How to get your employer to let you work remotely


I know the blog is called "Retire Earlier". I guess that means that we technically aren't retired as much as we are semi-retired. I don't have a J-O-B at all (other than making sure the sailboat we live on is maintained as well as managing our investing) but my wife works full time. Usually, when you hear that someone works abroad and remotely, most people assume they do websites, or writing, or graphic design, or something like that. My wife is actually a paralegal...for a law the United States. We haven't met another one of those yet. So if you have a job that may not seem like it would be congruent to working remotely, read on to see how you can transform your commute into a tele-commute.

It usually has to be able to be done over the internet (duh!)

First things, first. Unless you work for a company that has locations around the world for you to transfer to, then you need to be doing a job that is electronic and able to be done over the internet. Sorry, but your bank teller or auto repair job isn't going to allow you to go globetrotting and keep your employer sending you money every month. If you are a burger-flipper at McDonald's you actually might have a chance, though. Those things are all over the world!

But just because you don't have any co-workers working remotely doesn't mean you can't. If your job requires you to spend your entire schedule in front of a computer, there is a good chance that it can be done remotely. If you are working for a company with an IT department, your chances increase dramatically. That usually means that the infrastructure is there to get it done. If you have higher-ups like managers and executives doing work from home remotely, then you definitely have the capacity to work from home. Now you need to convince the boss to give you access to this awesome remote system.

You need to be one of the top employees in your department, or better yet...the company

If you aren't excelling and exceeding at work, no employer is going to give a hoot about any special perks you want. If you aren't highly-respected at work and the person who others go to when problems come up you probably don't have the leverage to work remotely, not to mention the self-control that comes with being able to be top-notch while not in the office anymore. My wife has an impressive resume and is highly sought-after and recruited in her field. She is a paralegal that has worked for some large and prestigious law firms/lawyers. In her last several positions, she has been the one dictating the terms of her employment. Not the other way around. If this does not sound like you, then get to work busting your ass. My wife didn't get that respect by hanging out by the water cooler and making sure she didn't miss happy hour. She did it by working overtime, being extremely detail-oriented, and going above and beyond expectations. I can't count the number of times I have heard lawyers who charge over $700 an hour thanking her for catching a mistake they made which could have been disastrous had she not intervened and fixed them. You have to be like that. Proactive, no mistakes, hard-working, and saving people's ass. Because then they owe you, and you WILL collect.

You need to have a good reason to not be where you are now

Noo, "I want to travel the world and work from white, sandy beaches" ain't gonna cut it. For us, it was my training to swim the English Channel. My wife approached her employer and let them know we might leave so we could move to a place where it was more beneficial for me to train (as opposed to the high desert region of New Mexico). They basically then said she could work anywhere in the world she wanted as long as she didn't leave. Bingo! That's what you need. Find something you want to do somewhere else that can't be done where you live/work now. If you are a valuable member of your company/team and have a valid reason, most employers will do what they can do keep you as opposed to having to replace such an important cog in the wheel.

Your company needs to be doing well

Depending on your position, you may or may not know with any accuracy how well your company is doing, but most people have some sort of idea. If things have been a drag and there has been a rumor or two about "cutting back" or layoffs...this is NOT the time! You wanting to leave will just give them the excuse to let you go and they'll have one less person to fire. Just ride this one out or go work for a better-performing company with a history of tele-commuting workers.

Don't be afraid to be selfish

Yes, being selfish is selfish. But this is your future and your sanity/happiness we are talking about. Unless you are under contract, you don't owe your company anything. It is up to you to find a way to live your life the way you want to live it. If you have to threaten to quit in order to work remotely, do it and be prepared to actually quit if they say no. Then go find another job, hopefully one better suited to working remotely. Of course, if you have been saving a large percentage of your income like we've been telling you, then you might be able to retire today and get started traveling. Maybe even start your own business doing what you already do on the side to supplement your income.

Be prepared to negotiate

Your first response from your employer is likely to be either 'No' or 'Let me think abou it'. Rule #1 in negotiations is to never take the first offer. When you ask again (and you will ask again), be ready with some backup. Offer to take lower pay, or reduce some benefits that may be appealing to the bottom line. One of the best tactics with a hesitant employer is to try a test-run where you work some days in the office and the rest of the week at home. Then you take the sting out of the changes and if it works out (which you should be working really hard while at home to prove you can) you can gradually reduce your time working in the office. As time goes on you are working at home 100% of the time, then sold all your stuff, and ready to move to your new locale.

Just do whatever it takes and go for it

Whatever it is you need to do to get to work remotely is worth doing. If you have to change employers, jobs, careers, cities, states, or even countries...believe us when we tell you it's worth it. The world then becomes your office and your playground at the same time. Stop complaining about your commute, your co-workers, or your boss. No one's tombstone said they'd wished they had worked a little longer. Totally the opposite. So get out there and do what you have to do so you can retire earlier already! You have my permission.


Chris grew up in the United States but felt the world calling. After working throughout his twenties climbing the executive ladder, he left the corporate world in order to have the free time needed to focus on family more than money. Since then he has never held a regular job and spends his time honing his skills to make money grow on trees.He now travels the world with his wife and two sons.

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