Go Ahead, Ask to Work Remotely. (You Won’t Get Fired)

8. Jan. 2024

Group of people working on laptops, laughing

What is the one thing holding you back from working remotely? Are you afraid of what other people might say if you stop living your life the “normal” way? Do the logistics of the decision overwhelm you so much that you find yourself adding it to the “list of things you’ll do one day” instead of taking action? Does your boss’s potential reaction to what you want to ask keep you up at night?

It all boils down to this: fear.

Fear of doing the ‘wrong’ thing. Fear of discomfort. Fear of consequences. Fear of change.

Break out of your comfort zone by joining a work and travel program

This mindset, when applied to any aspect of life, is pretty dangerous. Fear will stop you from pursuing any path that has an unknown outcome (which *ahem* describes most of the paths out there) and keeps you inside the bubble that you’ve created for yourself, or that someone else has created for you. It will make you weigh every last pro and con when making a decision so that in the end, all you are focusing on is the worst-case scenario. Fear is growth-inhibiting, stress-inducing and, most of the time, irrational.

So why are you letting it hold you back from pursuing your dreams of working remotely?

Why, when life is so fleeting, would you stop yourself from living every single day in a way that sets you on fire? Why would you give up the chance to pursue every passion that you’ve been putting off, while making moves in your career?

Working remotely could be the first step you take toward creating your dream life. It allows you to become even more engaged in your work, while taking you outside of the traditional workplace and giving you control over your environment. If the idea of working remotely sounds enticing, or if it’s something that’s been on your mind for awhile, now is the time to take the leap.

First, you’ll need to change your mindset. Though you probably felt a bit of apprehension creeping up again with just the mention of the word ‘change’, you’ll need to turn your fear dial way down and switch on your capacity for hope and opportunity to make this happen successfully. This is not the time to worry about your boss firing you (they won’t) for bringing up the idea of remote work. It’s the time to consider what life could be like if you worked remotely, and fuel yourself with those possibilities.

Think about what remote work can offer you - not only personally but professionally. In addition to an adaptable schedule, you could see increased productivity, better health and you’ll feel so much more happy and fulfilled by your work.

Find your next remote job opportunity here

‍So… how do you start to have the “remote work” conversation?

If you’ve shaken off that fear that we talked about earlier (good riddance!) and are feeling like you’re up to the challenge of talking to your boss about working remotely, there are a few things that you should do to prepare.

‍If you want to start small...

Ease your way into working remotely by beginning with one day a week outside of the office. This small ask is the simplest conversation to have with your employer as it shouldn't noticeably impact your weekly schedule or routine. Even so, you’ll want to make sure that you go into the meeting fully prepared to answer any questions that your boss may have about why you want to work remotely and how it will impact your role. Good news: we’ve already put together some tips and tricks on how to have that conversation.

If you want to consistently work remotely...

If working from home one day a week isn't enough, or you’re already working remotely one day a week and you want to take it to the next level, you may want to ask to work remotely for a week or two at a time. Just think of the joy that would fill your life if you had an extra week of time every month to be around your family. Maybe you're even ready to go fully remote. Working remotely everyday gives you the freedom you’ve been yearning for, and its effectiveness is backed up by some serious stats. For this more intensive conversation with your employer, it is pertinent to create a presentation deck outlining the why, the how and the KPIs that you’re going to track as you test the remote work waters.

‍If you want to go big or go home...

If you’re thinking of taking your job completely remote and want to learn how to work remotely and travel the world, you might want to consider talking to your employer about taking your job on the road. In this situation, you have two options: you can either go out on your own, or look into a work and travel program. These programs will take care of all of the heavy lifting for you, from booking flights to setting you up with accommodations and impressive workspaces, so your boss will have peace of mind. Like the point above, you’ll need to be prepared to walk through every angle of this decision with your boss, so do your research!

If you’re interested in joining Remote Year (we knew we liked you!), we can help you plan the conversation that you’ll need to have with your employer. In fact, we’ve developed an entire process to make sure that your talk goes as smoothly as possible.

Learn how to talk to your boss about working remotely

How to Talk to Your Boss About Working Remotely: A Case Study

Katelyn is currently traveling the world and working remotely with Remote Year Ohana, and she’s just one of the many examples of how preparation and an open mind can turn any conversation with your employer into an opportunity to stand out and advocate for yourself.

"In my journey to pitching Remote Year to my company, I went through three stages,” Katelyn said.

“Stage one is all about proving your worth. Remote Year can be a big ask, particularly if your company doesn't already have remote employees, so being really diligent about showing up every day and doing your best work matters when it comes time for you to bring up Remote Year to your manager.”

