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Coping with the Not-So-Freewheeling Life of a Freelancer


April 16, 2018 | Stephen Jackson

How things change. When I was a teacher and I wanted to go on a little trip, I’d call a substitute in advance, save up some money, and do it. After school, I was just done with work, and I got a paid vacation all summer long. I had it made.

After quitting teaching to become a freelance writer, I was suddenly putting in 10-hour days for a fraction of the pay, nowhere near a financial situation to take a vacation (much less a day off), and deeply missing that feeling of just being done for the day. It got rough, and it remained that way for a while. Like many creatives, I’m prone to anxiety, and often found myself worried and uncomfortable most of the day.

I learned how to manage these feelings more than eradicate them, and while I’ve now been working a steady gig on top of freelancing for some time, feelings of dread still come up. But I know I’m not alone. A quick Google search will also tell you you’re not the only one with the self-employment heebie-jeebies (my search bar auto-populated to say “is freelancing good for anxiety disorder”).

“Freelancers worry about so many things. Not having a steady paycheck, not having steady hours, not knowing when to quit, not knowing what jobs to take and what jobs to turn down, not having the expertise in the diversity of fields necessary for your own success,” says Sarah Larkin Birdsong, a licensed mental health counselor who works with developers and freelancers. “All these things can cause a lot of stress.”

So I’m right to worry as much as I do. But Birdsong points out some pretty helpful things we can do to help cope with the inevitable anxiety that comes with a stressful — but after all, pretty cool — job.

Build Your Own Structure

One of the main sources of anxiety for freelancers is the lack of structure associated with the gig. While a office job might be a drag, it does provide a great deal of stability both in terms of schedules and professional support. To combat this, you must think about what an office provides that freelancing doesn’t, and fill those gaps.

“I often recommend that my freelancing clients create that structure artificially,” Birdsong says. “Write out a calendar of your day broken down by the hour. Ironically, this is what people in recovery from substance abuse do. These are baby steps to a highly functioning lifestyle.” She suggests assigning different tasks to specific hours of the day, and moving onto other things as planned.

“With creative endeavors, it’s actually sometimes good to stop when you’re on a roll so you have something you’re excited to come back to,” Birdsong says. She points out that this approach is also successful in tackling all the non-creative endeavors you may not be as excited about, such as bookkeeping or managing your social media outreach.

Freelance Ain’t Free

When I used to sit behind a desk in a classroom going haywire, sometimes I’d dream about my future as a freelancer. I pictured a cross between a Corona ad and an episode of Friends, casually sipping coffee in some cafe as I tapped out witty musings for a variety of publications.

Not really. But I did expect to have a lot more freedom than I was ultimately afforded. And this expectation of being out on the open road is from where some of the stress associated with freelancing is derived. Whenever we picture things to be a certain way and they turn out to be the contrary, it bums us out — it makes it easy to think we’re failing.

“Don’t take this personally. It’s important to realize that freelancing is actually pretty scrappy, that it’s oftentimes a struggle, and that it’s OK to feel stressed out,” Birdsong says. “We seem to have this perspective of what it’s going to be like, maybe because ‘free’ is in the title, but also because we like to glamorize creatives and independents. But, anecdotally, I don’t know anybody who has less stress as a freelancer than they did at a corporate job.”

Basically, work to normalize your stress, since it’s really common to feel the way you do. “Limiting your inner critic or limiting your perfectionism will better serve your ultimately goals. It’s a marathon, not a race,” she says.

…Which Brings Us to Self Care

If you work an office job, it’s possible to have an off week or two and then right the ship. If a project here and there isn’t greatest example of your work, you can continue to improve in the long run, provided you are hitting your larger work goals. But with freelancing, it can often feel like every job is the be-all end-all of your professional existence. This can lead to burnout, and it’s important to understand that working ever-harder isn’t always the best move.

“More and more research is coming out that says daydreaming is fantastic for creativity and that unstructured play is fantastic for creativity,” Birdsong says. “We can get lost into thinking that the more hours we work, the harder we hustle, then the better our product. But that can also mean the opposite. Self-care can actually be the most productive use of our time.”

And while self-care can sometimes mean going hard on your to-do list because it feels good to clear stuff off of it, it can also mean hanging out with your friends, getting exercise, eating healthy foods, and taking more breaks. “And what’s cool is that you are completely authorized to do it. You’re the only person there to say you can’t,” she says. “Start noticing when you’re getting in the way of your own process.”

The idea that one’s inner critic is a profound source of motivation is bullshit. Over the years I’ve learned to work smarter, not harder, and a lot of that has to do with taking care of myself in between nasty, looming deadlines. I can’t think of a single time I dropped the ball as a result, and I wish I had known that when I was first starting out.

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