The do's and don'ts of working remotely on vacation

With limited PTO, so many of us find it challenging to maximize our vacation time. For many, working remotely on vacation is an appealing solution, offering up an opportunity to explore new destinations, break out of your routine, and have more adventures without having to leave the comfort of a secure job and salary. However, it’s crucial to understand the legal and logistical aspects to ensure a smooth and successful experience.

The work landscape is constantly evolving, and by 2026, over 40 million Americans are expected to work fully remotely. The idea of combining work with vacation is gaining traction, as social media is filled with images of people working from stunning locations, sharing images of their iced coffee and laptops next to rainforests or beaches.

Key things to keep in mind

More companies are introducing “work from anywhere” (WFA) programs, encouraging employees to explore new places while keeping up with their work responsibilities. That’s not to say working remotely on vacation isn’t without challenges. If your company doesn’t actively promote or support WFA, navigating the logistics can be daunting. Here’s what you need to consider to make your work vacation a success.

Employer policies and communication

You’ll want to present your plans to your employer in a way that makes it easy for them to get on board. Even if your company doesn’t have a formal WFA policy, it’s important to understand their stance and much easier to get their buy-in before you leave. Develop a detailed plan outlining how you will manage your work, maintain communication, and ensure productivity. It can help to get support from other stakeholders such as your managers and team members to create something comprehensive and improve the likelihood of success.

Your plan is less about telling your employer where you are going and more about how you will work, complete tasks, collaborate, and communicate effectively. This shows your employer that you can handle remote work without compromising on your responsibilities. You want to make it clear that you can and will continue to deliver in your role as you work from vacation.

So, your first step is going to be gathering research and building out your business case and presentation…

Technology and cybersecurity

Included in this plan, and your own preparation, will be a breakdown of the technology that you will use to stay productive, engaged and available for communication and collaboration. Many companies already have a tech stack that includes tools like Zoom, Microsoft Teams, Slack, or Google Workspace that will support you in your working vacation.

Cybersecurity is a top priority for most companies, and should be high on your list. You want to be proactive in addressing any concerns here. Some tips to consider include using a VPN to encrypt your internet connection and protect sensitive information, avoiding public WiFi, which is often unsecured, and investing in portable hotspots, a USB Dongle or local SIM cards for privacy. You’ll want to be mindful of your employers IT policies and factor this into your decision making and presentation on how you will succeed while working away.

Legal and visa considerations

It’s crucial to understand the visa and immigration requirements of your destination to avoid legal issues for both yourself and your employer. You want to make it clear to HR that you won’t be exposing the company to danger, or legal risks that could be costly for them. Many people opt for digital nomad visas, offered in 60+ countries, designed to simplify working vacations. These visas often come with specific requirements, such as proof of employment, minimum income thresholds, and health insurance coverage. Be sure to have the requirements set up before applying for your visa for a speedy and successful process.

If you plan to work from a different state within the US, be aware of state-specific laws affecting benefits, wages, and insurance. Once you enter a state, you are often immediately subject to the laws of that state, and this can have huge implications. For example, California mandates overtime pay for employees working more than eight hours a day. Going to a different state can complicate your tax situation and may require additional legal work for your employer. This is why it can be hugely beneficial to be at a company that already offers a WFA program, or where someone has already taken the opportunity to work on vacation. Consider that it may also become obvious that certain places are easier to work from than others, and that’s good to understand.

Staying healthy and keeping safe

You’ll also want to manage and minimize any health and safety risks while working on vacation. In the unlikely case something happens to you, you will want to be covered and cared for. Be sure to set yourself up with adequate insurance before you go, or if you extend last minute you can update your current insurance. Insurance is often a requirement for a digital nomad visa anyway. You can check to see if your employer’s insurance covers you while traveling, although most won’t and it’s strongly recommended you don’t rely on this without thoroughly checking.

Other general considerations, for any travel really, include bringing any necessary medical documents or medications, and researching any required vaccinations before traveling. You don’t want to arrive somewhere for an extended stay only to discover that your usual medication isn’t unavailable. The best way to avoid this scenario is to plan ahead and take excess medication with you. When it comes to your health and safety, you’d rather be over prepared than under prepared.

Your finances & financial planning

The great news about working vacations? You’re getting paid while on vacation! That can work really well for you if you’re somewhere where the cost of living is lower than it is in your hometown. However, that’s not always the case and sometimes you will end up somewhere more expensive.

The local cost of living is definitely something you want to be mindful of, and aware of in advance, so you can budget accordingly. Plus, just being on vacation will expose you to potential additional costs that you don’t have to cover at home, like short-term rentals, health and travel insurance, transportation, and potentially even a coworking space.

There are also many great options to supplement your income like subletting your apartment, home-swapping, or house-sitting that can help pad your budget.

Practical steps to success

1. Do your research. Online blogs, social media, etc. - there’s no shortage of information, such as Remote Work Community.
2. Speak to others. Especially if you have colleagues that have done this.
3. Document your plan. Clearly outline how you’ll manage your workload and be productive.
4. Present to your employer. Make it easy for them to say yes - include potential objections and solutions.
5. Check you will comply with legal and tax requirements.
6. Book health checks, get extra medication and any pre-travel vaccinations.
7. Decide where you will go and book your flight (once approved by your employer, of course).
8. Have fun! Become the person sharing about their working vacation online and inspire others.

This may sound like a lot of work upfront, and it is, but the payoff is huge. The key to your success is in the preparation, communication and simplification - how can you make it easy for them to say yes?

The choice is yours, and the world really is your oyster, in a way it hasn’t been for previous generations. The idea of working vacations is already spreading, and now it’s your turn.

This process doesn’t have to take long, you could be living it up on your work vacation by next month, depending on how much time and care you give to this process.

Photo: Welcome to the Jungle

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