Chad D. Thomas: How I Became a Successful Travel Blogger

How did I become a successful travel blogger? It sure wasn’t intentional from the start! Back when I started Adventurous Kate in 2010, I had no idea it was even possible to make money with a blog.

Recently I read the book Outliers by Malcolm Gladwell, which explains how certain individuals became successful. People tend to believe that genius leads to success — for example, that Bill Gates became successful because he was so smart.

But that’s not all of it. Intelligence is a huge factor. So is hard work. But so is opportunity — whether it’s being born at the right time, having the right background, or spending years on a new hobby that eventually becomes a viable career.

Bill Gates was smart and worked hard, but he also had unlimited access to a computer lab as a teenager — something so unusual at the time it was almost unprecedented. This allowed him to get in far more computing practice than his peers, giving him nearly unmatched experience by the time he founded Microsoft.

After reading this, I began thinking of every event in my life that put me in a position to become a successful travel blogger. After a bit of thinking, it came into clear focus. It was being obsessed with an early social network that taught you how to build your own website. It was a professor identifying my potential during my first semester in college. It was getting one of the earliest jobs in social media for a travel company. It was moving to Europe at a time when the travel blogging industry was strongest in Europe. And far, FAR more.

When all of this information added up at once, I was flabbergasted.

When you look at my life, from my birth to today, not only is it unsurprising that I ended up in this career — it seems inevitable that I would eventually become a professional travel blogger.

I had awesome hair when I was born.

A Privileged Position from Birth (1984-present)

You can’t begin to examine my life without first acknowledging my privilege. I grew up white and Catholic in a middle-class community in Massachusetts with a good school system. I didn’t grow up anywhere close to wealthy, and my childhood was difficult in some ways, but I was overall in a very privileged position.

My life was never made more difficult due to my race, religion, sexuality, gender identity, economic background, or nationality. As a result, opportunities came more easily and frequently to me and I didn’t have to work as hard as most people.

It didn’t feel like it at the time, especially when I went to college and was surrounded by kids from obscenely wealthy families, but I now realize how my privilege set me up for success.

Girl reading book (via Pixabay)

An Intellectual Upbringing with a Geography Obsession (1989-1995)

From the moment I began school, I was expected to excel. This translated into being pushed to work as hard as possible and supplement my schoolwork with other activities, like piano lessons and constant reading. Drama and music were my main interests; I did sports but was never a skilled or enthusiastic athlete.

I couldn’t tell you when my geography fascination began — I can’t remember it ever not being there. All I know is that whenever I got my hands on a map, I would get lost in it. As soon as we were allowed to check out nonfiction books in school, I would make a beeline to the 900s section and choose a book about a different country every week.

I had a placemat with a world map on it. I was obsessed with it and my family would quiz me on countries every night. (My mom took a picture of me with the placemat the day I left to travel.)

What kind of kid was I? I was the kid who got in trouble for leaving her Ethiopia library book at her after-school Math Magic class. (God, I hated that class. I was the youngest kid and the only girl.)

Being pushed academically is what gave me my lifelong work ethic, and my love for geography eventually grew into a love for travel.

Growing Up a Dreamer (1989-2002)

There’s a Jack Donaghy quote from 30 Rock that I love: “The first generation comes to this country and works their fingers to the bone. The second generation goes to college and creates new innovations…the third generation snowboards and takes improv classes.”

My family has been in the US for a long time, but I was a classic third generation kid. Both of my parents were the first people in their families to go to college. And both of them lost their fathers when they were teenagers, which meant that their mothers had to go to work, money was tight, and they had to pay for college themselves. They both commuted to state schools, chose “smart” career paths — business for Dad, teaching for Mom — and eventually earned graduate degrees.

My parents wanted me to have a childhood without constantly worrying about money. To be able to go to the best college for me and live on campus. To eventually have a career I loved.

This translated into a freedom to dream in a way that many of my friends couldn’t. My friends who grew up with immigrant families, or in conservative cultures, were more or less forced into medicine, law, or engineering from a young age, spending their time on extracurriculars that could lead to a better future.

