August. There’s no recording of the event, but it was an incredible honor to get a chance to speak with everyone there — and the organizers even managed to build in some networking time where I made some new friends. (Difficult to do over Zoom!)
What’s coming up in 2021?
2020 gave us all a bit of whiplash. And I don’t think I’m alone in my newfound reluctance to make big plans at the moment.
But my main goal is to double down on fiction, refining my process and focusing my time in order to grow this part of my business like it deserves. If you want to stay up to date on that, join my newsletter.
Enough about me now. I’d love to know — what are your plans for 2021? How did your 2020 go?
Leave me a note in the comments.
And here’s to a fresh start and an amazing new year!
–Jessie