The Conversation We Would Be Having

Adventurous Kate contains affiliate links. If you make a purchase through these links, I will earn a commission at no extra cost to you. Thanks!

Kate at Table Mountain


I met you at a party. Or maybe a bar. We’re friends of friends. Very likely total strangers.

I hope that right now you and I are talking about life in New York. Or hilarious dating disasters. Or our favorite slow cooker meals. Or the fact that we’re still not over how Bill Murray lost the Oscar for Lost in Translation. Or you. I want to know all about you, your life, your work, and what excites you.

Basically, I’m trying to avoid “The Conversation” and I haven’t figured out a polite way to do that yet.

Ana Desetnica

The Conversation

I have The Conversation several times a week. People find out that I’m a professional travel blogger and ask me several questions about it — the same exact questions each time. Open-ended, complicated questions that aren’t answerable in quick sound bites. And while I know it comes with the territory, having The Conversation is one of my least favorite things to do.

I totally understand why people want to talk about this. I have what a lot of people consider a dream career, and yet there’s no barrier to entry. People want to know how it’s possible.

I’m writing this post because at the last two parties I attended, I ended up having The Conversation over and over for half the party and wished I had spent that time making new friends instead of repeating the same things again and again. I didn’t even bring travel blogging up — it tends to travel through the grapevine.

So, instead, I’m writing this post. I hope in the future I’m able to smile at a party guest like yourself and say, “You know, I actually get burned out on talking about work and I’d rather spend my time getting to know you. I can send you a link to a page where I answer all those questions. For now, can we talk about something else instead?”

Here are your questions and my answers:

Koh Lanta Sunset

So, what’s your favorite place?

The truth? Most travel bloggers hate this question. It’s so hard to condense so many years of travel, a whirl of countries and cities and experiences, down to just one place. It’s practically impossible, which is why a lot of bloggers refuse to answer.

But I know you want an answer, and this is as close as I can get to my “favorite place”:

My top five favorite countries are Croatia, South Africa, Italy, Japan, and Thailand.

Beyond that, a few more: my favorite region in the world is the Balkans; I also love Central America and the Nordics.

Some of my favorite cities are Paris, New York, Melbourne, Bangkok, Berlin, Edinburgh, Savannah, Granada (Spain), Bologna, New Orleans, Hong Kong, San Francisco, and Boston.

Some of my favorite culinary destinations are northern Italy (particularly Emilia-Romagna, Tuscany, and Umbria), Japan, Vietnam, Paris, Mexico, and the American South.

And one place that means a lot to me is the island of Koh Lanta in Thailand. I wouldn’t go so far as to call it my favorite place in the world, but if I had to pick one, that would probably be a finalist.


What about the worst place you’ve ever been?

Poipet, Cambodia. It smells like rotten fish and waiting for hours at the border is a hellish experience.

Manila. So dirty and unpleasant, it makes my skin crawl. (No offense to my wonderful friends who live there.)

Port Authority in New York. It’s like the Twilight Zone.

Alberobello Trulli

So you’ve been everywhere, right?

Not remotely! I’ve been to 67 countries at the time of publication. That number is probably somewhere in the middle as far as full-time travel bloggers go. I know some travel bloggers around my age who have been to 90+ countries; I also know a lot who hover in the 30s or so.

Could I have been to more places in that time period? Sure. But keep in mind that I’m only one woman — there’s only so much time and money that can be spent on my travels without me losing my mind! I also prefer not to duck into a capital for two days and then move on to the next country. I like to explore three different destinations within a country when possible.

I have no desire to visit every country in the world. It’s not my thing.

I do have a list of destination goals, though: the Galapagos, New Zealand, Brazil, Madagascar, the Caucasus, and Hawaii are high on my list of priorities.

Osaka in Black and White

How did you get so many followers?

The most important factor to keep in mind is that I started in 2010. That is a lifetime ago in digital years, and the internet was a completely different place. Instagram didn’t even exist when I started. Back then, the only relevant social network was Twitter, with a few bloggers making inroads into Facebook and YouTube.

So you can’t do what I did and expect the same results. It’s just impossible.

What I personally did was network with bloggers, joining groups, being active on Twitter, and constantly linking to other bloggers and letting them know I linked to them, hoping they would share my posts (and they often did).

If you’re looking to grow your audience, the single best thing you can do is produce quality content, followed by networking and being active on social media. I also recommend the Travel Blog Success course, which is the single best resource on the web for travel bloggers looking to go professional.