I was told I could do anything, study anything, be anyone I wanted to be. I wholeheartedly believe that growing up with this mindset led me to quit my job, travel solo, start a business in a brand new industry, and live unconventionally.

A Technology-Filled Childhood (1990-2002)

My dad has always been interested in computers and technology; he passed on this excitement to me. On Christmas when I was six years old in 1990, I was led downstairs to see the latest addition to the family and I squealed, “It’s a computer! And it’s a Macintosh!”

That small, square, early 90s computer was the beginning of my love for technology. I was only playing games and creating art as a kid, but I was hooked. The computer was a million times more fun than anything else.

I grew up in the nascence of the internet and was immersed in its early days. My dad went on to train his colleagues in how to use the internet. Around the same time, we brought the 1990 computer to my fifth-grade classroom and I taught my teacher and classmates how to use it.

I was never interested in coding or the engineering side of computing. But growing up with computers, being comfortable with them, and constantly learning what they could do gave me an edge that came to fruition in high school.

Building Websites in the Early Days (1998-2002)

When I was around 13 in 1998 or so, I spent my time on a website called Bolt — it was one of the early social networks predating MySpace. They had message boards, quizzes, badges, private messaging. There were different sections for music, movies, sports, astrology. I was obsessed with Bolt and spent so much of my internet time on there.

And one thing you could do on Bolt was create your own website. I was fascinated and decided to build an astrology website.

It was simple — a home page with twelve links linking to separate pages for each astrological sign. On each sign’s page, I posted a description of the sign’s qualities. I copied and pasted the description from another site (holy plagiarism!).

I kept that simple site immaculate, though. It was neat and clean. Each page had a “go back home” link at the bottom. I spent time targeting the colors to each sign. It wasn’t overloaded with counters or 90s clipart.

But then Bolt featured the site on its astrology homepage. I was thrilled to high heaven. People were visiting a site I made!

For my second website, when I was 14, I turned to Angelfire and decided to build a fan site for my favorite Backstreet Boy, A.J. McLean. (Amusingly, 15 years later, I would learn that we are actually cousins.) I was already an expert on all things A.J. — this site would be a place to put it all together. I created pages with his biography, his favorite things, pictures of A.J., videos of A.J., his songwriting credits.

Angelfire was where I began teaching myself rudimentary HTML. I wasn’t hardcore coding or anything like that, but I loved learning the basics. More importantly, though, I was learning how to structure content in a way that would entertain readers.

My third site, also created at age 14, was definitely my most embarrassing site: a Backstreet Boys humor site called Out the Dizzo. Yes, a Backstreet Boys humor site. Around 1999, they were a thing and there were tons of them.

I would constantly create new content for the site: funny alternate lyrics to Backstreet Boys songs, funny quotes for Backstreet Boys pictures, links to the funniest Backstreet Boys fan fiction, and of course, commentary on “All I Have to Give: The Conversation Mix.” The name Out the Dizzo came from a random quote Kevin Richardson once gave in an interview that was an ongoing joke in our community.

My fourth site was my most professional site yet, and it served a purpose: it was called “Who’s Going Where” and I built it my senior year of high school as a directory showing where everyone was going to college. There were headings, there were colors, it was laid out professionally, and I was proud of it.

These days of building websites were absolutely blissful — I fell in love with it. But more importantly, when it became time to build a professional time, I wasn’t slowed down by learning HTML and how to structure content. I already had years of experience.

My First Trip Overseas Trip to France (2001)

From an early age, I was a hardcore francophile, thanks to the influence of my French Canadian grandmother. She taught me basic French, gave me French books, and made me proud of my French heritage. I signed up to take French in the eighth grade; the vast majority of my classmates took Spanish.

Every other year, my high school did an exchange with a school in Rouen, France. Their students would come visit for two weeks in the fall and stay with our families, then we’d visit them in the spring. By the time I was a junior, I had been dreaming of this trip for years.

