There are plenty of benefits to being a full-time employee. Let’s face it, health insurance, paid vacation, and a steady paycheck are all pretty nice. But if you’re burnt out from being stuck in an office—and daydreaming of becoming a digital nomad—how do you keep said benefits and convince your boss to let you make the transition to remote work?

Maybe you’ve seen photos of digital nomads working on a beach in Bali and decided it’s what you want to be doing. Maybe you simply want the freedom to be location independent and work from home, a cafe, or a co-living space in Lisbon. Whatever the reason, you don’t know how to bring up the topic of remote work with your boss and have it go your way. You’re not alone. Many people—including yours truly—have been in this exact position, and luckily succeeded in the transition from office to, well, anyplace.

At the time of this post, I will now have been working remotely full-time for about 2½  years. And the good news is that it’s more possible now to make it happen than ever before. That said, be prepared—it might not be a breeze for you to make the leap from working at the office every day to 100% remote. Although the signs point to the fact that the business world is definitely coming around to working remote, it may still take a herculean effort to convince your boss to let you detach from the office.

We totally get that. As a fully remote team at Anyplace, we believe in the huge benefits gained for both the employer and employee, and want to do what we can to help you make the jump. We’ve put together 6 steps to set yourself up for the remote work conversation, and hopefully, leave the meeting with a smile on your face 😄

Step 1: Build trust & be a kick-ass employee

Trust is the cornerstone when it comes to making the transition from the office to working remote. Trust is immensely important to the success of a business, and trustworthy employees are hard to find. The journey to remote all starts with building trust with your managers and being a kick-ass employee.

Most of the time, it’s better for your employer to hold onto you—someone who knows the ins-and-outs of the company and the job responsibilities—than to hire and train someone completely new. But this is only the case if you bring serious value to the company directly from your work. If you’re not really good at what you do, it will make the remote transition conversation much more difficult. Think about this—if your higher-ups don’t trust you when you work in the office under their watch, it’s highly unlikely they’ll trust you working remote full-time, or especially when traveling as a digital nomad.

Before you set up your remote work meeting, consider these questions:

  • How is your relationship with your direct supervisor?
  • How have your recent performance reviews gone?
  • Have you made any huge blunders? How did you make them right?
  • What kind of positive feedback have you received from management?
  • How is your rapport with your teammates and clients?

If you’re satisfied with your answers and they show you’re an outstanding employee, make mental notes that you can reference for each during the meeting. If the answers seem to work against you, it’s ok—don’t quit on your dream. Instead, use it as an opportunity to identify why you’re not performing up to par and focus on how to make improvements. When you feel confident with your answers to the questions above, you’ll be in a better position to have the remote conversation.

Step 2: Know your “why”

When you walk into your manager’s office and make the request, they’re going to ask for a reason. Not just because they’re curious, but because this change will affect them, your teammates, and potentially your clients. Your reason can be a variety of things, but be clear on what it is. Even if it’s that you want to explore the world or live in a different city than where your office is located. That’s valid.

Getting clear on your motivation will also help you put things into perspective if your boss eventually says no. If they do, is it a deal-breaker for you? It would be fantastic to know for sure beforehand that your boss will give you a resounding yes, but the truth is that not all conversations will be that simple. Know what your backup plan is ahead of time so you don’t get caught off guard if the answer is no.

Step 3: Understand logistics & present solutions

If you want your boss to take your proposal seriously, make sure you’ve got the logistic details worked out before you bring it up. If your office has anything special in place—like a VPN—figure out how you can connect to it from home. How will you handle regular meetings that you have with teammates or clients? Does the company already use Slack or Zoom for communication? Be ready to explain the ways you have planned to overcome conceivable hurdles that could prevent you from working remote. Think about how you currently work at the office and how you can make it successful anywhere.

Step 4: Be ready with research

Be ready to back up your claims about remote work with actual data! Thankfully, you should have zero trouble finding research to support your ask. There is a slew of research proving that both employees and employers benefit from remote working, with more studies/articles coming to the surface every day.

Two big ones to mention: remote work can lead to astonishing productivity and it greatly reduces costs for employers. You can find 15 other solid reasons in this post.

Step 5: Focus on the value it brings the company

This goes along with Step 4. Quick role-play exercise—pretend you are your manager. Someone walks into your office and tells you about this thing they want you to let them do that will make their lives amazing and that doesn’t necessarily bring any value to you or the business… how would you react? Probably not favorably.

As a manager, why should you bother putting in the effort to change the current arrangement if it only benefits one person? We hear that loud and clear. So please, avoid the approach above, because it could go badly. When you bring the idea to your boss, use the research you’ve done to craft a message that shows the value that your move to remote brings them—not you.

For instance, talking points like these:

“Studies have shown a X% boost in remote productivity over office-based productivity”

“If I work from home, it can save the company over $X each year”

“Remote workers are more likely to take ownership of their tasks.”

Again, the goal is to make sure your talking points don’t sound selfish, and on the contrary, make you sound like a team player with the company’s best interests in mind.

Step 6: Start with a trial run

If you’ve never worked remotely before, it’s highly unlikely you’ll be able to propose that starting next week you just don’t come into the office anymore. That’s quite a tall order. Instead, propose something on a smaller scale, like one day remote per week. If you are granted it, make sure that remote workday is your most productive for the week to prove the point that this is better for everyone! Once you’ve established that you’re reliable as a remote worker, attempt to increase the number of days out of the office.

Over time, you’ll be able to prove that you’re better when you’re not in the office and that nothing went wrong without your physical presence. Use the evidence to support your case to go fully remote.

You can make it happen—digital nomadism is within your reach

If you’re coming from a traditional 9-5 office position, convincing your boss to let you go 100% remote could be a feat. But don’t let that discourage you. Big changes take time, and often resistance to an idea isn’t due to someone disagreeing with you, it’s just new and outside of a person’s comfort zone. Be prepared for you talk when it comes to your ability to produce results away from the office; back it with your personal performance to date and oodles of research supporting remote work. Good luck—you got this!


Where to next? Find flexible month-to-month rentals across the globe on Anyplace.

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