7 Points to Ponder Before Accepting a Jet-Setting Job

If your idea of porn is scrolling through Condé Nast articles, or your idea of scrapbooking is cutting out clippings from AFAR Magazine to file into a binder, believe me, I get you. You’re my people. I’ve suffered from an incurable sense of wanderlust for as long as I can remember.

Sitting in Mrs. Hopper’s dimly lit sixth grade classroom, shades drawn, motivational posters sprinkled across the cinder block walls, my eyes were glued to the screen of that mammoth of a TV on a rolling cart (do you guys remember when TVs weren’t flat? Weird, right?). We were watching a video about Holland, and I was hypnotized by the sway of the tulips in the wind, the whirling sails of the windmills, and the Lisa Frank-esque colors splashed across the houses lining quaint cobblestone streets. I was seduced by the “other,” thrilled by the different, and lured into a lifelong love affair with exploring cultures, languages, foods, and customs that differed so radically from the familiar suburban surroundings where I was raised. I vowed then and there that Holland would be the first of many countries I would visit in my lifetime (it wasn’t).

It’s no wonder that this insatiable desire to travel ended up leading me to job opportunities that would support my addiction. You know what they say: find a way to get paid for doing what you love. Right? Well, maybe. In my 10 years in the workforce, there have been instances when doing something I loved for a living turned out to be the fastest way to ruin something I loved. This is why I’ve never pursued a career as a chef (cooking soothes me–why introduce the stresses of a job into such a sacrosanct experience?), or as a full-time writer (it could also be because no publisher has ever serendipitously tripped over my hobby blog to suddenly exclaim, “WHO is this shockingly undiscovered mind mecca of a wordsmith, blessing us all with her indelible grasp of the subtle struggles of humanity, and dusting our minds’ eyes with the shimmering wisdom in her words??!!” I mean, OBVIOUSLY, that’s what they would say, right…?)


Given that writing is free, cooking is cheap, and traveling is neither, it made sense that I jumped at the chance to take a travel-based job and absorb all the glorious perks that came with it. There are certainly many benefits to being in a travel-based career. You get to visit new places on the company’s dime, meal and entertainment expenses are covered, and you can rack up an abundance of airline and hotel points. If you’re certain that you are the exact type of person who is built for life on the road, in the air, and atop the rails, feel free to skip this post and re-read the article on work dresses that travel well.

If you’re on the fence about whether a travel-based career is right for you, here are seven questions to ask yourself. Sure, nothing is ever as romantic as it seems, but that doesn’t mean you throw the baby out with the bath water. In order to fully reap the benefits of a travel-based job, you must first do what you can to preserve the passion that led you to it in the first place. These questions and your answers to them can help you identify any potential hang-ups that could threaten to leave you more exhausted than exhilarated by the demands of travel.

1 – “How often am I expected to travel?”

Eventually, I came to find out that the industry standard for travel frequency for my position was 1-2 weeks per month, 9 months per year. In my first year, I traveled 2-3 weeks per month, 11 months per year, twice the industry norm. It didn’t exactly foster a reasonable expectation of long-term sustainability. Severe burnout at the end of my first year led me to set an ironclad policy for my second: no back-to-back trips, no trips two weeks in a row, no exceptions. If I was going to be able to do this job without collapsing, I had to learn to acknowledge my limits and set boundaries to protect them. Get a clear idea of how much travel is expected, and how much autonomy you have in making your own schedule.

2 – “Am I predominantly introverted or extroverted?”

(If you’re a raging extrovert, you can probably skip to Question 3.) This shocks a lot of people, because I’m neither shy nor socially awkward (unless I’m on a first date), but I am highly introverted. I get my energy stores from being alone, mulling over my thoughts, processing the events of the day, and basking in silence. I find small talk cumbersome. I have zero FOMO. Networking events are my worst nightmare.

This question will largely matter in regard to what it is you do for work when you travel. If you’re introverted, but spend most of your travel work day at an office or in front of a computer, this may be a winning combination for you. I was in sales, which meant I spent all day in a revolving door of pitching products to potential customers, and chatting with sales reps in the car between sales calls. Easy breezy for a bonafide extrovert, but by the end of the day, my brain and barometer for social interaction were, more often than not, completely fried. As such, often the thought of going out to enjoy the city’s social scene and cultural offerings paled in comparison to putting on pajama pants and binge watching Game of Thrones.


3 – “Am I comfortable going out and doing things by myself?”

I actually don’t mind doing things in public by myself. In Chicago, I saw Jim Gaffigan by myself. In Sedona, I ate dinner at a romantic resort overlooking the desert by myself. In Denver, I saw Deadpool, ate quail, and ordered an entire bottle of wine at an Alamo Drafthouse by myself.

I had a blast doing all of those things, but unless you’re one of those rare people who is instant friends with nearly everyone you meet, life on the road can get a bit lonely. Most museums and other cultural experiences are closed in the evening, which limits your choices to dinner, concerts, and movies. Can you eat in a restaurant by yourself, enjoying the ambiance instead of staring at your phone the entire time? Do you feel weird not having someone to laugh with at a movie? Are you secure enough to dance by yourself while checking out a local band?