WHAT A TRIP. I felt such freedom traveling with my friends. I felt electrified when I spoke French and was understood. I got to know French culture while staying with a family in the countryside. My language skills improved rapidly thanks to the immersive environment. I took more photos than any normal human would. I saw so much of Normandy, from Etretat to Caen to Giverny. And I fell madly in love with Paris, a love that remains to this day.

I look back at that trip with fondness — but also with embarrassment. I got roped into paying for shitty portraits and bracelets woven on my wrist without my consent by men who approached me at Montmartre. (Looking back, I find it absurd that our teachers didn’t warn us about the Montmartre scam artists but made a big deal about the word “bagel” being code for pickpocket.) And our behavior at the Normandy battlefields was appalling — we called it “Teletubby land” and took goofy pictures.

But that first trip began everything. For the first time, my love of reading travel books and studying maps had grown into something more real. I was a traveler — and I was good at it.

A Professor Who Saw a Spark (2002)

When I started college at Fairfield University, I planned to double-major in psychology and French — then I decided to keep my options open and go in undeclared. I’d chosen a Jesuit university because they force you to study so many different areas in depth; I wanted to learn about as many subjects as I could.

During my first semester of college, I took the introductory writing class required for all freshmen. Papers were due every week and I wrote them in a way I thought college writing was supposed to be: intellectual, distant, emotionless.

Then one week I was bored and decided to write an essay about how I loved to take on dares when I was in middle and high school. If someone dared me to do something crazy, I would do it. I had a blast writing about all the adventures resulting from my dares. If my professor hated the essay, I’d do something more normal the next week.

I got my paper back and the entire back page was covered in red pen. My professor had LOVED it. He himself loved to do silly things to make people laugh. “SEE ME!” It read at the bottom of the paper.

I went to see him after class and he raved about my paper, telling me how much he loved it and what a talented writer I was. He was expecting to see more great things from me in the English program.

“Do you think…I should major in English?” I said, dumbfounded. I had never considered majoring in English; it sounded like such a boring major.

“If you didn’t, I would be disappointed,” he told me, his face suddenly serious.

Though I didn’t declare for another year, I ended up majoring in English with a concentration in creative writing. It wasn’t remotely boring. I overloaded on the electives, from poetry writing and journalism to literature of the Irish Famine, and I felt so intellectually fulfilled.

My whole life, I had taken my love for writing for granted — I assumed it was easy and fun for everyone. That professor helped me see that my writing was exceptional, and while I never had him as a professor again, he set me on a path to making writing my career.

Laptop (via Pixabay)

Starting a Blog in the Earliest Days (2002)

Early during my freshman fall semester in 2002, I discovered the concept of an “online diary.” You could write anything you wanted and it would be put online for anyone to read. How cool would that be?

I wrote my first blog post on Diary-X one afternoon — and I loved it so much that I immediately wrote two more! I was hooked on blogging (though keep in mind that the word “blog” was barely used back then). From then on it was a near-daily habit that continued for the rest of college and beyond.

Oh, and I had no filter back then. I got in trouble for writing about who was hooking up with whom and which girls on my floor were feuding with each other!

During my spring semester of senior year, Diary-X’s server failed. Every online diary had disappeared, and all my years of writings were lost.

Well, it was time to start something new. I started a new blog on the much more reliable platform of Blogger. I called it “Adventurous Kate” — the first emergence of that name — and continued writing constantly.

Sometime during college, I was asked what my true dream job would be. “Getting paid to blog about my life,” I replied, laughing at the concept.

Studying Abroad in Florence, Italy (2004)

For years I had dreamed of studying abroad in Paris. But at the last minute, I decided to apply to be an RA my junior year instead — a resident advisor in a dorm. RAs had to commit to a full year, so I wouldn’t be able to study abroad at all.

Then the tables turned — I didn’t make the cut to be an RA. As I reeled in shock, I decided in that moment that having the year free meant I HAD to study abroad. But the Paris program was through another school, and it was too late to apply for the fall semester. If I had any chance of going abroad in the fall, it would need to be through one of Fairfield’s own programs.

