Digital Nomads Travel Tips

How to Convince Your Boss to Let You Work Remotely

If you’re like most of the world and enjoy a steady paycheck but dislike working in an actual office, you may wonder if there’s an option to work remotely. Working remotely would free up your time to travel more and commute less, but how do you get this privilege at your existing job? Check out my tips below on how to become entirely or partially remote.

For the purposes of this article, being “remote” can mean working from a home office (aka a desk and computer) or working from wherever you’re currently living or traveling (for you digital nomads). This advice is geared toward full-time office/cubicle workers.

Evaluate Whether You CAN Do Your Job Remotely

Most office jobs can be done from any location thanks to amazing technology tools like Slack. The first question to ask yourself is – can you actually do your job remotely? For example, if you’re a waitress you probably can’t do any of your duties from home but a nurse might be able to work remotely doing paperwork once a week.

Be Realistic About Your Self-Discpline

Many students struggle to take online-only classes because they don’t have the self-discipline to sit down at a computer and study. Are you that person? If you’re allowed to work remotely, will you actually work? There are a million ways to distract yourself these days and it can be very easy to get off track. If you aren’t the self-disciplined type, no big deal! Just know that working remotely is not for everyone.

Decide On Your Remote Setup

What kind of equipmentwill you need to work remotely? Here are some items to get you started:

  • Laptop and mouse
  • A GOOD computer chair – here’s the one I use
  • External screens – great for laptop and serious spreadsheet users
  • Printer/fax/scanner
  • Awesome Wi-Fi/a secure internet connection/VPN

Consider Your Perfect Workspace

Some people are lucky enough to have the perfect setup – on-demand coffee, fast Wi-Fi, and a peaceful remote workspace. Others are not as lucky and live or work in bustling homes filled with lots of pets/children/loud people who make it hard to concentrate. Be realistic about your ability to work from this space. For example, if you’re on the phone often for your job consider what other noise the caller may hear (i.e. loud kids, neighbors, or dogs). If you need to video-conference with colleagues, where will you do your conferences so your work buddies don’t see your Weird Al poster from 1999?

Check Into Alternative Workspaces

You may not actually want to work from your home or a hotel room, so what other options do you have? Check out some suggestions below.

  • Starbucks, cafes, and coffee shops
  • Local libraries (Remember to be quiet!)
  • Shared workspaces like WeWork

Ask Yourself What You’ll Gain

Ok, so you feel like you can be disciplined enough to actually work. Ask yourself what you’ll gain out of this arrangement. Are you gaining hours of your life back by not commuting? Can you travel easier if you can work in another city? Do you get to see your kids more? Are you trying to save on gas money and have less road rage? Be prepared to answer this question with a good solid answer.

Be Strategic About Asking

You’ll know if it’s not a good time to ask for special permissions to work remotely, either for the company or your boss personally. Set up a formal meeting to discuss this with just your boss so you have time set aside for it. Bring all your plans and answers with you and outline the schedule of when you’d like to do this.

Be Ready to Overcome Your Bosses’ Objections

Most bosses will be hesitant to give you the ability to work remotely, so you’ll want to have a plan in place. If they ask how you’ll work when your hotel Wi-Fi goes out, be prepared to tell them that your phone hotspot is a great subsitute. Run through your plan with a friend and have them ask questions your boss might ask. If you have a remote worker friend or colleague, ask them about some of their challenges.

Start Small!

If you work in an office 5 days a week and you ask to never come to the office again, your boss WILL get nervous. If you prepare them by working remotely in small ways first, they will be much more comfortable with the idea.

Here are some suggestions on small ways to start working remotely:

  • Ask them if you can start working remotely on one day a week such as Fridays, or even just Friday afternoons.
  • Schedule permitting, let them pick the day you work remotely so they feel more in control of the situation.
  • Give them tools to access you – they should have all your phone numbers, your Slack channel info, and a way to get to you easily and quickly.
  • Suggest a trial period – work remotely every Friday for a month and set up a meeting with your boss after the month is up to discuss the new arrangement and their feedback.
  • Never say you’re “working from home” – when you say this, people assume you’re at home watching Netflix because that’s what we associate with home.
  • Show the boss your workspace setup – most bosses immediately picture you sitting on a beach sipping margaritas when you ask to work remotely. Set up your workspace and snap a photo to show them that you have a quiet corner of the office or even a designated room to do your work in.

Accept That Some People are Old-School

You may work for a company that is okay with remote workers, but your boss isn’t. You could work for an old-school type of person who won’t even entertain the idea of you working remotely. They will ask things like “Well how can I show you the plans if you’re not here?” Be ready for those questions. Find software that helps you collaborate without being physically there. FaceTime your boss if need be! You may just need to accept that your old-school boss will take more convincing than your average manager.

Other Tips To Convince Your Boss

Still not convinced that remote work is a good idea? Check out the below tips that have actually worked!

  • Offer daily check-ins – some people like to constantly check in on their employees and if you have a micro-managing boss it will be hard for them to let you work in a different location. If they’d like, set up a call daily to discuss projects, questions, and anything else that may come up.
  • Point to your colleagues who work remotely – if you have any, they can be a great example. “Well Joe records his audio at the office and then finishes his training videos from home, so I’ll do that.” If you can use someone who is a successful remote worker as an example, it will help greatly.
  • Back up your claims of productivity remote work with data. There’s a growing amount of research showing that remote workers are happier and more productive! Be ready to whip those articles to prove it. Find some examples here.
  • Focus on the benefits to the company – will you working remotely free up a desk for someone who needs it more? Can you work more hours since you don’t have to catch the 5 PM train home? The company needs to benefit from this arrangement in some way too and you need to prove it. See an example below.

If I work from home, you’ll be saving the company over $9,000 each year. Studies have shown a 13.5% increase in remote productivity over office-based productivity too!”

-Backed up with real data!

How to Keep Your Remote Status

If you were granted temporary or partial remote status, congrats! Now here’s some tips to keep it.

  • ALWAYS be available – keep your Phone and Slack on, even if you take a lunchtime break to walk your dog or run to the store. Remember that being seen and heard are two different things!
  • Work when you would’ve taken a sick day – if you have a runny nose and not a major sickness, tell your boss you’re feeling sick so you’ll stay home today. Work through your sickness to prove that you CAN work remotely even while “sick at home”.
  • Keep the same work hours – while you may wake up later on remote days, be prepared to keep the same hours. Your colleagues will expect you to be working from 9-5 so you should plan to be available normal hours. If you have an appointment or meeting, put it on your calendar or let them know so they don’t think you’ve taken a Game of Thrones break instead.
  • Always make your boss look good! If you produce the best thing-a-ma-jig ever, your boss is going to look like a ROCKSTAR and way more willing to let you keep working remotely.
  • Be insanely productive – especially if you’re doing a trial run of remote work, keep track of what you’re accomplishing each day


Working remotely is an awesome privilege to have for any job, but it’s not for everyone. Evaluate whether it’s a good fit for you and your career. Follow the steps above to get your remote life started, and let us know in the comments if you come across any issues!

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