How to convince your boss to let you work remotely, written in collaboration with @annieergo

There was a time when full-time employment was synonymous with commutes, cubicles, and industrial coffee makers. Thanks to technology, more Americans are skipping the gas-guzzling commute to work remotely. In 1995, only 9% of U.S. workers telecommuted (Gallup). In 2015 this number was up to 37% of U.S. workers. There are some estimates that suggest that half of the world’s workers will be working remotely by 2020!

Technology tools have encouraged workers  to pack up their computers and work remotely. And not just at the home office or cafe around the corner, but abroad. It is predicted that there will be one billion digital nomads roaming the earth by 2035. For many people pursuing nomadic life, the love of travel is only part of the appeal. For those who live in cities where the cost of living is rising faster than wages, the ability to spend less while traveling more is the ultimate arbitrage.

It is possible to join the ranks of nomadic professionals and keep the job you’re currently working. Even though employers are becoming far more open to teleworking opportunities and flexible schedules, being able to convince your boss to let you work remotely and support your digital nomad dreams can be a tricky and complicated compromise. Unless your company already has employees in similar arrangements, you’ll need to be prepared to make a compelling argument that proves they benefit from supporting your remote work rather than you find employment elsewhere.

Before you try to convince your boss to let you work remotely, here are a few tips to make sure the conversation goes well.

Be Really, Really Good At Your Job

Any negotiation requires leverage, and top employees have considerable bargaining chips. Before you approach your employer, make an honest self-assessment of how you would expect them to react. Are you a top employee that has brought considerable value to the team? Do you have indispensible skills or knowledge that will be highly difficult to replace? Have you proven to be a loyal or tenured employee? If the answers to these questions are yes, more often than not your employer will be willing to at least think through how to accommodate you working remotely. If you do not fit the description, you will have considerably less leverage. Even if your employer does not love the idea, keep in mind that it is expensive and time consuming to recruit, hire, train, and retain new employees. Their perceived downside of you working remotely will be weighed against these costs and operational risks.

Own Your Productivity

If your company does not have remote workers, you’ve just asked them to take a risk in order to accommodate your lifestyle decisions and you’ve asked them to do a bunch of work to figure out how to make it possible. The best way to drive the discussion towards a “yes” is to take initiative, figure out the logistics, and answer the obvious questions. How will you stay in close communication with your team and avoid becoming a blocker? What will your working hours be if in a different timezone? Will you have a reliable, physical place to work where you can access the internet and be productive? How frequently are you able to return to the office if needed, with how much notice, and for how long?

One of the best ways to demonstrate you can be productive is to already have a history of successful teleworking. It does not need to be full-time, but even if you worked remotely a few days a month and have a track record of equal or improved productivity, it will be easy to use this as a way to calm concerns. In the end, it’s up to you to prove that this can be a “Business As Usual” arrangement. By owning research and planning from the beginning, you’re giving a strong indicator that you have the maturity and drive to be both highly productive and easy to work with while remote.

If you don’t have a history of productive remote work, Tim Ferriss recommends a plan in The 4-Hour Workweek: “Use a pre-planned ‘emergency’ like sickness or any personal issue that requires you to take a couple of days out of the office. After doing that, say that you prefer working from home rather than taking vacation days. Now, make these ‘off’ days the most productive ever!” Then, “create a bullet-point list of how much more you achieved outside the office” and “suggest two or three days at home per week as a trial for two weeks, and make them ultra-productive.” He concludes, “Ensure that your days outside of the office are your most productive to date. Show how great you feel with the change in routine, which definitely leads to better work in the future. Be prepared to suggest quitting if the boss refuses. Losing a valuable employee is less appealing to any company than arranging remote work.”

Make Remote an Advantage

There are lots of advantages for a company having a distributed workforce. Are there any additional responsibilities you can take on that are better for your company or team as a whole? Especially if traveling to different time-zones, can you take a lead on after-hours support or emergencies? Can you potentially approach new customers where you are traveling and help expand the business geographically? It’s a big world, and having you remote help makes it smaller.

“One of the golden rules of making someone do a favor for you is not going on about what you will get out of it, but rather letting them know what they’ll be gaining,” writes Elen Veenpere at “Try and think about what your company will gain from letting you have this extra freedom – will you be happier and therefore more productive? Will your time away score you some extra skills or knowledge you can use to benefit the entire team? Will your move help with office space constraints? Will you save the company money?”

Meet Them In the Middle

While the arbitrage of “make my NYC salary while living in Hanoi” is appealing, you can potentially make this a financial win-win for your employer. The reality is, your current compensation considers both your skillset and local cost-of-living. If your cost-of-living is going to change with the remote move, do the math ahead of time and come up with a compensation package you would be willing to continue working for in order to make it appealing for both sides. While reducing your paycheck ideally won’t be your first bargaining chip, it could be the difference maker. Be sure to have an agreement ahead of time that your compensation and benefits will return to its original or increased level if you return home.

If your employer listens to all these reasons, but is still hesitant, offer a trial period to demonstrate how the new arrangement will work. Let them know that if at any point it becomes too much of an inconvenience, you will return home (or quit).

Remember, getting your employer to “yes” is just half the battle. Once you convince your boss to let you work remotely, it is up to you to continue to be a top-notch employee and pave the way for all future digital nomads!

Get How to Become a Digital Nomad on Amazon here:

How to Become a Digital Nomad is a practical, step-by-step guide to living a location independent, digital nomad lifestyle – regardless of your career – while making money and doing the work you love.


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How To Convince Your Boss To Let You Work Remotely