At the time, Fairfield had study abroad programs in Galway, London, and Brisbane — but the most popular one was in Florence. Of those four, Florence was easily the most exciting and the most exotic to me. ITALY! I had to do it.

I ran around campus, securing transcripts and begging for recommendations, and applied the same day. I was accepted less than 24 hours later.

Florence was an incredible, life-changing experience. I wrote a 10-year retrospective about it here; it’s a great read. I lived in a huge apartment with eight other girls. We spent our weeks eating and partying in Florence and spent our weekends traveling to different places. Budapest, Interlaken, and Capri were some of my favorite spots.

And I did go to Paris after all — as part of my fall break with my friends. I was their navigator, translator, and tour guide.

While I was away, I kept a meticulous diary and wrote long, detailed emails to my friends about my adventures in Europe. People began looking forward to my weekly emails, and I began sharing them as blog posts.

I had no idea of its significance at the time, but I was in my first days of travel blogging — something that would become my full-time career six years later.

Discovering the Concept of Long-Term Travel (2006)

After graduating college, I got a job at a company in Boston. While my interviewer described the company as a marketing firm with celebrity clients, it turned out to be more of a call center (yes, with a few celebrity clients). We were a high-end concierge service for rich people; I was hired as a research assistant for the extra tough requests.

It was possible to have a lot of free time at this job if you did your tasks quickly, and I was a speed demon. I’d browse the web when I could, and I can’t remember how this happened, but I came across a website called Gone Walkabout. It was a collection of journals by a guy named Sean who had gone backpacking around the world for a year.

This guy spent a year traveling the world alone. Just because he wanted to.

My heart raced. I’d heard of entire families traveling together for a year, but a single person, alone? THE THOUGHT HAD NEVER EVEN CROSSED MY MIND. Keep in mind this was 2006. The internet was nothing like what it is today.

Right then and there, I knew I was going to do exactly what he did. I would save up for a year around the world.

Every day at work, I would go in, get my work done, and sneakily read more of Gone Walkabout, nearly jumping out of my seat with excitement. I vowed to do a similar route to his, starting in New Zealand and heading westward. I knew I had to visit Railay in Thailand, just like him.

At the same time, I became active on another travel site: BootsnAll. In those very early pre-travel blogging days, I hung out on the message boards with people like Beth of Beers and Beans, who went on to create the Speakeasy Travel Supply scarves that I share with you often, and Brooke from Her Packing List and Anne-Sophie from Sophie’s World. We talked about our favorite places, planned our future trips, and gave each other travel tips.

In the early 2000s, long-term solo travel was so uncommon among Americans that I had no idea it was even possible. That revelation broke my world open so wide that I knew immediately I would do the same.

The Grammar Vandal (via Boston Globe)

Starting a Famous Blog A Little Too Quickly (2007-2009)

In 2007, Reebok ads appeared all over Boston reading, “RUN EASY BOSTON.” The lack of a comma drove me crazy and I decided to take a comma sticker and put it after the EASY.

I blogged about it, of course. I blogged about everything back then. But this seemed like such a good idea, it could be its own blog. The Grammar Vandal became my newest website.

Almost immediately, The Boston Globe contacted me, wanting to do a feature about me. I couldn’t believe it. After it was published, The Grammar Vandal went viral and I instantly had tons and tons of visitors.

I had no idea what to do with this fame except create more and more content. Every day would be a new post — I’d be changing grammar on signs, or musing about grammar rules, or ranting about something a celebrity said poorly.

After the Boston Globe interview, I was interviewed on NPR and for MSNBC.com (now NBC News). The blog got even bigger.

I knew I had a huge opportunity with this instant fame. But monetization didn’t even cross my mind, and something darker was happening — the fan mail was terrible. Almost every day, people would send me examples of bad grammar and would add, “That editor should be shot.”

“That editor should be shot”?! Are you actually advocating murder?

