Naps, Dinner at 4:30 and Other Side Effects of Freelancing Writing

Naps, Dinner at 4:30 and Other Side Effects of Freelancing Writing

It’s 3:52 on a Sunday afternoon.

While I wouldn’t say I’m on vacation, per se, I’m out of town, having traveled for an event. After a rather-too-raucous Saturday evening, I’m hanging out in an Airbnb just minutes away from one of the best beaches in the country.

And guess what? I’m working.

Despite how it sounds, I’m not complaining — or at least, not loudly. I have a full day of non-work-related activities planned for tomorrow, and I haven’t written a word since Thursday night.

But I must admit, when I first envisioned my life as a full-time freelance writer, weekend power hours on way less sleep than I’d like were not part of the fantasy.

And speaking of sleep, this is hardly the first time my schedule has gotten weird.

Freelance writing: It gets weird

I’ve always been a little bit of an insomniac. Whether falling asleep eluded me entirely or 2 a.m. made a silent, unsolicited wakeup call, slumber’s more complicated than it really seems a basic biological function should be.

(I hear they make medication for these problems? I may be in the market.)

So when I transitioned from an office job that required my physical presence for eight hours most days to a fully flexible, self-directed schedule, I was thrilled to say goodbye to anxious nights lying awake, waiting desperately for the Sandman to come take me.

Who cares if I can’t sleep? As long as I meet my deadlines, I can get stuff done whenever the mood strikes me, be it mid-afternoon or in the wee hours of the morning. I can even use tools like Boomerang to answer emails at oddball hours without coming across to clients like the weirdo I truly am — or, at least, not tipping them off any further than my writing already must.

But as it turns out, a structured schedule does more than make office work feasible.

Time is a social tool.

It allows us to do things like eat together at a set mealtime or gather for a yoga class.

And as a freelance writer living on my own, time quickly became all but irrelevant.

Suddenly enabled to fully indulge my insomnia, I ended up with very strange sleeping patterns — say, four hours starting at midnight, followed by a productive pre-sunrise burst and a long, listless day punctuated by a nap or two. This, of course, of course, wreaked havoc on my meal schedule, which became less “schedule” and more “I don’t know, I get hungry sometimes.”

After finding myself standing in the kitchen eating dinner in my PJs at 4 p.m, or calling four heaping mouthfuls of 3 a.m. peanut butter off the spoon breakfast, I started to think I might benefit from some self-imposed structure.

How to maintain structure when you work from home

Listen. I totally get why working remotely is so attractive.

I mean, yoga pants are 100 percent dress-code friendly and you’re never more than three feet from the refrigerator. What could possibly go wrong?

But remote hopefuls might not realize the impact of some of these unintended side effects I’ve mentioned.

Don’t get me wrong: Schedule weirdnesses don’t necessarily have to be a bad thing. It might be healthier to listen to your body’s hunger signals instead of forcing down a meal simply because the clock says noon, for instance.

And as it turns out, sleeping for four-hour blocks rather than eight isn’t unprecedented — or even necessarily unhealthy.

But if you’re trying to maintain relationships with people who are still beholden to a traditional 9-5 schedule, the whenever-you-feel-like-it lifestyle can become a serious obstacle.

Not to mention the fact that when your home is your office, it can be difficult to ever feel like you’re truly off hours — especially for the driven, type-A, color-coded-calendar types who so frequently make good freelancers. I mean, you can always write one more paragraph, right?

Although it may seem like a non-issue in the face of all the benefits of a flexible, self-directed career path, maintaining work-life balance is imperative if you want to stay happy and productive in the long run.

So. How can you avoid the 4 p.m. dinnertime fate?

Here are five ways to add structure and sanity to your life when you work from home.

1. Set and maintain a regularly-scheduled social activity

It might be a standing weekly dinner date, monthly girls’ outing, local trivia night or weekend volunteering — but whatever you do, prioritize creating a regular opportunity to leave your house.

Not only will you actually interact with other humans (imagine!), but you’ll likely refuel and recharge your creative batteries, too.

2. Actually get dressed in the morning

It’s a lot more difficult to turn what would have been an eight-hour workday into a 12-hour, nap-and-Netflix-and-also-some-work day if you’re not sitting in your jammies all day long.

Yes, I know that yoga pants forever sounds like nirvana, but comfort can be a fickle mistress.

Go ahead and throw on some jeans. If anything, you’ll be motivated to finish your workday so you get to take them off again.

3. Partition off a specific place to function as an office

Working from literally anywhere makes it that much more tempting to drag out the laptop when you should be relaxing.

So as extravagant as it may sound to work in bed or while lounging poolside, consider setting up an actual home office — and promise yourself not to work anywhere else.

(OK, at least not very often.)

4. Decide on days off ahead of time, and stick to them

No, you may not answer that client email on Saturday if you decided Saturday is a day off. No, not even if your hiking trip got cancelled because it’s raining.

Sit down, watch a movie, and pretend work doesn’t exist. You’ll be a better creator in the long run if you take the opportunity to turn your brain off.

Want a tip on making this feasible for us workaholics? Do yourself a favor and disallow push notifications for your work email address on your smartphone — or, better yet, disconnect the account altogether.

You can do it. I believe in you.

5. Make good use of a to-do list

This could just be me and my crazy type-A tendencies, but writing tasks down does wonders stop me from passively obsessing over whether or not they’ll actually get done.

Then again, I carry around my planner like a security blanket and write down things I’ve already finished just for the satisfaction of crossing them off. But whatever: It’s a lot cheaper than Prozac.

Hopefully, these tips will help even the most eccentric freelance schedule feel a bit more livable.

Who knows? Maybe if you’re really diligent about maintaining these self-imposed parameters, you’ll come across to non-freelancers as normal.


Filed Under: Freelancing


  • Ty Blade says:

    Hi Jamie.

    Thanks for sharing. I really enjoyed reading. I relate to so much of it, especially the weird sleep schedule. Currently, I’m still a college student. Between writing and studying I’m not even sure what sleep is anymore. Sometimes I close my eyes and I don’t know if I was asleep or just laying there. Not working the traditional 9-5 has given me the chance to expand as in individual though I’m not sure how long I can keep this up before I’ll feel the need for more structure.

    Thanks again

  • Wendy says:

    Who needs a “home job” for a weird schedule? Try working at a bakery when you start at 5-6pm and work until anywhere form 11:30pm-8am depending on orders! That was 15 years ago and I STILL haven’t gotten back to a “regular” schedule. (Of course, there was 11 years at a movie theater, too. Not quite as crazy as baker’s hours, but still not terribly compatible with “lark” habits.)

  • Megan Sharma says:

    Great article, Jamie!

    I did the corporate 9-5 thing for so many years, and I am a creature of habit, so I still follow that timetable fairly loosely.

    I have embraced my 2-year-old daughter as my alarm clock, an actual lunch somewhere around the midpoint of the day, 1 hour in the gym 5 days/week purely as an excuse to read my latest book on the elliptical machine, and retrieving my daughter from daycare as the official end of my workday (until I poke around on my computer more from 8-10 pm).

    We all have our ways of getting things done!

  • Felix Abur says:

    I’m the ultimate insomniac and outlier. But once I married, my wife and daughter keep me to a fairly regular schedule in and out of the home

  • Matt Barton says:

    This is all very true, but I often welcome the schedule weirdness. I tend to be most productive in 2-3 hour bursts, so spacing that throughout the day (and the week) works for me more often than not. Otherwise, totally on board, except for it being so hot here right now that I’d rather not get dressed at all.

  • Jamie, thanks for sharing your experience. I’m contemplating free-lance work, and this will be helpful.

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