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Bleisure Travel: Business In The Front, Leisure In The Back

It’s not exactly a new concept, combining work and pleasure. Quite the opposite, business and pleasure started off together but, with human progress, had to be separated in the name of getting things done and, in some extra pleasure-intensive cases, for the sake of common decency.


However, modern possibilities are opening up new ways to combine work and relaxation. It has been dubbed “bleisure travel” (business + leisure) – and it’s all the rage among professionals who are not entirely tied to a stationary office.


What Is Bleisure Travel?


Before we go on – I am aware of how silly the word “bleisure” sounds. I recently mentioned to someone that I was going to write a blog post about “bleisure” and I could tell that everything I said thereafter was not registering as they wouldn’t stop giggling.

Then again – did I succeed in coming up with a better word? No. *sigh* The term popped up as early as 2009, but the concept didn’t blow up until 2020, when people started realizing that a whole lot of their work can be done remotely. So, I’m using “bleisure” because it has caught on with the general public (as many ridiculous portmanteau words do) – and as a linguist, I bow to that.


OK, back to talking about bleisure with a quasi-straight face…


Simply put, you take your work on the road “digital nomad”-style, except it’s temporary and you just go to a singular destination and work from there.

Owing to the “business” aspect of the trip, bleisure travel is not a vacation. It is better described as getting geographically creative with your work environment. You are moving your office someplace different, fun, and distant from all that is familiar and mundane. So, even though you don’t stop working, the idea is to bring vacation-y elements, accents and possibilities into your work week by transporting your office to a place that excites your senses and – very importantly – lets you do different and fun things with your free time after work.


And, in case you think that it would be daunting to arrange such a combination in practice, you can bet your business flip-flops that hotels are wising up to this trend – and are recalibrating their services to offer both wellness activities and business spaces. And, yes, it can be done on a moderate budget in budget destinations around the world


Is Bleisure Travel For Everybody?


I don’t know of any singular activity in the world that’s “for everybody”, and bleisure travel is no exception. If you really like to keep work and play separate, combining them in a bleisure trip may not be your jam. Then again, when you take your work on the road, you can still technically keep work vs. non-work times strictly separated – it’s really up to how much discipline you can put into it.

Bleisure travel is not exactly something you choose out of all the options: it’s more of a compromise you make with yourself when you can’t interrupt your work to take a proper vacation. While it should not be a substitute for a real vacation, it can bring some re-energizing effects vacations are known for.


It’s also probably a good fit if you’re a total workaholic that must feel “busy” in order to feel alive. For people like that, I’d say bleisure travel may be a gateway baby step toward working their way up to a real vacation.


Professionals most fitted for bleisure travel, in my observation, are:

  • Freelancers. I mean, come on, it’s made for people like us! Chances are, your work is already portable, schedule more flexible than most and you don’t even have a boss whose permission to ask for!

  • Professionals with jobs whose offices are easy to convert into mobile offices. If your work centers around laptop and phone, you can sneak away for a week or two just about anywhere, as long as internet is available.

  • Individuals who are well-organized self-starters (wow, them’s are some big resume-padding words!!) It’s true, though: self-discipline is essential when you’re trying to get work done in a gorgeous and enticing environment. You have to be able to set your own schedule day after day as well as – and this is the challenging part – stay focused and stick to it!


Fun And Productive?? Surely, There’s A Catch?


The only two “catches” are:

  • Being realistic about how much work you actually have at the moment – and if it allows for any leisure

  • Exercising self-discipline about the work plan you set for yourself

You need to be realistic about how much you can get done and how much free time will be left for you to chill. Don’t go on a bleisure trip if you know that you will be working 12-hour days: chances are, you’ll be too exhausted to go out and explore/party, so there isn’t much point to that. It has happened to me, causing frustration and stress – not recommended!!


If you do have the time and decide to go on such a trip, don’t just “wing” your work schedule! Put some thought into it – in accordance with what fun activities are available for you to take advantage of. This really depends on when you’re most mentally active – for some people, it’s the wee hours of the morning, for others, it’s late at night – this is up to you.


(Be warned though, if you spend a whole day on a tropical beach – good luck getting anything productive done afterwards! You may be a night owl who does their best work after the sunset – but a day around the ocean and the blasting sun will completely drain your work energy – and all you are going to be capable of when you get back to your room is take a nap!)