Suddenly I had built a successful blog with an audience I couldn’t stand.

I kept The Grammar Vandal up for a few years, but my heart wasn’t in it. As much as I enjoyed writing about grammar, I couldn’t deal with the mean, rude emails from my readers. Eventually, I stopped.

This taught me that I couldn’t blog about something I wasn’t genuinely passionate about. I began to entertain the idea of writing a blog about a subject I actually loved.

A New Career from a Blogging Friend (2008)

In the early post-college years in Boston, I kept up my blogging — still as Adventurous Kate on Blogger — and discovered several blogs by locals. One was called The Missus and was run by a woman a few years older than me. We commented on each other’s blogs and developed an online friendship.

The Missus worked in search engine marketing at a travel booking site. When it became time to hire an assistant, she reached out to me to see if I wanted to interview. “Anyone can learn SEO, but I need someone who can write, and I already know you can write.”

Yes. I was interested. I had been trying to get out of the call center job for months without success. And a travel company? How perfect!

I got the job, and a 25% salary bump. I was ecstatic — then because I had heard never to take the first offer, I emailed them asking for $5,000 more. (They offered $3,000 more and I couldn’t believe my luck.)

Those early days at the travel booking site were idyllic. It was a respectful professional environment with amazing coworkers and a fun, social atmosphere. I enjoyed my work and was eager to learn more. I even got to go out to business dinners at fancy restaurants like No. 9 Park.

In the early days, I did a lot of travel SEO content writing and was a natural at it. Later on, the job changed and became more about paid search, which I found incredibly tedious and boring.

My years of blogging for fun became my greatest professional asset, getting me noticed by a connection who gave me a great job. Learning the art of SEO content writing gave me one of the most important skills I used to build my career as a professional travel blogger.

A New Specialty: Social Media (2009)

Soon, my responsibilities at the travel booking site grew and I was put in charge of the company’s first social media accounts. Back then, social media was just Twitter and Facebook, there were almost no analytics, and their feeds were based on content curation more than anything else.

But this gave me an early opportunity to get to know the people on travel Twitter. Back in 2009, the entire conversation was happening on Twitter. As the human behind the accounts, I got to know who the big players were — and I used my knowledge to befriend them with my own profile, where I talked travel with them as well. When I eventually left that job, I messaged several of them privately and told them to head over to my personal profile.

This job gave me a reason to spend hours on social media and get to know the main players in the travel space, and those relationships I built with them led to them sharing my travel blog’s posts in the future.

Dipping My Toe Into Freelance Destination Writing (2009)

I wanted to try my hand at freelance travel writing, and I combed Craiglook (a site that crawled all Craigslist sites) for writing gigs I thought I could do. One was for Boston nightlife. As a girl who hit the clubs every weekend, it was a perfect fit.

For $20 an article (they were just a few paragraphs long!), I’d write about Boston’s nightlife for sites like AOL Travel and TripVine. It wasn’t much, but eventually I started getting invited to different parties and events around the city.

Starting my freelance writing career while I worked a full-time job gave me a leg up when I eventually quit, giving me the connections and portfolio to earn a writing income once I started traveling.

Laptop Image via Pixabay

Starting Adventurous Kate — A More Professional Travel Blog (2009-2010)

By this point, I had been blogging almost daily for seven years. Blogging wasn’t just a hobby — it was a major part of my life. I was ready to do something bigger.

After the success of The Grammar Vandal followed by my ambivalence for writing about grammar, I decided the next logical step was to start a new, more professional blog centered on my absolute favorite interest: travel.

It was the easiest decision of my life.

I began laying the groundwork in fall 2009 and AdventurousKate.com went live in late January 2010. I wasn’t one of the very first bloggers, but I was part of the earliest travel blogging community.

My plan was to write about my past travels and, when the time came, eventually write about my dream trip around the world. Thanks to Twitter and blogging, I made tons of new friends in the industry. People like Cailin, Stephanie, Michael, Lillie, Ayngelina, and Michael. Nearly a decade later, we’ve accumulated marriages, babies, breakups, career changes, and trans-continental moves, but I’m still friends with all of them.

