How To Actually Convince Your Boss To Let You Work Remotely

This post is crucial to read for just about anyone. We all have massive roadblocks standing in the way of a life of travel. We have financial responsibilities, apartment leases, and a bevy of other things shackling us to a stationary life. The king of all these responsibilities, however, are obviously our jobs.

Last Friday I gave some advice on how to get your first remote Upwork job, but many of us are completely happy employed where we’re at.

I’m a Digital Nomad, but by no means do I look down on people that choose to stay and make their life in one place.

But, even those who do hunker down want to travel, right?! How do they do it? How do they convince their boss to let them work while traveling at the same time? Maybe some of us even want to incorporate a little bit of that Digital Nomad style into our lives while maintaining a traditional office job.

Let me show you how. Follow these three steps exactly, and you’ll have a chance. Keep in mind these ideas come from The 4-Hour Workweek.

1. Call In Sick

To start, you’re going to call in sick to work one day. The day before you go, install a trial period of GoToMyPC on your office computer so you can connect to it from home.

You’re calling in sick, but you’re still going to work. Sorry.

The point of this is to show your boss how much more you get done at home. Trust me, without the commute, distractions, and meetings, you should be able to increase your productivity a good bit.

Try to figure out what you would need to get stuff done at home. Obviously I don’t know what your line of work is, but I trust you’ll find clever ways to solve that problem.

Leave a trail of emails behind as proof of what you accomplish, and figure out a good way to measure productivity so it’s easy to understand for your boss.

2. Propose A Trial Period

Armed with data from your “sick day,” schedule a meeting with said boss to go over your results. Now, there’s a specific set of key words and phrases to use as you speak with them, which Tim Ferris outlines brilliantly in The Four-Hour Workweek.

But even if you choose not to read the book, it’s not a stretch to imagine the benefits for businesses to allow employees to work remotely. Decreased costs and increased productivity are just a few of the painfully obvious reasons.

To quote my own article on Huffington:

The folks over at Global Workplace Analytics came up with a report regarding this data. They found that businesses could save $11,000 per person per year if they decided to let just half of their employees work remotely.

Office space, office supplies, and work computers are all costs they wouldn’t have to incur.

Cite these things in your meeting, and propose a trial period where you’re allowed to work from home on Monday and Tuesday of every week. Make sure to emphasize the fact that it makes sense on so many levels. If they decline, suggest just one day per week.

3. Expand Remote Time

Now it’s time to get to work. On Monday and Tuesday, blow through everything. Drink twenty cups of coffee. Get up at 6 a.m. Eliminate any distractions at home. You’re on the clock, but you’re also on the clock to prove that allowing remote work is a flat-out good business decision.

You’re essentially doing what you did in step one, just on a larger scale.

Cutting out unnecessary business meetings, office distractions, and commutes should help you out significantly. The funny thing is, you’ll find you actually do get more done. There is so much more time in the day when you don’t have to get dressed and drive to work.

Repeat step two with your boss after the trial period, and attempt to convince him you only need to come in once per week, or better, once every two weeks. By this point if you’re working hard enough, and really benefitting the company, this shouldn’t be too steep of an ask.

4. You See Where This Is Going

If you’ve gotten to this point, congratulations! You’re now working from home most days and have the flexibility to start traveling a bit more because of it. If you’ve found it tough to get to this point, well, you can still try to grab remote work opportunities from Upwork and other sources until you make enough to quit your job.

If you really want more information, you need to read The 4-Hour Workweek. Tim Ferris drives the point home and makes the reader really feel like they can achieve this lifestyle–quick! If you don’t want to fork over the money, I have a few ideas for you in my ebook below. Click on the image to download.

Note: This post contains some affiliate links. If you choose to click through and purchase these products, you’ll be helping me with the costs of running this site at no additional cost to you.




Life in your 20s and beyond. A Medium publication focused on Work, Freelancing, Money and Life Advice.

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Tom Kuegler

Tom Kuegler

Travel blogger. 28 years old. Currently in Mexico. Get my free 5-day Medium course via email →

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