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Have to Work on Vacation? Here’s How to Master the Workcation If You’re a Freelancer

If you’re a freelancer or run your own business, working on vacation might seem like a necessary evil. The problem is that when you’re trying to combine the two, neither of them comes out right: the quality of your work suffers, PLUS you don’t get to enjoy a much-needed vacation. And after all, you’ve started working for yourself because you need more flexibility, not less.

Hailey Thomas is joining us today to explain that this doesn’t have to be a lose-lose scenario. Here’s how Hailey plans her work around her vacation, and why working a maximum of 90 minutes a day (and not every day) is the way to go when you’re trying to relax away from home.

Working while on vacation gets a bad wrap. And honestly, I get it. If you’ve ever spent any time in the corporate setting, there’s a very distinct line between work and play; rest and productivity.

Usually, mixing work and pleasure stirs feelings of angst and guilt.

And that mindset is hard to shake loose once you begin the sweet adventure of working for yourself. It’s hard to put on the boss’s hat and indeed create the lifestyle that lets you serve your clients while also helping yourself and your family.

Enough of that, I say! I think pleasure and productivity don’t have to be exclusive anymore! I challenge the idea that work and vacation should always be separate and that you can’t experience both together well.

Today we’re talking about how to flourish while vacationing and working in a way that you won’t leave you feeling guilty, overextended, and exhausted.

But first … how I miserably failed at working while on vacation.

Four months into my VA business, we took a two-week trip to my in-law’s farm for some summer fun. I had been fantasizing about using my newly found freedom as a virtual assistant to travel, and this was just the opportunity to try it out.

I jumped right into the trip without mentioning to my clients that I would be gone for two weeks. I also hadn’t planned ahead and hadn’t taken into account the weak wi-fi and lack of quiet spaces to work. And to top it all off, I was responsible for delivering several pieces of a project about eight days into that trip! I’d set myself up for failure without realizing it!

To say it was painful would be an understatement. It didn’t take long for the frustration and tantrums to mount. I was waking up early trying to get work done (but wasting half of my time trying to figure out internet problems) and staying up late trying to “be fun” with my family.

I was exhausted! And I was driving everyone nuts working late into the day and responding to requests for hikes and ATV rides with, “Hold on, this will just take 10 more minutes!”.

It was a miserable trip. I felt like I missed out on most of the fun, succeeded in making my family very frustrated, and to top it all off, wasn’t able to fully deliver on what I said I would with the client. Ouch!

How to get working on vacation right

After that experience, I was determined to get this right. One of the top reasons for starting my VA business was to enjoy time and location flexibility!

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Now, I do enjoy that flexibility, and I attribute my successful workcations (which include a six-day family trip to Shawnee National Forest, a three day “Friendsgiving” in Indianapolis with my spouse, and several more trips to the farm) to three things: correctly setting expectations, planning how we used our time, and giving myself ramp-up time after returning.

My love for the well-planned workcation doesn’t stop me from acknowledging that NOT EVERY TRIP NEEDS TO BE A WORKCATION. There is terrific ROI (return on investment) in unplugging completely; it’s good for you, your business, and your family! There are a time and place for everything!

Step #1: Set realistic expectations

The hard part about this step is being honest with yourself and sharing out your plans early.

For yourself:

You need to proactively design your workcation to fit your lifestyle and your needs for each trip. Not every trip will have the same purpose, and your job at this step is to take an honest assessment of you and your family’s desires for this outing.

Ask yourself; do I need to unplug entirely during this trip (it’s totally ok if the answer is yes!)?

Who’s going and what’s their capacity for sharing duties like childcare, meal prep/clean up, etc.?

Based on my business and my client load, what kind of work is essential and what can wait? What would “success” look like at the end of this trip? How many hours do I want to work?

Personal example: The next trip we’re planning is part anniversary trip, part family road trip to Michigan. I know I want to be completely unplugged for the first three days (our anniversary celebration days). But after that, I’ll likely work 90 minutes each day. That’s about how many minutes at a time I can focus when it’s nice out! And I can do most of my MUST BE DONE tasks in that time frame. Plus, there are plenty of tasks that take less than 15 minutes to achieve that I can get done in short bursts of work.

With your family:

The goal here is to tell your travel companions your plan to work part of the time.

Work on vacation freelancerPaint a clear picture, give reminders of what you’ll be capable of, and give them permission to call you out when you are doing more than you said you would.

Along with sharing your plan of attack, you’ll want to share how you plan to make things like extra childcare duties more manageable for them.

