I fell in love with freelancing

And I feel kind of guilty about it.

It’s hard for me to admit this, but here goes: I don’t want to return to a full-time job.

I left my salaried position at the end of 2017. It was a decision I fully believed was a grief-fueled whim, one that I’d snap out of sooner or later. I figured I’d eventually return back to a demanding office job, one with a respectable salary and benefits, and that my friends and family would breathe a collective sigh of relief.

Last weekend, I went down a social media rabbit hole. I was feeling nostalgic, and wound up exploring my Instagram story archive, curious to see what I shared online a year ago.

Many of my updates were the sort of vague-posting you might expect from someone who’s at the start of a relationship with promise. I was a month into dating my now-partner, a period in which I spent inordinate amounts of time wondering when would be appropriate to say “I love you.”

(The answer, past Katie, is whenever you’re ready. And don’t worry; it will be well received.)

What I wasn’t expecting to discover were so many posts about another burgeoning relationship: My love affair with freelance work.

I really enjoy freelancing, as it turns out. I’ve embraced the freedom of working from home, running errands on weekdays, and taking regular breaks for walks or other attempts to clear my mind. I’ve been thrilled to discover how beneficial this lifestyle is for my mental health.

As it also turns out, I battle a lot of internal guilt for loving those things. On average, I now work around 35 hours a week. I receive a handful of emails a day. I start my days with a long walk around the neighborhood, read a book or the newspaper with lunch, and take breaks for afternoon errands or snuggles with my dog. I am much less stressed out than I used to be, and actually look forward to the work I get to do.

As someone who’s only known demanding, all-consuming, responsibility-heavy jobs, this new relationship with work feels strange. And as someone who runs a leadership program for women, it feels slightly disingenuous. My happiness as a freelancer has forced me to question some damaging long-held beliefs I had about productivity, money, and worth. If I’m not at least slightly miserable, am I even working?

(The answer, dear Katie, is yes. And I’m sorry it’s taken us so long to figure this out.)

That’s why I was especially grateful to read two well-timed essays this week. First, Livia Gershon defended the freelance lifestyle:

“It’s rare to see public calls for more and better part-time jobs. The fact that there are few news features, think-tank reports or cable TV rants on the topic says a lot about whose ideas get taken seriously, punditry itself being a round-the-clock obsession. Those of us who don’t work that much, or would rather not work as much as we do, are unlikely to number among the weirdly ambitious outliers extolling the modern work ethic in the Sunday press.”

And then there was the transcript of Anne Helen Peterson’s commencement speech at the University of Oregon. This gem was exactly what I needed to hear:

You are not your job. Your job is a part of your life, but it is not an expression of your value. Working hard is not, in itself, good. Not working hard is not, in itself, bad. And if, for whatever reason, you find yourself in a place where you cannot work in a way that society values — you’re disabled, you decide to stay at home, you care for your parents — that does not make you a bad or less worthy person. You might think you already believe this, but you probably don’t.”

Freelancing has offered me the healthiest relationship I’ve ever had with work. And while I think the idea of friends and family worrying about me freelancing is almost entirely in my head, I’m also discovering that I don’t actually care whether people approve of my work decisions.

I realize I’m in a position of privilege; I have no idea if freelance life would be possible if I had significant debts to pay down or children to save for. I sincerely wish more people had the option (or belief in themselves) to work as much as they wanted to, and not as much as society tells them they should.

My decision to leave full-time work may have been a choice fueled by grief, but, as my therapist challenged me last week, it’s possible that grief gave me permission to do things that I’ve always wanted to do. I have always wanted to be a writer, but I convinced myself that life just didn’t work out that way — that I was better suited for the management track, or for solving organizational problems. That’s what other people saw in me, and what I figured I should see in myself.

But I wasn’t happy. I might be good at leading people and projects, but those things don’t fulfill me — at least not in environments that require demanding, yet arbitrary work schedules, or for bosses who push goals that I ultimately have no say or personal investment in.

I am much happier doing work that I believe in, on a schedule that suits my lifestyle, emotional needs, and energy levels. But, like any other job, there are drawbacks and frustrations. The toughest thing so far about freelancing is feeling isolated; I miss the various office outings and camaraderie with coworkers.

So I tried to fix that, too.

For the past few months, I’ve hosted a monthly meetup for a half-dozen female friends who all work remotely and are chasing their own dreams. We all bring food and drinks, talk for hours about our wins and struggles, and share what we’re aiming to accomplish in the weeks ahead. Besides committing to freelancing (and sticking with that A+ partner of mine), hosting these get-togethers has been one of my best decisions of the year so far.

I’ve posted about these meetings on Instagram, and almost every time a handful of people message me, saying things like, “I wish something like that existed where I live!” But here’s the thing: It didn’t exist in St. Pete until we made it happen in St. Pete.

Sometimes you have to make things happen that you want in your life. And sometimes you have to give yourself permission to enjoy those things, especially when they’re different from what other people have or what you’re used to. And sometimes, once you relax into it, those brand new things will represent some of the best decisions you could have made.



Good job, brain

I'm (still) currently reading:Mostly Dead Things” by Kristen Arnett. Wow this story is intriguing, and wow Arnett’s writing is incredible. Also: What a treat to read a novel where the protagonist and narrator is a lesbian! This book has made me realize what a rare perspective that is in literature — or at least in my reading experience.

I’m currently inspired by: My friend Natalia, who’s one of the members of that monthly gathering I mentioned. She’s chasing her dreams of owning a vegan bakery, and doing it with so much passion, grit and purpose. Plus, her creations are delicious. I’m so impressed!

I'm currently aiming to: Set aside dedicated time — at least several hours; ideally, a day — to write each week. This is still very much a goal in progress, but it’s a good one. This book I want to write someday isn’t going to write itself!

Additional resources

  • A friend gave me Marlee Grace’s “How to Not Always Be Working: A Toolkit for Creativity and Radical Self-Care,” and I’ve gotten so much out of it. At just over 100 pages, it’s a short read, but it’s packed with helpful tips and thought-provoking exercises.

  • Hey, maybe there’s something to this whole working less thing: “Figures as different as Charles Dickens, Henri Poincaré, and Ingmar Bergman, working in disparate fields in different times, all shared a passion for their work, a terrific ambition to succeed, and an almost superhuman capacity to focus. Yet when you look closely at their daily lives, they only spent a few hours a day doing what we would recognize as their most important work. The rest of the time, they were hiking mountains, taking naps, going on walks with friends, or just sitting and thinking. Their creativity and productivity, in other words, were not the result of endless hours of toil. Their towering creative achievements result from modest ‘working’ hours.”

  • Need another reason to not work so much? Read this beautiful and heartrending essay about the passage of time.

For your sweet dumb brain

I firmly believe that there are lots of ways to improve your relationship with work that don’t require quitting. One of those (often underutilized) tools is delegation. Delegating tasks can be a win-win situation: It gives you more time to focus on the work that brings you joy, and gives your coworkers a chance to take on more responsibilities or visibility at work.

Choose one day this week to write down everything you did at work. Document all of it — the meetings you attended, the emails you wrote, the conversations you had. Then, using this matrix, see how many of those things fall into the “urgent but not important” category. Chances are, you can delegate some of these tasks, freeing you up for the work that matters. Bonus points if handing those duties off to someone else makes them feel more empowered in the office.

This newsletter is written by Katie Hawkins-Gaar. It’s edited by Rebecca Coates, who’s traveling cross-country with an infant this week. Send thoughts and prayers.