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Lessons Learned

The Counterintuitive Career Lesson I Learned By Traveling The World

How to separate the possible from the probable, then act accordingly—even when it's risky.

The Counterintuitive Career Lesson I Learned By Traveling The World

[Photo: Flickr user Milosz1]

I purposely don’t tell my family about the "crazy" things I do when I travel. They only found out that I'd hitchhiked through Burma, motorbiked across southern India, or walked alone across the Egyptian-Israeli border at sunrise well after the fact. Because I know what they’d say: Can’t you get kidnapped like that? Can’t you get robbed? Or harassed? Or hurt? And they'd have a point.

Sure, all those mishaps are conceivable, but they aren't all that likely. It’s within the realm of what’s possible, but it’s not probable, so my time and energy aren't best spent preparing too much for a very unlikely outcome. That's not to say there's no risk in these cases, just that it doesn't overdetermine my decision.

There are two converse principles I've learned to apply to my life whenever I’m contemplating taking a risk, but which one I choose to apply depends on whether the risk relates to my career or to travel:

  • For travel: Focus on what’s probable, not what's possible.
  • For career: Focus on what's possible, not what's probable.

Different Spheres, Opposite Approaches

Over time, I’ve learned to be safe when I travel. I don’t take unnecessary risks, but I don’t worry about things that are so unlikely to happen that they’ll prevent me from having a unique and serendipitous travel experience.

Night buses in countries with high, narrow, treacherous roads? Not a chance. Walking through a crowded street in Delhi where I’m likely to be harassed? No, thanks. But accepting an invitation to join a woman and her children for dinner in Muscat? Wonderful. Hitchhiking with a partner in a country known for its kind and gentle culture? Probably fine. For me, these are pretty reasonable guidelines to work within.

With travel, I’d do almost nothing if I only thought about what maybe, potentially, possibly could happen. I have to focus on what most probably is going to happen.

In my career, though, it’s just the opposite; I’m a ruthless risk-taker. I quit a corporate job in New York with a leadership track so I could move to Nigeria with a global media company that promised on-the-ground international experience and rapid advancement—or so they said. I really had no idea at the time whether it would pan out that way. I left my last job for a year because I wanted to see if I could become a professional writer and build up a coaching business. Now I’ve been accepted to a fellowship in a completely new career arena, and I’m going to try that, too.

In these cases, I’m not focusing on what’s likely to happen, and I’m not managing my risk taking by telling myself not to worry if the new job doesn’t work or if I can’t make it freelancing. On the contrary, I’m actively narrowing in on the best-case scenario that lies two standard deviations away from what usually happens: I find my dream job, I make a killing freelancing, I build my ideal international lifestyle that spans three continents, and I meet highly influential and inspirational people who play a role in my life for decades to come.

Weighing Risks And Managing Expectations

For me, it’s not about setting unrealistic expectations, it’s about deciding whether your life is going to be led by aiming for the bottom of the bell curve and trying to do everything in your power not to let that stuff happen (going broke, getting stuck, being ostracized from important communities, failing, and feeling ashamed) or eyeing the top of the bell curve and doing everything in your power to make that stuff happen (wild success, intense love and support from others, dreams coming true left and right).

Life falls somewhere in the middle, of course, but you can often push yourself toward one end or the other. I can’t say I’ve necessarily achieved the top of my curve yet, but I’m soaring way above where I’d be had I just focused on the median all along, or let my fear of the worst-case scenario limit how hard I’d really try, how far I’d really go, or how deeply I’d really care.

If you ask me, this goes for personal relationships, too. Did you know every time you start something with someone, the likelihood of it working out is approximately 0.00009%—or something like that? It’s low, anyhow. But does that mean you begin dating thinking that it’s not going to work, or that this person has nothing valuable to add to your life because someday he’ll have moved onto someone else? Of course not! That's a self-fulfilling prophecy every single time.

In fact, the outsize optimism that dating fundamentally requires may hold the key to managing expectations in other spheres of our lives, too—the ones where it's often harder to aim for what's possible than to settle for what's probable. Even if this particular romance or career move doesn't work out, you didn’t undermine its potential by only giving it 50%. You set your sights high, acted with integrity and vulnerability, and eventually that formula will reward you.

Whether it’s travel, life, career moves, or relationships, it all comes down to championing love over fear. So focus on the love, choose to move toward the big exciting things, and don’t waste time maneuvering around the small scary stuff. Not all risks are worth the taking—but you always need to know which ones are, and why.


Elaina Giolando is an international sales director and digital nomad who's lived and worked in more than 50 countries. She writes about global careers, unconventional lifestyle design, and meaningful travel on Life Before 30.

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