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Story & Lesson Highlights with Alan Stenback of Fairplay, Colorado

Alan Stenback shared their story and experiences with us recently and you can find our conversation below.

Good morning Alan, it’s such a great way to kick off the day – I think our readers will love hearing your stories, experiences and about how you think about life and work. Let’s jump right in? Are you walking a path—or wandering?
Definitely wandering, with purpose though. I’m drawn to the edges of things, whether that’s a mountain ridge at sunrise or a creative idea that hasn’t fully taken shape yet. I don’t need to know exactly where the path leads, as long as it keeps me curious and inspired.

Can you briefly introduce yourself and share what makes you or your brand unique?
Sure! I specialize in landscape, night and astro photography and video, and I lead creative workshops from my home base in Fairplay, Colorado. My brand is all about connecting people to wild places through photography, storytelling and hands-on experiences.

My wife Gina and I run Roam With Us, where we lead photography retreats and adventures in places like New Mexico, Puerto Rico and the Colorado high country.

I also work with real estate clients, do commercial drone work and sell fine art prints. Whether it’s capturing the Milky Way at midnight, printing a large-format image for a modern interior or delivering a polished set of photos and videos to help sell a property – I combine creativity with technical chops to deliver high-quality results.

Lately, I’ve been diving deep into hybrid content: stills, audio, video, drone footage and timelapse – exploring how to blend those elements into cinematic visual stories.

Amazing, so let’s take a moment to go back in time. What’s a moment that really shaped how you see the world?
When I was younger, I played a lot of golf. I was maybe just above average, but I stuck with it. Over time, I realized it wasn’t the game I loved, it was being outside, walking the fairways and watching the light change. I always preferred to walk instead of taking a cart. Looking back, I think that rhythm – slow, quiet, present – was a preview of what I’d later find in hiking, exploring and landscape photography. For that, I have the sport of golf to thank.

Was there ever a time you almost gave up?
I’ve definitely had (and still do!) moments where I’ve questioned the grind. I joke that “the struggle is real” and “every day I’m hustling,” but there’s truth in that. Running multiple creative endeavors across fine art, photography workshops, aerial video and commercial work takes more than vision, it takes stamina, adaptability and a strange mix of faith and grit. I’ve had to learn to trust the process, trust my eye and believe that what I’m doing matters – to others and to myself.

So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. What’s a belief or project you’re committed to, no matter how long it takes?
This isn’t my first creative rodeo. I came to photography after years as a musician and DJ, and much of what I’ve learned behind the lens has been self-taught through curiosity, mistakes and time in the field.

I’m committed to the long game: refining my craft, sharing what I learn and creating work that connects. Whether it’s one of my personal photography projects or helping someone finally nail manual focus on the stars and Milky Way, I’m here for the slow burn.

Okay, so before we go, let’s tackle one more area. How do you know when you’re out of your depth?
Usually when I feel that mix of excitement and panic, it’s a sign I’ve stepped into something that’s stretching me. It happens a lot when I’m teaching, leading in the field or learning something technical (hello, star trackers). But I’ve learned that being out of your depth is where growth lives. I try to lean into that, ask good questions and stay open to learning, even when it’s uncomfortable.

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Image Credits
Alan Stenback Photography

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