This Is Me, 20 Years Later: 20 Years of Travel Blogging

This article may contain affiliate links where I make a small commission for purchases you make from links that you click from this article. By purchasing through these links, you support me at no additional cost to you. Thanks for your support.

I’m skeptical of many things and people. Not unfriendly — I’m actually really good at being your fun, awesome new friend on the outside. But the whole time, the voice in my head is running its checklist: Is this really true? What kind of person is this? Are they smart? Do they know what they’re doing? It takes a lot to win me over. I got that from my dad, a Midwestern engineer who never made a big deal out of anything because he never assumed anything would work unless he did it. (Probably not a great thing to admit to all of you. Too late now!)

So it makes no sense that 20 years ago, terrified, I handed my whole life over to the one thing I had no reason to trust.

I trusted travel.

Twenty years ago I was standing in a Manhattan apartment saying goodbye to my Blackberry. That’s not a metaphor. I actually had a Blackberry. It was 2006, “podcast” was still a new word, and I had just quit a corporate IT job to buy a one-way ticket to Kenya, kicking off my career break (year of travel). I was scared of what I was doing. I did it anyway, trusting that somehow everything would be ok. I started a website so my family wouldn’t worry about me. I didn’t call it a blog because I didn’t know that word yet either. I called it a travel journal, because that’s what it was.

You can see what’s left of that original Travel Journal Here…it still lives….

I’m Type A, so of course I made a plan and bookings — but only for the first three months of my trip. I left the rest loose on purpose, and I told everyone that I’d be disappointed if I actually stuck to it. I wanted answers. I wanted to come back a different person. I was not disappointed.

Two months in, on a bus somewhere on the South Island of New Zealand, I realized I was never going home. Not that I’d never set foot in America again — I would, a lot. But the woman who bought that one-way ticket to Kenya wasn’t coming back. Out the window were landscapes so unreal I remember thinking someone must have retouched them just for me! Every hour the bus stopped somewhere more beautiful than the last, and I was 36 years old and I had never felt anything like it — not once in 14 years of climbing a corporate ladder I didn’t know if I even want to be on.

The genie was out of the bottle. How was I supposed to go back to an office and try to be normal, when every single day had something in it I’d never seen before? Back then everything was new — every place, every person. (I miss that.) So I just kept moving, and kept being open to whatever happened next. And things I couldn’t have imagined happened. Like building a career out of it.

Smiling woman with glasses holding a Sherry Ott influencer badge at a conference.

That’s why the Gilda Radner quote I stuck at the bottom of my very first post has followed me around for 20 years:

“Some stories don’t have a clear beginning, middle, and end. Life is about not knowing, having to change, taking the moment and making the best of it, without knowing what’s going to happen next. Delicious Ambiguity.”

The woman in that apartment was terrified of change. She cried on her couch about her disliking her job in 2003 and then waited three more years to actually do anything about it. The woman writing this goes looking for change on purpose, and gets restless when she can’t find any.

Twenty years of traveling. I can’t even believe it. This post is about how one of those women turned into the other.

Table of Contents

Why I Keep Writing These

This is a habit at this point. Every few years I sit back down and write one of these — “This is the Middle,” “This is Now,” six years later, nine, thirteen. Same assignment every time: stop moving long enough to take stock of who I am and what actually matters to me right now. I reread all of them before writing this one (a little embarrassing — I used a LOT of ellipses back then!). Different writer, different person, every single time.

So here’s the 20-year version, in six eras. (Yes, eras. Taylor Swift is not the only one allowed to have them! Hers have sequins. Mine have laptops, cameras, backpacks, hiking boots, and compression socks!)

Era One: Letters Home (2006–2009)

I got my first passport at 30. I did not know what SEO was. I did not know what a “niche site” was. I wrote like I was writing letters, because I was — to my parents, to friends who thought I’d lost my mind, to anyone who wanted proof I was still alive. Kenya was only ever the first stop — I’d planned three months and left the rest open — but the one year I’d promised everyone turned into a year and a half, and 23 countries, because that’s what happens once you start.