Back then I blogged short posts daily. Monetization didn’t cross my mind. I wanted only one thing — to be one of the most popular travel blogs in the world. I wrote constantly; I networked with my travel blogger friends on Twitter; I became obsessed with this new and interesting community.

My old personal blog, the version of Adventurous Kate on Blogger (and then WordPress.com), became a relic of the past as I focused exclusively on the new self-hosted AdventurousKate.com.

This started it all.

An Exit, A New Job, and a Revelation (2010)

The travel booking site was so wonderful in the early days — until the founders changed their strategy and decided that we needed to “get to 10X.” That day, they let go several longtime employees. Starting with some people I liked very much, including my blogging friend who had hired me.

Every few months, there would be another purge — two or three more people would be let go (we had something like 24 people in our office) — but bizarrely, they would be replaced with two or three new people doing essentially the same jobs. As you can imagine, it was terrible for morale.

I began searching for another job and landed one at an agency in the suburbs. I’d be doing paid search work for a variety of clients.

BOY was that fortuitous timing, as days later, I was told I no longer had a job. (I called the agency and asked if I could start a week early. They said sure.)

While I lucked out in missing only three days of unpaid work (who fires someone on a Tuesday?!), I soon learned that taking the job at Catalyst was a mistake. I hadn’t enjoyed paid search work at the travel booking site, but I loved the people — and now I was doing exclusively paid search work in a company with no social atmosphere whatsoever.

I was miserable at the agency. I hated every minute in the building and would spend my lunch hour listening to D’Angelo and Maxwell and Robin Thicke while walking all over the neighborhood.

So why didn’t I leave? I was terrified that if I went for a new career, I’d have to start over with an entry-level salary. I had moved into a more expensive apartment in downtown Boston and couldn’t afford that. I was terrified that I was stuck forever in an industry I hated.

That awful job was a blessing in disguise — it would be the push I needed to go after my dreams.

My going-away party in Boston

Planning an Escape — and a Trip (2010)

Around this time, I was tired of Boston and began weighing a move to New York. The logistics would be complicated if I moved without a job. I could transfer to one of the agency’s New York offices, but why would I want to continue in an industry I hated?

Day and night, I kept dreaming of traveling the world long-term. Soon enough, I realized that living in New York wasn’t my dream — traveling was my dream. I needed to move my travel date up a lot sooner.

But I wouldn’t have enough money for my dream trip, starting in New Zealand and moving on to Australia, Southeast Asia, India and Nepal, and westward to Europe. So what else could I do?

I could move to Korea, teach English for a year, and save a ton of money for my dream trip. But I had a close friend’s wedding to attend, and I knew that teaching in Korea would make it difficult to take the time off to come home. Not to mention all the other wedding activities.

Then it hit me. I didn’t have to do my dream trip — I could do a shorter trip in a cheaper destination.

Like Southeast Asia. For seven months. Southeast Asia was the place I wanted to visit the most anyway.

I would leave October 21, I decided, and I planned to work until October 15. I saved up $13,000 in seven months. I booked a round-trip ticket to Bangkok. My lease ended on August 31 and I moved into my mom’s house for the last few weeks.

I gritted my teeth through the workday. October 15 was too torturous; I decided to stick it out until October 1. I didn’t last. On September 14, 2010 — a day I celebrate each year — I picked up my belongings and walked out with my belongings, never to return.

These months were among the hardest of my life — not only was I working a job I hated, I was blogging in my free time and doing a ton of freelance work, only sleeping four hours on weeknights. I was also barely eating and lost 20 pounds in a very unhealthy way. I spent as little money as possible. Living this way made the coming trip even sweeter.

Specializing in Solo Female Travel and Southeast Asia (2010-2011)

It sounds crazy now, but back in 2010, few people were blogging about Southeast Asia exclusively and few women were specializing in solo female travel. By focusing on these two areas in this time, I was able to differentiate myself from other travel bloggers, who were mostly doing RTW trips on a budget or traveling part-time.

