I just got home from one of the most memorable and meaningful trips I’ve had in years: My alma mater, Ohio Wesleyan University, invited me back to campus to talk about how my college experience prepared me for my job as a travel writer. I get a lot of strangers telling me, “You have my dream job!” But now I had to sit down and really think hard about how I got to where I am, and what it means to create a meaningful career doing something you love.
How do you distill 20 years of travel into a one-hour talk? Come to that, how do you get to be a travel writer? Beats me. But I can tell you how I became one, and throw in a few tips for anyone who’s just starting out. Since I’m in a nostalgic mood, first I’ll tell the story of how I got to where I am. Then I’ll zoom out to offer some advice that worked for me…and might just work for you, too.
My Travel Writer Origin Story
Travel runs deep in my family. Before I was born, my parents lived abroad — in North England and in Switzerland — for four years. This was at a time when long-distance calls were so expensive that they could only afford to talk to their parents twice a year: on Christmas and on Mother’s Day. Other than that, it was letters — written on crinkly, blue-and-red-striped “aerogram” stationery. Back then, “living abroad” meant being entirely cut off from your home culture. It required a deep cultural immersion that sent you home with a funny accent. (Returning to small-town USA, my parents were informed by friends — much to their surprise — that they had started talking like Brits.)
When I was in high school, my father — a professor at a theological school — set up a language-study program for his graduate students in Oaxaca, Mexico. He invited me to tag along and work on my rudimentary Spanish. Sensing that this was an alternative to getting a menial summer job, I said, “Sure.” I wound up spending one month each of the next three summers living with a wonderful host family, becoming fluent in Spanish, having my hometown blinders pried open, and — most important — discovering a deep affinity for the everyday adventure of travel. My sepia-toned world had suddenly been colorized.
When it was time for college, I attended Ohio Wesleyan University, in my hometown of Delaware, Ohio. (A generous scholarship trumped the fact that it was just 15 minutes from my parents’ house.) I majored in English, and I decided to take a break from Spanish and tackle German. Eight semesters later, I had a second foreign language — and a second degree — under my belt.
For a semester abroad, I took a “sabbatical” from my German classes to join Ohio Wesleyan’s esteemed program in Salamanca, Spain. The first time I set foot in Europe, I stepped off a plane in Madrid, boarded a bus, and rode across the sun-baked Castilian Plain to be introduced to my host family. I took classes at the Universidad de Salamanca, got acquainted with one of Spain’s finest small cities, stomped grapes to make wine at the family farm, and traveled to places like Galícia, Toledo, and Barcelona.
Returning home, I completed my studies and graduated valedictorian, Phi Beta Kappa, summa cum laude. Clearly, I had the world by the tail!
Except…I truly did not. In fact, I had no earthly idea what to do next. I had spent too much time striving to get straight A’s, and not nearly enough time considering what I’d do with that flawless transcript.
Thus began what I think of as “The Wilderness Years.” As if to scream to the world just how rudderless I felt, I grew a deeply unfortunate scraggy beard.
For the next couple of years, I floated through life like a cork in a river. Feeling drawn to the Pacific Northwest — where I had many relatives — I drove cross-country to the Oregon Coast. Upon arriving, I realized I had no clue what to do out there, either. After a couple of months, I drove home, moved in with my parents, and got a job at the local movie theater…just to hang out with my friends who also worked there. Thinking I might want to become a teacher, I did some substitute teaching — but that wasn’t for me, either. A lone bright spot was when I got a gig writing weekly movie reviews for my hometown newspaper, at $25 a pop. I considered going to film school, because clearly another $100,000 in debt and another marginally useful degree would be the answer to my prayers.
Obviously, I was waiting for something — anything — to inspire me. And what do you do when you can’t figure out anything else to do? You go to Europe! My high school sweetheart, Shawna, suggested we take a trip to Great Britain. And then, I decided, I’d stick around and do some solo backpacking around the Continent.
