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Can you work from anywhere with a remote job?

Things to consider when working remotely.
September 29, 2022
Oyster Team
Woman working in the countryside

If the thought of reporting to an office five days a week makes you shudder, you aren't alone. Today's workers are increasingly demanding remote work—one of the many changing employee expectations in the modern workforce. Remote work saw a sharp uptick during the COVID-19 pandemic, and it looks like it's here to stay.

It's understandable. If you work remotely, you have greater flexibility on where, when, and how you work. This arrangement also gives you greater flexibility on where you call home. You can pick a city you love to live in or switch locations every few months, seeing the world while making a living.

The good news is that remote jobs are projected to increase in 2023, meaning you'll have more options to choose from.

The bad news? Working remotely doesn't necessarily mean working from anywhere you want. Digital nomads may paint a rosy picture of a globetrotting lifestyle, but their experiences aren't representative of the entire remote work community.

Even if a job is remote, that doesn't necessarily mean you can do it from anywhere in the world. There are practical obstacles, from not being able to enjoy comprehensive employee benefits abroad to time zone differences.

This guide covers some of the key points to consider if you're hoping to work remotely from anywhere in the world, like common challenges and tips for overcoming them.

Can you work remotely from anywhere?

In some cases, yes, you can work from anywhere with a remote job. However, before you start packing your bags, beware that working from anywhere isn't always realistic. Here are some barriers you may face.

Interested in Oyster but want more information about how the platform works? This product overview should help.

Restrictive company policies

While companies are increasingly open to remote work, that doesn't mean they're necessarily open to employees working from anywhere. Some companies may require you to be present in a certain time zone, for example, or within a certain state. Others may require you to be located within the United States.

Insurance and benefits limitations

One reason companies have restrictive location policies is that they don't want to deal with the administrative process of determining how to provide insurance and benefits to people abroad. Alternatively, they may only hire people outside of the U.S. on a work-for-hire basis. Since such freelance contracts don't offer benefits, you’d have to make your own arrangements for benefits like health care and retirement savings.

Tax implications

Another reason some companies may restrict remote work locations is because of variations in employment tax withholding across state lines. Additionally, be aware that if you're an American living and working abroad, you're still obligated to file U.S. taxes. Depending on where you claim residency, if your income exceeds a certain threshold, you may have to pay double taxes—to your country of residence and the U.S.

Operational practicalities

There are also day-to-day hurdles to consider before you jump on the digital nomad bandwagon. For example, time zones are one issue. If you live in Berlin, Germany, and have to be on a call at 4:00 p.m. in New York City, you'll have to dial in at 10:00 p.m. from Berlin. Also, some locations—like remote islands—may not have the internet infrastructure you need for calls and large file transfers.

Do all remote jobs allow you to work from anywhere in the world?

Although remote work presents some challenges, they don't have to be prohibitive. If you're determined to do your job from Tulum one month and Thailand the next, it requires some planning.

First, do your research. When applying for jobs, educate yourself about the company's remote work policies. Do they require you to be in a certain city, state, country, or time zone?

Some types of jobs are more amenable to remote work than others—like affiliate marketing. Here's a roundup of companies with remote work policies, including some international options.

Beyond figuring out whether your current or prospective employer offers remote work from anywhere, verify what benefits you'll get as a far-flung digital nomad. Tools like Oyster make it easier for companies to take care of workers abroad, for example.

Once you've snagged a job that lets you work from anywhere, you still have to take some steps to make your digital nomad life a success:

  • Check local laws: If you're planning to camp out in a foreign country, verify whether you need a visa, both for entry and to stay there long-term. For example, some countries only allow tourists to stay for three to six months.
  • Invest in your equipment: Make sure you have the tools you need to work abroad, like a laptop and VPN. Also, check that wherever you're headed has the infrastructure you need for your job, such as a reliable internet connection.
  • Communicate with your employer: If you're going abroad, clarify expectations in advance. Are there certain times when you should be online? How will you communicate with your team or your manager? Being transparent about your work-from-anywhere plans will make your life easier in the big picture.

Clearing these hurdles gets you set up for a life of freedom working from anywhere. While it will take some preparation, that effort will be well worth it once you're sitting in your dream location with your laptop.

Oyster helps companies take care of workers who work from anywhere. Let us help with the hard parts so you can focus on offering employees the environment and experience that helps them do more.

About Oyster

Oyster is a global employment platform designed to enable visionary HR leaders to find, engage, pay, manage, develop, and take care of a thriving distributed workforce. Oyster lets growing companies give valued international team members the experience they deserve, without the usual headaches and expense.

Oyster enables hiring anywhere in the world—with reliable, compliant payroll, and great local benefits and perks.

About the Author

Oyster is a global employment platform designed to enable visionary HR leaders to find, engage, pay, manage, develop, and take care of a thriving distributed workforce.

About the Author

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