Get Your Boss on Board with a Travel Leave of Absence

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Last updated on March 25th, 2019 at 04:33 pm

So you think you want to experience life as a world traveler, but you don’t want to leave your current 9-to-5 job permanently. Did you know that there is such a thing as a travel leave of absence?

Last week I brought you into the lives of my friends, Angela, and Jason of the blog, “BodesWell,” and their epic journey across the world in a VW bus. But many readers then inquired about what to do if you are not in a position to leave the office or house behind to live abroad–so I wrote this article is for you.

You can travel the world and keep your day job.

Here’s the big dream question I will answer for you–

How to Ask for Travel time from a Full-time Job

I promise this is possible and not another lofty travel feature that is written by someone who gets paid to country-hop for a living.

This is also for the real 9-5ers of the world who still haven’t figured out the 4-Hour Work Week.

Today’s question, How can I travel the world with a full-time job is real, and entirely possible. How do I know? My friend and former co-worker, Megan, recently returned from living that dream–an extended vacation with her boyfriend in Southeast Asia for six weeks. Amazing.

Megan and Ralph went to Bali, Vietnam, China, Thailand, and Cambodia and safely returned to steady paychecks after six weeks in the world. The good news?

You can too.

In fact, Megan hopes her story inspires more women to take time off to have meaningful fun. You don’t have to have a million vacation days or dollars saved up to do this, you just have to say, “Yes!” Before Megan set-up an out-of-office auto-reply to answer 30 work days worth of e-mails, she shared the steps of how she got her boss to agree to her extended vacation.

4 Steps to Get Your Boss on Board with Your Big Travel Dream

Step 1: ASK!

Megan says, “I only studied improv for one semester in college, but I carry with me two valuable lessons from those Friday night rehearsals… the first is to always say “YES, and…” because that’s the only way to move a scene forward, to make it work. True for life, as well. The second isn’t an improv maxim, but logistically can provide more concrete results on the day-to-day; Fairfield’s Director at the time, Heather Parody, told us “You won’t get what you need unless you ask for it.”

And you know when a little nugget of advice plants its seed? That’s what happened. Six-and-a half-years later Megan sat down with her boss at work and asked for what she needed: “Can I have six weeks off next spring to go travel?” Without hesitation, her boss shot back, “Absolutely, I fully support it.”

BOOYAH! She did not think it could be that easy. All that nervousness and held-back hope–and her boss said YES!

At the time Megan and her boyfriend were planning to go to Buenos Aires, rent an apartment and take tango and Spanish lessons, como muy romantico, no? Alas, the major dictator of all budget travel ruled: Megan’s financial resources would not cover that destination. No worries, though, there are 5 entire continents (count them) left for them to explore. So Megan and Ralph headed to Southeast Asia, where the sun is hot, food is on the street and temples and beaches are happening.

Step 2:  Request a copy of your employee handbook and read through the section on employee leave.

Megan was surprised to find her company had a policy about unpaid leave that was unrelated to medical and family leave. It should include all the details you need to know on how much time is allowed, what your medical insurance looks like during your time off and also if your job is guaranteed or not upon your return. You could also see if your company is OK with the idea of you working while remote. You just have to make sure where you are headed has good coverage for you to be able to work digitally and that the company is Ok with the time difference.

Step 3: Soft-sound your HR contact before reaching out to your boss.

In Megan’s case, her HR manager was able to tell me that people request leave all the time (just not in her particular office) and that she fully supported the adventure. But in the end, it was up to Megan’s boss to approve or decline Megan’s wish.

Step 4: Prepare “The Ask” for your boss.

Make it easy for your boss to say YES. Ask as early as possible and give an outline of a plan for coverage while you’re out. Megan asked about six months ahead of when she wanted to take the trip and there was ample time to prepare Megan’s work to be transitioned to other team members. Then it’s the fun part of the conversation—talking about the trip. Your boss is a big reason you’ll be taking that longer-term trip and if they say yes then they will likely also be excited for you–share your enthusiasm, joy, and appreciation.

When you’ve secured all approvals, it’s so fun to talk with your co-workers about my upcoming journey: getting tips, hearing stories and connecting. Which is the bottom-line what makes traveling so enjoyable and satisfying in the first place.

In four steps, you can be closer to a six-week travel dream than you realize. Now that you know a real-life 9-5er who asked for and got a leave of absence from work for travel–you can do this, what are you waiting for?!

Katie Eigel

Psst! If you are curious about finding work to help fulfill your travel dream wanderlust, check out this video on how to get paid while traveling the world: