Planning a multi-stop content-gathering trip as a freelance writer or photographer is no easy task. Since starting at Western Horseman in 2010, I’ve planned more of these trips than I can count. From building stories around unique sources to navigating rural terrain, I’ve learned a lot along the way—and I want to share five key challenges you’ll face when chasing your dream trip, and how to tackle them with strategy and heart.
Without physically being in Moose, Wyoming, I never could have taken this shot of the Stidhams with Grand Teton National Park in the background. This ran in Seth Stidham’s “Craftsman” article for Western Horseman.
1. Content Saturation & Standing Out 📷
In today’s content-heavy digital world, breaking through the noise is harder than ever—especially in the equine and Western travel niche. Popular locations like Montana or Wyoming, often boosted by shows like Yellowstone, dominate the pages of many magazines. With countless blogs and Instagram accounts out there, it’s increasingly difficult to stand out or offer fresh perspectives to magazines and digital content buyers. Building an audience and maintaining engagement requires strategic branding, consistent content, and a unique voice—and looking outside the box, literally, on the map!
Instead of heading to the area surrounding Yellowstone National Park for story ideas, or the ever-popular Jackson Hole, Wyoming, for example, look into more rural, remote areas. The challenges here can include airfare or hotels (which I’ll get into later in this blog) but it can also show you a few gems off the beaten path. When you pitch a few stories in Idaho, for example, it can be more appealing to an editor than another story based in the same popular areas, or using the same popular sources others have written or photographed more recently.
Be sure to search a magazine’s archives online and perhaps any old issues you have to ensure you’re not pitching the same sources or places they’ve recently covered. Last year, I traveled to California, Colorado and Arizona, so you can bet I’ll be shifting gears to pitch stories in other locations this year and next, to keep the content and source list fresh.
2. Balancing Creativity with Commercial Deman ds 🤹
While travel is inspiring, creators (writer, photographers or videographers) often find themselves compromising artistic vision for what's marketable, especially when advertising heavily influences editorial decisions today. Editors and clients may prioritize SEO keywords, product placements, or overly curated aesthetics that can clash with personal storytelling or authenticity. This starts with your pitch, be clear on why an unknown ranch family is perfect for that audience, or why profiling a silver maker that only sells online from their remote location is worth the trek and page count. Then, when you have the assignment, be sure that you not only gather the information you need to fulfill the story needs, but that you allow yourself the freedom to gather images or content you love.
One thing I enjoy is photographing with sun flare, in super contrasty light or simply taking photos of the barn cat or ranch dog. These images are for me, but several have been printed over the years. If a story only requires 3 images, don’t only take three shots. Take more! Be ready to include a few of your favorites that didn’t run in a personal blog (ahem, like this one!) or a social media post that can help promote your work and that magazine.
While we often tailor our work to the assignment, do not allow that to stop you from taking personal joy or a deeper interest in interviewing your subject. You never know when that fun image or random question will generate the bit you need to make the story truly special.
These mule ears didn’t factor into my October 2024 feature on Lee and Jen Roeser, but I sure loved taking the shot!
3. Logistical Hurdles & Constant Planning 🗺️
Behind every breathtaking photo is often a logistical headache—traveling with gear, unreliable transportation, changing weather, or *GASP*gear failures. Planning, scouting locations, and managing permissions (don’t forget those model and location releases!) can be exhausting and time-consuming. It feels like as soon as I home in on an idea in one location, the wheels start to turn on adding other ideas, sources or pitches until I may as well be a travel agent for that part of the country. It becomes constant, even setting Google flight trackers for better airfare.
When you decide to gather content out of state, or even out of country, there is added pressure financially and performance based. Though you bought the ticket, booked the hotel and have the rental car, and the source’s schedules lined up, the weather could make your trip into a nightmare. Boy, I’ve been there!
Back up locations, back up plans for photos and being backed by travel insurance is key to reducing a bit of that anxiety. Know that when you travel, especially to a rural location, not everything will go as planned. Not every image will be in the perfect light, and not every interview will sound like an American Horse Publications winning profile.
The key is to not give up, to continue to ask questions, seek new ways to photograph a subject or to be flexible in rescheduling or rearranging a trip due to weather.
4. Emotional & Physical Fatigue 😴
Constantly being on the move can lead to exhaustion. I’ve been there in Glacier National Park, to be truthful. Over the years, I’ve had content gathering trips that lasted four days and those that lasted 10 days. For me, the ideal trip is no more than 6 days, including travel on the front and back. When I was younger, I crammed so many stops in – two a day – and drove the wheels off that rental car. Now, I prefer to spend more time, even building in some personal sight seeing stops.
Travel writers and photographers may deal with loneliness, jet lag, culture shock, or the physical strain of carrying heavy equipment through remote or rugged terrain—all while staying creative and productive. It’s not easy. Taking time for small things like getting a coffee, or pulling off at a scenic lookout, can be the way to stay sane and keep calm on a long trip.
I also ensure I bring allergy medicine, other medicines that can handle potential stomach issues or travel illness, all to help make sure the trip is a success and I’m at my best. Small comforts—like a phone call to a friend or a scenic roadside stop—can make all the difference.
5. Inconsistent Income & Job Instability ⛰️
Freelance writing and photography professionals often carry the financial burden of the travel and cost to gather an assignment. This is one of the many reasons I do not travel as often as I used to do for stories. Assignments can be seasonal, unpredictable, and highly competitive, as we all know. Many creators juggle multiple gigs, from blogging to content licensing, just to maintain a livable income, and that isn’t always doable while on the road.
Before I contact sources or book any travel, I determine how much my estimated cost for the trip will be, and how much the stories I have listed for the trip will garner. At the least, I want the trip to break even, but we all want to make a living doing what we love, of course. I pitch the stories to editors and ensure I’ve got the expenses covered before ever booking a flight or charging a hotel room reservation.
Yes, it can mean that I gather a story in January that doesn’t run until a December issue, and therefore, I get paid nearly a year after that trip, but sometimes the experience, shining a light on that source, is worth it to me. If I am gathering seven stories in one state, that means they can be spaced out over two years, to prevent too many stories saturating the readers.
Every writer, photographer or content gatherer will need to weigh the cost against their decision to travel.
In the end, the connections and experiences outweigh the costs—and that’s why I keep going. Traveling for work has not only allowed me to visit 36 states, and two other countries, but provided me with friends and contacts that have changed my life. The personal benefit is greater than the cost, in my opinion, and the ability to share the Western lifestyle with readers is the driving force in why I love to plan and execute a traveling work trip.
I’ve packed into the Bob Marshall Wilderness twice, and each trip was worth the travel it took to get there.