We had no idea where to begin planning our trip. Around this time, the local public TV affiliate was airing a show called Travels in Europe with Rick Steves every evening around dinnertime. It became my family’s tradition to watch this goofy American, in his leather jacket and aviator glasses, work his way around Europe. We had a stack of Rick’s free travel newsletters on our coffee table, too. One night, my mom said, “I think Rick also writes guidebooks.” I suggested to Shawna that she check it out. A couple of days later, she called me and said, “I got that Rick Steves book out of the library. Now I know exactly what to do on our trip.” (Clearly, Shawna was very astute. But I must have been even more astute…because I wound up marrying her.)
We had a wonderful time in Britain…guided each step of the way by our Rick Steves guidebook. We still speak fondly of the “chirpy attic room” in Keswick, and the many other just-right places Rick directed us to.
Shawna went home (for, you see, she actually had a job) and I was left alone in England…again rudderless. So I got in touch with my friend Trevor, who had graduated with me and immediately entered the Peace Corps, stationed in Slovakia. His sister Abby was coming to travel around Eastern Europe with him…would I like to come join them?
I was staying with family friends on the moors of South England, and Trevor wanted to meet up in Poland — which felt very, very far away. But, in possession of a Eurail pass and lacking other options, I decided to make the two-day trek: boat to France, train to Paris, night train to Munich, train to Berlin, another night train to Kraków. Walking bleary-eyed from Kraków’s train station to the main square, I marveled that this crazy plan might have actually worked. And a few minutes later, when Trevor popped into view at the far end of the square, I was hooked. (You can read my full account of the journey at the bottom of this post.)
Trevor, Abby, and I spent a week traveling around Eastern Europe: Kraków, Prague, Dresden, Budapest, and back home to Slovakia. And I was flabbergasted by this corner of the Continent. Something about Eastern Europe got under my skin. I continued on the rest of my trip with a renewed energy, hitting my groove as I traveled through several more countries, eventually running out of money in Ireland and flying home.
Back in Ohio, I returned to the throes of The Wilderness Years. But something was different. I was more at peace, while also more excited. I had seen a glimpse of a world that felt like it would become important to me in some way. I just had to figure out how.
But first, I decided I should write a thank-you letter to Rick Steves. The letter ballooned to several pages, as I waxed poetic about the glories of Eastern Europe that were inexplicably not included in his guidebooks. C’mon, Rick, I chided — why no Budapest? No Kraków?!
At the end of the letter, I figured I might as well throw in my resume and mention that I was looking for work. I dropped the letter in the mail and got right back to the important business of not having a job. Somewhere in there, my mom said, “Cameron, you’ve got to take some initiative and figure out what you want to do. It’s not like Rick Steves is just going to call you up and offer you a job!”
A couple of days later, the phone rang. A familiar voice said: “Hi, is this Cameron? This is Rick Steves.”
After an embarrassing exchange in which Rick repeatedly assured me that he was actually Rick Steves, and not my mischievous friend Andy, we had a great conversation. He liked my letter. He agreed that he could do better in Eastern Europe. And, by the way, was I serious about coming to work for him?
It was November — the slowest time of year in the travel business — and Rick wasn’t hiring just then. But, he said, if I was ever in the Seattle area, I should drop in to meet him. I hung up the phone and called my Grandma in Portland, Oregon. “Grandma — I’m coming for a visit!”
I flew out to the Pacific Northwest and made the rounds with my relatives, working my way north toward Seattle. A couple of days before I was to be in town, I called Rick to be sure he knew I was coming. He answered, and I told him that I was on my way to see him.
There was a long, awkward pause. “Um, who is this again?”
You know — Cameron Hewitt. That guy from Ohio. The one who wrote you a letter. You said I should come out to meet you.
Rick ended the call with a very noncommittal, “Well, I still have no idea who you are. But if you want to come to my office, I guess I’ll talk to you.”
I could have — probably should have — hung my head and flown home to Ohio. But I’d come this far…and, frankly, I didn’t have a lot of other prospects. So I made the lonely drive north on I-5 to Seattle, and showed up on Rick’s doorstep.
At first, Rick eyed me suspiciously. But, relentlessly, I recapped our previous conversation — and finally he remembered. We had a lively conversation and hit it off. It was clear that our travel styles were perfectly in sync. He said they may be hiring in a few months and took me to meet the HR manager. She was just arriving at her desk for the day — still wearing her jacket and holding her car keys — and she looked at us like a deer in headlights.
A few months later, they were indeed hiring — and I got the job. In March of 2000, I moved to Seattle and started working at Rick’s Travel Center, where customers can come to buy our luggage and guidebooks and get advice on their trips. I worked hard there for two years, and when an editorial position came open in our guidebook department — which was my target all along — I became a guidebook editor and researcher. I continued to work hard. And I never stopped. Over the last two decades, I’ve been spending three months each year in Europe, contributing to guidebooks in more than 40 countries, from Iceland to Sicily. (Here’s a partial summary.)
(tl;dr: Overachiever-turned-loser goes to Europe, writes Rick Steves a letter, and winds up with his dream job.)
While my story is extremely specific (and, upon reflection, nothing short of bizarre), I find that many people’s stories have their own twists and turns. It’s hard to give universal advice to someone just setting out, but here are what I consider the takeaways from my journey. While these tips may not be relevant to everyone, they’re what I wish someone had told me on graduation day.
Someone has to do your dream job…so why not you?
OK, try this: Picture your dream job. Close your eyes and imagine what you would consider the coolest thing you could get paid to do. Got it?
Here’s the thing: Somebody does that job. Somebody has to. So why shouldn’t you be that somebody?
This isn’t to say that you deserve that job just because you want it. You’ll have to earn it. But why not be the one who earns it? If it’s something you have a passion and an aptitude for, why not dedicate yourself to working tirelessly, proving yourself indispensable, and being the person who gets to do what you dream of doing?
The big caveat here is that your dream job is probably much harder (and much less glamorous) than you imagine. I realize that I will never get one ounce of sympathy from any of my friends, but…my job is very hard work — with long, tedious days, exhausting assignments, and unforgiving deadlines. And I would imagine any career considered a “dream job” would be commensurately more challenging.
But if you don’t shy away from hard work, give it a shot. It might take a long time. You’ll be precipitously steep on the learning curve as you pay your dues. And it will require patience and persistence. But why not you?
A career is like a trip: have a plan, but remain flexible.
I help a lot of friends and acquaintances plan their trips to Europe. (Occupational hazard.) And I find that the people who have the best approach are those who know what they want to do, without being too rigid about it.
Some travelers have every single hour plotted out. I have seen itineraries that read like they were designed by aeronautical engineers (because, well, they were): “Day 10, at 10:00: Visit the Accademia to see Michelangelo’s David. 10:35: Ponder humanity’s place in the universe and relationship with God; if time, also see Michelangelo’s Slaves. 10:45: Coffee break in museum cafeteria. 11:00: Walk 15 minutes to the Uffizi for our reservation there…”
These people invariably have troubled trips. They can’t possibly live up to their own rigid standards, small setbacks derail their precision plans, and spontaneity suffers.
I have also seen “itineraries” that barely qualify: A sketched-out list of places that might be in the cards, and a reluctance to book even a single night in a hotel. These entirely spontaneous trips may work for some people, but my sense is that they miss out on things they may have loved, simply because they didn’t do any homework. They waste a lot of time improvising — for example, calling around to find a room when they stumble into a town that’s unexpectedly jammed with a big convention — and less time experiencing Europe.