Unlike vacations, when you can decide to blow off your culturally-saturated day plans and just do nothing if the fancy strikes you – blowing off work is not really an option, when you’ve got clients and deadlines looming. And the thing about going to a fun destination is that the temptation to blow everything off goes way up. Hence, being able to stick to your work plan is key.


In case you are wondering if I’m relying purely on my own experiences here – nope! Thanks to my own lifestyle, I’m up to my neck with being surrounded by digital nomads and bleisure travelers – and at least some of them are quite well-paced and productive at it.


A good friend and colleague of mine came down to where I live in Mexico and truly demonstrated the meaning of “work hard/play hard”. She woke up early, took a beach walk, spent the morning and day taking calls with clients and composing legal briefs, then did a work-out and – and by 6 pm, we were out painting the town red. And then, the next day, she would do it all over again.

Now, not all of us can aspire to that level of self-control and stamina, though I certainly admire it greatly in the rare individuals who possess it (did I mention, my friend also brought her teenage son that she managed to get to attend school and do homework from the hotel room every day??)


Personally, I got waaaay too much chronic pain in my life to do tightly-scheduled bleisure trips (or anything) – but I do pretty well on my own terms, if I say so myself. I have an internal little time accountant that just “knows” how much time I need for familiar tasks and shuffles them around my downtime and my pain-time.


It’s all about striking your own balance based on how you operate – it’s a highly individual thing and you should have faith that, whatever others do, the “right” way is simply what works best for you. It might take a few tries to discover the most optimal way to travel "bleisurly", but there’s its own fun – as well as a sense of accomplishment and growth – in the process of getting there.


Some Practical Bleisure Travel Tips


If you decide to take the bleisure plunge, here are just a few considerations to keep in mind.


Make sure you have good internet where you go. It’s just a modern necessity for both business and leisure – unless you’re intentionally going off-grid, which you wouldn’t do on a work trip.


Stick to a singular destination (at least initially) where you can set up your virtual office in your lodging and venture out on day trips in various directions. Work requires some amount of stability, especially if you’re used to having stability when you work. People who try to cover too much ground while also working end up being overwhelmed – and you don’t want to end up miserable and turned off to bleisure just because you went overboard with a demanding travel itinerary.


If you’re someone who needs the structure of a workplace, consider using co-working spaces that are cropping up in pretty much all tourist destinations. I recognize that I’m in the minority for liking to write in the middle of techno raves and other loud ragers. Most normal people, though, prefer at least some semblance of order in their work environment – and bringing your work to a co-working space will signal to your brain that it’s “time to work”, making it easier to focus.


You might want to be discreet about the fact that you are working from not your usual place. It can rattle a client (or boss) a little bit to know what you’re talking/working with them from a foreign country a whole world away. The pandemic has shifted this perception somewhat but remember, most people used to conventional offices associate travel with vacations and vacations with doing nothing. Which could also lead to coworker resentment.


So, take a cue from digital nomads who log into their work accounts through a VPN set to show their location as wherever they’re “expected” to be. And, if you’re talking with clients, it’s best to call them from a number that does not show as “foreign”. This is why Mexico is such a convenient location for US-American digital nomads and bleisure travelers – our US phone plans work there, allowing us to be selective about disclosing our locations.


And speaking of conveniences, mind the time difference when you’re setting up your bleisure travel plans. For example, if you’re trying to talk to clients in New York from Bangkok, that’s a 12-hour difference: this will mess with you big time (unless you are very used to conference calls in the middle of the night – which some people indeed are).


As such, I would not recommend making your bleisure trip to a dramatically different time zone. I would start somewhere without a huge time difference – to be on a similar schedule as your clients and colleagues back home – and to spare yourself the brutal jetlag that comes with flying halfway across the planet.


The Bottom Line


The whole point of going on a bleisure trip is to bring some extra fun and relaxation into your workdays. If, instead, the traveling is causing you stress and endless FOMO (feeling restless wondering what cool stuff you’re missing “out there” as you’re working), it does not make sense to take such a trip -- physically, emotionally and financially. Make a real vacation your top priority – and go on one as soon as it’s feasible.

That said, if you love to travel and bleisure sounds like something you could get into, give it a shot! Try it out when the work stakes are relatively low or when you can reduce your load to part-time for a few days.


We don’t know how well we do in certain settings until we’re there: for all you know, bleisure travel could be a great addition to how you conceptualize and do "work".




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