How to Ask Your Boss to Let You Go Remote and Work From Anywhere

Woman working in cafe. Matehavitally/

While work-from-home jobs became more common during the pandemic, work-from-anywhere and location-independent jobs are still not typical.  According to FlexJobs, about 95% of remote jobs require employees to be based in a specific state, city, region, or country.  If you want to become a digital nomad and transition your current job to work-from-anywhere so you can travel or live in another country, you will need a smart strategy before approaching your boss.  

This article will teach you tips and the secrets of negotiating with your current employer to become a digital nomad and work from anywhere in your country or the world.

Disclaimer: This article is provided for general information purposes only and is not intended to constitute career other professional advice. You should obtain professional advice before taking, or refraining from, any action on the basis of the content in this publication. Deskless Nomad makes no representations, warranties, or guarantees, whether express or implied, that the content in the publication is accurate, complete, or up to date. Please see the full Deskless Nomad Disclaimer

Before You Begin

Check with your Human Resources department to see if your company already has a remote work policy

Your company may already have established guidelines for remote work.  In a Gallup survey, 76% of remote workers said their company will continue to have a policy for at least partially remote work and 27% of remote workers expect their companies to continue allowing fully remote work in the future. If your company already has a remote work policy then check to see if it allows working from anywhere, not just from home.  

Know why your employer may not allow you to work remotely from another country or across state lines

Understanding the issues that complicate work-from-anywhere policies will help you to anticipate the concerns your employer may have and how you can address them.  Here are the key management, legal, and tax concerns your employer may have about work-from-anywhere and remote work in general:

  • Remote worker availability for staff or client meetings during travel or across time zones. TIP: Detail the hours you will make yourself available and your commitment to attending all necessary meetings.
  • Impact on company culture when workers are spread across the world.  TIP: Bring up specific tools that can help facilitate interactions between employees that spark creativity (think beyond zoom and slack).
  • Distractions and decreased productivity. TIP: Bring up stats from Forbes showing remote work can decrease distractions and increase productivity.
  • Required state-specific licenses and certifications that may no longer be valid if you work from another location.  TIP: Check the website for your state licensing board for further information.  Also check the licensing website of any state where you plan to travel.  Call your state licensing board to ask if your license is still applicable if you work while abroad.
  • The legal question of whether or not a worker has the right to live in and work from another country.  Each country has their own laws about rights to work and work permits, even if the employer is based in another country. TIP: Research remote worker visas for your destination(s). One of the many advantages of these visa programs is they allow you to legally live and work in another country for 6 months or more.
  • Paying taxes and social security when the employee is in a country that differs from where their income is sourced.  Even if you stay within the United States, you may encounter different state tax requirements.  Many states tax any income from work performed while in their state.  For example, professional athletes submit tax returns for every state they play in, even if only there for 2 days.  TIP: Consider applying for a remote worker visa since these visas often specifically address tax issues. Make sure to read our tax guide for digital nomads to help you plan ahead.
  • The legal liabilities in the event a work-related accident occurs in another country while the remote worker is performing their duties.
  • If the employer has an obligation to provide employee medical insurance, they may worry the insurance plan won’t provide coverage to an employee working remotely in another country or they may worry about the cost of additional coverage.  TIP: Research travel health insurance for digital nomads and negotiate a stipend for coverage rather than using the company plan.
  • Concerns about corporate data protection and security as employees access sensitive data online from a remote location. TIP: Get a VPN to keep data secure. Talk to your IT department about other security software.
  • How to adhere to foreign labor laws, especially those regarding leave and termination.
  • For many companies, the biggest reason they may not allow workers to work remotely abroad is that some governments may count the presence of employees in their countries as evidence of a Permanent Establishment, a designation that requires the company to pay corporate taxes derived from income made in one country (where the company is located) in another country (where the digital nomad employee is traveling). This could cost the company thousands if not millions of dollars, depending on the size of the company.  Larger companies that already have business entities or branches in countries where remote workers choose to live or travel long term will be less concerned about legal and tax ramifications because they can arrange to employ and pay the worker through the branch in the foreign country.  TIP: Apply for a remote worker visa. With these programs you can work in another country and your employer does not need to register as a local entity or pay local corporate taxes.
Women remote working online. Shellygraphy/


Figure out what you want and know exactly what you are asking for 

Think it through and write it down.  Make sure you are clear and specific.

Do you just want to extend your vacation by a couple of weeks and work remotely from the beach?  Do you want to travel for 2-3 months per year?  Or are you looking to become remote permanently?  More companies may be open to allowing workers to briefly become digital nomads on extended vacations. 

