Picture this: a beach breeze, a home office overlooking a sparkling pool, and the perfect balance between work and play. I’m on a family vacation, but before diving into relaxation, I need to finish a few projects. On the plane ride over, I’m hammering out the details of a project brief. By the time I land in Massachusetts, I’m still working—this time on the drive to Cape Cod. I wrap up those last few emails before jumping into the pool for an afternoon swim. It sounds like the perfect scenario, right? Well, balancing remote work and travel is not not as easy as it looks, even for those of us lucky enough to work from home.
Many people dream of a lifestyle that combines flexibility with a steady paycheck. For some, working remotely seemed like the answer. In fact, 59% of people reported that a remote or hybrid work model motivates them, their friends, and their families to travel more. But the digital nomad lifestyle, while ideal in theory, comes with its own challenges.
Before the pandemic, the idea of working remotely was a rarity. In 2019, I was busy preparing my office wardrobe, fully expecting to work in an office. Fast forward to now, remote work is the new norm. My office is a desk in my living room. According to reports from Forbes and Upwork, by 2025, nearly 32.6 million Americans, about 22% of the workforce, will be working remotely. This shift has completely transformed my day-to-day life. I traded the commute for walk to the living room and a blazer jacket for pajama pants. Now share lunch breaks with my partner instead of a coworker. Plus, squeezing in household chores like laundry between meetings? Huge perk!
There is nothing like being in the comfort of my own home. While the benefits far outweigh the cons for me, the question remains: Does working from home mean you can work from anywhere? There are a few things you should consider before packing your bags.
Company Policies
First, company policies vary widely. Depending on your employer, you may only be permitted to work from specific states. While I can work from Illinois (where I live), I’m restricted from working in certain states like North Carolina. Luckily, Massachusetts and Cape Cod are fair game. Before planning your next workcation, check with your HR team to see if you legally can. This is due to the taxes a company pays goes to the state they practice business in. Before learning this information I assumed working remotely meant work from anywhere. Often times it doesn’t.
Wifi issues
Once you secure with the location issue, another thing to consider is the dangers of public WiFi. With the increase of AI there are more security attacks than ever. Unfortunately, connecting your devices to public WiFi at airports and hotels can increase the risk of a breach. My friend Emily works in recruiting for a local law firm. All of the databases she manages consist of private information. For legal reasons she is not allowed to work anywhere except the privacy of her own home. Depending on the industry you work in, remote work and travel might not be permitted.
Even with secure WiFi, unreliable internet can turn a day’s work into a nightmare. Imagine losing half a day’s productivity because of spotty service! When working remotely on the go, be sure to plan your tech setup ahead of time. If you plan on traveling while working remotely, please have all of your technology in place beforehand.
A quite space for meetings
Once you tackle the WiFi problem, there’s another hurdle: meetings. Depending on your company, meetings are often a regular part of your day, including being on camera. While working from a picturesque cafe sounds lovely, the reality is that they’re usually too noisy.
When I started working remotely at a marketing agency, I naively thought taking my first calls from Starbucks was a great idea. Initially, it is fine—I answer emails and organize my calendar. But when the meeting begins, the background noise made it impossible for anyone to hear me. As a new employee, I stress and worry about leaving a bad impression. I stay on mute for the rest of the meeting, but quickly drive home afterwards. While the idea of working from a coffee shop sounds appealing, it’s often more stressful than productive. Now, I only go on Friday afternoons for focus time, when I know I won’t have meetings.
Libraries can be the opposite—too quiet. At my local library, there are designated sections for talking and others where it’s so quiet you can hear a pin drop.It’s a classic Goldilocks situation—only my own home feels “just right” for ideal working conditions.
Overall, I need a quiet space to concentrate on working and meeting with my coworkers and clients. Hotels or shared workspaces like WeWork are the best options for conducting meetings while traveling.
Full time work still means time
And let’s be honest, your work responsibilities don’t magically disappear even though you’re traveling. Balancing remote work and travel is complicated. The reality of juggling a full-time job while exploring new places often limits your sightseeing. Incorporating work into your travel plans can bring flexibility, but you’ll still need to give your job the time and attention it deserves.
Can you travel while working remotely? Yes, but I don’t recommend you turn it into a lifestyle. I could travel full-time with the proper dedication. It’s nice having the option of a change of pace, but realistically, I am seldom away from my home office. Working from home doesn’t change your job responsibilities, and traveling complicates things.
Ultimately, working remotely has granted me more freedom and flexibility than I ever imagined. Whether it’s taking an important call in my sweats or having the ability to work at my Grandma’s house, I’ve found a work-life balance that fits my lifestyle. Remember: a little planning goes a long way when mixing remote work and travel.
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