“Stage two is all about the lightweight ask. For me, this came in the form of a casual professional development 1:1 I had with my manager. I hadn't created a pitch deck or anything yet - I simply brought up the idea of remote work and asked what he thought about it. That conversation was a casual way to set the tone for a more formal presentation about why Remote Year would be a great option for me and for the company.”

“And last, but certainly not least, stage three is about doing your homework. When I presented my Remote Year pitch to my manager and eventually my company, I felt confident that 99.9% of the questions that would be asked were already researched and answered either in the deck or in my own notes. This preparation showed my team that I was serious about this experience and that I had thought it through from every single angle."

While every professional situation is unique, Katelyn’s three step system worked for her - and now she’s working from places like Cape Town, Lisbon, Buenos Aires, and Mexico City. Don’t worry if you felt a bit of anxiety while reading through Katelyn’s process. We’ll work with you to develop a plan that works for you and your company.

If you’re still worried that your boss will have a bad reaction to you bringing up a remote work agreement, we’re about to blow your mind. In our experience, many employers think more highly of you after you bring up the idea of working remotely.

What Asking to Work Remotely Says About You

You read that right - employers actually respect it when you present them with the idea of working remotely. Remember the fear that we talked about earlier? Set it aside. It’s doubtful that your employer will fire you over asking to work remotely. Here’s what we’ve heard from managers who have had this conversation with their employees:

They see you as a risk-taker

Because you are one! By laying it all on the line and asking your manager about an opportunity to work outside of the office, you show that you are comfortable with challenging the the status quo. You are proving to them that you are not afraid to bring new ideas, and the evidence to back them up, to the table. This kind of attitude is what managers are looking for in employees when they are considering promotions and raises, so having an in-depth conversation with them about working remotely is a great way to stand out.

You show that you are committed to the company

You wouldn’t be setting up time to chat with your boss about testing a new working style if you were considering leaving your position anytime soon. By showing that you are looking for ways to be more productive, while piloting new programs for the organization, you are putting yourself in a position to be recognized as an upcoming leader in the company.

It shows that you are interested in personal and professional growth

Though sales goals and profit margins mean a lot to your manager, they are looking for more than execution from their employees. With their eyes on the horizon, they are also searching for employees who want to better themselves personally and professionally. Remote work supports this growth by encouraging a self-starter mentality and allowing employees to work when they are most productive and inspired. By having a one-on-one talk with your manager about how working remotely can work for you and your team, you are showcasing your passion for personal and professional development and making a name for yourself with the company’s higher-ups.

What Allowing You to Work Remotely Says About Your Employer

Having a conversation with your boss about working remotely will not only reveal to them the type of employee that you are, but will also reveal to you what kind of company you are working for. Their reactions to having the conversation will bring a few things to light and either affirm your decision to work with them, or make you rethink a few things about your future with the organization.

‍They’re forward-thinking

If your company doesn’t have a remote work policy already, and they’re interested in pursuing one after you’ve spoken with them, it shows that they’re open to fresh ideas that come from their team members. They are dedicated to testing out new concepts so that their organization can become more productive, efficient, and remain in-the-know on changes occuring in the workplace or maybe they just know that remote work is the future. That’s the kind of company that’s going to persevere in a world where norms are constantly evolving.

They’re committed to employee development and retention

Going all-in on a remote work trial run shows that your employer values your personal and professional development, and wants you to stick around for the long haul. They’re devoted to helping you move in a direction that will result in better, more creative work done in a productive environment, which can only mean good things for your morale and their bottom line.

‍They trust their employees

Most of all, allowing you to go out on your own and work outside of the office shows that your manager has trust in you. If you have built a close connection and rapport with your boss already, this may not come as a surprise, but for others it can be an indicator of a job well done. If your company takes on the task of implementing a larger-scale remote work policy, it’s an even clearer sign that they’re operating from a healthy, trusting workplace culture.

Working remotely is not an impossible dream. While the fear of talking to your boss, explaining it to your friends and family, or figuring out where in the world you actually want to work can make you want to stop in your tracks, we’ve got your back. This is the first step to finding what could be your most creative, productive, engaged, efficient, happy self. Don’t let it pass you by.

If you feel like your current role isn’t allowing you enough flexibility to live life on your terms, maybe it’s time to look at a remote job board and search for your next opportunity. Life’s too short to hold yourself back from finding your perfect remote job and to take it on the road with a like-minded community of professionals who want to travel the world while working remotely.