You might not get exactly what you want so try to be flexible and willing to negotiate.  Consider offering to be local for part of the year or doing a trial run/probation period to see if the arrangement works for your employer.

Decide where you will travel

If you plan to travel within your own country, your employer may be more lenient.  If you are traveling within the United States, your employer may still have concerns about you working from multiple states due to tax issues.

Some people who work from home choose to travel and not tell their employers.  The legality and ethics of this decision are beyond the scope of this article.

Create and detail your work plan

Make a list of all duties and activities related to your job to be sure everything can be done remotely.  If there is any question about where the work needs to be done, have a plan you can propose to your boss. Make sure to include the following:

  • The hours you will be available when working remotely
  • Your meetings and how you will participate (Zoom, Skype, etc)
  • How you will communicate with coworkers and clients (instant messaging, daily check-ins)
  • How you will track your work hours and performance (apps like MyHours or Quickbooks Time)
  • What work tools will you need (laptop/tablet, printer, headphones/microphone, camera, internet access, additional software licenses)
  • How you will access the company’s database or website and the tools you will use to keep your company’s data safe (VPN or any security software approved by your IT department)
Woman sitting on carpet working remotely. Surabky/

Approaching Your Boss

Pick the right time 

You will have more negotiating power if you have been in your position for a longer period of time and have had the chance to prove your value to the company.  If you have just started with a company or recently changed positions, you may have more success waiting a few months to approach your boss.

This is an important discussion so don’t approach your boss during a coffee break or social event.  The best time may be during your annual performance review when you will be discussing your productivity and accomplishments.  If you don’t have a review scheduled, then request a personal meeting with your boss.  Never ask over email!

Confidently discuss your strengths

You don’t need to brag or threaten to quit but be prepared to confidently discuss your productivity, past performance reviews, and excellent track record in meeting deadlines and managing your time.   Don’t forget to mention your organizational and communication skills which are essential for successful remote work.

Explain how you will commit to making a work-from-anywhere position successful.  Detail how you will continue to complete your tasks and stay on top of your responsibilities, communicate and check in regularly with clients and coworkers, provide project status updates, maintain constant internet access, and remain available during the company’s working hours even if you are in a vastly different time zone.

List the benefits for your company

This is probably the most important part of your argument.  A company is not going to agree to employees working from anywhere just to be nice.  Your request needs to focus on how it will benefit the company as a whole rather than just you. Be prepared to provide stats and specific examples.  You can draw from your company experiences during the pandemic.  Remote work has many benefits for companies including:

  • Attracting the best talent and retaining valuable employees who value work-from-anywhere flexibility
  • Allowing those on maternity or sick leave to return to work part-time sooner
  • Increasing productivity and improving performance (decreasing commutes and office distractions)
  • Zoom meeting transcripts can be used as notes, making it easier to focus on the conversation
  • Meetings can be easier to schedule without having to factor in commutes
  • Employee wellbeing and improved morale.  Many employers have become more concerned about worker burnout and potential loss of talent during the great resignation.

Suggest a trial or probation period

Propose a remote work trial and discuss what the success of the trial would look like.  You could also consider a first trial where you extend a 2-week vacation with an additional 4-6 weeks working remotely.  

Make sure you over-deliver during the trial: stay active on chat tools, make yourself available, communicate and give regular updates, participate in video meetings and call-ins, and track your tasks and productivity. 

Offer to help develop an official company remote work policy

To avoid appearing as if you are requesting special treatment, show that you are part of a larger cultural movement.  A Gallup survey in September 2021 revealed that 9 in 10 workers wanted to continue working from home.  Of those, 54% would prefer a hybrid work arrangement and 37% wanted to switch to work from home permanently.  3 in 10 remote workers surveyed, said they are extremely likely to seek another job if their company eliminates remote work as an option.  Offer to help to create an ongoing remote work policy that benefits the organization and everyone in the company as this cultural change evolves. 

If your negotiation to work from anywhere is unsuccessful, don’t despair. Times are changing rapidly and it may take a little longer for your company to adapt.  Do your best to understand what your boss’s concerns are, address them, and prepare yourself to try again in the future. If you don’t want to wait or think a future negotiation would still be unsuccessful, there are more and more companies offering remote work positions.  Embrace this as an opportunity to shift your career and check out my article on how to find a work-from-anywhere remote job.

Jamie Dubois

I am a freelance writer, wanderer, kayaker, rock climber, and adventurer.

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