I was a bucket-list traveler then, and I’m not embarrassed about it. Kilimanjaro, the Great Wall, Machu Picchu, Sydney Opera House — I wanted to check off the places everyone dreams about. I failed to summit Kilimanjaro in my first month out and wrote about it anyway — altitude sickness, tears, all of it. My sister made the summit. I got sent down to 10,000 feet to recover. Looking back, that post set the tone for the next 20 years: tell people the part that didn’t go well. It’s the imperfect parts we remember best anyway.

Then I sold almost everything I owned and moved to Ho Chi Minh City, where I taught ESL, sold photography, and rented a motorbike I was too scared to even start for the first few weeks. I wrote a whole series about learning to ride it that I’d sum up now in one line: Fear: 1, Sherry: 0. Then, eventually, Fear: 1, Sherry: 100, because I just kept facing that fear and kept riding.

This isn’t staged, I actually used this public phone in Athens in 2006!
Sooooo blue!
Camping – with a clear view of Mt. Kilimanjaro
Traveling together in Thailand
Photo taken prior to the Helmet law in 2007
Me and my motorbike – and one flat tire…
Dinner with my writing students
Me with my furry, flatulent friends

That’s the era’s whole personality. No plan, no polish, just a stubborn refusal to be the version of myself crying in that Manhattan apartment again!

Era Two: The Corporate American Refugee (2010–2012)

For two years, Ottsworld wasn’t the biggest thing I was running. This was.

In 2007, midway through that first trip, I spent a month volunteering as an ESL teacher in India through an organization called Cross-Cultural Solutions. A program manager there named Michaela Potter started following my blog for work. She and her boyfriend Michael had just quit their jobs together to travel. By early 2008 all three of us had landed back in New York City at the same time, each of us changed, each of us asking the same question: why is it so hard for Americans to take extended time off to travel?

Other countries encourage gap years and sabbaticals. Americans wear our productivity like a badge and act like that’s what makes us valuable — and then we wait until 65 to see the world. Time away from a routine is how people grow. Other countries do this. Why couldn’t we? We were taking on the American work ethic itself, and our Big Fat Hairy Goal was a career break on every resume in the country.

We called the first version Briefcase to Backpack. In January 2010, over coffee in San Francisco, Michaela and I decided a blog wasn’t enough — people needed to be in a room together — and Meet, Plan, Go! was born. The idea was simple and a little crazy: one night, one shared program, hosted at the same time in cities all over North America by volunteer hosts, most of them career breakers or travel bloggers themselves. The first national event was September 14, 2010. Eat, Pray, Love had hit theaters six weeks earlier (a friend gave me that book before my own trip in 2006, back when nobody had heard of it — I’ve always said if I wrote mine it would be called Eat, Pray, Reality), and suddenly a whole country was asking why they’d never taken time off. We had an answer ready. A month later the New York Times wrote about us. The next year we were in 17 cities! I did a CNN interview about career break myths from a family’s apartment in Beirut. I got called a “corporate IT refugee” in print so many times I started using it myself.

That same year, 2010, I turned 40 and wrote the third post in this series: “This is Now.” The subtitle was “40 and Happy.” I meant it. I was leading something. I was helping people make the same leap I’d made, and I could see it working. Looking out at a sea of people who wanted to change their lives, knowing you have an answer for them — that’s a drug I still haven’t found a replacement for.

It was also the era where I figured out this blogging thing could be a career and not just a hobby. I was one of the first travel bloggers working directly with brands and destinations — in spring 2012, a European apartment-rental company sent me to ‘live like a local’ in Rome, Venice, Vienna, and Berlin for a campaign called “Living La Vida Local,” back when “sponsored travel” barely had a name. I drove a tiny car from London to Mongolia for the Mongol Rally in 2011. I was busier than I’d ever been in corporate America, and a whole lot happier.

