A solopreneur’s guide to working (or not) while on vacation

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should i work on vacation

Do you read those tantalizing stories about other creatives working remotely while traveling the world and wonder if it’s right for you?

Or are you hoping to sneak in a family vacation and you’re on the fence about whether or not to work while on the road?

This has long been an internal debate for me because I travel a lot. (Case in point: we’ve put 25,000 miles/year on our car since 2008.) And I’m not willing to not go places; this is, after all, one of the big perks of creating a flexible career I love.

In fact, I’m writing this from a hotel room in Oklahoma City while I’m here to watch the Women’s College World Series with my best friend.

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But when I was planning the trip, I had some decisions to make:

  • Would I set aside regular time to work while out of town?
  • Realistically, would I really do any work at all?
  • How would I handle client needs while I’m gone?

By answering the following questions, I was able to make the executive decision to vacation from everything but Millo (which I mostly already had planned out before I left anyway).

Feel free to use these to determine the best course of action for you when planning your next getaway.

(PS: Yes, freelancers CAN go on vacation!)

1: Are there any client projects that absolutely need my attention while I’m out of town?

If the answer is yes, you either need to get on it NOW so they don’t need your attention anymore or plan to carve out some time while on your trip for just this project only.

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2: Do I want to work while on vacation?

While I realize some part of everyone is like “heck no!”, almost all of us also have that nagging boss voice in the back of our heads that freaks out at the thought of abandoning our work for any amount of time.

If your boss voice is going to prevent you from enjoying yourself while you’re supposed to be unwinding, scheduling a small portion of time for working may actually help you relax.

3: Do I need to work while on vacation?

If you’re planning on an extended trip, the answer is almost undoubtedly yes.

So for these trips, taking care of these housekeeping items beforehand can make a HUGE difference in your overall happiness while on your journey:

  • Let anyone else traveling with you know before you leave approximately how much time you’ll need to work.
  • Put some thought into what work schedule would make you most productive (every morning for 3 hours, one day all day per week, etc.)
  • Determine, if possible, what local amenities you might need – and where you’ll need to go and how to get there. If this isn’t possible pre-travel, do this first thing when you arrive.

By creating a rough outline of what your work schedule might look like and what you’ll need while working enables both you and your travel companions to be on the same page before you find yourself in a strange land with different expectations of who’s doing what when.

4: Is it realistic to expect to work while on vacation?

Sometimes, your trip is either so short or so jam-packed with activities that while you might be okay with working, it’s just not likely to actually pan out.

For example, if I’m going to be around family for less than one week, I’m probably going to bed well after midnight while getting up before 9am every. single. day. So it’s really not feasible for me to carve out much, if any, work time.

However, if your answer to #3 is yes, you don’t have much choice in the matter or you have to change your travel plans.

5: If a client needs something urgently, how will I handle it?

It’s always important to have a plan in place in case something goes horribly, awfully wrong and your client NEEDS your attention ASAP.

This also can be really tough for some one-person shops.

Whether you bring tools to handle your clients’ potential emergencies or ask a trustworthy peer to cover for you (or tell your client nothing can be done…as we all know, some clients use the terms “emergency” and “ASAP” rather loosely) is your decision to make.

Defining your vacation strategy

Now, after your first few vacations, you start to realize that your answers to these questions tend to be pretty similar and you get a sense for how well you tend to execute your plans of attack.

So when you plan future similar vacations, you can either:

  1. tell your clients you’ll be unavailable from this date to that date, or
  2. explain your abbreviated schedule.

Personally, I’m a “get away from it all” kind of vacationer. (I say as I type this from my hotel room on vacation.) I’m happy to take care of little things, answer questions, and make plans for when I return, but I’m really not good at setting aside regularly-scheduled work time while traveling. However, I make do when necessary.

I’ve also never traveled for long periods of time (i.e. over 2 weeks straight).

But I know several amazing creatives who happily take working vacations with no problem at all.

What type of vacationer are you?

Am I the only crazy fool that skips town scot free after cramming a ton of client work into pre-vacation week?

How do you pull together the self-control to work while the wonders of a new city, country, or continent beckon you to experience them?

Share your tips, ideas, and thoughts in the comments!

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  1. Hi April:

    Thanks for covering this topic. I think that’s one of the best and worst parts of this kind of work. Everyone always brings up how awesome the whole flexibility thing is but I think it’s both a good or bad thing.

    I remember my first ever vacation as a self-employed copywriter. I was a bit anxious that I’d lose clients if I wasn’t open to working at least a little bit. At the same time, it gave me the flexibility to write an entire blog post while on a train to Paris, with my significant other sleeping on my shoulder. That was pretty cool.

    The one thing I would add is that automatic email notifications really come in handy when going on vacations, especially if it’s an email from a new client.

  2. Great advice here April. I can almost always plan far enough in advance that I am able to warn my regular clients and like you I work to wrap up anything that is time critical before I know I will be away. I’ve even gone so far to send a ‘hello …and by the way…” email to some clients several weeks in advance that have spurred them to get a project they had been planning to contact be about going and done before I’d be away.

    1. Yes, I often let my clients know well in advance when I’m leaving, too.
      That way I (usually) don’t have something urgent come up during my vacation.
      Thanks for sharing!

  3. Nice post April. I’ve been working while on vacation for so long now that I’m not sure there’s another way. When I had my own agency it was a requirement, when I ran someone else’s art department it was a matter of control, and now that I’ve been freelancing full time for almost 12 years it’s a no-brainer. I’ve travelled all over the world for anywhere from 1-7 weeks and there’s always something that comes up, especially Italy on longer trips. That said, most of my vacation time tended to fall in July and August when most of my clients were either gone or so slow there was minimal work to concern myself with. Usually a quick email check in the morning and then schedule the time required.

    That said, the last couple of years have seen my biggest clients go bankrupt or retire and it’s caused a definite cut in my finances. Time to step back out of my comfort zone and hunt down some replacements. Add in the time commitment for running a review blog site, tending to my kids, and ensuring the household runs smoothly and there are days when I wonder if it would be easier to go back to the 9-5. Nah!

    1. Hey Gordon,
      I’m with you – 9-5?! Nah! 🙂
      One of the things that’s hardest for me is that I’m often on vacation with family that I don’t see very often, so I don’t want to miss a second with them. (Literally, I just got back from my adopted dad’s 70th birthday party, and I was up from 6:30am – midnight every day because he wakes up super early. So I then would stay up about 1-2 hours after him to check in with business and wind down.)
      So that’s how I got into the “vacation” mode when I’m out and about. But it’s whatever works best for you!
      Thanks for sharing!

  4. Thanks for this very timely article! I’m heading on a family trip next month and have already told my husband that I may need to do some work while we’re gone. One of my clients is a monthly publication that has a set schedule, so if the schedule overlaps with the trip, I’ll have to do my part and meet the deadlines. I planned the trip before I got this client, otherwise I’d have planned around the production schedule. The good news is that we are traveling with the in-laws, so any time that I need to work is really a blessing in disguise. 🙂

    1. Ha! 🙂

      Monthly clients are both wonderful (recurring income) and a bit restricting on a flexible schedule, aren’t they? After having worked so long with a “whatever, whenever I want” attitude, I’ve recently “tied myself down” a bit, too, and at first it was kind of scary to commit to always being available at certain times.

      You’re welcome!

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