Adventurer At Law: How to Travel with a Full-Time Job

A man walks through the snow with a small peak behind him
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Nicholas LeRoy is an attorney who preaches calculated risk to his clients and enjoys formulating and implementing legal strategies at one of Florida’s largest law firms. He is also an adventure travel enthusiast who enjoys running up mountains, climbing rocks, scuba diving, and jumping off of high things. Because of this, Nicholas often trades in his briefcase for a backpack. And in the past few years, he has begun embracing this dual identity: what he sees as a Clark Kent/Superman juxtaposition.

We caught up with Nicholas to learn more about how he balances these two contrasting worlds and what he’s gleaned from the process of traveling with a full-time job.

Walk me through your decision to start traveling so much. At what point did you decide you wanted to inhabit this lifestyle?

I have always had an insatiable appetite for new experiences. When I’m too stuck in routine, I find myself longing for adventure the most.

As a child, I read a lot. I can remember reading countless books, thumbing through page after page, and obsessing over faraway lands. While I didn’t grow up in a family that traveled frequently, I did have extremely supportive parents who stressed the importance of hard work and always chasing your dreams. But another frequent topic in our household was the importance of education. Throughout my teens and into my early-20s, I focused on my studies until I was admitted to the practice of law by the Florida Bar in 2012. Shortly thereafter, I started my legal career, and through my own personal ambition and hard work, I gained some professional success.

For a brief moment in time, I felt complete. However, something was clearly missing. Everyone has some form of personal struggle, but my own occurred when my father was diagnosed with a life-threatening disease. Through conversations with him, I began to realize that despite my successes, I had not truly discovered myself. I had forgotten about exploring faraway lands, and I had a longing for growth, both spiritually and physically.

A pair of feet with a mountain peak in the background

Most people who travel as much as you do (including most people we feature on this site) do so full-time. Why did you decide to keep your job as a lawyer as well?

A man in a suit on the left, and in hiking gear on the rightFor me, the choice to balance career and travel was an easy decision. I am passionate about the law and giving my clients the best legal representation possible, but at the same time, I am passionate about adventure and travel. At 31 years old, I am a partner at one of Florida’s largest civil trial litigation law firms, and I am also a world traveler. I think that’s really cool!

Also, I personally experience the same joy and thrill being in a courtroom as I do atop a mountain. Both of my passions are inherently similar. To be a successful trial attorney and an advocate for a client requires a strong work ethic and analytical reasoning skills. The same can be said for an adventure traveler. One will face adversity and difficulty over the course of a legal case, just as one would in attempting to summit a famous peak. It all depends on how you respond when faced with adversity, and I have always welcomed the challenge.

In addition, and even more significantly, for me, travel has never been an escape from reality. I am not a “live for the weekend” type of person, nor will I ever view travel as a vacation. I believe in living life to the fullest, and since career and travel are both substantial parts of my life, I have never even considered walking away from either. 

A mostly dry river wends through grassy hills
A bridge crosses a raging river

Can you talk a little about how you manage to carve out time for travel as a lawyer?

What are the obstacles that keep us from traveling more? The answer is usually time or money, and, in some instances, a combination of the two. With work, family obligations, bills, and more, it might never seem like the right time to book a flight.

For me, time has always been my greatest challenge. While some countries have governments that mandate 20-plus vacation days per year, in the U.S., many full-time professionals in private practices are extremely limited in the amount of time off they receive from work.

A man smiles at the camera with a shoreline behind him

So what’s my big secret? It’s actually really simple: travel is a priority in my life!

In my first year as an attorney, I took only seven days off from work, including vacation, personal, and sick days. Yet, I utilized those seven days with a trip to the Bahamas, Mexico, and two U.S. National Parks. Fortunately, I now get more days off from work, and incorporate national holidays and weekends into the mix, so I’m able to stretch those days into more frequent world travel.

Do you have any examples of how you’ve made travel your priority?

While at a wedding in San Francisco, recently, I decided to rent a car and drive a few hours to Yosemite to hike. I was able to attend the wedding and reception, and in addition, I had an amazing time hiking and caught up on rest when I got back home.

Other things I’ve learned along the way are to pass on luxury resorts and opt for Airbnb or other accommodations when possible, book travel 90 days in advance, work long hours for two weeks prior to traveling to get ahead and prevent potential issues while out of the office, work while abroad, and take late-night flights after work to save time.

Do you see any crossover between your — as you put it — Clark Kent and Superman identities?

To people within my profession, travel means vacation. It is assumed that when you travel, you are relaxing on a beach and enjoying the comforts of resort life, all while your colleagues are working tirelessly in an office. On the contrary, I am the guy who travels to Hawaii for 10 days and goes to the beach once. I define “adventure traveler” as a minimalist who does not need possessions or comforts that society deems necessary. I have met many travelers around the world and more often than not, “shock” would be the best way to describe these individuals when they find out that I am a lawyer.

I am always the same person no matter if I am in my office or completely off the grid. The only difference is that when I’m in the office I have a briefcase, but while I’m traveling I have a backpack. They are one and the same as far as I am concerned because I carry the same things inside.

A man looks out over a rocky formation
A man sits on the coast of a Mediterranean city

You’ve mentioned a time when you drafted a memo while traveling through a storm on a fishing vessel to go shark diving. Can you elaborate on that story?

