2020 Year in Review

Welp…2020 did not go how I expected it to.

I know you can relate with that sentiment; we’re all in that boat.

But even with all of the uncertainty, the cancelled plans, and the pivots that happened this year…it was still a good one. I was fortunate in a big way.

This was my seventh year of full-time freelance writing, and somehow it was my best year revenue-wise to date: As of the end of December, my revenue was up 76% over 2019.

I’m breathing a huge sigh of relief and gratitude with that statement, as I vividly remember back in March when I was considering applying for a PPP loan (I opted not to in the end) and feeling super anxious about the future of my client work. 

I had no idea if companies would cut freelance support as they got conservative with budgets or if they’d lean into online content creation with events and in-person marketing off the table.

Thankfully it’s been the latter, and I’ve kept so busy this year that I’ve been getting help with overflow assignments and sending referrals to fellow writers a handful of times each week.

So what else happened in 2020?

Solo writing retreat + socially distant meetups

The first week of January, I took a three-day solo writing retreat up in Galena, Illinois to work on finishing the first draft of a creative writing project I’ve been working on. 

That’s still a work in progress (in need of some major rewrites which will be starting soon), but it felt so good to hole up by the fire in a cozy cabin for a few days with no client work just to focus on writing something *for fun.* 

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During warmer weather, I also got to see a few fellow writers via outdoor, socially-distanced meetups.

My local writer friend Courtney Westlake came over up a few times to co-work with me on our back patio, and I got to see Allie Decker for a bit when she was nearby on a solo retreat of her own. It’s always so great to get face time with people who “get” what you do.

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New business developments

Launching digital products and productized services

In January I officially launched my first digital writing resources. I’d been putting it off for a long time in fear of coming across as a spammy salesperson, but finally got past that and just, as they say, “shipped it.”

It was a good decision: I’ve sold just under $10,000 in digital products this year, and hope that number will go up in 2021 with a transition on the horizon around these offerings (more on this soon!)

I did a lot of experimenting with different teaching formats, too. I did a handful of live sessions on Crowdcast where I taught various writing lessons. In the second half of the year, I started offering one-page website copy audits as well. Together, these generated another $14,000-ish in revenue.

I continued my coaching work as well, and was excited to have a more diverse mix of both male and female clients this year.

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Upon reviewing the increasing demand and surveying past students, I decided to finally increase the cost of the four-week program to $2,200 to better reflect the results and ROI the program generates for participants.

I hadn’t raised the price at all in over three years of offering this service, but looking at the impressive results and feedback from past students, I realized it was time to re-evaluate that.

Newsletter transition and reporting work

In July, I moved my newsletter from Mailchimp over to Convertkit. It’s been a great decision so far, as performance and deliverability have both gone up significantly since making that switch.

I also landed some new and exciting online bylines this year with places like Vogue Business, Protocol, and Modern Retail, as well as in print for Mission Magazine. 

The most interesting piece I wrote for a publication this year was based on a video chat I had with Shep Gordon, the “Supermensch” Hollywood talent manager for Alice Cooper and Blondie (and many others.) I loved what he had to say about taking a service-based approach to networking and was nodding along the whole time.

The end of the road for Creative Class

The other big development: My Creative Class co-teacher Paul Jarvis and I have decided to wind down our efforts around our freelance business course and podcast in early 2021.

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Paul and I are both at a point where we’re largely focusing on other things (him on building Fathom Analytics, me on building out more resources for freelance writers), so it seems like the right time for both of us.

We’ll have one more season of the podcast come out (releasing January-March) and one final course launch window in January, but those will be our last.

It’s bittersweet, but I’m looking forward to the next chapter and building out some more robust offerings of my own!

Travels (pre-March)

In January, my husband Brandon and I went to NYC for a few days. We stayed at the PUBLIC Hotel and did lots of walking: We went to The Met, ate at Freeman’s Alley and had drinks at Ray’s Bar, saw a movie at the Roxy Theater, sat in the cozy pit at Sky Ting’s yoga studio in Brooklyn, and so much more. It was cold and snowy for much of the trip, but that’s one city that’s even prettier in the snow.