Share a few local places they can explore like a nearby park. Bring along bubbles or water guns just for this time. Or if your work time will crossover into meal prep or clean up time, plan a few recipes they can quickly make (or grab the number of the nearest pizza place for them). The idea here is to make them feel supported, and not like they are a second thought.

Personal example: My travel companions for this upcoming trip will be my husband, and my three-year-old. I already told my husband of my workcation plans and given him times I’ll likely do that (the first 90 minutes of the day seems to work for us). I also gave him the caveat that I’ll probably also use 30 minutes after our son has gone to sleep to check-in, and he has strict orders to shut my laptop after that!

With your clients:

I tell my clients that I’m going on leave four weeks out and then send reminders two weeks out and a few days before I head out. I’m explicit in my reminders; letting them know three things:

When I’m leaving and returning: I try to add two business days to my trip so I can successfully transition home-more on that later.

How we will communicate: By email or call, on our regular schedule or only if they need something. I also share my expected turn around time.

How work will be completed in my absence: I make sure there are no significant deliverables due while I am out. In the days leading up to the trip, I ask specifically about each milestone/task’s due date and cross check that with each project goal to make sure nothing gets dropped. If there is a crossover, I pass that task off early to a team member or a fellow VA to help out.

Personal example: In this case, I’ve already notified my clients of our upcoming trip at the 4 weeks out point. I’ve specified that I will be out of communication for three days, and then available for limited contact for another four business days. I also shared that I will only be available by email and will have a 24-hour turn around time for communication.

Step #2. If you plan to work on vacation, you have to PLAN your time

Plan your time

Plan out what type of work you’ll be doing each work session. It sounds simple, but I know we’ve all sat down to accomplish a vital task just to waste the first 30 minutes sifting through email.

The more specific and focused you can be during these work times, the more productive you’ll feel and the easier time you’ll have to pull yourself away to go have some fun when you’re done. You’ll be surprised by what you accomplish!

Personal example: I ask myself two questions when I’m trying to be productive with shorter work blocks.

1. What single thing is going to make my client most successful right now?

2. What single thing is going to move my business forward right now?

Usually, the answers to those questions give me enough to do within my small work blocks. Additionally, I tack on 30 minutes for routine items such as invoicing and replying to emails.

Plant your family’s time

As we mentioned above, it’s a good idea to spend some time planning a few simple things for your family to do during your absences. A few fun things for your family to do, such as pool time, nature walks, or special toys gives everyone something fun to look forward to. Everyone stays engaged, and your family doesn’t feel like they are just waiting around for you to be done with work.

Personal example: On our trip to Shawnee National Forest, I bought pancake mix (which I never buy at home) for my son and mother-in-law to make with breakfast. They had a blast trying to create shapes and impress everyone with their culinary skills! They now have a fun memory, and everyone was entertained as I worked up until breakfast.

Step #3. Plan for a successful return

I find that the last step seems like the simplest, but it’s the most difficult one to enforce. Even though I know that I can avoid feeling haggard if I add two business days to my workcation expectations with my clients, I’m still an overachieving people-pleaser (which I know many of us are!).

It’s tempting to jump back in to be of service to our clients and try to be productive. But it’s actually counterproductive! Without some space to decompress and prepare for them, you’ll head back into the full swing feeling like you need a vacation from your vacation!

Personal example: This buffer gives me space to deal with the inevitable “post-trip” chaos without losing my mind. All the unpacking, refilling of the fridge, laundry, happens in the space I was just holding for the fun activities on the trip. I also spend an hour or two making a plan for upcoming client work. And when I do return fully to my clients, I am organized and not harried. A win-win!

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Virtual Assistant
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If you’re a freelancer or run your own business, successfully working while on vacation boils down to planning and giving yourself enough time and space to execute it well.

By setting realistic expectations, making a plan for your time, and giving yourself a buffer for smooth return, you can make mixing work and vacation part of your reality!

Do you have any workcations planned? What do you do to make things successful for all?

Hailey is the head Project Manager & EA at BrainSpace Optimized. She and her team are obsessive about helping tech leaders become more available, generous, and accomplished. Want to get in on that? Get in touch! At home, Hailey is wife to a talented carpenter, mom to one wily toddler and spends her free time reading fiction, traveling and weightlifting.

Gina Horkey

Gina Horkey


Gina Horkey is a married, millennial mama from Minnesota. Additionally, she’s the founder of Horkey HandBook and loves helping others find or become a kickass virtual assistant. Gina’s background includes making a living as a professional writer, an online business marketing consultant and a decade of experience in the financial services industry.

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