For me, a good trip has a general plan: I book overnights and a few can’t-miss experiences (like a museum that requires reservations, or a world-class restaurant), but leave the specifics of each day wide open to flex with the weather, surprise opportunities, and unplanned setbacks. Sometimes everything works out perfectly — as if I’d plotted it out, hour by hour, months before. But other times, I’m glad I built in wiggle room to deal with changing circumstances.
Nobody setting out on a career path can know exactly what lies ahead. Saying to yourself, “I have to get my first job by August, become a senior manager in three years, and make partner within ten” is a recipe for disillusionment. Beware the bullying “Bucket List,” especially one with deadlines baked in. On the other hand, having no direction is a great plan for winding up nowhere at all. But if you have a general sense of roughly what you’re aiming for, that will keep you on track.
To that end…
Figure out what you’re passionate about.
During my Wilderness Years, I had skills and motivation, but no direction. All of that changed with a trip to Europe that lit a fuse in me. I knew that travel — and specifically Eastern Europe — had to be a big part of my future, even if I didn’t know yet exactly how. My aimless and halfhearted job search narrowed considerably, setting me — eventually — on the course that brought me to here.
Your passion is your compass — it’s what keeps you on track. Even when you don’t know exactly where you are or what’s around the next bend, it reassures you that you are, at a minimum, heading in the right direction. (In this analogy, your “career plan” is like a map. But if a bridge is washed out or a new path has been laid out, your compass makes it easier to improvise.)
I love the famous quote by Howard Thurman: “Don’t ask yourself what the world needs. Ask yourself what makes you come alive and then go do that. Because what the world needs is people who have come alive.”
A few years ago, when I started my blog, I sought advice from a trusted colleague: Is there a structure that works best? What’s my target word count? How long is too long? How many pictures should go in each post? What kinds of topics will interest people?
She said essentially the same thing as Howard Thurman: People want to read things written by someone who’s passionate about what they have to say. What they don’t want to read is a rigid template that’s been half-heartedly filled in. There’s so much soulless clickbait masquerading as “content” out there. You may have to do some of that to pay the bills, but make sure you’re also making time to create something that’s fresh, personal, and bursting with enthusiasm. Write what you’re excited about, period. And people will enjoy reading it.
Find an organization that matches your values.
When I first started working at Rick Steves’ Europe 20 years ago, I noticed a funny thing: Although it’s a for-profit business, the organization had a distinctly non-profit philosophy. My co-workers would talk about “our mission” and “our travelers” and the importance of helping people have great trips to Europe…but nobody seemed the slightest bit preoccupied with the bottom line.
It turns out that Rick Steves’ Europe was way ahead of its time. Today, every jobless (or underemployed) millennial dreams of finding work at a “values-driven company.” They don’t just want to be paid well to work hard — they want it to mean something. They want their work to draw an income, but also to make the world a better place.
I see now that we were “values-driven” long before it was trendy. And we’re just as obsessed with it today as we ever were. We take every opportunity to remind each other that we are travel teachers first. At a recent leadership retreat, Rick reiterated his longstanding philosophy that what matters most isn’t gross revenue, but what he calls “gross travel happiness created.” We succeed when we make one more person’s trip better. (This works like a charm. Turns out, when you channel all of your energy into creating top-quality content and getting it into the hands of people who need it, the money will follow. Who knew?)
Back in 1999, this scraggly-bearded backpacker recognized that I was dealing with a company that did a great job at accomplishing its mission (i.e., helping me have a better trip). I took a gamble to come work here, because I had a sixth sense that I was more likely to find a meaningful career here than I would somewhere else.
When I loaded up my Honda Civic and drove from Ohio 2,400 miles to Edmonds, Washington — ahem, to sell backpacks — my friends must have thought I was nuts. But it was worth the gamble. My hunch paid off.
If you find an organization that feels like a good fit, take a chance on it. It might not pan out. But, then again, it might.
Once you get your foot in the door, work hard to prove yourself.
I realize “paying your dues” seems hopelessly old-fashioned these days…but I’m living proof that it works.