Then in 2012 Michaela stepped back from Meet Plan Go, and I ran the third national event mostly by myself. It went fine. It just wasn’t nearly as fulfilling. I already had Ottsworld, which I was running completely on my own. I was traveling on my own. I was tired of doing everything by myself — and when Michaela left, I was alone in this too. Meanwhile Ottsworld was taking off in other directions, and I simply wasn’t capable of running both while living out of a suitcase. So I let Meet Plan Go get smaller, and eventually I let it go.

I don’t count it as a failure. A lot of people took career breaks because of those events. And the person I built it with didn’t go anywhere — Michaela shows up again in Era Six, driving a support car behind my bike across the Dakotas and producing the documentary series about it. Fifteen years, two completely different projects. That partnership is the real thing I built in this era.

Era Three: The Only Thing Certain Is Uncertainty (2012–2014)

That was my line for this whole stretch of my life, and the next one too: the only thing certain in my life is uncertainty. I didn’t know where I’d be sleeping in a week, how I was going to make money that year, what projects I’d be working on – everything was completely fluid during this nomadic stretch. This is when I learned to trust that uncertainty.

In 2012 I walked the Camino de Santiago — 500 miles across Spain, solo, on foot. At the Cruz de Ferro I left a rock with my Gilda Radner quote on it, the same one I’d put at the bottom of my very first blog post in 2006. I picked up a second phrase on that walk that I still use today: Make Your Own Way.

Something else happened on that Camino that I didn’t write about at the time. Crossing the meseta — the flat, empty stretch most people skip (I loved it, I love an underdog) — I walked past a farmer tilling his field, and the smell of fresh dirt hit me like a tidal wave. Childhood memories came flooding back to me of working in my dad’s garden outside Peoria. The one I resented weeding every single summer as a teenager, because all my friends lived in subdivisions and rode bikes and nobody else’s dad made them weed gardens and can vegetables. Back in the 80’s – no one even had gardens! He always had to be different. He always had to be contrary. I hated that about him. And there I was, standing in a field in Spain, walking alone across a country — exactly like his weird quest to walk alone across America to state capitols. I realized I had spent the last 6 years traveling, trying to be different, bucking the norms. How did I become my dad? WTF.

That question is the reason there’s an Era Six.

The Camino also started something I didn’t have a name for yet. When it ended I felt flat, and the only cure I could think of was another one. So over the next few years I went looking for every long-distance pilgrimage route I could find: the Kumano Kodo in Japan, the Lycian Way in Turkey, St. Olav’s Way in Norway, the Camino de Ronda in Spain with my dad. I’d rather walk 100 miles through somewhere I’ve never heard of than fly to somewhere everyone has. And in 2014 I drove a 7-horsepower auto-rickshaw — a glorified lawnmower with three wheels — 2,000 miles from the bottom of India to the top with my friend Charlie, raising money for clean water and getting asked “where is your driver?” at every single gas station. It will press your limits. It will also give you back more than it takes.

My travel style was changing underneath all of this. The bucket list didn’t interest me anymore. I’d figured out that what I actually loved were the harder countries — the ones where the culture was as far from mine as I could get, where nothing worked the way I expected and I had to figure it out. That’s where I felt most alive. I wanted big journeys, I wanted to challenge myself. I wrote a post at 44 about learning to surf and canter a horse on the same trip, and asked the question that’s been bugging me ever since: when did life stop being fun and start being scary? Staying the course and not trying new things is the quickest way I know to get old.

Read “How to Overcome Fear in Your 40s”

I wrote “This is Me 6 Years Later” from a ferry in Patagonia in early 2013, and it’s the first time I said the quiet part out loud: this life was getting lonelier. I wrote, more or less, that people love meeting an independent, worldly traveler right up until they realize she doesn’t fit into their five-year plan. That’s a hard sentence to publish about yourself. I published it anyway.