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A few weeks later, I went to Oahu to watch the Billabong Pipeline Masters surfing competition. Hawaii was so beautiful, and it was such a welcome escape to perfect weather coming from the dead of winter in the Midwest. I even got to do an outdoor aerial yoga class one morning!

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I turned 31 a few days after getting back from this trip, and that’s when things started closing down due to COVID. We had more trips planned for later in the year (California, Boston, and NYC again), but all of them were cancelled. Once things started closing down in March, we decided to play it safe and haven’t taken any trips since then.

Since we didn’t do much traveling this year, we decided to donate some of those previously-allocated funds to causes we care about, like the Central Illinois Foodbank and several local no-kill animal shelters.

The great outdoors

One of the benefits of not traveling this year is that Brandon and I have been able to spend way more time doing outdoor activities we don’t normally get around to. 

We biked hundreds of miles with my brother on new trails we found in a nearby town, foraged and found lots of tasty morel mushrooms, kayaked, hiked, and took Brooks (our doggo) on lots of walks and Jeep rides. 

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I also started stand-up paddleboarding this year, which I love! I even got back into running. All of these physical activities have been a saving grace for my mental health.

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Life things

In the fall, I had a friend cut more than 10 inches off my hair (outside, with masks on) so I could try out short hair for the first time since 5th grade. Turns out: I like it! It’s faster, it’s lighter, and I think it makes me look a bit older.

During quarantine I haven’t gone into any sort of salon, so I figured I’d just highlight my own hair with a box kit (like I used to do in high school.) That was a very bad call, as my roots turned orange. 

A cosmetologist internet friend sent me corrective color, but while I waited for that to arrive in the mail, I experimented with some fun colors to cover up my oops (pink was super fun, as was lilac.) The moral of the story is don’t try to bleach your own hair at home, k?

In October, my husband and I bought a new house, which, hilariously, is right across the street from the house I grew up in. Didn’t see that in my future!

The house is still a work in progress as we make some changes before moving in, but we’re hoping to be moved in there this spring. It’ll be so strange to have a new office space after working in the same spot since the start of my freelance career seven years ago.

Favorite reads

I had plenty of time for reading this year, and these were some of my favorites.

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The Woman Destroyed by Simone DeBeauvoir: I really enjoyed the first and third stories in this book (the middle one was written in a writing voice I couldn’t really get into.) This was excellent female perspective during my Existentialism philosophy kick this year.

The Midnight Library by Matt Haig: A fast read with a great original story and a positive message. If you’re into the idea of multiverses, this is up your alley.

The Lying Life of Adults by Elena Ferrante: This author is one of my all-time favorites for her ability to tease out characters’ emotions and to put you inside their heads.

The Harvard Psychedelic Club by Don Lattin: I had no idea about the magic mushroom experiments that went on in the 70s at Harvard and the careers of these famous folks that emerged from it. Loved this piece of nonfiction!

French Exit by Patrick DeWitt: Writer Rachel Syme recommended this book as a fun story with larger-than-life characters, and it delivered. A quick, light read.

Goals for the year ahead

I’m hoping that 2021 will be a year where I can branch out a bit more, diversifying my work beyond writing and getting a bit deeper into digital products and consulting. 

My biggest goal: Teach more than 2,000 people how to run a successful freelance writing business. I’ll be doing this through some new resources that are on the way (coming soon!) as well as the resources I already have for sale now.

My long-time writer friend Emma Siemasko are also launching a podcast together that’s aimed at freelance writers. I love chatting with her anytime I can, and with both of our combined years of experience as freelance writers working with clients in the US and internationally, we have a whole lot to talk about and share.

I’ve also got a few virtual speaking gigs lined up for 2021, so while I don’t plan to put a big focus on presenting in the coming year, I will be doing a few of these with sizable audiences. The first one is coming up with SEJ’s eSummit in January.


Did you do a post like this—or do you have an accomplishment from 2020 you’re really proud of? I wanna hear about it. Tweet me @kaleighf.

This originally appeared in my newsletter, A Cup of Copy. Sign up and get future editions delivered to your inbox.