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.

Pre-Vacation Update

I’m going on vacation TOMORROW, y’all.

Six days at Walt Disney World, six days in Portland, Oregon to celebrate my grandfather’s 90th birthday, and three days of post-travel recovery (resting, restocking groceries, getting over any crud I might catch along the way) at home.

I gave myself the three extra days first because I subscribe to Kelly Conaboy’s It Should Be Vacation + One Or Two Days theory — “after you return from vacation you should have a mandatory one- or two-day period to readjust before you go back to normal life” — and second because I told myself that the one thing I was going to do in 2019 was take two consecutive weeks off.*

(I have not done this in forever. My last vacation was four days long.)

I will not be posting on vacation, so here are some updates before I leave:

  • I went through and blocked out the rest of NEXT BOOK’s plot using the technique I showed you last week, which means I know where I’m going with the draft and all I have to do is use Jami Attenberg’s 1000 Words of Summer (write 1000 words every day between June 17 and July 1) as motivation to finish it up.
  • I also gave NEXT BOOK a title: A COINCIDENCE OF DOORS. I am fighting very hard against the impulse to make the cover look like a door that you open to read the book, because that is not the Trend For Covers These Days and I know I need to put a Dreaming Woman on the front. (I wonder how much it would cost to do one of those covers where it looks like a door with a cutout keyhole that you can see through and then when you open the door you can see the full-color illustration of what’s behind the keyhole. This is also not On Trend, but it would be super-cool.)
  • I’m also fighting very hard against the whole “what if I was able to get this book self-published this year” thing. I want this book to be THE BEST IT CAN BE, not THE FASTEST IT CAN BE. (I’m also thinking about how much money I’m willing to put towards “the best,” but that’s a discussion for another day.)
  • I’ll owe you a financial update while I’m on vacation, so here’s the gist: May was my highest-earning month EVER. I brought in $13,311 in freelancing income and $14.51 in publishing revenue. I also got a $1,337.74 tax refund I wasn’t expecting because it turns out I did my taxes wrong (long story, can tell you when I get back if you want, good to know the IRS keeps an eye out for your mistakes). Current net worth is $116,293.34.
  • However, this vacation is going to cost me roughly $4,500 in unearned freelance income (which is to say that if I weren’t going on vacation and were able to complete my usual schedule of work, I’d earn $4,500 over the next two weeks). This is in addition to the $2,200 budgeted for the Disney trip and the $1,100 budgeted for the family trip. Soooooooooo…. actually, I’m fine with this. Paid time off is great, but I’d rather be a freelancer any day of the week. (Including the vacation days.)

See you all in June! ❤️

*Yes, I did realize that Thursday to Thursday to Thursday is actually two weeks and one day. Bonus!

How to Create the Systems/Structure in Which to Do Your Best Work: Part 1 (of Many)

Last week, I wrote a short post about how we know when we’re doing our best work.

Over the next week (or so), I want to write several posts about how to create the systems and/or structure in which we can do our best work — because although I absolutely agree with the whole “putting your butt in the seat is 90 percent of doing THE WORK” thing, it’s that other 10 percent that can transform THE WORK into your BEST WORK.

(Yes, I know that not all creative work involves a butt in a seat, don’t @ me.)

I’m going to kick this discussion off with something I heard on a recent episode of the Rope Drop Radio podcast, since I currently have Walt Disney World on the brain.

Also, it’s super-relevant.

In Episode 148, Bad Disney Advice, Derek Sasman and Doug McKnight explain why the whole “don’t get your FastPasses 60 days in advance because you don’t know what mood you’ll be in when you visit the parks” thing is terrible advice:

DOUG: I’ll tell you what mood you’re going to be in, in each park, 60 days out. You’re going to be in the Pandora mood, you’re going to be in the Slinky Dog mood, you’re going to be in the Space Mountain mood, what other mood am I missing? Test Track, Soarin’ mood? Come on, folks. Maybe a Frozen mood? I don’t even know you, and I know what mood you’re in when you’re going to walk around the park. But then you’re going to be miserable —

DEREK: Because you’re going to be waiting in line for two hours [without a FastPass].