Blogging was SO different back then. I miss it. Blogs were narrative-driven, people commented like crazy, you didn’t have to worry about Instagram and Pinterest because they didn’t exist. And if you were making money from your travel blog, you were selling text links.

I remember those early days in Southeast Asia so clearly. I didn’t sleep a wink the first night — I got up at dawn, went to the Grand Palace and Wat Pho, and came back to my hostel to write about them. Writing about real-time travel felt so unnatural at first, but soon I found my groove.

This was the ideal way to start my travels — I was experiencing an interesting, cheap region and educating women on what it was like to travel Southeast Asia solo.

Taking a Leap to Continue Indefinitely (2011)

Most people think quitting my job to travel the world was a ballsy move — but I think what I did the following year was even more terrifying.

After coming home from my seven-month trip and being present for my friend’s wedding, I had found myself in an unexpected situation: with a new English boyfriend I had met in Vietnam.

He was coming to visit Boston in July, so it made no sense to get a job before then. I got offered trips to Sayulita, Mexico, and San Antonio, Texas. I hung out at home and continued to blog; he visited; all seemed good. Shortly after that, I was invited to a travel blogging conference in Austria in late August, and it seemed like a great way to tie in a visit to my boyfriend.

I went to England. I went to the conference in Austria, and visited Germany and Liechtenstein for the first time (the latter as their hosted guest). I got invited on two sweet press trips: Emilia-Romagna, Italy, and Jordan. I added a side trip to Turkey after Jordan and planned for Portugal and Spain in the winter.

It made no sense to go home. Europe was great. I had a community of travel blogger friends. Things were good with my boyfriend. I stayed.

What I didn’t realize at the time was that Europe was the best place I could have been — the travel blogging industry was far more advanced here than anywhere else. There were more press trips, more conferences, and more PRs that took blogging seriously. I had put myself in a very strategic relationship-building position.

Moving to Affiliates at the Right Time (2014)

Those early years were tough. I was in love with my work and addicted to the freedom, but I was barely getting by financially. My income came from text links, poorly paid freelance writing, and the occasional odd writing or editing gig. I lived off press trips and generosity.

I hit a breaking point during Chinese New Year in 2014, while I was in Boracay. That day, my most lucrative writing gig, a steady $1500 per month, disappeared. In the coming weeks, I wrote a post called How to Start a Travel Blog, linked to some affiliates for web hosting, and forgot about it.

Google updated and I suddenly started getting tons of web hosting commissions. By the spring, I was making thousands of dollars per month off that one post alone. I did so well that my highest-earning affiliate massively increased my commission.

Somehow I had cracked the code. Finally I had the job I loved — and money as well.

It didn’t last. Within a few months, virtually every other travel blogger copied my post, and in a few years I was pushed out of the top rankings. But I had laid the groundwork for other successful posts. Plus, at this time, I started getting paid campaigns on a regular basis.

I should have gotten into affiliates years earlier — but I was still ahead of the game. Building a passive income took a lot of pressure off me and allowed me to continue creating content that made me happy.

Moving to New York (2016)

In early 2016, I moved to New York. This decision was crazy in so many ways — if you can work from anywhere, why move to a cold, expensive city that makes life so hard for you?

I did it because I wanted to. After moving abroad twice for relationships, finally I was choosing a place for me alone. And also because my sister and best friend were here, among other friends. But despite the high cost of living, being a travel blogger in New York provided lots of other advantages.

I got some opportunities in part because of my location. My campaigns with Austrian Airlines, ANA, Kenya Airways/Fairmont Kenya, and Guyana Tourism, as well as several influencer opportunities, would not have happened if I hadn’t been based in New York. Brands will always fly you from New York because it’s so well-connected.

