What I Learned in My Year of Freelance

My mousepad at Superhuman, courtesy of Van Horgen

I had a very cool job for six years. And then I quit. That’s scary stuff. I had some money saved and some opportunities lined up, so I took a leap. I had always fantasized about working on my own schedule, spending a couple days a week in my pajamas, and seeing what would happen without a 9-5 grind. In some ways, it was as great as it sounds. In other ways, it was harder than I expected.

I learned a lot, and I would recommend trying it yourself if you’re curious and able to. If you’re interested but can’t cut it in your own life, here are the cliff notes.

1. I Chilled Out

The vision I had of working from home wasn’t actually that far off. I started sleeping in till nine every day. I ate breakfast in pajamas while watching Live with Kelly. My dog and I took a lot more walks. I stopped neglecting my plants. I even lost weight because I had less stress and more time to exercise.

2. I Threw a Lot of Expectations—and Resentment—Out the Window

I used to get annoyed when I was stuck at the airport across the country for work and other people were having fun. Only a constant state of being busy seemed like “real life.” That wasn’t my job’s fault—that sense of constant pressure was coming from within. Once I started freelancing, I occasionally became the person at the beach on Instagram while everyone else was at work—and it ruled. I stopped being jealous and resentful of people who seemed like they were leading more interesting lives, because I realized the risks they’d taken to do that. Even now that I work full time again, I have a much more relaxed and open-ended view of what “adult life” can look like.

3. I Learned to Cook

I used to come home from work, grab a glass of wine and throw something from a box into a pan. Voila. Freezer mac and cheese. Why would I want to work and cook? Once I started spending more time at home, I made friends with my kitchen. Breakfast slowed down, becoming an elaborate smoothie or oatmeal bowl. I started meal planning and trying all kinds of recipes from scratch. I realized that cooking doesn’t have to be a stressful obligation, but can instead be a great way to check out mentally and get in touch with your senses. Now that I work full time again, I still look forward to coming home and spending an hour or so chopping veggies, appreciating the smell of sizzling meat and making my own colorful sauces. Plus I’m so much healthier than I used to be.

4. I Worked Fewer Hours, and They Were My Hours

Before I quit my job, I was incredibly skeptical of bloggers who insisted they work more than people with traditional jobs. But aren’t you still taking pictures of cupcakes in your kitchen, on your own time, in your slippers? Whatever the case for other people may be, I was definitely working less—and working on my own terms. Sometimes I would work from 10-3. Other times I would finish three projects on the weekend and spend Monday with my mom. Working overtime felt less like a drag, because I was getting paid hourly for it.

5. But I Didn’t Necessarily Stress Less

I’ve made it sound like fairy tales and roses so far, but it wasn’t all easy. First, you have to get enough hours to pay for your life when you work freelance. (I mean duh, you knew that.) You also have to plan for the eventuality that you won’t. I had some gangbusters weeks and some dead slow weeks. You also have to make sure you have the right connections to get enough work. Hustling for work becomes part of your work, and adds hours to your day. That said, it’s thrilling to have how much you make be so directly tied to how much you work.

Speaking of Money …  You have to seriously plan ahead. I skimped and saved, not just for slow periods but for taxes. Now that I work full time again it’s amazing to just get a paycheck and not have to immediately hide 1/3 of it from myself for taxes. It’s also amazing to just get a regular paycheck. But I don’t think I would have appreciated that if I hadn’t freelanced for awhile.

6. I Also Didn’t Become Magically Successful at All My Other Creative Ventures

My biggest hope for working freelance was that without a FT job I’d magically write a successful book, pursue new journalistic connections and somehow make money from blogging. Instead, I found I was spending so much time structuring my unstructured life and chasing down security that I put all of these things on the back burner. In fact, it had been easier to put aside time every night to work on a book when I was working full time. Why? When I was getting paid hourly, I almost always prioritized paid work over personal work. Would I rather spend a half an hour working on a 90,000 page book that I’ll probably never show anyone, or making $XX amount of dollars? The latter.

7. That Said, I Did Get A Lot of New Opportunities Once I Put Myself Out There

When you let people know you’re open to collaborate, they do come knocking. I got to start writing for some new publications and partnered with some awesome small businesses for freelance work. I also had to learn to turn down projects that weren’t the right fit, which can be hard to do when you’re young and trying to get as much experience as you can.

8. I Got Lucky

I can’t say my freelance year was typical. I didn’t spend as much time hustling for work as most freelancers do, nor did I scoot around every ad agency in town as a perpetual freelance table nomad. Instead, I wound up spending most of my time at one place, Superhuman. Everyone I found there was a kindred spirit. We all wanted to do great work, both professionally and personally, and really enjoy ourselves while we did it. We called ourselves “outdoor cats,” because we had all taken risks to end up where we were. In January, I took a full time job as Creative Director, because I felt like I’d found my place. Superhuman’s work felt personal for me, because I was so invested in what we were building.

Here’s where I get to the obligatory section about freelance life not providing enough quality time with people. I was lucky enough to get to collaborate with my current co-workers most days, so I never felt very isolated, or like an outsider at new agencies. I imagine that makes freelancing a lot harder.

Everyone’s experience freelancing is different. Mine was wonderful, but I ended up finding a place I liked better than my couch (which is such high praise—love you, couch). If you quit your job and work from your bed every day, more power to you. I will no longer resent you for how fun that looks, cuz I’ve had my turn. I wouldn’t change anything about my year freelancing, because it gave me a new appreciation for work. I never would have known that feeling if I’d never taken time away from the 9-5 world. I was lucky enough to get to do it, and I hope this helped you see what it’s like.