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How to Convince Your Boss to Let You Work Remotely

There are a lot of benefits to being an employee. Things like health care, paid vacation, and — of course — a steady paycheck are nothing to scoff at. But if you’re sick of being stuck in an office, how can you convince your boss to let you work remotely?

Whether you’re ready to take off and see the world, looking to cut down on your commute, or if you’d just like to have extra time with your loved ones, telecommuting is the solution.

And while the business world seems to be coming around to telecommuting, you may still be facing an uphill battle to convince your boss to let you cut the cord.

So how can you convince your boss to let you work from home?

how to convince your boss to let your work from home

Work Out the Logistics Ahead of Time

If you want your boss to take your proposal seriously, make sure you’ve got all the details worked out before you bring it up.

If your office has anything special in place — a VPN, for example — figure out how you can connect to it from home. Be ready to explain, in vivid detail, all the ways you’ll be overcoming hurdles between you and your goal of working from home.

Arm Yourself with Research

Make sure you’re ready to back up your claims with actual data.

Fortunately, you’re not going to have any trouble finding research to support your claims. There’s a growing mountain of research papers proving that employees and employers benefit from remote working.

If you look for it, you’ll find data proving that remote workers are less likely to quit, more productive, and less expensive for the company.

And that’s just the tip of the iceberg; for a more in-depth look, read how remote work is a win for everyone.

Focus on the Benefits to the Company

Put yourself in your boss’s shoes: if someone walked into your office and started talking about this thing they want you to let them do that will make their lives super awesome but that makes no difference for you, what’s your initial reaction?

At best, you’ll probably be nonplussed about the whole idea. Why should you bother putting the effort into changing this arrangement if it only benefits one person? There are surely other projects you could work on that would benefit everyone.

At worst, you might be inclined to turn down the idea because it sounds awesome and you want it, but you can’t have it, so no one should have it.

When you bring the idea to your boss, compare these two statements.

Option 1: How Working Remotely Benefits You

“If you let me work from home, I’ll be able to spend more time with my family and friends, avoid the commute, and have fewer distractions when I’m trying to get stuff done.”

Option 2: How Working Remotely Benefits Your Boss

“If I work from home, you’ll be saving the company over $10,000 each year, studies have shown a 13.5% boost in remote productivity over office-based productivity, and remote workers are also more likely to take ownership of their tasks.

If you’re the boss, which one sounds like a better call for the company?

Because if you’re not the boss, you’re asking for exactly the same outcome with both statements; one just makes you sound selfish, and one makes you sound like a team player looking out for the company’s best interests.

Start Small with Trial Runs

If you’ve never worked remotely before, it’s unlikely you’ll be able to propose that you just…don’t come in anymore.

Instead, propose something small, like one day per week to work remotely. It should go without saying that your teleworking day needs to be your most productive for the week to prove the point that this is better for everyone. (To give yourself a running start on your remote days, make sure you have a clear plan for what you’re going to work on.)

Once you’ve established that you’re reliable as a remote worker, attempt to up 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. You can use the evidence to support your case to go fully remote — it’s much easier to make the case if you’ve got metrics, so use something like RescueTime to keep track of how your time was spent.

Ask Forgiveness, Not Permission

If your company isn’t receptive to a trial period, you can always adopt a different tactic and drag them, kicking and screaming, to victory.1

Call in sick on a weekday — probably not a Monday or Friday so you don’t look like you’re trying to squeeze out a long weekend — and just work remotely. Get your tasks done, keep in touch with your team, and handle the day like you would if it was a normal, remote working day.

Make a note of how much more productive the day was. If you can prove it, prove it. If not, make sure your boss is included on the task completion notices so they can see that you cranked things out from home — even while “sick”.

My dad used this technique to build up to the point where he was only coming into the office a couple times a month. After a while, he would take his phone as a mobile hotspot out on his boat and work while fishing.

His boss was none the wiser — after several months of working from his favorite fishing hole, his boss finally asked him to come into the office. “I can’t,” he said, “I’m in the middle of a lake right now.”

Rather than getting in trouble for surreptitiously working from wherever he felt like for months, my dad was able to remove all ties from his office because they realized that, really, he’d already done it without their knowledge. They never had a clue because he never faltered in his productivity or responsiveness.

Don’t Give Up

If you’re coming from a traditional 9-to-5 role, convincing your boss to let you leave the office is going to be an uphill battle in most cases.

Just remember that big changes take time, and often times the resistance to an idea isn’t due to someone disagreeing with you; it’s just too new and uncomfortable, and they need some time to chew on it before they can consider it objectively.

To recap, when you’re trying to convince your boss to let you work remotely:

  • Have all your ducks in a row and be ready to overcome any logistical objections about your ability to get the job done.
  • Be ready to present research to back up all your claims that remote work is a win for the company as much as it is for you.
  • Focus on the ways that remote work will benefit your boss; people are much more motivated by self-interest, and bosses want to look good.
  • Don’t go for full independence right out of the gate. Instead, start with trial runs to prove that you’re willing to work with your boss to prove this is good for everyone.
  • If you can’t convince your boss, you can try to just do it anyways and ask for forgiveness instead of permission.
  • And, of course, if all else fails, you can look at other ways of becoming location independent.

What To Do Next

If you're like me, the idea of traveling permanently while making a living probably seems like a dream — but you don't think you can pull it off.

I felt that way right up until I actually boarded a flight to leave the United States back in 2014 — and now I can't believe I didn't start living this life sooner.

The secret to a life on your terms — work where and when you want, living anywhere in the world — is remote work. And there's good news: it's easier than ever before to join the ranks of location-independent workers around the world.

I want to help you. The best remote workers all have a set of non-technical skills, and I’ve put together a free 6-point checklist to help you master them — and ultimately master your time and ability to work anywhere in the world.

Click here to get the free checklist now.

Jason Lengstorf in Tokyo

Escape the Office: Get My 6-Step Checklist and Learn:

  • How to create a location-independent income source (or how to make your current job remote-friendly).
  • The additional skills remote workers need to master if they intend to remain remote workers.
  • A remote worker’s most valuable tool for balancing work and play. Because what good is having the freedom to live anywhere if you can’t go explore?

  1. This technique is not for the faint of heart. You need to be willing to 100% own this decision — if you falter, or seem anything less than unwaveringly convinced that you’re in the right, this technique could end up harming your career. Use at your own risk.

About the Author: Jason Lengstorf

I’m living Post-Hustle.

I don’t believe in extremes. You don’t have to make a choice between a successful career and a fulfilling life outside of work. I’m living proof that you can have both: I work 40 hours a week while traveling the world — all while saving money and feeling happier than ever.

Learn More
Jason Lengstorf in Tokyo