Working Vacation vs Working on Vacation

a woman sitting on the beach with a laptop

There is a big difference between a working vacation and working on vacation. And that’s something I’ve been learning this past year, the hard way. My new job allowed me to work from anywhere in the world and I decided to test it right away with a 3 week trip to Asia.

Now I had already mastered the art of working on vacation. I would wake up and drink my pot of tea while checking email and handling anything that had come up. It might take an hour or two. Then I would go off and enjoy the day, not thinking about work, and over evening cocktails check my email again and respond to any issues.

It worked great — my colleagues were getting responses within a day or less and since I was checking in twice a day nothing was piling up so I felt relaxed and away from work.

Well, as you may already know, working full-time in a vacation destination is a lot more challenging. I would need to put in 6-10 hour days, but also wanted to put in a full day of siteseeing! So of course the first thing to go is sleep.

And that works just fine on a 2 day trip. Not really sustainable for 3 weeks.

I got into a weird schedule. I’d be exhausted and in bed by 8PM, then I’d wake up at 2AM and get straight to work, then try to nap mid-morning and then try to go siteseeing and make the most of my afternoon, which left me falling asleep over an early dinner. Rinse. Repeat.

It didn’t take long for that to get old and for me to try a different approach. I would try to do one or two things a day and if that wasn’t enough, I would plan to return on another trip.

My travel philosophy has always been not cram everything in and wear myself out. “If I like it, I can come back.” But it felt wasteful to be in a cool new city spending most of my time working in a hotel room. And much of what I needed to do was not conducive to coffee shops or bars, so that wasn’t an option.

Now I have figured out for new destinations I either need to either stay longer than a few days or make sure that my stay includes a weekend so I have more time, but I still struggle with finding the right balance.

I’m still a newbie when it comes to working full time while traveling, so would love to hear others’ insight and tips!

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  1. I’m also still figuring out the balance, but when I’m traveling and working, I average about 6 hours of work + 6 hours of sightseeing daily. Throw in some sleep, meals, getting ready and some “necessary routines” (I still like a little me-time and a quick workout) and you’ve got a pretty well-rounded day. That’s enough sightseeing for me to feel like I actually did something and enough work that I can make up the slack either before/after the trip from home.

  2. This is my life, and it’s so so hard. I have spent many a trip where I didn’t leave the hotel for three days because it just wasn’t practical work-wise, which just makes me cranky and resentful, so I’ve put a lot of effort in to finding technical solutions, and managing my own expectations of myself.

    For me:

    • Timing is everything. Figuring out the busiest times of the day/week/month and factoring that into my travel plans has been key.
    • WiFi. I make a point of having internet everywhere I go. This isn’t a solution for everyone, but being able to glance at my email while I’m queuing or in a taxi helps me feel calmer, and like I’m more in control. Otherwise the deluge of email and notifications walking back into the hotel can be life-ruining.
    • Offline mailboxes and scheduling. Being able to get to Inbox Zero on a flight, then scheduling everything to send at a time that’s convenient for me has been a game changer. So much better than having emails come in faster than you can reply.

    And then I try to be reasonable about what I can do. Maybe it’s only 2-3 hours of sightseeing in a day, and I need to stay somewhere longer. But I’ve generally come to terms with the idea that travel is just different when you work remotely, and that 3 hours in a city is better than 0 hours in a city.

  3. I work full time, but also have my own business, so that means when I go on vacation (from my “real” job), I’m still “working” on my business.

    For the past two years, I have gone to Australia for two weeks’ vacation, so I usually sleep between 9pm and 3am, get up and work for 5 hours before my parents get up, and then I have a day to spend with them and do my sightseeing.

    So, it’s 5 hours of work a day, but I do that 7 days a week, essentially giving me a full work week, yet full days to spend with my family.

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