Travel Insights Blog
Travel Insights Blog
After settling into the comfort of working from home — or couch, or even bed — it’s no surprise that young workers aren’t exactly clamoring to get back in the office.
Many of us even entered the workforce remotely, making in-person office culture seem like a relic of the past, like typewriters and fax machines — charming but essentially useless. At the same time, vegetating at home 24/7 has its drawbacks: loneliness, boredom, isolation... the list goes on. It turns out humans just aren’t designed to sit in a little box alone all day.
Luckily, there’s another way: not WFH or RTO, but a secret third thing–remote work with a little travel on the side. For those with gigs that offer a remote or hybrid option, the so-called workcation can provide some much-needed novelty, connection and rejuvenation outside the conventional boundaries of PTO, holiday vacations, and long weekends.
If you’ve ever worked remotely in any capacity, this probably isn’t news. Long before the pandemic, at least since the first laptops hit the market, the dream of working from anywhere and traveling the world has brought us the digital nomad. But today, this dream isn’t just for the lucky or daring few. More and more workers are taking advantage of remote arrangements and abundant wifi to stretch the definition of “work from home”; as @loewhaley put it in a recent TikTok, “home is where the wifi is.”
It’s easy to see why. After years of pandemic travel restrictions, everyone is eager to make up for lost time, and a couple weeks of PTO just isn’t going to cut it. In the US especially, true time off tends to be limited if not totally nonexistent; ironically, the higher up the corporate ladder you climb, the harder it is to go totally off the grid, since you’re expected to join in on key meetings and decisions. If you’re already working while you travel, why not just travel while you work?
With remote work increasingly the norm, many more people can sample the digital nomad lifestyle without having to commit. Before, traveling the world usually meant sacrificing career in one way or another — quitting your job entirely, or at least choosing an industry that lets you move around, whether it’s language teaching, seasonal service work, or fully online work, like the mythical freelance copywriter earning six figures from their laptop.
But post-pandemic, even as many companies push for RTO, remote options look like they’re here to stay, with hybrid coming out on top. Now, anyone with at least a remote day or two a week try it out without fully buying in. Instead of selling off everything you own and bouncing around cheap capitals with a simple visa process and fast wifi, it’s increasingly becoming the norm to shift locations for a week or two — or even just for a long weekend.
Traveling on the boss’s time might seem like a luxury, but in the modern economy, the physical and mental relief that travel can provide is more like a necessity. Obviously, all workers need time off for their health and wellbeing, whether they work in an office, on their couch, or from a laptop in a hammock in Bali. But especially for those of us working from home, a change in location can provide a crucial change of scenery and human interaction. Despite all the perks of working from home — sleeping in, banishing pants from your wardrobe — IRL work culture could provide some much-needed change of scenery and human interaction, without which it becomes all too easy to feel like a brain in a jar, eternally planted in front of a screen in some unspecified location deep in the space-time continuum. Even the most die-hard introvert needs to talk to a real human every once in a while.
Enter the workcation. Travel might not solve all the world’s problems, but it’s a good start for tackling the boredom, isolation and burnout of modern work culture. Below, we’ll dig into some of the practical considerations to keep in mind when planning your own workcation, whether it’s a long weekend upstate or a weeks-long gander around the world.
The first step, of course, is choosing where and when to go. Naturally, this depends on your work arrangement: are you remote or hybrid? While fully remote workers clearly have more flexibility to extend travel time, many hybrid workers are embracing the so-called erosion of the M-F workweek to extend weekend trips from Monday to Friday, days less likely to require in-office attendance.
In terms of timing, consider: are there any particularly slow or busy seasons at your workplace? Common sense suggests planning a trip during a lull in business, so your days can skew a little less work and a little more vacation without raising any eyebrows.
Once you know how much time you have and when you can get away with a little workcation, the next step is to choose a location. Often, workcations come in response to a particular event, like a wedding, which means the timing and location are decided for you. Still, you might take advantage of remote work to extend an already planned trip to explore the area. In this way, remote work can make a long-distance trip possible that just couldn’t happen over a weekend — think, your college best friend’s wedding in Australia.
In the absence of any particular event, you could always plan your trip around a visit to friends or family. This can be a great way to connect with college or high school friends who ended up in different cities. Since you’ll be working while you’re there, it takes a bit of the pressure of hosting off, so your friends don’t feel like they have to entertain you every minute of the day. On the other hand, visiting friends could mean saving on hotel or rental costs — assuming they have enough space, physically and mentally, to host you.
But don’t limit yourself to preexisting excuses to travel — make your own adventure, drop a pin on the map, and take off. A workcation can be a perfect way to plan a trip that’s never quite made it to the top of the list when vacation time rolls around; explore a new city you’ve always been curious about, check out some cute small towns in your state, or just camp out by the beach for a week or two.
If you’re traveling solo, consider choosing a destination with opportunities to meet locals and fellow travelers — spots with a vibrant local culture, an existing digital nomad community, or both. In the US, besides the obvious coastal contenders, this could be any one of the rapidly expanding mid-size cities like Austin, Denver, Nashville and Portland, which attracted thousands of remote workers leaving New York, L.A., San Francisco and the like during the pandemic. If you’re headed abroad, try checking out a popular travel hub in Mexico like Tulum or Playa del Carmen, a smaller, digital nomad-friendly European city like Lisbon or Prague, or, if you have the time and funds (and aren’t scared of the time difference), you can venture even farther, to Latin America, Asia or Australia.