I often find time to work while traveling. In this particular instance, the plan was to get a head start on a legal memo on a boat transfer from Bluff, New Zealand, to Stewart Island. I had done all of the legal research and printed the applicable case law a couple of days prior, and the 2.5-hour boat trip was the perfect opportunity to get some work done. 

View off a shark diving boat

The waters to reach this location were horrendous, though — think of the movie, “the Perfect Storm.” Ok, maybe not that bad, but the waves were extremely high, we had to go fast to beat the storm, and we were on a small fishing boat.

I only made it through the first paragraph of the memo before getting sea sick. Then, there was an engine issue and the boat stalled on the open water. With every wave, it felt as if the boat were going to capsize, and because of the storm and all of the chaos, all of our dry clothes got soaked. My iPad keyboard also got wet and was unusable, and all of the case law that I had printed was not much better. Eventually, we made it through the storm, and the sky became clear. Many of us (all strangers at the time) still communicate on occasion, and we all refer to the ordeal as “the boat ride from hell.”

You also said that one of your goals is to complete the Seven Summits. Tell me about that.

My uncle is a successful businessman and an avid mountaineer. In 2002, he joined an expedition to climb Everest and was able to summit in May of that year. Many years later, he led approximately 15 family members, including myself, to Tanzania to climb Kilimanjaro. Although the mountain is 19,341 feet (5,895 meters) above sea level, it is often considered to be a relatively safe, non-technical climb. Having been an athlete my entire life, I thought it was going to be fairly easy.

It wasn’t! The problem with living in Florida is that you are directly at sea level, and altitude sickness is a real thing. Although I eventually pulled it together, I had never experienced a challenge like that before. Quite frankly, it excited me.

A man dives into water-filled canyon

What made the trip so much more amazing was that we were guided by Vern Tejas, who was the first person in the world to complete the Seven Summits (summiting the highest mountain on each continent) 10 times. Even more impressive is the fact that he has guided 54 Denali ascents and completed the first Denali winter ascent. Having the opportunity to spend seven days with the man and listening to his stories inspired me more than any photograph ever could.

They say “the practice of law is a marathon, not a sprint,” and the same is true for me in terms of mountaineering. The biggest issue I face is obtaining the time away from work necessary to complete the summits. The important thing that keeps me grounded is that I am patient. I have narrowed my focus to one mountain at a time, and Aconcagua at 22,837 feet (6961 meters) is currently in my sights.

A man overlooks a dry plain with snowy peaks in the background
A man overlooks a snowy peak with a lake in the foreground

A man looks out over a rocky formation

Mountaineering is a very dangerous sport, both physically and mentally. How have you developed the mental discipline required not only to push yourself to the top, but also to know when to turn around?

Like most lawyers, I am very competitive. When I travel, I am always looking for the most difficult challenges, and once you start completing a few of those challenges, it gets harder and harder to top the last. The only difference between me and most other lawyers is that I am competing with a mountain rather than on a golf course.

Yes, mountaineering is inherently dangerous. However, in my opinion, pop culture often influences the general public to think that mountaineers are just insane risk-takers booking flights to mountains as casually as people vacation at beach resorts in Hawaii. This line of thinking could not be further from the truth. Mountaineers are not in an office for six months and summiting the world’s highest peaks a few days later. A lot goes into planning and preparing, processes that include selecting a guide, collecting the necessary equipment and practicing with it, completing endurance training, and much more. Also, few realize that the amount of time needed to summit Aconcagua is approximately 18 days, and guides estimate nearly three months for Everest. The idea is to strategically prepare for all potential scenarios on the mountain, and plan ahead in order to alleviate any risk.

In terms of the mental discipline, on guided expeditions like the ones I join for the Seven Summits, if the guide turns around, then you turn around. Moreover, as I discussed above, having experienced some altitude issues on my very first mountain taught me the importance of not only preparation, but knowing the warning signs when something is wrong.

What advice would you give to someone who wants to travel but thinks it’s impossible due to their work life?

Travel is subjective. The photos may look the same from each destination, but no one will ever have the same exact experience or memories. We are all storytellers. That’s what exploration really is all about: going to places where you haven’t been and returning to tell a story someone hasn’t heard before.

A man sits in front of a graffiti-covered wall

One of my goals is to inspire working professionals to travel. I have met so many people who are unable to balance career and travel, and I want to help them to understand that travel can be enjoyable even on a “time crunch.” I’ve learned that missing one city or one place or one mountain is not going to define your memory of a trip. It’s better to visit Italy for one week and miss out on Rome than to never visit Italy at all.

So start slow, commit to future dates, and plan a Thursday-night flight and a Monday-afternoon return. If you’re a solo traveler, it’s okay to start even smaller. Pick a nearby city that you haven’t visited, plan an itinerary, and try it out. If you want to make travel a priority in your life, you really only have a few options, since we unfortunately can’t add more hours to the day or days to the year.

With the recent passing of Anthony Bourdain, I’d refer you to his words, which hold great significance to me. Maybe they will have the same effect on you:     

“Travel isn’t always pretty. It isn’t always comfortable. Sometimes it hurts, it even breaks your heart. But that’s okay. The journey changes you; it should change you. It leaves marks on your memory, on your consciousness, on your heart, and on your body. You take something with you. Hopefully, you leave something good behind.”

To join Nicholas LeRoy for travel inspiration as he explores the world while maintaining a successful legal career, follow him on Instagram.

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