10 Tips For Convincing Your Boss to Let You Work Remotely

Don’t let a desk job keep from your adventure goals.

Imagine doing your job from a campsite in Yellowstone or a café in Bar Harbor.

If you’ve spent countless hours in your cubicle dreaming about living an adventure travel lifestyle, then it may be time to talk to your boss about letting you work remotely.

After all, if you’re like many corporate citizens, your job relies heavily on a computer, and that computer is your gateway to remote work.

Here are a handful of tips you can use to help make your case to convince your boss to let you work remotely, giving you the freedom to make money and travel on your adventure.

Prove Yourself Worthy

The first and most important thing that you need to do is prove to your boss that you are a responsible and passionate employee.

Do whatever you need to do to make it clear that you are an asset to the company. If your boss already likes the work you do, he or she is going to be more willing to work with you.

There is a mistake that can be made here.

If you spend so much time daydreaming about your adventure travels, especially as your planned exit gets closer, then you can hamstring your ability to convince your boss to let you work remotely.

It’s kind of like “senior-itus”. Remember those last days of your senior year in high school, before graduated to head off to work or college. It’s hard to stay motivated during that period, to show up on time and put forward the same effort on exams.

Don’t let a few months of poor performance at the end of your tenure overshadow several years of professional and stellar work.

Consider Other Positions You Could Fill

Before even approaching your boss, consider if there is another position in the company that would make more sense if it was done remotely and that you have the right skills to fill.

This is especially true if you’re job doesn’t lend itself easily to remote work.

For example, if you are a front desk receptionist, you will have a difficult time convincing your boss to allow remote work. Someone has to be at the front desk to greet visitors.

Instead, perhaps you could reposition your skills and value as a virtual assistant for an executive or coordinator for a marketing team.

You may have many realistic options within your reach, so give it some thought.

Get Prepared to Approach the Boss

Would you trek into the Gobi Desert without some sort of plan? Likely not.

When you walk in to your boss’s office to pitch the idea to work remotely, be prepared and have a plan.

Be prepared to counter the objections.

Many bosses may initially resist the idea, so be prepared with responses to the objections that you expect to hear.

Don’t go into the first meeting unprepared.

If you’re idea to work remote is half-baked, don’t risk throwing up the red flags that you are a flight risk.

Confirm your commitment to the company, and show how you will be just as, if not more productive, through a remote working option.

You may have to strongly sell this position, so be prepared to spin the facts and story in your favor.

One last thought on preparation, have an exit plan.

Have a contingency to get out if the conversation turns south.

Do not let your ship go down in the first battle. Be ready to retreat to safe harbor to regroup for the next attack.

Productivity is the Magic Word

Whether your position is overhead or revenue generating, there is a certain amount or productivity that your boss and company except from you.

In a well functioning organization, you have your job because the cost to employee you is less than the value you contribute to the organization.

Use facts and data to prove how you would be more productive when working remotely.

Perhaps removing distractions will allow you to work more efficiently. You can make more calls. Write more articles. Better manage projects.

Whatever your job entails, spin how working remote will add to productivity.

Working Remote Saves the Company Money

When you’re not using the company’s Wi-Fi, electricity, bathrooms, office space, parking space, key FOBs, and so on, you’re reducing the company’s overhead costs.

For your job in particular, explain how you think working remotely will help your employer save money or time.

Show how it will be worth it to your employer to let you work remote.

If it is unavoidable that the costs for your employer will go up as a result of your working remote, then be super prepared to cite some of the intangible benefits of work from home (i.e. better quality of life, employee satisfaction, or happiness)

Start Small by Working from Home

Your boss may be more open to the idea if you start by asking to work one or two days a week from home.

Call it a trial period. And be sure to excel.

Do this well ahead of your plans to travel, and don’t divulge that your planning to travel long term.

Instead, work from home. Ease into the remote working lifestyle.

When you are ready to go full-time remote, and when you’re ready to divulge long-term travel plans to the boss, you’ve set some positive groundwork for the case.

Stay Visible

During your trial period, make sure that you’re instantly available to answer emails and phone calls.

You want to make your boss feel like you’re just down the hall and that they can talk to you whenever you’re needed.

Maybe even ask them more questions than normal to remind them that you’re only just a message away.

The idea here is to stay visible and valuable to your boss. Don’t go dark and make the boss conclude the trial period is a failure.

Convince the Boss that the Decision Will Make Him or Her Look Good

Does your boss report to people higher up the corporate ladder?

If so, you’ll need to assure them that you will be doubly focused on productivity so that the boss doesn’t take on too much personal risk by making a bad personnel decision.

Try to highlight your commitment to making it work, and that your boss’ boss will be impressed with the increased productivity and reduced costs that your remote working situation provides.

Promise to Make the Weekly/Quarterly/Monthly Meetings

In a lot of companies, it’s important that employees stay engaged, guard their time, and attend the right meetings.

When working remotely, a boss may be concerned that you’ll be less inclined to attend meetings or perhaps not be aware of the meetings you need to attend.

Stress that you will attend meetings remotely and be better able to manage your time without typical office distractions.

Also, show how you will keep informed of the informal discussions and ad hoc meetings that regularly occur in the workplace.

Rely on chat, email, and regular informal touch points with key colleagues to ensure that you’re aware of the conversations, trends, and politics in the organization.

This will help keep you relevant while you are traveling and working.

Be Persistent and Bold.

The first time you ask to work remotely, your boss may shut down the idea immediately.

Don’t give up.

Keep working hard and revisit the idea several times, building a strong argument.

If you’re persistence falls short, even when you have a list of great reasons that your boss should let you work remote.

Bail out.

Find a new job that will let you make money and travel.

Got another tip?

Got other tips that you want to share with our readers about convincing a boss to let you work remotely?

Leave a comment. Maybe it will help someone reach their adventure travel goals.