New York is the center of the travel industry, and it’s amazing that I can meet for coffee with different PR agencies whenever I feel like it. New York has industry events like Travel Massive, IMM, and the New York Times Travel Show, where I’ve spoken annually since 2015. There are always events being thrown by different tourism organizations. I get offers for free Broadway shows, restaurant openings, and all kinds of events.

But the most important thing is the city’s work culture. People in New York work extremely hard and it encourages you to work even harder. I wouldn’t have had that same kind of motivation if I had moved to a digital nomad hotspot where people work only enough to get by.

Conclusion

What does success as a travel blogger look like today, in 2019? Everyone’s definition is different. For me, I live in Manhattan and have a large apartment all to myself. My sister lives a short walk away, my best friend lives a subway ride away, and I have lots of friends in the city. My family and friends in Massachusetts are a short train ride away, and I’m a loving auntie to two sweet little boys, one in New York, one in Massachusetts.

I’m in New York about 75% of the time and I travel the other 25%. I have friends around the world. I work out in the mornings and work in the afternoons and evenings. I love exploring New York, going to literary events, obsessing over politics, Zumba classes, taking long walks in Central Park, and spending time with friends. I don’t work while traveling anymore; I prefer separating those aspects of my life these days.

Is my life perfect? HELL NO. There are LOTS of things I’d like to improve; I have worries that keep me up at night. But it’s a good life, and it’s a life that I built for myself. It’s worlds away from when I was on a sweatbox of a train in Bulgaria, down to my last $200 and owed $9,000 from late-paying vendors, and sobbing my eyes out. Or working in that terrible office in suburban Boston, marking a line whenever 15 minutes had passed.

I think when you look at the events of my life, themes begin to emerge. Three major things:

1. I had a privileged upbringing that put me on a much higher footing than many of my peers in terms of education, work ethic, and opportunity.

2. I grew my lifelong loves of writing, geography, and technology into obsessive storytelling, travel, and website-building.

3. I made a lot of smart decisions at the right time, even when I didn’t realize it at the time.

I also think it’s equally important to examine what I didn’t do. Today, most people start travel blogging because they want to make money and get travel comps. I was never in that position because making money and travel blogging comps didn’t exist in 2010. Hell, when I started my travel blog, I thought the only way to make money was to get a book deal or TV deal.

I didn’t look to replicate the success of others because I was one of the originals. Almost everything I did was based on instinct, and I had already developed my voice from seven years of near-daily blogging.

I started this career because it was my favorite hobby. I’ve kept it going since because I still love it. That is my greatest motivation — work that I greatly enjoy, and knowing I can help women along the way.

How to Replicate My Success

Unfortunately, you can’t do it exactly the way I did. So much of my success comes down to timing, from being a teenager when Angelfire was at its height to being a college student when blogging was in its infancy to starting a travel blog among the first generation.

But I do have advice for parents or teenagers or college students who are looking to glean lessons from my life:

Cultivate your interests and lean into them. I grew a career that I’m passionate about because I had been spending years and years preparing for it — without even knowing it. My obsessions with writing, travel, and technology eventually knit together into travel blogging. They say it takes 10,000 hours of practice to master a subject, and I had definitely been blogging for 10,000 hours for fun before I even started Adventurous Kate.

Get involved in technology from a young age. Learn to code. Learn to build websites. Master a social network and content creation. Learn cutting-edge techniques of photography and video production. When you put in hours developing these skills, you’ll be in a better position than your peers. Of course, be sure to have a healthy amount of time away from technology, too. It’s good for your brain.

Forcing yourself to take a leap can be the greatest motivation. I wouldn’t have worked nearly as hard to succeed at blogging if I hadn’t quit my job, or moved to Europe when I was broke, or lost my plum freelance writing gig, or moved to expensive New York. Had I taken the easy way out, I could still be making $2,000 per month, drinking every night in an expat hangout, and wondering why my blog was getting less and less popular.

I know that my life will continue to evolve — I might not always be a blogger, but I know that travel and storytelling will always be part of my life. I’m looking forward to the next step, and the step after that, and the step after that.