I started writing this on Friday, July 5th* — which, this year in the US, was a freelancer’s weird murky day between Independence Day and the weekend. Consensus felt mixed on the “long weekend” of it all. On July 3rd, one of my US clients wished everyone a happy holiday weekend. The morning of July 5th, a different US client contacted me to set up an afternoon call. A hurried prospective client in the UK may have shifted focus when I was busy on the 4th, because I never heard from them again.

The last week of the year often feels similar, when I try to step away and stay in my pajamas during the stretch between Christmas and New Years. But It can be hard to create rest when other people are on the job. By default, unless our national calendar says otherwise, we are expected to be “on” and productive.

Being tied to workweeks

Working for myself does create flexibility, but I still sometimes struggle with meshing client and project expectations with my own schedule.

For one thing, I don’t like working Fridays. I feel much better and calmer when I’m not available for meetings and check-ins and deliverables five days a week. 

If a project calls for Friday “on”-ness, it wears me down very quickly. The more Fridays I bend, and the more off hours I field emails and messages, the more I start thinking, “I need a vacation.” 

Now, after wrapping up one of those energy-sucking projects, my head is 1,000% focused on a huge Japan trip that we had luckily already booked for next week (!!!).

Of course, telling current and prospective clients I’m going to be unavailable for two weeks can feel a little shaky. Practically speaking, I don’t want to miss out on opportunities and income because I’m making myself completely unavailable for a little chunk of time.

Luckily, though, folks are often really supportive about planned time away. I think people are starting to better recognize just how important rest and vacations are for wellness. (And, yes, long-term productivity.)

Vacations as a break from stress

Time off resets us to feeling like ourselves again.

Travel, in general, is fun and enriching, though I do categorize travel and vacations differently. Here I’m talking about a relaxing, brain-shutdown, forget-about-real-life vacation. Can some trips incorporate both travel and vacation? Sure — in fact, that’s what I plan on doing very soon in Tokyo. Can you take a vacation without going somewhere? I think so, kinda.

Vacations are a mode; a temporary timeframe that you’ve decided to deliberately disengage from responsibilities. Going someplace really helps us emotionally distance ourselves from our stress, but it isn’t required. 

We really do need stretches of time to disconnect from our work selves and reconnect with our own thoughts and feelings, and the important people in our lives. It’s how we create lifelong memories, and how we reframe our thoughts around novel experiences. It’s how we gain renewed perspective before returning to our daily grind.

Vacations exist because of how we define work

Why do we think about vacations the way we do — a week or two each year (don’t laugh at me, Europeans) to take a break and enjoy the fruits of our labor? 

Before humans defined work as a job earning money for a boss, the concept of a vacation probably didn’t need to exist as a contrary, I’m guessing.

For most of humankind, people largely “worked” because they were providing for themselves and their families — by gathering food and supplies, farming, or offering a specific service for trade or money. (Or because they were enslaved, or servants.) For our ancestors, the work was finished when it was finished, not because it was 5pm.

Taking a declared break became more popular as social classes developed, and some groups earned more money to afford leisurely getaways. The term “vacation” emerged in the US to replace the British “holiday” because wealthy New York City industrialists would “vacate” their city homes for upstate nature getaways.

As the middle class emerged, more and more people could take a week each year to pack up the car, schlep the kids out to a lake, and cosplay as a different worry-free version of themselves.

For many people, working hard is the default — and occasionally we get to switch off for a predetermined number of days, subject to the approval of those around us (and subject to our bank accounts). But truthfully, weekends and holidays and annual vacations aren’t enough. And that’s barely even considering that for many other people, breaks and vacations simply aren’t feasible.

Rethinking leisure

Being lucky enough to relax and take a trip is wonderful. But, there is also something very depressing about potentially working miserably each day, with only weekends and vacations and eventual retirement to look forward to. For a lot of people, that’s just how life has to go.

I don’t think we were meant to work 40 hours per week, most weeks of the year. (In fact, I definitely don’t. But I’m lucky!) There’s not much we can do as small cogs in the capitalism machine, based on how this society’s been designed, but what if things were different?

Imagine if real rest were part of your routine

Ideally, maybe we should be able to incorporate more leisure into everyday life, without seeking approval for paid time off or putting up an email autoresponder as a protective barrier.

