How to Work Creatively on Family Trips and Vacations

Laura Leavitt is a writer, editor, and teacher in Ohio; she has a pet gecko and likes a good game of Ultimate Frisbee on occasion.

When I went full-time freelance, I assumed that one of the benefits of freelancing would be the ability to spend more time visiting extended family and friends, since I could just “work from wherever.” In reality, working while simultaneously visiting family is… more complicated than I thought.

I’ve heard great things about working while traveling and living that digital nomad life, but it hasn’t worked out so well for my own trips and vacations. I’ve had to figure out when to fit work in and when to just take the day off, even if it hurts my payday. A lot of this effort has to do with figuring out my rhythms, so it may not be the same for you as a creative worker, but finding your own rhythms is probably a skill that you’ll be able to put into practice as well.

Experiment 1: Staying with family and working

My first effort involved visiting my in-laws for a four-day trip, assuming I’d find time to work. I was wildly unrealistic, telling myself, I’ll be able to wake up at 6 a.m., work for two or three hours, and then join the rest of the family for a long and exciting day of family togetherness.

There are many reasons why this didn’t work:

  • This family stays up late. I failed to account for the fact that I’d have to peace out to sleep before the card games and campfire stories really got going. I don’t need to shut the party down every night, but I also didn’t want to be the person who left early to go to bed; it looks too much like I’m sick or unhappy or something.
  • I don’t really want to get up before 6 a.m. and make coffee and start working instantly; I don’t even do this at home. I have managed it a couple of times while traveling (including on this trip) because of deadlines that I couldn’t change, but it wasn’t a smart move. It certainly didn’t help me get into a creative groove.
  • Even if I did wake up early, I wouldn’t get that much quiet time before the rest of the household got up; this family somehow wakes between 7 a.m. and 8 a.m. even after a big night, so I would have very little private time for writing even if I stuck to my schedule. 
  • By making these unrealistic demands on my time, I got impatient and frustrated with every aspect of the rest of the day. This was arguably the worst result: when my family took understandable amounts of time to decide what to do, or ended up lazing around for an afternoon rather than making an ambitious plan, I couldn’t enjoy it with them because I felt “behind” in my work, and all I wanted to do was find a corner where I could work in peace. This was an awful feeling and made me feel like a workaholic… which I was being.

I resolved to do better, but I also accepted a truth for these kinds of trips: I can wake up 30 minutes early or whatever amount of time I need to finish last-minute deadlines, but otherwise, when staying in people’s homes and being offered time to spend with them, I am going to accept that this time is fully allocated for togetherness.

Experiment 2: Staying in a hotel near family and working

We just had a family reunion with a group of relatives that we don’t see that often. Due to the large number of people coming, many of us stayed at a hotel a short drive away from the relatives who were hosting, giving us our own private spaces in addition to the common spaces we shared for most of our meals, game playing, and chat. This trip went so much better than the previous family vacation, partially because I tried not to have super high expectations for how much I was going to work each morning (I aimed for 90 minutes, not three hours), but also because I built a structure that worked for me. 

Here’s how it went:

  • This side of the family had many more young children, so when the parents of the group decided to turn in, I eased myself out of the group early as well. I slept more and better, because I’m just fundamentally not a night owl.
  • I woke early (between 6 and 7 a.m. each day) but didn’t rush anything: if I wanted to go for a swim first, I did that, but if I had a good creative idea first, I did that. I let my husband sleep in and I never made plans with the family until after 10 a.m. 
  • This way, I got at least my 90 minutes of work in during my best brain-hours of the day, but I didn’t pressure myself (while on vacation!) to wake up and instantly work.

While I cannot always stay in a hotel or a separate space from family, it made me realize that if I want to get work done while I’m on a trip, I need my own space. Ideally, this space needs to be completely separate from the family gathering, so I don’t feel like I’m making the whole event “less fun” by sneaking away to work on my laptop.

Experiment 3: Visiting a new city with a friend and working

I also recently took a vacation that was peak vacation/work. My friend and I were on the same page: we wanted to see a new city but we also wanted to make a big dent in big creative projects we were working on. We booked a cheap apartment rental for a week, flew to Austin, Texas, and bought groceries to cook together to keep the costs down. Here’s how we made the trip serve both our work and our vacation goals:

  • We figured out our priorities together: what would make this most relaxing for each of us would be waking up at our own pace, exercising, writing for a block in the morning and a block in the afternoon, eating fresh food, and going to see something inspiring/interesting/creative every day. 
  • We aimed to have around four hours per day devoted to writing, but the rest of the time we went for walks, tried every kind of taco we could find, talked about our projects, watched movies, and went to art museums and local theater performances. 
  • It ended up being a very inexpensive vacation, but four hours a day of work felt great, not like a sacrifice: we’d both chosen to work on our least monetized projects, which meant we were really making a dent in work we otherwise rarely got time to prioritize.

This was my first experience that really felt like being a “digital nomad,” and it was really fun and freeing. While I cannot necessarily implement this method of combining work and play on family trips, it made me realize that, if given the opportunity to exercise my creativity while also seeing new things, I really enjoy balancing work and vacation this way.

All in all, I still have things to learn about avoiding being a workaholic, but I think that you can still prioritize your creative work during trips and vacations if you know what you value, realistically estimate your own bandwidth, and take advantage of having your own space. Knowing how to fit in work during a trip can also help you keep your freelancing goals on track, especially during those times where a family visit is more of a necessity than a vacation. You can’t always “work from wherever,” but you can learn how to turn “wherever” into a place where you can get work done.

Read Laura’s previous guest post on how volunteering helps her creative practice.

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