How to Make a Freelance Sabbatical a Reality

By Jackie Lam January 19th, 2022

Forget the four-day workweek—a ten-month year may be just what you need for a productivity boost.

Michelle Jackson is living proof that such a lifestyle is possible. A freelance personal finance writer and podcaster, Jackson finds that working nonstop throughout the entire year is counterproductive. “Endless focus on work [for 12 full months] is a problem,” she said. Taking periodic breaks, on the other hand, allows her a much-needed respite to regain focus.

So Jackson designed a schedule that works for her needs, wrapping up the bulk of her client work by the beginning of November, then going offline and not engaging in social media or Zoom calls until after the new year.

Ultimately, the flexible schedule pays off. “I end up making more money because I’m refreshed and energized,” she said.

While not all freelancers have the luxury of taking off two full months, particularly during fourth quarter, a freelance sabbatical might be more attainable than you think. Here’s how Jackson and a few other freelancers manage it.

Step 1: Evaluate year-over-year trends

To figure out the best window to take time off, look at trends from past years. Evaluate when your workload and client requests tend to peak, as well as when your pipeline tends to thin out. Then, consider your personal flow—when you’re running out of steam, nearing burnout, and in need of rest. Keeping a simple log of your energy and productivity levels throughout the year can help you track when burnout is on the horizon.

Jackson pauses for the last two months of the year as that’s when her contracts and sponsorships typically taper off. It’s also the time of year she notices her productivity nosediving. To reset during her break from client-facing work, Jackson reviews her goals and thinks deeply about the kinds of projects she wants to tackle, her dream clients, and how much she wants to earn. “I review that information at a pace that’s sustainable,” she said.

“One of my favorite things about freelancing is the way you can flow with natural rhythms.”

Depending on your industry and niche, as well as the types of clients, projects, and publications you write for, your annual trends may look different. Maybe it makes more sense to take a month off in the spring and another in the fall, or a few weeklong retreats strategically scattered throughout the year. Or maybe a lengthy break isn’t in the cards for this year—but it’s something you can plan for next year.

Step 2: Plan according to your personal flow

Work-life balance isn’t a one-and-done deal that you figure out once and becomes set in stone. Instead, it’s a fluid cycle you might work on throughout your career as your needs, challenges, and priorities shift. Carving out time to define what work-life balance looks and feels like to you can help you get closer to reaching it.

“One of my favorite things about freelancing is the way you can flow with natural rhythms—of your body, like when you want to wake up, or with the weather, or with seasons of nature or your life,” said Paulette Perhach, a freelance writer and author who took a three-month backpacking trip to South America to work on the second draft of her book, “Welcome to the Writer’s Life.”

Amanda Castleman, a freelance journalist and founder of the writing academy Write Like a Honey Badger, said she leans into writing retreats to boost her creativity and double-down on goal-setting. During retreats and writing residencies, she tends to work on specific projects like book proposals. Other times, Castleman tries to just drift and daydream. She believes that unstructured time boosts creativity (and studies back her up).

“Breaks give me the energy and inspiration to take steps forward—to launch projects, break into fresh editorial markets, draft award-winning stories, and expand my partnerships with corporate clients,” Castleman said.

Jackson also enjoys a couple of “working retreats” throughout the year, including a week off in the fall when her workload tends to wane. She does more than just relax during this time—she re-evaluates her business strategy to figure out what has and hasn’t been working.

Step 3: Be flexible and have a plan in your back pocket

Ideally, you should plan your time off strategically. But as all freelancers know, workloads can be unpredictable. You might get a monster project at the exact time you wanted to take that weeklong retreat. In this case, you’ve got two options: Embrace flexibility and be willing to change your plans last-minute, or commit to your time off at all costs. If you choose the latter option, you may need to get comfortable turning down work. (A healthy financial cushion is a key part of adopting this mindset.)

On the other hand, a window to take a break might appear unexpectedly. Maybe your managing editor takes a new job elsewhere and there’s a lull in assignments until her role gets filled. Perhaps a major client merges with another company and their content is temporarily put on pause. In these cases, having an idea of a retreat in mind can come in handy.

Perhach, who is also a writing coach and instructor at the writing community A Very Important Meeting, suggested having a rough game plan that you can put into action quickly. “Have a place in mind. For instance, ‘When I need a break, I’m going to go to that cabin by the stream.’ Keep it in your back pocket. You’ll be able to feel when you need it,” she said.

Step 4: Give your clients as much notice as possible

Giving up a full eight weeks of work—and income—requires some serious financial planning and likely some sacrifices. For this reason, a ten-month year might not be a possibility early on in your freelance career or if you’re living paycheck to paycheck.

You’ll also want to keep your client relationships healthy when planning for a sabbatical or long stretch of time off. This ensures you’ll have work to return to when you’re ready. If you’re building significant vacation time into your 2022 schedule, be sure to give your clients as much advance notice as possible.

Castleman emails her corporate and copywriting clients about blackout dates a month in advance, then again two weeks out. “I’ll check in a few days beforehand to tie up any loose ends, then I set my OOO alert and go for it,” she said.

As freelance writers, it’s easy to adopt a scarcity mindset and say “yes” to every single assignment. But this approach isn’t always the best for mental health. Castleman points out that, at the end of the day, business relationships are partnerships. “If you’re financially able to, fire clients who don’t respect your clearly stated boundaries, whether they’re about turnaround times, off-hours availability, or time away,” she said.

Jackson added that the whole point of being in business for yourself is that you don’t have to work for someone else. “Thoughtfully designing a business that serves you best, keeps you happy and healthy, and energizes you means that your clients are getting a happy you 100 percent of the time,” she said—and typically, happy freelancers are productive ones.

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