How do you make money?

This is where the questions start to make me uncomfortable. Would you ask this question to someone in a traditional industry? Probably not.

At the same time, though, I get the curiosity. Again, it’s a cool-seeming industry with no barrier to entry. Here’s how I do it:

Affiliate marketing. I link to products I use and recommend, and if you click through and buy them, I get a commission (at no extra cost to anyone).

Campaigns. I work with tourism boards or travel companies on campaigns designed to promote the destination or company. Sometimes this takes the form of content on my site or one of my social media accounts; sometimes it’s producing written or photo content for their own sites and marketing materials.

Advertising. I run advertising on the blog and my social media channels. I only choose ads that are for relevant products (very often contests to win trips to destinations), and I write the ads in a way that will get them read and enjoyed by my readers. There’s also display advertising on the site.

Photo sales. I sell my photos to magazines, tourism boards, and travel companies.

Tours. I co-ran two tours in Central America in 2015. There are no plans to do another tour at this time, but I would love to partner with a professional tour company in the future. As much as I loved running these tours, I’m nervous about what would happen if someone got seriously ill or injured, and I’d want to partner with “real” company for that reason.

Writing/consulting/etc. There’s a lot of random work that finds its way to me.

Beyond that, I’m not going to tell you exactly how I do these things — it took me nearly seven years of figuring it out on my own. I don’t give away those secrets.

Melbourne Arcade

How much money do you make?

Dude, honestly? That’s a rude question.

I live alone in Manhattan; that should answer whether travel blogging can be financially sustainable.

Manhattan Bridge

Why do you live in New York if everywhere else is so much cheaper?

Well, why would you live anywhere else if you could live in the place you loved?

I get the merits of basing yourself somewhere cheap. Most full-time travel bloggers do that. Chiang Mai and Bangkok and Playa del Carmen and Medellín and Berlin are some of the hotspots. Sayulita was big one year. Oaxaca was super-popular last year.

But these places have drawbacks. It can be exhausting to live 24/7 in a culture that’s not your own, especially if you don’t speak the language. It’s tough to live somewhere with a revolving door of expats, where your friends arrive and depart on a regular basis and nobody really sticks around.

I live in New York because I love it. My sister lives four blocks from me, my best friend lives a subway ride away, and I have tons of friends scattered across the five boroughs, including friends I’ve met on my travels. My travel blogger friends are always passing through and I love hosting them. I’m a 4.5-hour bus ride away from my parents in Massachusetts.

But most importantly — New York will never bore me. I might decide to live somewhere else in the future, but for right now, New York is where I’m meant to be.

(Plus, it’s not quite the most expensive place I could be! Rent is more expensive in San Francisco. And my day-to-day costs would be much higher in places like Australia, Norway, Iceland, and Switzerland. London is relatively on par with New York, but it’s a bit cheaper now if you earn a non-GBP salary.)


What’s the most dangerous situation you’ve ever been in?

I was shipwrecked in Indonesia in 2011. We hit a reef in the middle of the night and had to swim to shore before we were rescued by a nearby dive boat. Later, I realized that the waters could have been shark-infested and the island could have been home to man-eating dragons.

You can read the full story here and the retrospective on it, five years later.

Beyond that, nothing too dangerous has happened to me. I’ve been pickpocketed a few times. I’ve spent a few nights lying wide awake because I didn’t feel safe and my intuition was pinging like crazy. I get catcalled in most places in the world, and sometimes it escalates to me being threatened. There was one driver in Cape Town who had no idea what he was doing and he scared me to death.

It’s worth noting that two of the scariest incidents actually happened in my hometown of Boston. I was violently mugged in front of my Fenway apartment; I was assaulted two days in a row by the same man on an orange line train on my morning commute. Bad things can happen if you never leave the country.

Here are my top travel safety tips.

Flying over Miami

So, how can I get free flights?

Free flights don’t exist.

You can play the points and miles game, which can earn you very cheap flights if you’re crafty (and you always have to pay some kind of fee for award travel), but totally free flights for no reason at all do not exist. People don’t give away something in exchange for nothing.

On the same wavelength, you can’t get a free upgrade to business class if you just dress up and act polite. This is one of the biggest lies in pop culture! The best way to get a free upgrade to business class is to become a loyal flyer with one airline and earn status.

Blue Bottle Coffee

Can I buy you coffee and pick your brain sometime?

