How to Make a Working Vacation Still Work For You

You may be thinking, ‘wait, why are we talking about working on vacation?’ of course it’s not ideal. But the reality is, sometimes you may have to consider it, especially when a ‘working vacation’ is better than no vacation at all. If you need to work from vacation, it’s possible to reduce the tradeoffs and maximize your enjoyment.

This month, I had a two week childcare gap during an intensely busy season. My first book, Repair with Self-Care: Your Guide to the Mom’s Hierarchy of Needs is launching September 3rd. And I knew, completely checking out for two weeks, would have compromised the book launch. An incredible opportunity I’ve worked on for over two years.

However, I was crispy and desperate for time away. Running a business through economic plot twists, near constant interaction with teachers or specialists for my kids and feeling under resourced through all of it, was draining my natural optimism. Certain things were working but a lot felt broken. I didn’t just want to escape; I wanted to reset.

Choose Your Location Wisely

Vacations don’t always feel restful, there are a lot of logistics before, during and after. Like baby proofing a rental, ensuring older kids have separate space to sleep or navigating multi-generational meal preferences. And then of course, there’s all that packing, laundry and unpacking.

Start with what you need. Do you want respite or adventure? To be in or out of your comfort zone? After years of trying too hard, I wanted to be in an environment where I knew the rules. I also wanted it to be somewhere beautiful and free myself from the relentless weight of household operations. Basically to pause some of my top stressors, which led me back to Barbados.

Pick Themes That Resonate

Okay, it can’t be “every” theme but pick one or two priorities you need to return feeling whole. Family connection, deep rest, or adventurous play are themes that can lead in different directions. If you are partnered, it helps to align on this in advance.

I wanted to be on island speed. Steeped in the rhythm of where my story began, largely to reconnect with family. After losing my father last year, seeing older relatives and walking the streets where my parents grew up, was soothing.

Use Breaks for Clarity

It might seem odd to seek transformation in a familiar place but psychological safety and familiarity enables that for me. It may be completely different for you. However you choose to break with your patterns, give yourself the space for it. I spent a lot of time listening to the ocean and disconnected from technology.

Decide to Rest

How rested do you feel? Right. Sleep deprivation is real and not just for new parents. The intensity of parenting and physical shifts we experience, from postpartum to perimenopause, often lead to sleep disruptions.

Although I knew I’d have to work, I didn’t make any morning commitments during the trip. I wanted to wake up naturally and have the option to fall back asleep. You might feel differently, especially if you seek an active “see new things” type of experience.

Know What you Need a Break From

If you know you will have to do some work on vacation, it helps if you have discretion over what the work looks like. Not everyone does but if you can choose, separate what drains you from what fuels you and if possible, focus on the latter.

I decided to take a break from meetings because I’m heavily scheduled most of the time. You might choose synchronicity over asynchronous work, depending on the nature of what you do. The “live” time is what I find hardest to manage, especially without childcare. So, for two weeks even though I had some work, without meetings, it still felt glorious.

Consider Childcare Coverage

Many parents will seek a sitter, kids club or vacation buddies with kids the same age to keep their children entertained. If you want to enjoy romantic dinners, extra rest, vacation classes or quiet time.

When my son was a baby, we went to Maine for a few days with our nanny at the time. I shifted her schedule so my husband and I could have a couple of dinners on our own and she could enjoy time exploring Maine. If you’re on a working vacation, and have meetings, deadlines or other projects that need focus, you may want to consider some childcare.

Choose Your Work Time

During the Barbados trip, I carved out early mornings to work from the patio before I went running and could see the ocean. It was a nice departure from my faux-home-office, which is really a desk behind a divider in our dining room. It also helped to maintain my usual movement routines, although my runs there were shorter than at home.

Delegate Responsiveness if Possible

Your options for delegation depend a lot on your role and org structure. I introduced a trusted colleague for time sensitive communication from my ‘out of office’ message. We discussed the priorities in advance to keep as much as possible running in my absence.

Before the trip, I gave key clients, my agent, and publisher my mobile number so they could call for anything time sensitive. Although I did scan my inbox once a day, I focused on messages related to the book launch.

Know What Work Fuels You

If possible, minimize the type of work that drains you if you can while you’re away. On this trip, I limited email responses to one hour a day, typically in the early mornings while the rest of the family was asleep. Writing is something I love to do so I continued with my weekly posts and newsletter but paused social media writing. I’m very active on LinkedIn, but it has a certain synchronicity to it. For the business pages, my colleague who handles social media had me review her posts and scheduled them in advance.

Dedicate Family Time

My main themes were family connection and clarity. You might decide to choose rest, revival or learning, depending on your season. In Barbados, we spent afternoons swimming in the ocean. My husband taught the kids to kayak and paddleboard, and it was wonderful to have the screen-free time and presence. I’m looking for ways to replicate this dynamic in our ‘real life’ now that we’re back home.

Like most things, you can choose the flavor of vacation that suits your circumstances. That includes your budget, goals, work needs, desired mindset shifts and overall infrastructure. With intention, structure, support and communication with family, you can emerge from time away feeling like the conditions matched your needs.

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