Get Your Boss on Board with a Travel Leave of Absence

Last updated on June 17th, 2024 at 10:49 am

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

In a past article I submitted to 8WomenDream.com, I introduced you to the lives of my friends Angela and Jason of 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 for you.

Today’s question: how can I travel the world with a full-time job? Is it real and entirely possible?

My friend and former co-worker, Megan, recently returned from living the travel with a full-time job 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 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 emails, she shared her steps to get 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 what she needed: “Can I have six weeks off next spring to travel?” Without hesitation, her boss said, “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 was hot, food was on the street, and temples and beaches were happening.

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

Megan was surprised to find out that her company had a policy about unpaid leave unrelated to medical and family leave. It should include all the details you need on how much time is allowed, what your medical insurance looks like during your time off, and whether your job is guaranteed upon your return. You could also see if your company is OK with the idea of you working remotely. You just have to ensure where you are headed has good coverage for you 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 told me that people always request leave (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 so that she could 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, they will likely also be excited for you–share your enthusiasm, joy, and appreciation.

When you’ve secured all approvals, talking with your co-workers about my upcoming journey is fun: I get tips, hear stories, and connect. This is the bottom line that makes traveling so enjoyable and satisfying in the first place.

You can be closer to a six-week travel dream in four steps 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?!

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:

Katie Eigel

Born and raised in St. Louis, Katie Eigel has lived in Switzerland, San Francisco, Arizona, Sonoma, California wine country, Brooklyn, and Chicago. She has published wine and travel stories in Wine Folly, Chicago Sun-Times, Image Chicago Magazine, TimeOut Chicago, Travelers’ Tales: Leave the Iguana, Take the Lipstick (book), Billboard (music business), WhichWinery, and more.