Here’s a deep, dark secret that nobody wants to tell you: An organization’s top priority is not ensuring that you feel challenged or fulfilled. A good organization does care about this…somewhat. But they care even more about whether you’re making an impact and earning your keep. Are you contributing to the mission and/or the bottom line enough to justify what they’re paying you?
When I started at Rick Steves’ Europe, I desperately wanted to work on guidebooks — but I was perfectly happy, instead, to work in the Travel Center for what turned out to be two years. I could have spent that time complaining that I was being underutilized or asking about when my dream job posting would come available. But I didn’t. I put my nose to the grindstone and worked hard every day to get to know our content and our customers, while making sure that the company was getting more out of me than I was getting out of it. I volunteered for every task and did it with pride. If someone needed to dress up like a Viking for the Travel Festival, I was their guy.
Here’s another secret: “Paying your dues” isn’t just about proving yourself to someone else. It’s an essential boot camp for understanding what the organization is all about. In retrospect, those two years I spent in the Travel Center were far from wasted; they were an invaluable opportunity to understand every corner of our business and to really get to know the people who do business with us. To this day — 18 years after I left the Travel Center — I still think back with gratitude on that opportunity. And I believe that I still “get” our customers better than many of my colleagues do, because it was my job to interact with them all day, every day. I know what makes them tick. It’s the foundation the rest of my career is built upon.
If you’re an aspiring writer, “paying your dues” means actually writing. It’s great that you have an English degree. Now show the world what you can do with it. When young people ask me how to break into the travel writing field, my answer is simple: Travel. Then write about it — a lot. Start your own blog. Build a real portfolio. This helps you develop your skills. And it demonstrates not just that you want to be a travel writer, but that you are a travel writer. When I first met Rick, I showed him the stack of yellowed movie reviews that I’d written for my newspaper. It wasn’t “travel writing,” but at least he could see that I knew how to produce content on a deadline.
Patience, grasshopper. Later on, you’ll be very glad you did this. Have you ever heard a successful person say, “Boy, I sure wish I hadn’t paid my dues”?
Tackle big challenges like eating an elephant: One bite at a time.
Part of paying your dues is stepping up when someone needs to tackle a big, imposing job. And that can be intimidating. But you just have to begin with that first step.
The first guidebook chapter I ever updated was Lausanne, Switzerland, in May of 2001. And I was terrified. By this time, I knew that working on guidebooks was my ultimate goal — and I desperately wanted to do it well. But I’m naturally shy, and a perfectionist, so I spent the weeks leading up to the trip tying myself in knots about whether I’d be able to pull it off.
I rode the train into Lausanne, my heart thumping in my ears, my mind racing. And then, around the time that train pulled into the station, an unexpected calm washed over me. It was go time, and the only thing left to do was what they had taught me to do: Go to the first hotel on my list and ask the first question. And then the next question. And then the next question. And when I was done at that hotel, I’d go to the next hotel. And the next one.
So that’s what I did. And by the end of the day, almost without noticing it, I had updated the entire chapter. And I did the same the next day, in Murten. And the next day, in Bern. And a couple of weeks later, I flew home with an updated guidebook.
A few years later, Rick accepted my pitch to co-author a brand-new guidebook to Eastern Europe. It was, in retrospect, a foolishly ambitious task (at the time, Rick likened it to the Louisiana Purchase). But I flew to Warsaw, went to that first hotel and that first museum and that first restaurant, and gradually worked my way south, all the way to Dubrovnik. I came home with a new guidebook, which is now a bestseller in its 10th edition.
Sometimes corny cliches contain deep wisdom. When faced with a daunting task, my father-in-law says, “How do you eat an elephant? One bite at a time.” Writing a book about Eastern Europe wasn’t easy. But each individual task, out of the ten thousand tasks it took to complete the project, was doable. And so…I did them, one at a time.
Play to your strengths, and collaborate with smart people who play to theirs.
