This year I celebrated six years of full-time freelance writing, and it was my most productive and interesting year of self-employment to date.
Client work picked up, Paul Jarvis and I partnered on the Creative Class course and podcast again (cracking 100K downloads!), and I still find myself excited when I sit down to work each day. I’m so grateful to have found a job I enjoy doing and am truly interested in…the novelty of that never wears off.
This year I also leaned into writing about direct-to-consumer retail and sustainable fashion, which started as an outlet for my interests but transformed into a whole new world of connections, opportunities, and friendships. Writing for publications like Forbes, Adweek, and Glossy opened doors to conversations I likely wouldn’t otherwise have had access to and gave me a place to share my expertise on eCommerce in a new way. Win-win.
What else happened in 2019?
The Domina Retreat for Female Freelancers
In April, my friend Emma Siemasko and I hosted our first ever retreat and brought together a small group of women at an Airbnb just outside of Austin, Texas. I wrote up a full recap of that if you want more details on what it was/how it went, but in short: I’m so proud! It was a wonderful time, and Emma was the perfect partner to do this with. Face time with these smart women was incredibly valuable for me.
More Freelance Writing Coaching
This year I continued my one-on-one freelance writing coaching work (year three!) and I loved having the opportunity to work with more international freelance writers, including a few living in India, the UK, Australia, and Japan. While the time zones made scheduling a little tricky, we always made it work! I also got to meet up in person with a few of my past coaching partners. I love that some of these business relationships have blossomed into real friendships over the years.
Freelance Writing Business Performance
My busiest months this year were January through April and October through December, which worked out well because it allowed me to enjoy the summer months and do some non-work travel during that time.
I brought on some incredible new freelance writing clients like Monday.com, Packlane, Freshworks, and ChurnBuster while continuing to work with some of my long-standing SaaS/eCommerce clients as well. Again, I am so grateful to have had some fellow freelance writers support me on different projects, which helped me stay sane. I didn’t surpass my freelance business revenue from last year, but I’m really happy with what I invoiced over the past 12 months.
A huge perk of living in the rural Midwest and working with clients in major metropolitan markets is that the low cost of living here means higher margins for me. The trade-off is that we’re not really close to much and travel takes longer. Pros and cons, just like everything in life.
Other highlights:
Started teaching yoga. I’ve been going to classes for years now, but when a local studio opened up this spring I got the chance to start teaching a morning class of my own. I’m loving it!
Joined the “Friends of the Library” Board in my hometown. So far I’ve gone to a 20-minute meeting and been asked to make cookies for children’s story time. Best Board gig ever? I think so.
Work Travel, Life Travel
2019 was full of travel again. I was in LA twice this year: Once for a fun trip with my husband and our brothers, and once to attend Yellow Conference. Both times I went to Rosie’s dog beach in Long Beach, which is pretty much my favorite place on earth.
In September, Brandon and I went to Colorado to participate in the Fjallraven Classic: A three-day, 25-mile trek through the Rocky Mountains. Despite some training beforehand, it totally kicked our flatland Midwestern asses. Carrying our 30+ pound packs, we ended up walking for 8-9 hours each day (because, well, we were slow.) It was both physically and mentally challenging, but I mean…look at those views. You can’t really complain when you’re looking at these gorgeous landscapes.
The entire trek was so beautiful, and the people we met during the event were the best, cheering us on the whole way. The community this event brings together is incredible and everyone was so kind. I never thought we’d climb a mountain, but it was an amazing experience and I’m glad we did it. A Snickers bar at the summit of the highest peak never tasted so good.
Seattle was one of my most favorite places we visited this year for the first time. Brandon and I spent a few days exploring the city, hiking, eating all the food, and even took the ferry over to sleepy Bainbridge Island. There were so many dogs, the people were great, and we found this city to have a very ‘livable’ feeling to it. My big highlight was having pastries at a little coffee shop on a rainy/foggy day. So relaxing.
We took Brooks north to Racine, Wisconsin not once but TWICE this year on his own little adventures where he got to splash around in Lake Michigan, stay in a hotel, and go to the fancy dog park in the Chicago suburbs on the way back. Clearly he had a very good time.
Other travel highlights:
St. Louis: This is the closest city to us, so we visit it often. In 2019 we had amazing stays at both the Angad Arts Hotel and the newly remodeled Union Station. If you’re in the area, I can’t recommend these hotels enough. Very cool.
Fermilab: I toured the particle accelerator at Fermilab in Batavia, Illinois (and the nerd in me loved it.)
Boston: Brandon took another executive education course this April, this time at MIT. I tagged along and worked remotely from Boston, and we both loved how walkable the city was. Also went to my first baseball game at Fenway Park!
Chicago: I took a couple of trips to Chicago this year both for work and pleasure. I loved getting to check out the Wicker Park neighborhood while I was in town for a 2PM Executive Members dinner and again just about a month ago while we were in town for a sustainable holiday market. This Airbnb and The Robey were both *so* lovely!
Favorite reads
As usual, I put my library card to good use this year. My top five reads were:
How to Change Your Mind by Michael Pollan: Interesting look at psychedelics, the stigma associated with them, and new research that indicates they can be beneficial in new contexts.
The Great Pretender by Susannah Cahalan: I loved Cahalan’s first book Brain on Fire, and after my husband and I saw her speak about her newest book in St. Louis, I was hooked. Quick read with a fascinating look at mental healthcare over the years and one very unique study.
Daisy Jones and the Six by Taylor Jenkins Reid: A fun, easy read with strong characters who are rock star band mates. I can’t wait to see this made into a TV show.
Bitter Brew by William Knoedelseder: If you liked the show Succession, you’ll like this book. It’s the true story of the family behind Anheuser-Busch beer...and it’s a roller coaster.
Lost and Wanted by Nell Freudenberger: This was an oddball fiction choice for me that I just happened to pluck off the shelf at the library. I loved it: Thoughtful and extremely well-written.
Goals for the Year Ahead
A theme for me in 2020 is stepping out of my comfort zone as a freelance writer.
For a long time, I’ve held a very anti-conference/speaking stance because 1) traveling to speak isn’t often a lucrative activity and 2) it takes a lot of time and energy. Public speaking still gives me the nervous sweats, but this year, I want to challenge this point of view.
I’d like to dip my toes in the water by participating in more panels and maybe even doing more speaking/moderation, especially on topics about retail, eCommerce, direct-to-consumer brands, and sustainable fashion.
If that doesn’t pan out, I’m at least going to make an effort to be present at more gatherings where my internet friends/peers are meeting up in person, because I’m finding that those face-to-face meetups are some of my most favorite/impactful experiences for my business.
Did you do a post like this—or do you have an accomplishment from 2019 you’re really proud of? I wanna hear about it. Tweet me @kaleighf.
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