DOUG: Have fun with that.

I agree with the gist of this — like, most people who visit WDW are going to want to ride one of the big headliner rides, and getting a FastPass in advance will help with that — but I want to look more closely at the word mood.

Because, as anyone who’s ever done a family vacation (or any kind of vacation) knows, you can spend six months thinking about how much fun it’ll be to ride Space Mountain and then, on the day of, you’ll be in the tired mood or the hungover mood or the my feet hurt mood or the if my dear loved one complains or whines one more time I’m going to scream mood.

So what you actually have to plan for, in addition to the FastPass, is how to be in a Space Mountain mood on the day you’re going to ride Space Mountain.*

I’d say “what does this have to do with creating your BEST WORK,” but I’m pretty sure you’ve already put it together. Planning to work on your project at a certain time, getting your butt in that seat, is only half of it.

The other half is doing your best to come to that seat in the right mood.

This is why you see many creative types say things like “I don’t check the news or social media until I’ve completed my work session, because I don’t want to see something that might turn my thoughts away from THE WORK.”

Why Tara K. Shepersky’s writing ritual included an early-morning walk before she sat down at her QWERTY.

Why I don’t do email until 10 a.m.

Those are just some of the systems and structures people put into place to help them do their BEST WORK — but, as this post title suggests, they aren’t the only ones.

We’ll discuss more tomorrow. ❤️

*Take this advice from someone who had Blue Bayou reservations and then ate this nasty Galactic Grill** meal that made her feel so gross that, two hours later, she wasn’t in a Blue Bayou mood. HUGE REGRETS. 

**Do not make the mistake of walking up to the Galactic Grill and thinking “yay, a place with no line!”

On Preparing Your Audience for the Experience They Want to Have

Soooooo… as I hinted last week, I’m going to Walt Disney World this summer.

(Technically, since I’m going at the end of May, it’s this spring. But it’s after Memorial Day so most of us will consider it “summer.”)

At first I thought I liked Disney parks (and other amusement parks) because I liked rides; after I made my first solo trip to Disneyland two years ago I realized that I loved the solo Disney experience.

I am not the first person to discover that exploring the parks on your own can be, to borrow Disney’s favorite word, magical.*

I haven’t visited WDW since I went with my family in high school literally twenty years ago (I was seventeen); it’s changed a lot since then. Unlike Disneyland, which you can do on a morning’s notice, Walt Disney World now invites — if not requires — you to plan your vacation several months in advance.

And they guide you through the process in a way that is — did I use the word magical already? — fascinating.


The first step in the typical WDW vacation planning process is choosing a resort hotel. (This step tends to go hand-in-hand with picking the vacation dates, though it’s kind of a chicken-and-egg thing depending on whether you’re more flexible on dates or more flexible on resorts.)

As of this writing, you have thirty-four resort options. Each with a different theme, a specific price point, and the promise of a certain type of experience.

I picked the Port Orleans Riverside resort (which falls in the middle of the price points) because it promised me the experience of elegance combined with nature; I paid $10 extra per night for a garden-view room, and I am already fantasizing about the walking trails.

Port Orleans Riverside is also one of the quieter resorts (it literally has “quiet pools” that are separate from the big waterslide pool where you take the kids, which is in turn very far away from the hotel rooms), so it also promises the experience of being able to retreat and relax after the excitement of the parks.

And, to ensure I get to fulfill that promise of retreating and relaxing and rejuvenating myself amidst all this elegance and nature, I booked a stay long enough to allow me to enjoy both the parks and the resort.

So Disney makes even more money off my visit.**

Win-win.