What if we could weave in and out of work and rest modes as needed? What if, more often, we felt like we could take an afternoon to go kayaking when the weather is perfect, or a morning to sleep in when we feel worn down? Some jobs require specific hours in a specific spot, sure, but what if we had fewer work hours in general?

Vacations could actually be even more enjoyable if we were more rested in general.

Imagine if we didn’t feel like we needed to “earn” a break

What if we never had to get to that point of “I neeeeeeed a vacation”?

What if we stopped thinking about vacations as much-deserved breaks from working hard?

If you work for an organization where you earn paid time off, then technically that time is something earned. But philosophically, breaks shouldn’t necessarily be a reward — everyone deserves rest, consistently.

Imagine if productivity didn’t follow a calendar

Of course, we have practical commitments and constraints, but we don’t experience each workday, work week, or work year the same way. Our energy level changes, our family needs change, our emotional capacity ebbs and flows.

If you’re feeling run down, your commitments and work schedule might not be aligning with what’s best for yourself, right now. Vacations help temporarily, but don’t fix burnout.

What if we could more easily ramp up and ramp down responsibilities based on our season of life? Maybe it’s not a vacation that we need at all, but rather a slower, gentler pace of life.

Small acts of resistance

I suggest a few small ways we might all work to shift how we approach rest and vacation, for the betterment of everyone. Depending on your job, these might work, or not! But some thought starters:

• However you can (without overly burdening other people, yadda yadda), set work boundaries and plan for time you are taking away.

• Encourage other people to use their paid time off. Use yours, too.

• Do not contact coworkers or collaborators while they’re on vacation. Let them enjoy their time not thinking about work. And hopefully they return the favor.

• Do not send emails or messages outside work hours. If someone contacts you outside work hours, unless it’s for real an emergency, don’t answer right away.

• Actually, in general, don’t answer people immediately all the time if you don’t have to. Most things can totally wait a few hours.

• If you work for yourself, think about the work schedule that best fits your life, and try to proactively communicate that ideal schedule with partners and clients to set expectations. (That’s like my “no Fridays” thing, and I could honestly be firmer about it.)

• If you’re into reading about rest or burnout, I’ve now read a bunch of books over the years I can recommend. (Let me know about others!!)

  • Feel Good Productivity — Ali Abdaal

  • Burnout — Emily Nagoski and Amelia Nagoski

  • Niksen: Embracing the Dutch Art of Doing Nothing — Olga Mecking

  • How to Do Nothing: Resisting the Attention Economy — Jenny Odell

  • Time Off: A Practical Guide to Building Your Rest Ethic and Finding Success Without the Stress — John Fitch and Max Frenzel

  • Wintering: The Power of Rest and Retreat in Difficult Times — Katherine May

miscellany

• I’ve badly played a few here and there (thinking of you fondly, Lord of the Rings machine in the Las Vegas Pinball Hall of Fame), but I hadn’t given much thought to how modern pinball machines create unique opportunities for physical/digital gameplay. I spent more time skipping around this two-hour stream of the Iron Maiden: Legacy of the Beast pinball machine than I’d have anticipated.

• And something I’m better at than pinball: the new-yet-classic 2D top-down Zelda game, Echoes of Wisdom! I liked this Nintendo interview that offers a peek into how the creators evolved their ideas for gameplay. It started as Link “copying and pasting objects” from Hyrule in a create-your-own-dungeon setting. That idea evolved into using those mechanics as Princess Zelda, creating magical “echoes” of objects and creatures to solve puzzles and battle meanies.

• The Casa Bonita documentary shows us what happened when Trey Parker and Matt Stone bought, restored, and reimagined the beloved Denver restaurant during Covid. (Side note: before that time, I thought South Park was inventing a fictional Mexican-themed playland.) An interesting part of the movie — and something we can file at the top of “gigs I wish I got to do” — is their soft opening, when they tested their new entertainment and menu with real customers, uncovering creative and operational issues that resulted in some sweet, quick pivots (plus narrative drama in the doc, of course).

• I often can’t share stuff I’ve worked on, but here’s something: my client HSA Store is launching a Learning Center that I helped create as a resource on how to open, use, and get the most out of health savings accounts. For free, no strings attached! (Phase one is for Open Enrollment, with manyyyy more modules to come.) I think HSAs are a rich people secret that a lot of us don’t know much about, so it was a fun challenge for me to simplify complex information and structure it for easy learning. Get those tax breaks!!!