The adventure travel writer talks to founding editor Natasha Khullar Relph about traveling on assignment to 13 countries, including Mexico, Peru, Sweden, Germany, and Japan.
Kassondra Cloos is a freelance writer and editor who travels the world and writes about it for publications including Outside, Backpacker, 5280, Travel Channel, Gear Institute, HGTV, the REI Co-op Journal, Gossamer Magazine, and The Denver Post. She also writes for gear, apparel and adventure companies, as well as organizations committed to sustainable tourism.
She’s traveled across four continents since taking her career completely on the road in 2019. Her more recent work examines the concept of home, and captures the complexity of starting over—and over, and over, and over. In her essays and columns on slow travel, she encourages readers to find adventure and intrigue within their own neighborhoods.
How did you get into freelancing?
I don’t think I ever knew that you could be a travel writer. I didn’t think it was a real job. But when I was an editor for Outside Business Journal, I worked with freelancers who were doing that. We had some opportunities offered to us as staff writers and editors, but we just couldn’t take that many press trips because we were a two-person team. So I just started seeing people doing the kinds of things that I wanted to do and just kind of tried to position myself to take those opportunities.
I started a relationship between our publication and the ATTA (Adventure Travel Trade Association), and tried to create an adventure travel section on our website and got a lot of my press trips through them.
I’m fascinated by the trade versus consumer side of things, because when people think of travel, they always think of consumer publications. What are the opportunities on the trade side?
The last big sponsored thing that I went on was an ATTA trip to Switzerland in October. And as part of that, they had a trade day. There are different sectors in this industry. ATTA is made up of not just media, but also people who run tours and people who buy tours. They combine media and tour buyers in a way that I am sure happens elsewhere, but I haven’t personally seen it elsewhere.
I’ve also met a couple of reporters who write about trips for the trade magazines, such as magazines about cruises and luxury travel. It seems like those are pretty fun to work for.
How should writers be thinking about this from a business perspective? Free travel is great, but you also need to make a living.
I’m gonna kick it back to you. When I was first starting out, I was reading your newsletter constantly. After I went through your 30 Days, 30 Queries course, I just started thinking about things differently. You have to think about this as a business. And I learned that from you.
You have to like go into it saying, okay, this could be fun, but if it’s not, if it’s not a hell yes, immediately, then there needs to be some other reason for doing it. If you’re not getting paid for it or getting paid a low amount, you have to say no. You have to find better opportunities. And I think it’s really, really easy in travel to trick yourself into thinking that it’s a vacation. It’s not. And you can’t think about it that way. First of all, if you do, you won’t make any money. And second of all, you’re not going to advance.
You really have to be committed to being serious about it. There are a lot of places who will pay you no money to take a free trip. And a lot of these places will pay you $50 or so for a story. You just have to say no.
Right. The trip is not the payment. The trip is the business trip you take in order to get the story.
Especially because the vast majority of the time the magazine is not paying for your trip. I’ve never had a magazine cover my trip. I’ve been paid to travel by brands.
You should charge not based on your time, but on your value. So if you’re writing a blog post for a company and that one blog post will get them, say, $20,000 worth of business, it’s not outrageous for you to get paid $1,000 for it, even if you’re only spending an hour. And if you are spending weeks of your time planning something, going out and then spending a week on the ground, and then coming back and spending weeks of your time writing and editing, you deserve to be paid for that. Even if you had a good time. Having a good time is a bonus. You should like it.
You shouldn’t have to suffer in order to get paid a living wage.
A lot of new writers think of press trips as holidays. I’m curious to hear your opinion on how these things actually go and what kind of schedule you have.
It’s so hard to talk about press trips with people who want to go on them and haven’t done it because you don’t want to sound like you’re complaining about amazing free travel. It’s super fun. It’s not a vacation. It is exhausting. It’s very scheduled.
When I was first starting out, I basically said yes to absolutely everything. I said yes to all the assignments, I said yes to all the press trips, yes to all the gear to test, yes to everything. I was exhausted, and it was super fun. I don’t even think I would go back and change all that much because it was all really good experience that led me to where I am. But I think about press trips really differently now. Now it has to be like a hell yes, like I would spend my own money to go on that trip, and I really want to write an article about it.
When you’re on a press trip, not only are you like throwing yourself out of your routine, you’re probably jet lagged and you’re working from maybe 6 or 7am until 11pm for four, five, six days in a row. You’re doing this with people you’ve never met before, and everyone’s there for work.
It’s super fun and I’ve made some of my best friends on trips like this because your relationships grow so fast and so quickly and so deeply when you’re in this compression chamber, and it’s amazing. I love it. It’s just not a vacation.
Well, your time is not your own.
Right. You can’t make any of your own decisions. You can’t decide where you’ll eat dinner, what time you’ll eat breakfast, what time you’ll get to bed. Sometimes you’re exhausted and you’re still two hours away from the hotel. And then you get to the hotel and you’ve got 15 minutes to throw your bags in your room so you can take a tour of the hotel.
You have to do your due diligence as a writer when you’re being invited on a press trip. Ask to see the schedule ahead of time, ask what the vibe is going to be, and how many people are going to be on the trip.
What I’ve found for me is that it’s so much nicer to like go and do something. I was on a press trip with Chaco, a gear company, for example, and they took a group of us to an island in Mexico for three days. We had no cell service, and it was pretty chill. We went hiking, we went snorkelling with sea lions, we took a boat trip and went fishing. And we just ate fresh fish on the beach every night. It was phenomenal. We were there to use their gear and have an experience, not to see six hotels in six days.
So let’s get to the question on everyone’s mind: How do you get on these press trips?
When I reflect on where the best trips have come from, they mostly are from the ATTA and two sister PR companies, Backbone and rygr. It’s so important to build and maintain good relationships, especially since people move around a lot and open doors to other companies when they do.
A good piece of advice for people who want to get on press trips is to join regional writers’ groups and find local trade events for the travel industry and find a way to get in there. There are tons of regional and national travel markets where marketing teams from city and state tourism boards go to meet with media. TravMedia/IMM, IPW, and the New York Times Travel Show are three of the big ones in the U.S. but there are lots of smaller ones, too. The Outdoor Writers Association of America had a small destination showcase at their conference that I went to a few years ago. If you’re a new writer, you may find it hard to get comps from destinations by cold-emailing them, but if you meet them in person and make a good connection, you can toss story ideas back and forth and you’ll likely have an easier go of getting invitations.
You’re not gonna get a press trip unless you have some bylines and so, this is not new advice, but the best way to become a travel writer is to write about travel in your community. This is something that I started doing, too, when I first started out. Like, how can I write about travel for the Denver magazine 5280? How can I write about travel for Elevation Outdoors, the Boulder adventure magazine? And so you start small, you can write about hikes in your town or city or region for magazines in your town, or city or region.
When I first decided that I wanted to start freelancing on the side, I wanted to get my bylines out there, and I wanted to practice. So I went around to coffee shops and started picking up all the free magazines just so I would know what was out there. And I started emailing them. I don’t think I ended up writing for any of those magazines, but I think it was a good exercise.
I was thinking, where am I going to find places to pitch and also how do I pitch? Before I took your class, it would take me weeks to write a pitch because it needed to be perfect and I was so afraid of getting rejected. At some point I started tracking my pitch attempts but framing it as expecting to get rejected because that it wasn’t personal anymore. Now I’m like, I’ll fire off a pitch to Cosmopolitan. They’re gonna say no, whatever, I’ve tried. It’s not about me.
Does the travel impact your life and your relationships?
Oh, a lot. A lot. Lately, I’ve been much more interested in staying put and building a real community somewhere. A friend of mine said to me that it gets boring after a while to be constantly meeting new people. That really resonated with me. Moving around constantly is fun until that becomes your normal. And then you get bored of constantly readjusting and introducing yourself. And you get sick of hearing yourself talk because you’re just having the same conversation over and over and over again, because you don’t know anybody long enough to have a deeper conversation.
And there are exceptions to that rule. I’ve made some really really good friends travelling who are like still really good friends of mine today. But how many people have I met along the way that I haven’t had those relationships with? It’s hard when you’re constantly starting over and you have no community and you’re just reaching for anybody who will hang out with you.
There’s something really amazing and wonderful and beautiful about that. And there’s also something like really exhausting about it.
And then when you return to your base, you don’t fit in. You don’t have a regular job and you don’t have a regular life, so people don’t know how to figure you out.
You know what, I think it is actually that I don’t know how to figure myself out.
Last night we had this office party and when I say I’m a travel writer, I just end up answering the same set of questions. It just feels like I’m just always having a very one-dimensional conversation. I’m trying to move on.
So you’re in London now, but you’ve just launched a newsletter, Downcity Ink, about your home state, Rhode Island. Tell me about that.
Somehow, no matter how far away I travel, I always find myself talking about Rhode Island with strangers. I can’t help but explain our quirks and complexities, and I love the intrigue on people’s faces when I start getting into the specifics of the legacy of Buddy Cianci. Downcity Ink is a place for Rhode Islanders (current and former ones) to speak in the language of locals that we rarely hear beyond the state’s borders.
I just came up with this idea and then people liked it, so I had to do something. I started having fun with it. I do think it’s nice to remember where you’re from. It’s the classic you don’t realise what you have until it’s gone. So I’ve travelled all around the world, and I’ve never met anybody who talks about where they’re from the way Rhode Islanders talks about where they’re from, and it’s just fun to lean into that.
Where are you currently based and what’s next for you?
I’m in London now and I guess what’s next for me is I’m just like really excited to spend more time exploring one place more deeply. So I’ve been in the UK for a couple of weeks, I’m planning to spend most of the summer here, travelling around Scotland, explore London on foot and by canal, explore Scotland by canal. I just really love how easy it is to explore the outdoors here without a car, you just hop on a train or you go for a hike. And that’s amazing.
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