The downside to this is that even the most introverted among us still need close human connection, and eventually I started to realize that my travel schedule fostered a perpetual rotation of isolation. After being on the job for about six months, I started to find that I’d be too tired to hang out with my friends when I’d get home. After catching up on sleep, I’d have to do errands, laundry, bills, and pack again for the next trip, where I’d go out to eat alone, go to the movies alone, etc. It was getting difficult to maintain close connections. It was while I was out to dinner for the 100th time by myself at a restaurant in Portland, when I realized how sad I felt to be eating alone again. For someone who likes doing things alone, that was a pretty big sign to me that maybe I didn’t have the best social temperament to spend that much of my time constantly surrounded by people but connecting with none.

4 – “What am I sacrificing at home to be on the road?”

Your answer to Question 1 is important to take into account when examining what you’re leaving behind. Will you be able to maintain your life and your relationships at home with the ratio of time you will be expected to be away? Are you newly married, trying to settle into a new life with your spouse? Do you have kids who have soccer games, school plays, and science fairs? Are you single and trying to meet someone in your city and don’t want to be in a virtual long-distance relationship? Do you have close friends you’re used to seeing on a regular basis? Do you have a pet to whom you are the primary caregiver and companion? Do you miss being able to say yes to a spontaneous night out, or reading bedtime stories to your kids before they go to sleep?

I’ve always been more wings than roots, so it took quite a bit of time away from home before I started to feel really uprooted from my life, but it did eventually happen. I distinctly remember one time, having to schedule a hang out with one of my best friends, who also traveled for work, six weeks in advance. My dog started being less obedient, responsive, and attentive whenever I was home, either because he was mad I was gone so much, or because the dynamic of our connection was changing. And dating? Challenging. To be fair, I’ve always found it challenging on my best day under the best circumstances, but working a budding relationship into the priority wheel of my already dwindling friendships, connections, and social circles made me dizzy. I really started to miss the life and the relationships I had built and was building at home, and for the first time ever, I started to view my suitcase as a sign of restriction instead of freedom.

5 – “What kind of sleeper am I?”


If you’re one of those blessed humans who blacks out the minute your head hits the pillow, and can sleep soundly through the night in spite of hotel doors slamming, sirens in the streets below, insufficient light blockage by hotel curtains, and the inconsistent firmness levels of mattresses and hotel pillows, skip this section and know that I hate you. I’m a horribly light sleeper. In my bedroom at home, my windows have dimming film, my curtains are blackout curtains, there’s a sound machine across the room, and bottles of lavender and melatonin stored in my bedside table.

Unfortunately, there’s no way around it: travel is tiring, even when you’re doing it for fun. When you’re doing it for work, you need to make extra sure you’re well rested so you can wake up and hit the ground running at the top of your game. Plus, what’s the point of having a job with travel perks if you’re too tired at the end of the day to go out and explore the city? Sleep isn’t optional. We need it to survive. Staying well rested prevents sickness, lowers stress, and helps maintain a healthy weight. The best we light sleepers can do is to manipulate our nightly surroundings as much in our favor as possible, say our prayers, and hope for the best.

6 – “How often/easily do I get sick?”


Do you get motion sick? Better stock up on Alka Seltzer. Prone to colds? Get used to dumping hydrogen peroxide in your ears. Against getting flu shots? Eat your vegetables, take your vitamins, don’t touch anything, and wash your hands a lot. Airplanes are basically flying cesspools of air and surface bacteria. Thousands of people have inhabited your hotel room before you. You’ll be shaking hands with a lot of strangers. When you’re traveling, you’re less likely to hydrate properly, sleep well, exercise, and maintain healthy eating habits. Good health takes discipline all the time, but it requires a lot of extra effort on the road.

If your immune system still needs some fine tuning, consider how much more costly and complicated it is to call out sick in a travel-based job. You’re not just missing a day at the office; you’re likely canceling a (possibly non-refundable) flight, as well as a (hopefully not prepaid) hotel room, not to mention missing the opportunity to further grow whatever market you were scheduled to visit. If you’re not dedicated to staying on top of your health, you’re putting yourself in precarious (job) position.

7 – “How much will I actually be making for my time?”

Jobs that require a lot of travel have big price tags for a reason. Psychological studies show that people consider their work day to have started when they leave the house, and consider it to have concluded when they get home. Mentally, we lump in the commute with our workday, simply because it is time away from our lives. When you travel for work, your commute is constant, and sometimes, when you divide the hours spent away from your life by the amount of money you make, it doesn’t end up being worth it. Ask yourself what kind of compensation you’d expect for the actual work you do on the road, then ask yourself what compensation you’d expect for the inconvenience of having to be away from home to accomplish that work. After you’ve done that, take into consideration any extra expenses you’ll occur by being away, like pet care, day care, or help with house cleaning, grocery shopping, or errands. If the bottom line adds up to you, great. If not, consider looking for a higher paying job at home that will fund your travel hobby in your free time.


Fortunately, the travel bug is impossible to squash, and my love of new places hasn’t waned. I learned quite a bit from my jet-setting job, and enjoyed the new places I was able to visit because of it. If you’re ready to take the plunge into a jet-setting job, many adventures await you, and I salute you! May it never lose its sparkle for you. My goal for 2017 was that anytime I set foot on a plane, it would be for fun, not for work, and for the first time in a long time… I’m really looking forward to packing a suitcase again.



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