Once you take care of that hotel booking, you get to start making dining reservations. You can make these reservations 180 days in advance. This is where the typical vacationer starts heading down one of four paths:

  1. “Nope, we’re bringing our own food into the park” (a perfectly viable option)
  2. “Whatever, we’ll figure it out when we get there” (also viable, but it means you and your traveling party won’t be able to get into any of the most popular restaurants)
  3. “Wow, there are a lot of restaurants, this Be Our Guest place sounds good, let’s just pick that one” (totally acceptable)
  4. “I AM GOING TO LOOK AT EVERY RESTAURANT AND EVERY MENU BEFORE I DECIDE” (that one’s me)

Notice how each person and/or traveling party is beginning to refine the experience they want.

Also pay attention to the way that Disney is providing its guests with entertainment — because a lot of us consider shopping and planning and thinking about where we might like to eat entertainment — a full six months before we set foot on resort property.

This entertainment, in the form of choice-making and experience-refinement, proceeds at regular intervals. At 60 days out, resort guests can begin selecting FastPasses (to get a shorter wait on certain rides). Guests that want the best options can set their alarms to 7 a.m. Eastern on their 60-day mark, so they can book at the first possible moment. All of this is exciting and novel and full of possibility.

And then the customized MagicBands arrive. In a beautiful box, in the mail.

And then it’s close enough to your vacation that you can contact your resort to request the individual room or block of rooms you want, if you’re so far down the mouse hole that you’ve researched individual rooms. (That is also me. I am going to make that call. Apparently they try to honor as many requests as possible.)

And during all of this time you’ve probably been buying special clothes to wear on your trip or thinking about the souvenirs you might buy on your trip or drooling over photos of donuts and Dole Whips on Instagram. Maybe you just rewatched The Princess and the Frog because Port Orleans Riverside is Princess and the Frog-themed and you want to make sure to catch all the visual references. Maybe you’re going to watch James Cameron’s Avatar for the first time because you want to ride Flight of Passage.

Etc.

By the time you make your trip, you’ve already been experiencing your Disney vacation for months.


Sooooo…. what does any of this have to do with our creative work?

This:

That kind of tweet serves four purposes:

  1. It presents an honest depiction of what it takes to draft a novel.
  2. It encourages other writers who might be considering drafting a novel.
  3. It begins to prepare readers for the experience they might get with this particular novel. This is a book for people who know what a tetromino is (or who are willing to look it up).
  4. It gets those readers excited about the possibility of having that experience with this novel.

Not everybody is going to be part of your readership or audience, just like not everybody is going to enjoy a week at a Disney resort.

But for those people who are part of your audience, well… let’s just say that I am currently studying the Disney method of bringing you into the experience months before the experience actually begins.***

Because I know I’ll learn something from it. ❤️

*One of the reasons I like going to Disney parks alone is because it is one of the few experiences that feels like the type of immersive exploration you get to do in video games. If you want to wander down some path and see where it leads, you can. If you want to follow the fastest route to the scariest ride first, you can. If you want to sit and enjoy the sensory detail, you can. (You could do a lot of this at any standard nature path for free, but those tend not to have rides. Or soundtracks. Or detailed walkthroughs with six pages of hints and secrets.)

**Arguably Disney would have made just the same amount of money whether I had booked a four-night stay or a six-night stay; they could have sold those other two nights to someone else, after all.

***Yes, I know that Disney is not the only entity to use this technique. Every author with a cover reveal, every movie with a cast reveal and then a poster reveal and then a trailer, etc. etc. etc. does this. But Disney does it exceptionally well.

Saturday Open Thread

Time to discuss WHATEVER’S ON YOUR MIND.

I’ve got vacation on the brain, first because it’s Spring Break and a lot of people I know are either traveling or getting back from travel or preparing to travel, and second because I just started planning my own vacation for this summer. (More on this next week. It ties into the creative practice, I promise.)

So chat about travel, or… whatever you’d like! ❤️