How to Live the Dream and Leave Work to Travel

The following two tabs change content below.
8 Women Dream wants to hear your dream story. Do you have a dream you'd like to share? Do you have a dream success story you'd like to share with our community? Be a Guest Contributor on 8 Women Dream! To read Guest Contributor guidelines click here. +Contributor Stories Contact us only after you've read the guidelines

Latest posts by Contributor Dream Stories (see all)

Welcome to the second installment of my “How to live the dream” series. Last week I brought you into the lives of my friends, BodesWell, on their epic journey across the world in a VW bus. If you were inspired, but not quite in a position to leave the office or house behind, then this post is for you. You can travel the world and keep your day job.

Vietnam on my friend’s recent extended vacation. Photo: OftenbyLand

Here’s the question I will answer for you today:

How can I travel the world with a full-time job?

I promise this is possible and not another lofty travel feature written by someone who actually 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 Four-Hour Work Week.

Psst! If you are curious about finding a job to fulfill your wanderlust, check out these top 7 travel jobs:

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 at the Victory Gate in Angkor Thom. Photo: OftenbyLand

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.”

Reading on a Thai beach. Photo: OftenbyLand

Ao Thong Nai Pan Yai beach Photo: OftenbyLand

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.

A pre-trip excerpt from her blog, Ofter by Land, “Just Ask”:

“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 I sat down with my boss at work and asked for what I needed: “Can I have six weeks off next spring to go travel?” Without hesitation he shot back “Absolutely, fully support it.”

BOOYAH! I did not think it could be that easy. All that nervousness and held-back hope… and he said YES!

At the time Ralph and I were planning to head 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: my financial resources would not cover that destination. No worries, though, there are 5 entire continents (count ‘em) left for me to explore. This time we’re heading to Southeast Asia, where the sun is hot, food is on the street and temples & beaches are bumpin’.

For those of you who are ready to Google “how to ask your boss for time off,” let me give you a few tips to get started:

1. Request a copy of your employee handbook and read through the section on leave. I was surprised to find my company had a policy about unpaid leave (did I mention these 6 weeks off will be unpaid?) 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.

2. Soft-sound your HR contact before reaching out to your manager. In my case, my HR manager was able to tell me that people request leave all the time (just not in my particular office) and that she fully supported the adventure. But in the end, it was up to my boss to approve.

3. Prepare “The Ask” for your boss. Make it easy for him or her to say YES. Ask as early as possible and give an outline of a plan for coverage while you’re out. I asked about six months ahead of when I wanted to take my trip and there is ample time to prepare my 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 said yes then they will likely also be excited for you… share your enthusiasm, joy and appreciation.

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

Megan on a Moped in Thailand. Photo: OftenbyLand

In three steps, you can be closer to a six-week vacation than you realize. So now that you know a real-life 9-5er can do this, what are you waiting for?!

Where will you go when you leave work to travel the world? What meaningful fun awaits you in the world?


  • Katie

    Thanks, Cath. I love the poem analogy!
    I know travel changes me, even if I go somewhere just for the weekend. It’s nice to step outside of my normal life for awhile. I can’t even imagine how Megan in this post felt after 6 weeks out in the world!

  • Reading someones travel journey sounds like a poem to me.

    Travel changes you.

    I love these stories.


  • Katie

    Thanks, Lisa!
    Megan (and Ralph) are truly the ones who rock!
    So often people tell me how they want to travel and venture throughout the world, but they never think they can. I love this story because you do have to ask for it. Megan proves that the sky is the limit. And world travel is possible and accessible.

  • Lisa

    LOVE this Katie! Megan’s advice is great – ASK for what you want (so simple, but so often we don’t, because we’re afraid or haven’t yet figured out exactly what we want or think someone will say no or.. or… or…). And I love the “YES, and… ” from Improv too. So great! A great lesson for life – like the funny movie “The Yes Man” ;) If you really say YES to everything for a while and embrace all of life, it’s amazing how you can start living your dreams from WHEREVER you are!

    Thanks for making the travel dream feel a little more accessible and possible for all! :) You rock!