No. I know you mean well, and I appreciate your offer, but I don’t do this. I’ve spent years developing my skills and for that reason, companies pay me to pick my brain. It’s worth more than the cost of a cup of coffee that I can’t even enjoy because I’m busy helping you.

For more on why, I’ve always appreciate this piece: No, you can’t pick my brain — it costs too much.

San Blas Bay, Gozo, Malta

If I want to do this, too, how do I get started?

You’re in luck — I wrote a whole post on how to start a travel blog. The advice still holds today!

Vulcano Lodge Atitlan Guatemala

I’m planning a trip soon but I’m having some trouble — can you help me?

If it’s something I can answer off the top of my head, I’d love to help you! I love helping people plan their travels! Especially when you’ve already done most of the planning but are having trouble with an issue or two.

Should we take a cab from Heathrow Airport? Not unless you want to spend a lot of money. Take the tube or Heathrow Express. It’s easy, even with bags.

Should we go to the Caribbean in November? I wouldn’t. The weather tends to be its worst then.

Where’s somewhere cheap and awesome? Guatemala if you’re in the States. Macedonia and Albania if you’re in Europe.

I just have one request — this could quickly turn into an all-night conversation, so please let me have time to socialize with other people, too.

Thanks for being understanding.

I really appreciate it.

Get email updates from KateNever miss a post. Unsubscribe anytime!

27 thoughts on “The Conversation We Would Be Having”

  1. If it’s any consolation, I have the conversation a lot once people discover I’m a doctor. It usually starts with ‘are you a real doctor?’ (what with me being female and this being the 21st century). If anyone asks about lumps, bumps, rashes etc I nod wisely and say it’s probably going to kill them. Strangely, not many ask any more! (Now, about picking your brains, I have this great coffee machine….) ?

    1. I always love Sophia on Golden Girls — “Hey, doctor, how about a freebie?” It must drive you crazy!

      Also, the scene on Parks and Rec when Ann takes over some of Ron’s appointments and ends up examining everyone’s ailments once they find out she’s a nurse.

  2. Great post, I know exactly how you feel! I recently wrong a very similar post, I’m a Brit and recently moved to America, I get asked the same questions over and over again (I called it ‘Cursed as Soon as I Open my Mouth’)! At first I thought it was nice that people were paying an interest but now the novelty has just worn off. I’d love to be asked some more unique questions once in a while!

  3. Everything about this is perfect, especially the question about living in NYC. Why does anyone decide to live where they want to live when the option is entirely up to them? And why do we constantly have to justify it just because it’s more expensive than your average city?

    As a full-time photographer, I get a lot of those intrusive questions most people wouldn’t ask others in other industries so I feel your pain! Great idea with this mini FAQ, I definitely respect your decision to keep certain parts to yourself. I constantly am asked how exactly to make money with photography, or how I lit something in detail, or what my retouching process is step by step, as if my path to get to where I am and knowing what I know will work for another.

    It’s so strange that people assume they deserve to know what took you years to figure out (which you sometimes learned the hard way!) over a cup of coffee.

  4. This is such a great post, Kate! If this same thing can happen to me I can’t imagine how often/bad it happens to you. I get the curiousity but it does get exhausting. “How much do you make?” I don’t get why this asked so nonchalantly! It’s such a rude question in literally every situation and many cultures, yet when you have a “weird and cool job” it suddenly moves to an appropriate small talk question. Awkward! Good job coming up with this post but I’d bet it will still be hard to avoid this convo, unfortunately. Hopefully you get on ok, good luck hehe. 🙂

  5. I wouldn’t take it so close to heart ^_^ as a banker, I also get asked about how much I make quite often – it seems to be a sort of taboo in the Western world but notably less so elsewhere. Joking the question away with “not enough to retire yet!” or something goes a long way.

    I think your frustration stems more from reluctance to discuss what to you is work, all the time. That I can relate to very well: bankers strangely take the weird pleasure in talking about work all the time in their free time. Annoying and boring! Your job though is at least cool ^__^

  6. Loved this post- all so true. I have been feeling this way a lot lately, not necessarily with how I make my living but lately, people are asking me the same questions over and over. 1) How much does your flat cost? 2) How much do you make? and 3) Who did you vote for? I don’t mind so much answering the last one, but in general, these are three questions that I don’t really like answering and have been raised never to ask people…. however when you live in another country with different rules with people who are much more straight-forward about these things (they aren’t a big deal), I do feel kind of guilty not wanting to reply….