Unlike a regular vacation, the workcation comes with one extra detail to consider: to tell or not to tell? Depending on the explicit and unstated work culture, sharing your plans with your boss and coworkers might seem like a no-brainer or a no-no. Of course, we recommend following all official guidelines provided to stay out of trouble and maintain positive relationships at work. But seeing as many companies haven’t outlined clear protocol for traveling while WFH — or haven’t created a culture of trust and transparency — the true recommendation would be to weigh all factors carefully, feel out the vibes, and go with your gut.
Taking a so-called “hush trip” could be risky if your travel unexpectedly interferes with your work — a flight delay, for example — or if word gets out in some way. On the other hand, as long as you make sure that your work is completed just as it would be at home, there’s no reason why your employer should have access to your whereabouts at all times — we’re not teens with mom making us share our location anymore.
That said, it’s important to plan ahead so both the “work” and the “vacation” parts of your workcation run smoothly. I asked a friend and seasoned remote worker with several workcations under her belt for some of her tips; here’s what she said.
To avoid any connectivity issues that could put you into a sticky situation — not to mention turn your boss off the idea of the workcation and ruin the fun for everyone — double, triple, and quadruple check the wifi download and upload speed where you’ll be staying. Then, consider extending your connection with a portable WiFi dongle or hotspot to guarantee a strong and fast connection, especially if you’ll be video calling.
Once your wifi is secured, consider bringing along any other essentials for your workstation. Having all your equipment handy will make for a smooth (read: efficient) working experience, so you can maximize your time off the clock without sacrificing productivity. If you’re used to a second monitor, try packing a portable one to keep your workflow up to speed.
Likewise, investing in a good pair of noise-cancellation headphones can be a lifesaver, especially if you’re someone who’s sensitive to sound. That way, you’ll have more flexibility for your work location — you could even try working in the cute local cafe or coworking spot without worrying about distracting talking and music. These might seem like small details, but they add up, helping you get your work done smoothly and efficiently so you have maximum time for the fun stuff.
Now, onto the vacation part. If you’ve never workcationed before, you might worry that you won’t have time to take advantage of the trip. No one wants to spend hard-earned cash on transportation and lodging just to spend all their days holed up in the same room, or even a coworking spot. Luckily, with a little planning, this won’t be an issue.
The buzz of being in a new place will naturally motivate you to get off the couch at the end of the day, go out and explore, so don’t gauge your days by what you normally feel up to at home. Almost guaranteed, you’ll be able to fit much more in one day, just like when you’re actually on vacation. Of course, this can be tiring, but it’s also energizing.
A side note: by planning ahead and finishing up more work before you go, you can free up some extra time during your trip.
Workcation is a great time to practice setting boundaries between work and life. When you’re at home, it’s easy to continue plodding away on a project into the evening hours. To be fair, if it’s that or Netflix, it might not seem like such a big deal. But when you do have much better things to do — things you can only do here and now — force yourself to log off at the end of the work day. As a bonus, it’s a good habit to carry over into your regular WFH life, inviting you to treat your normal life a little more like a workcation.
When planning your time, factor in your work schedule as well as the activities you’d like to do. For example, if the museum is open until 5pm, maybe there are asynchronous tasks you can take care of in the evening to free up a couple hours during your normal work time. Also, take advantage of any time differences to extend your day — instead of dreading an early wake-up or late night on your workplace’s time zone, try to use the extra time in the morning or evening for your vacation activities.
To get to know the local scene, scope out a coworking spot and try to spend at least a few hours there instead of just working in your hotel or apartment. This way, you’re more likely to meet more locals (and fellow travelers), make some friends for your off hours, or at least get some tips for things to do around town.
Another great way to feel like a part of local life, even for a short while, is to frequent the same local spot — no, Starbucks doesn’t count. Scope out a cute cafe near you, and make it a point to stop in at least once a day. That way, you’ll start to see the same people — and be seen, which could make for some fun vacation meet-cutes. If you’re not quite brave enough to strike up a conversation with a stranger, you’ll still get to feel out the local vibe, observe daily habits and rhythms, and generally get a felt sense of life in the place — which, arguably, is the point of traveling.
This one might seem a little strange, but there’s a lot about a place that you can only learn from a trip to the grocery store — eating, shopping and spending habits; store etiquette; cultural demographics. Think about it: the grocery store is the modern market or town square, where people from all walks of life dip in at least once a week to meet their most basic needs. (A farmer’s market is also a great spot to visit, but it doesn’t quite capture the everyday-ness to the same extent as the grocery store.) By seeing the products available and how people shop, you’ll instantly get an intimate peek into the cultural and economic fabric of the place in a way that’s hard to glean from any other place.
A trip to the grocery store might be especially novel when you travel out of the country, but even subtle regional differences are worth the experience. Often, people’s allegiances to their home grocery store are emotionally charged, a sort of shorthand for attachments to place and certain ways of life. If you’ve ever struck up a conversation with a Floridian about Publix, a Texan about Central Market, or a European about Lild, you’ll know what I mean.
Now, onto the vacation part. If you’ve never workcationed before, you might worry that you won’t have time to take advantage of the trip. No one wants to spend hard-earned cash on transportation and lodging just to spend all their days holed up in the same room, or even a coworking spot. Luckily, with a little planning, this won’t be an issue.
Just as with any travel, there’s a lot to think about when it comes to planning the perfect workcation. At the end of the day, though, it’s all about balance — work and vacation, routine and adventure, comfort and novelty… the list goes on. Turns out figuring out workcations is a lot like figuring out life — you just have to keep trying until you find the mix that works for you. So take this advice — or not — and don’t be scared of a little healthy risk. Guaranteed, it will pay off in more ways than just a paycheck.
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