You’re not good at everything. But you are good at something. The secret is figuring out what that “something” is — and then working with people whose somethings are complementary.
If I had to pick my single favorite thing about working at Rick Steves’ Europe, much to my surprise, it would not be all of the travel. Nope, it’s the wonderful people I get to work with. Everyone does their job well and proudly, we are all passionate about our mission, and we all understand that the strange and beautiful alchemy we create works because we do it together.
A lot of people never get to meet their idols. I am incredibly lucky, because I get to work with two of mine. Rick Steves…and Gene Openshaw, whose prose about Europe’s art and history sparkles with razor-sharp clarity, profound understanding, and wipe-a-tear beauty. (Gratuitous plug: Check out Gene and Rick’s stunning, brand-new book, Europe’s Top 100 Masterpieces.)
Gene and I have collaborated on several guidebooks, including our titles on Greece, Barcelona, and Berlin. Gene writes eloquent self-guided tours of great archaeological sites, museums, and neighborhoods. If you’ve taken these, you know Gene’s unmatched gift for taking the traveler by the hand and introducing them to exactly what they came so far to understand. (The best part of my job is when I have privilege of being the first person on earth to follow one of Gene’s new tours. I feel like I’m a friend of the Beatles, and they’re playing me a demo just before laying down the final track.)
When Gene’s done his part, he hands the book off so I can do what I consider “the fun part”: Filling in the edges of what he’s built, fleshing out the restaurants and nightlife, writing up the minor sights and quirky sidebars and side-trips. In the Greece book, for example, Gene wrote the tours of the Acropolis, Agora, Oracle of Delphi, Ancient Olympus, and so on, while I did the street food and street art tour in Psyrri, plus Mykonos and Santorini.
Next, when Gene and I are both done with our work, we hand our contributions over to a crack team of editors and mapmakers. And then…we never have to worry about them again, knowing they are in excellent hands.
If there’s one thing I wish for anyone starting out on their career path, it’s that they find a collaborative environment that hums like a happy machine.
Relax! Celebrate serendipities. Because jams are fun.
Standing on stage in front of students at my alma mater — who sat in the same chairs where I sat 22 years ago — I could remember exactly what it felt like to be in their shoes: Enjoying “the college experience,” excited about my studies, but deep down terrified about what would come next. From the moment you get to college, an imaginary stopwatch begins ticking over your head — relentlessly counting down to the moment when you have to enter The Real World.
It’s easy for me to say, “Relax! It’ll work out!” But if I could talk to myself 22 years ago, I would say exactly that. Not that it would always be perfect. Not that there wouldn’t be Wilderness Years, or that I’d get exactly what I wanted, when I wanted it. But that all those twists and turns do wind up taking you somewhere. And while you’re worried about that “somewhere,” don’t forget to enjoy the twists and turns. Memorable problems and delightful serendipities may feel like road bumps and distractions — but they’re the good part.
Have you ever noticed that when someone gets home from a trip, and you ask them how it went, almost invariably they begin telling you about something that went wrong?
My wife’s Great-Great-Aunt Mildred is my travel role model. A single woman to the end of her days, she traveled the world far and wide — long before such a thing was common. Near the end of her life, Aunt Mildred wrote a memoir of her travels. The title: Jams Are Fun.
After seeing so much of the world, it wasn’t the cathedrals and the museums and the grand views that Aunt Mildred remembered most fondly. It was those moments when everything went sideways, obstacles had to be overcome, and the trip was more memorable for it. (Like, say, when you call up Rick Steves for your big job interview…and he has no clue who you are.) Aunt Mildred understood that jams make wonderful memories…and dealing with them makes you a better traveler.
If you’re embarking on a career — and I know this is very easy for me to say — try to relax, lean into it, and enjoy. You’ll wind up in some interesting places, but I certainly hope that your journey isn’t without challenges and “problems.” Because, after all…jams are fun.