That’s also when the Niece Project officially started — a promise to each of my six nieces that instead of birthday gifts, I’d take them anywhere in the world they chose when they turned 16. I never wanted kids. But I did want to be the travel mentor nobody was for me (I didn’t get a passport until 30, remember?). Evie picked Vietnam, threw up in her airplane seat somewhere over the Pacific (I will never travel without a barf bag again), and became the first person in her family — my brother’s — to leave North America. I took my dad to Antarctica in December 2012, our third trip together. The family trips were starting to matter more than the country count.

And then there was the blog itself. Somewhere in here, blogging changed. It stopped being a bunch of people writing letters home and became an industry — with keywords, and listicles, and “how to” articles, and people buying and selling links, and everyone chasing the same Google rankings. New bloggers flooded in, and they started their blogs as businesses and ran them like businesses from day one. I’d started mine out of passion and had no real idea how to run a business — I figured it out as I went, somehow, and survived. But I had a decision to make. I could write for SEO like everyone else, or I could keep writing like me. I didn’t want to tell people how to travel. I never did. I wanted to inspire people to go — and then let them figure out their own version. So I stayed true to that. For a long time. And I watched bloggers who started when I did catapult past me in traffic and in income while I stood still. That was hard. Really hard. Someone asked me around then what my overall goal was, and I told them honestly: I have no fucking idea. My life choices have always been more about what I don’t want to happen than what I do want to happen. And I did not want to become a content farm.

Era Four: Tired, Stubborn, and Still Going (2015–2019)

At nine years in, 65+ countries and seven continents deep, I wrote that I was tired. Stressed. That my relationships kept suffering. That I did not — do not — think most people should do what I was doing. I compared my need for new experiences to an alcoholic who used to get drunk on three beers and now needs three beers and two shots of whiskey. I was working with a literary agent on a book proposal around then, too. I’ll come back to that.

This is also the era where I caved, a little. I started paying attention to keywords. I wrote some of the how-to articles. I restructured old posts so Google could read them. I did it because I had to make money and survive, and the honest, inspiring, “here’s what it was actually like” essays I loved writing didn’t pay the rent I didn’t have yet. I had always told myself I would keep traveling until I had to start touching my savings — that was the only rule. It never happened. I got close a few times. But it never happened, so I kept going.

The whole time, though, the SEO game made me a little sick. It was turning the entire internet into the same article. Every “Things to Do in New Orleans” post had the same ten things in it — nothing new, nothing different, just the same list rearranged, because everyone was trying to rank for the same five words. Articles written by people who had never set foot in a place were outranking mine, written by someone who had personally eaten the thing and slept in the room and gotten lost on the way there. I was mad about it. I’m still mad about it. But I made the changes anyway, because being right doesn’t pay for a plane ticket.

At 46 I wrote a post called “Why I Hate My 40’s” and said I felt like the real me had been kidnapped and was being held hostage somewhere. Perimenopause, arthritis medication, knees that clicked. That year I slept in 95 different beds. Ninety-five! I wrote that I felt like I lived on jello.

In 2017 I finally got a home base, in Denver, after 11 years of having none. Not because the quest was over — because I missed real relationships, the kind where people actually know you, and because my body needed a regular doctor. A tweet I’d scheduled months earlier happened to post the same day I stood at the apartment deposit box: Certainty is overrated. I took it as a sign. A few months later I panicked on a flight because I couldn’t remember which bag my keys were in. I had been keyless for a decade. Keys were a new responsibility!

Then in 2018, almost by accident, I found the thing that would carry me into the next decade. My sister and her friends wanted to go to Ireland, so I designed a trip for them and led it myself. I expected to tolerate it. Instead I loved it — way more than I thought I was going to. Designing the trip was the part that lit me up: finding the corner of County Mayo nobody goes to, the hike nobody’s written up yet, the place that isn’t in anyone’s top ten. I see where everyone is going, and then I turn around and go the other way. It turns out you can build a tour company on that sentence! Ottsworld Tours started there, with my sister, and it has been growing ever since.

Then came the knee surgery, and the lower back that had, in my own words, become “the back of a 70-year-old,” and then, on what turned out to be the last Niece Project trip, three blood clots in my lungs after a long flight to India. I am lucky to be alive. Travel — the thing I’d trusted with everything — very nearly killed me that year. I finished the project. I also think about that flight a lot, which is why I now write and talk about how to avoid blood clots when you fly, and why I get up and walk the aisle every 90 minutes on every long flight now. At 13 years in, I wrote that the blog itself felt like it was turning into a teenager — old enough to have a history, young enough to still be figuring out who it was.

None of that made me stop. It just made me tell the truth about the cost.

Era Five: Pink Hair, Kittens, and a Bike (2020–2021)

I turned 50 and colored my hair pink instead of panicking. (Fine — it was probably a little bit of both.)

That year I wrote openly about perimenopause, about a rare form of alopecia that took my hair for good (I have eyebrows tattooed on now — no, I will not stop mentioning it, it’s funny and it’s true), about hot flashes and 20 pounds I’d put on in my 40s after backing off exercise from old injuries, about forgetting words mid-sentence. I treated all of it like material instead of a diagnosis, because that’s the only way I know how to survive a decade that keeps taking things from you while also, somehow, being the best one yet.

I celebrated turning 50 at a women’s surf and yoga camp in El Salvador with my sister, a niece, and old friends. Not because I’d arrived anywhere. Because I’m the person who, faced with a milestone that’s supposed to scare you, would rather go learn to stand up on a board she’s going to fall off of.

Then the world shut down, travel stopped, and for the first time in 14 years I had no next trip. I fostered 13 kittens — they saved me as much as I saved them. I bought a bike. And I finally sat down and did something with 14 years of trips: I wrote an ebook, Where to Go & When, a month-by-month guide to the places I’d actually been that nobody was writing about, built on the same sentence as the tours: find where everyone is going, and go the other way. It was the first time I’d looked at the whole 14 years at once and realized it added up to something.

Era Six: Turn Around and Go the Other Way (2022–2026)

Remember the farmer’s field on the Camino? This is where that thought ended up. In 1984 my father started walking, alone, to every lower-48 state capitol, with his own strict rules — no rides, ever, and you walk into and out of every capitol building. He made it to 23 before he stopped in 2009. In 2022, a little lost after the Niece Project ended and honestly flirting with depression from how predictable blogging had become, I asked him if I could pick it up on a bike. He said, more or less, “what the heck.” I started in 2023 with the route he’d left unfinished the longest, St. Paul to Pierre, with Michaela — yes, that Michaela — driving the support car and filming. My mom drove logistics on the next route. We call her the OG Logistics Queen, because in the 1980s, she was literally his. I’m eleven routes in now, with a lot of America still ahead of me!

Everything I do now runs on the same engine my dad’s did – be different. The tours grew — Patagonia on e-bikes, Alaska in the winter, the counties in Ireland no one goes to, a women’s surf camp in South Africa — and my favorite one I’ve ever designed is the Japan Cat Tour, for one simple reason: nobody had done it before. That need to be different, to be unique, to not do the thing everyone else is doing — I used to hate it in him. It turns out it’s the best thing he gave me, and I think it’s why I’m still here after 20 years.

I’ve done three separate expeditions to Antarctica now, crossed the Drake Passage twice, and taken the much longer, much rougher Southern Ocean route to the Ross Sea once — the trip where someone on our ship had to be helicoptered off within the first four hours. I still get seasick. I’ve just gotten better at admitting it and preparing for it. This July, at 56, I got back on the Camino — by bike this time, the Camino Português from Porto — 13 years after I first walked it. Same destination. A completely different body carrying me there.

The blog changed with all of this. I write with a lot more structure now — summaries, tables, FAQs — because 20 years in, people come to me for answers, not just stories. But I’ve made my peace with it, because the answers come from somewhere real. Oprah Magazine called me an influencer once and I’m still not comfortable with it. What I actually am is someone who wants to inspire people to do more than they think they can, and push their own boundaries a little further out.

I’m firmly an adventure traveler now, and have been for a while. What I want is adventure mixed with culture, in places people haven’t heard of yet. I like motion. I like to move. I like challenging myself and growing, and I like bringing my readers along, because I have a feeling they’d like it as much as I do. Few things scare me anymore. I roll with it.

But I’ll be honest about the cost of 20 years of this: it’s rare now that I get to see something truly new — a landscape, a culture, a way of doing things I’ve never run into. I don’t count countries anymore. I’m harder to impress, and I get a little down about that sometimes. The flip side is that when a place does impress me now, I know it’s really something. These days I’m mostly interested in getting other people off the beaten track — and I have to remind myself that it’s ok if they still want the bucket list stuff first. I did too, once.

What Changed

Twenty years ago I was terrified of change. Then I became a traveler. Then I fell in love with change and newness for its own sake. And somewhere along the way I became someone whose whole job is inspiring other people to take on a challenge and be a little different — not to travel the way I do, but to stop following the shoulds. The bucket list turned into hard countries turned into adventure. The letters home turned into an industry I fought with and eventually made a truce with. The woman who needed five friends and a host in Nairobi to get on the plane to Kenya now rides a bike alone down gravel roads in the Dakotas – and occasionally rides on interstates (which is much harder!).

Inspirational quote on practice and life with a black background and white dotted border. — ¯;

What Never Moved

Six eras, six very different writers/people, and somehow the same handful of things survived all of them. Chasing new over comfortable, even now when comfortable would be so much easier to justify. No kids, no spouse, no home base for 11 straight years — not a sacrifice, a choice, made on purpose and never regretted. Telling you about the industrial stretches of the Camino and not just the cathedral, because not everything in travel or life has to be good and perfect, and the unplanned parts are the ones you remember anyway. Doing hard things with people I love, because doing them alone stopped being enough somewhere around Era Two. And a few mantras, recycled for two decades: delicious ambiguity, make your own way, and see where everyone is going, then turn around and go the other way.

The One I Almost Didn’t Tell You

Somewhere around year nine, I had an agent. She found me through a mutual friend and asked if I wanted to write a book — my chance to take all of this and put it between two covers. I started the proposal. Most mornings I woke up thinking, I can’t write a book! And eventually I walked away from it. Not because I ran out of material — I clearly had more material than I knew what to do with (are you actually still reading this?!!) — but because I got scared. By then, “quit your job and become a digital nomad” had turned into a story a thousand other people were also telling, and I couldn’t shake the feeling that mine wasn’t unique enough anymore to deserve a book. That fear — of not being different enough — is the same one that’s driven every good decision I’ve ever made. It’s just usually pointed at a trip idea, not at myself.

Giving up on that book is one of the only things I’ve done in 20 years that felt unlike me. It’s bothered me ever since. I’m telling you now because writing this post — 20 years, six eras, one very stubborn woman — is the closest thing I’ve had to proof that the story was always unique enough. It just took two decades to see the whole shape of it.

No Ending, On Purpose

My parents are both 90. My nieces — the ones I dragged to Vietnam and Peru and India at 16 — are getting married and starting to have kids of their own. I own a condo now. Time keeps moving on and on, and somehow Ottsworld is still here. I can hardly believe it. And now AI has arrived and is changing my world, and my blog, all over again — the same way Google did in Era Three. I don’t know what that means yet. I do know what I’ll do about it, because it’s what I’ve done every time: figure out where everyone is going, and then go the other way.

Twenty years ago I put a quote about “delicious ambiguity” at the bottom of a blog post because I liked the phrase and I was 36 and terrified and had no idea what I was actually starting. I still have no idea what’s next — a couple dozen more capitols, another pilgrimage route, a tour to somewhere none of you have heard of yet. I’m still skeptical of almost everything. But I trusted travel, and it paid off. The ambiguity’s still delicious. I just finally know it’s not going anywhere — and neither, apparently, am I.