  7. I COMPLETELY understand the exhaustion from always being the person at a gathering that people want to ask a million questions. I was in the wine industry for 14 years and used to run California for an import company and travel occasionally to France, and threw a lot of events (both personal, charity and work). My life looked so exciting to people, and wine has been so trendy for so long now that it never fails that people want to ‘pick my brain’ on ‘what is the best wine’ (no answer for that), what do I drink at home (not just one thing), what’s the most expensive wine, is expensive wine better, what makes French wines better or different, what would you pair with…….

    the list goes on. Now I’m a travel/expat/lifestyle blogger and social media consultant living in Europe so I’m starting to get the same thing as you, but nowhere near the scale since I’m nowhere near as big 🙂

    I suggest making up a profession that sounds boring or saying your ‘between jobs’ when you want a break! 🙂 ahahah

    I also agree with all of your answers. I love trading information with other bloggers and wine professionals but when someone who needs help with the basics (aka needs a personal travel consultant or wine consultant) and hasn’t Googled anything or had any experience with it wants to ‘pick my brain’ it’s unfortunately just not time I can afford to spend and that doesn’t edify me in any way.

    Tough to be a curmudgeon though (how it feels sometimes).

    Keep on trucking-and I completely also understand the need for a home base in a country where you have friends and family and a good economy (much easier to pick up clients and well paying work at home if home isn’t a third world country full of expats living the cheap digital nomad life and unable to legally work in that country). And with so much travel, the familiar becomes the rare and thrilling almost more so than the new destinations sometimes.

    1. Truth? Occasionally when someone I’ll never speak to again asks me what I do for a living (usually a creepy guy who won’t leave me alone), I say, “I’m an accountant.” Boom and done. Conversation killer.

      I probably would have been someone asking you wine questions at a party. I know better now!

  8. That was an awesome read! Loved the way you started this whole piece. We are right now at a stage where the questions aren’t yet wearing us down. Besides, this travel blogging as a profession is still just starting out in India. We would love for more young Indians to travel etc etc. But when it gets to a “okay, this is too much” point, will keep your strategy in mind 🙂
    Happy travels!

  9. I’m a web editor, and the number of casual acquaintances I make who genuinely decide, without any indication from me, that I should build them a new website FOR FREE is staggering. Like I’m going to work for free for someone that I’ve met twice? I feel your pain.

    The thing is, you have what’s perceived as an “interesting” job and that makes people naturally curious. A lot of people genuinely believe that they have boring lives or careers that they don’t want to talk about, or that other people don’t want to hear about their lives. They might think that your job is much more exciting in comparison. I would recommend that you try to see them off by changing the subject to a quirky book/TV show/band/cuisine/hobby etc. Find something interesting that isn’t your career to talk about and stick to that line.

  10. I am a public defender, and I get a lot of this too. “Are all your clients guilty?” “How can you morally do that?” “Why do you choose that job when you went to such a good school? How much do you even make?” “That’s my dream job/office/law school and it’s a super hard job market will you get coffee with me?”

    It’s not the same. Your job is much more interesting and mysterious. But I do make sure to mentor some people, just when my gut tells me *this* person is worth spending time with despite my 80 hour work week, and worth giving out all the free advice too. I hope at least a few people meet that criteria for you, for the sake of future travel blogging!

    1. I can imagine how that would get annoying! Especially when it feels like people are judging your morality.

      I’ve met a few really impressive people who I think could be excellent bloggers with a little more direction. Mostly while traveling, not at home. They definitely get more advice from me!

  11. I am a Dietitian and work for the NHS in England. I tend to get a lot of people who feel they need to justify to me what they like to eat or they will say things like ” I don’t know why I can’t lose weight…I don’t eat anything ” . In reality my job has little to do with weight management since I work mostly with gastro disorders. Like you I prefer to talk about something else rather than what I do for a living. But I do love what I do and usually I can answer few questions and swiftly change the subject…usually to travel ?

  12. Thanks for this post! I think I would probably be that person cornering you for an hour to ask you every detail about your job and life, mostly because whenever I travel anywhere I have to tell every person I know about it plan a vacation for them. But it’s different when it is your job! In the future I will be more sensitive about it.
    P.S. I’m a physical therapist and once had a girl at a bachelorette party very seriously ask me to “work on” her foot injury. So yeah, I should really know better 🙂

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Subscribe to the blog: