Fact Checking Dance Parties

Kassondra Cloos on getting creative with your pitches and capturing color on the road

Hi writer friend,

I’m deep into organizing and draft mode for my Lonely Planet project, writing about Eastern and Southern Oregon for the next PNW guidebook. I love going through all my notes and photos, and puzzling together the details that will help travelers really sink into these places I love. It’s a ton of information to condense and shape into something that’s hopefully helpful and inspiring. I’m excited to share more about that process with you soon.

A quick note on my recent call for pitches! Thank you, THANK YOU, to everyone who sent me such thoughtful and interesting essay ideas. At this point, I’ve commissioned five stories for this summer and may assign a few more. But I have to put a cap on new pitches for now! I’d hate for more people to spend time on writing these pitches when I don’t have the bandwidth to consider any new ones at the moment. But keep an eye on this space for future opportunities.

Here is what you’ll find in today’s issue…

• Q&A with adventure travel writer Kassondra Cloos, who writes for Outside, Adventure.com, Trails Magazine, and many more.

• Upcoming deadlines for fellowships and grants (paid)

• Events and education opportunities for writers (paid)

• In the Weeds: The words I’m tangled in this week (paid)

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Whether she’s covering a wild week of dating at a ski resort in the French Alps or being half-dragged on a family vacation to Harry Potter World, Kassondra Cloos makes writing seem fun. The kind of sensory-rich, narrative-driven stories she pens for Outside, Adventure.com, and The Independent are a lot of fun to read and presumably to research and write. (Chair lift speed dating and champagne showers? OK!) They’re also clearly a lot of work. (Does one take notes before or after the champagne shower??)

Last year, Kassondra was awarded for her hard work and captivating stories by the British Guild of Travel Writers, who named her Travel Writer of the Year. I was excited to ask her about the mashup of finding assignments, frequent travel, and actually writing. We touched on all of that, plus press trips and how pursuing her master’s in creative writing has impacted her approach to pitching and story ideas.

So let’s get to it! Writer friends, meet Kassondra!

Photo by Anette Andersson

Last year, you were named Travel Writer of the Year, which is so exciting! A belated congratulations on that! Was there anything that you were focused on or doing differently last year that you think caught the judge's attention?

That was honestly such a surprise. It was one of those things where I almost didn't submit my clips because I really thought there was no chance I would win. But I think what was different is that in the last couple of years, my work has really gone in a much more creative direction. I recently finished a master's program in creative writing, and I was forced to be more creative. And that changed the way I thought about certain story ideas. I think I was able to develop my voice in that program in a way that I hadn't really been doing in my work previously. And then I got really lucky, and Adventure.com in particular has really encouraged me to develop that voice and use it—so I've had a lot more fun experimenting.

It sometimes feels like there are not a lot of publications that are open to more creative pitches. How have you cultivated those relationships, or found those editors who are willing to honor your voice and let you go in some more unexpected directions with your writing?

I think that might actually be a bit of a myth. I used to think that as well—that no one was going to be interested in my voice. Part of the reason I thought that was because I went to journalism school, and when you’re in a program that teaches you how to write for newspapers, you are really focused on not being in the story. When I became a freelancer, and when I started working in the outdoor and travel space, writing about things that are more based on personal experience, it was very hard for me to figure out how to be in the story in a way that didn't like feel super cringy, based on what I’d been taught.

I assumed for a long time that nobody was interested in me or my opinion, and then I guess I’ve just had some chance opportunities. I’ve pitched some ideas that felt pretty wacky and out there. And when I started getting responses to those ideas, I was like, ah, okay, this is different, and it seems to be different in a good way. I should continue down this track of trying to push my creative limits.

So to answer your question, I think almost every publication actually wants those super creative ideas, particularly now, considering there's so much conversation about AI taking over the low-level types of writing like SEO-focused writing. AI can do a listicle pretty well. It's not going to be accurate, necessarily, but it can do it. AI can convincingly write certain types of content. Because of that, the stories that really capitalize on a creative angle are the ones that are going to make you AI-proof.

What does your travel schedule look like these days as a full-time freelance travel writer?

In the last year or so, I've been a little more focused on spending time with family and finding story ideas in places that are really familiar to me, which has been a really fun challenge. So the one that you mentioned about Rhode Island came about because I was like, I'm in this place that I love very much, but I also don’t know it that well. So, how can I find a way to make it a work project that gets me engaged and excited?

It's like reverse travel, traveling inward and going deeper into places that I already know instead of looking for far-flung destinations. I came to visit my family. I went out to Vegas for work. Now I'm back in Providence this weekend. I'm going to Washington, D.C., then New York, then Colorado, then back here. When I go back to London in May, I'm working on a couple of things around the UK, and then I have some possibilities to go pretty far afield in June, but I’m still working out those details.

Do you typically travel with an assignment, or do you like to go somewhere and then find the stories?

That’s a good question, and I recently spoke to a class of students in a master’s program, and they asked this, too. I said we’re talking about a chicken and egg situation—when do you go searching for ideas, and when do you go searching for something to execute the idea you already have?

I guess it's an even mix of me going to do things because I want to do them, and then finding stories eventually, and me going places specifically for an assignment or with the hope of an assignment in mind.

Last year was a good example. My family wanted to go to Universal Studios, and I was so not excited about that initially. It’s just so not on brand for me, this is the opposite of what I usually do. I was like, honestly, you want me to fly across the ocean to a fake version of the city I live in?

Then I realized, actually, that's a really good story. I could turn this family vacation into a funny story. I got to have the experience with my family, and I got to experience a great story for The Independent, a publication I hadn’t written for before.

Something I've been talking to a few different travel writer friends about recently is press trips. A lot of publications don't take press trip stories, and they can be kind of hard to write about, just because you're doing the same thing as a bunch of other writers. How do you think about and consider whether to do press trips?

This has been such an interesting thing in the last few years for me, because I think press trips are seen very differently in the UK than in the U.S. In the UK and in Europe, I think publications pretty much accept press trips. I've spoken to many journalists and travel editors who are very confused about the economics of U.S. travel writing. They don't understand how these publications can expect writers to not go on press trips. Part of that could be that rates are typically lower in the UK and in Europe than they are in the U.S. You can make a lot more money, usually, writing for U.S. magazines than European ones.

Early in my career, I went on a lot more group trips and really enjoyed them. I made a lot of great friends and incredible connections. A lot of the editors I still write for today are people that I've met on press trips, so those have been really valuable.

But today I’m more interested in working with a destination individually to plan a trip. Going on something to experience it the way that a reader would actually experience it has been so much more valuable to me.

There have been many times that I've self-funded travel without any idea if it was going to turn into assignments later on. I'm thinking of a couple of really expensive trips off the top of my head, and in the end, I was able to not only cover those expenses but make a profit on the experience by pitching them later on.

Do you work exclusively in journalism, or do you do any copywriting or other types of writing work?

I do a lot of different types of writing, so it varies. Sometimes there's more journalism, sometimes there's more of the other things. The nature of freelancing is that things ebb and flow. I've done copywriting and blog writing for brands and for companies that have nothing to do with travel. Sometimes those are great gigs because it doesn't tax my creative energy as much. When I've had clients that have nothing to do with the travel industry, I can work pretty quickly on those projects, and then it kind of bolsters my other work and gives me the ability to self-fund travel and then pitch later on.

Yeah, it seems we all need to find those different types of work these days. When we need to market ourselves for different types of writing work to support journalism, it can be hard to figure out how to put yourself out there publicly, especially when you really want to be known as a journalist. But you also do this other work. Do you market your services for other types of work, or do you try to position yourself exclusively as a journalist?

I definitely position myself publicly as an adventure travel journalist. And some of the projects that I've had previously that have nothing to do with travel came out of just connections I made very, very early on in my freelance writing career that have just been sustained over time.

Sometimes I've thought about that when I was working on a project that wasn't about adventure travel, and then worried: Does this change my identity as an adventure travel journalist? I would say no, but it's so much easier to analyze someone else's career than it is to give yourself freedom or permission to identify in a way. Personal branding is tough.

Something I heard at college that I remember very clearly… I made business cards for myself, and I wanted to put something like “Aspiring Journalist” on there. The advice I got was don't do that. Just say that you're a writer, because no one will take you seriously if you say that you want to do something. Just tell them that you're doing it. So that's the advice I often give people.

Let's talk about your latest piece for Outside, which was so fun. You give some of the origin story of that trip in the article, but for those who haven’t read it yet, can you tell us how you wound up writing about a group dating trip to the French Alps?

So a few years ago, I came across this ski trip by the dating company, Thursday. They do events all over London, and they were advertising a singles ski trip. And I was like, that sounds fun! It's so cheap and it sounds massively chaotic. I will definitely get a good story out of that, and maybe I'll also have a good time.

I was planning to go, and then I started seeing someone and ended up canceling my trip because it was weird to be going on a singles trip when I was dating someone else. Then he broke up with me, like, immediately after I canceled and right before the trip.

This last year, I [still] needed to know what it was like. I pitched Abby Wise at Outside, as like a Love Island on skis. I figured if I had to go for work, I’d be grandfathered into it. No one could be mad at me for going for work.

I've worked with Abby a lot. It was amazing that she also liked this idea, and it was the most fun assignment I've ever been on.

Your schedule was packed with dating events and skiing and a bowling alley came up a few times. How do you collect the kind of details you need for a story when your schedule is go-go-go like that?

That is such a good question, because there were so many specific details in this story. I had a journal and took some notes by hand, in the mornings, in the evenings, whenever I had free time. I had a Notes app on my phone that I would occasionally put things into. And then I also recorded memos to myself. I sent some voice notes to friends, because my friends were so interested and they wanted to follow along. I was able to listen back to these things I was recording from the field. That provided a lot of color.

My favorite bit of that story is the chair lift speed dating. That was such a funny thing, because it was one of those moments that could have been absolutely mortifying. I got up in front of this crowd and was like, date me, please. And then realized I essentially had egg on my face. But in the moment, it was really funny that I was failing so hard at this.

I also had so many photos and videos that I could look back on. In the lede of the article, there are guys dancing on tables and I have video of that happening, so I was able to fact check the disco ball ski pants from the couch.

I noticed that there is a titanium pot in this piece. And I loved your unusual take on reviewing a titanium pot for Trails Magazine. Was that the same pot?

Yeah, that was the same one.

How did you pitch that review of your ex-boyfriend’s titanium pot? I loved that.

That was an instance of like, I've got this pot. How can I justify it? Ryan from Trails had put out a call for pitches, and they were looking for something for the “Unreviewed” category, which I interpret as unconventional gear reviews. So I was like, hey, how about a review of my ex-boyfriend's titanium pot? I thought it was so random and no one would want this story. It felt like a kind of joke that I was pitching it. But he said yes, and it became one of my favorite pieces I've ever written.

Do you know if your ex read it?

Oh yeah, we're friends now. What actually happened is I borrowed that pot from him, and then I scorched the bottom of it. I couldn’t give him back a pot that had been damaged—that could not be his lasting impression of me. So I secretly bought a new one and gave him back the new one. And I kept the one that I had damaged, which is why I was so keen to write about it. I needed to justify the existence of this pot in my life.

I'm asking everyone this right now, since there's such a bad vibe around journalism these days, but there's a lot to be excited about, too. You are doing a lot of exciting work. So I would love to hear what makes you optimistic and what makes you excited about writing these days.

There are so many new publications that are popping up out of passion. We keep hearing lots of bad news about layoffs and publications shutting down or changing in ways that feel uncomfortable, but I think there's also a lot of new things popping up, and there will always be new things. I think the medium of journalism will continue to evolve forever. We just have to do the best we can with what’s in front of us. Maybe that's a bit cliche, but I think my career has certainly evolved, and it will continue to evolve. And I think the best thing we can do is be optimistic. If you worry too much, then you'll just hide under your desk, and the worst will come to pass, because you won’t have the creative ideas that you would have in a place of more exuberance.

Thank you so much to Kassondra for taking the time for this interview! You can keep up with all her work and her travel adventures through her Substack, Out of Office and on Instagram.