Sheldon Wyman of Durango, Colorado on Life, Lessons & Legacy

We recently had the chance to connect with Sheldon Wyman and have shared our conversation below.

Sheldon, a huge thanks to you for investing the time to share your wisdom with those who are seeking it. We think it’s so important for us to share stories with our neighbors, friends and community because knowledge multiples when we share with each other. Let’s jump in: Have you ever been glad you didn’t act fast?
Absolutely! I’ve found that taking time to reflect before acting often leads to better long-term outcomes. A clear example is with my business. Instead of diving in headfirst, I invested countless hours in research and skill-building. I also recognized that it didn’t need to be “all or nothing” at the start; it was okay to begin small and gradually build momentum. That approach has allowed my business and artistic ability to grow sustainably, and like any venture, there’s still plenty of room for improvement and future growth.

Can you briefly introduce yourself and share what makes you or your brand unique?
I founded High Ability Imagery in 2019 after an opportunity arose to take photographs for a local real estate firm. What began as a simple project quickly grew into a vision: building a company that delivers the highest-quality media to help clients achieve their goals. Over the years, I’ve refined my skills, expanded services, and built lasting connections in the community.

While we started with real estate photography, High Ability Imagery has since grown to include advertising and commercial media, as well as special projects like sporting events, engagements, and weddings. Today, we’re proud to be the leading provider of real estate media in Southwest Colorado, with a team of three photographers and a lead editor, and we plan to continue expanding so we can provide the best media possible to everyone who needs it.

What makes us unique is our client-focused approach. We don’t just take photos; we listen to what our clients want to achieve and use our expertise to bring those goals to life. That dedication to both artistry and results is what continues to drive our work forward.

Great, so let’s dive into your journey a bit more. What part of you has served its purpose and must now be released?
I believe we go through phases of thinking in life. As children, we often believe anything is possible, but somewhere along the way society tells us to be “realistic” and conform. I went through that cycle myself, and for a time I accepted that settling was the definition of success.

As I’ve grown, I’ve realized that mindset no longer serves me. Letting go of conformity and returning to a sense of childlike wonder and belief has been essential to setting bold goals, including the courage to start my own business. High Ability Imagery wouldn’t exist if I hadn’t taken that leap of faith.

I haven’t fully broken free from the binds of conformity. Like all things, it’s a process that takes time. But embracing the belief that more is possible has allowed me to create something meaningful and continue pushing for new growth, both personally and professionally.

What did suffering teach you that success never could?
I believe that true learning comes from failure, not success. When you succeed on the first try, it’s easy to assume that’s the only way forward. But when you try something and fail, you’re forced to explore new approaches, adapt, and grow.

The fear of failure, and the suffering that often comes with it, is real and difficult. Yet it’s in those moments that the deepest lessons are learned. I’ve found that resilience is built not from success, but from failure. Each setback makes you stronger, more open to taking on new challenges, and better equipped to approach them with creativity and persistence.

Sure, so let’s go deeper into your values and how you think. How do you differentiate between fads and real foundational shifts?
As a photographer, trends are constantly shifting, and keeping up with fads is part of the job. That also makes it easier to see the difference between what’s temporary and what represents a true foundational shift.

For decades, photography has been rooted in human perspective and skill. But with the rapid rise of AI, we’re seeing one of the biggest foundational shifts in the industry. AI can now generate almost any photo or video, making it harder for people to tell what’s real and what’s not. In some ways, that diminishes the beauty of photography, when images can be created at the push of a button, it raises the question: why invest hours or days into capturing the “perfect photo”?

For me, the answer lies in the dedication to the craft. AI has shifted the technical foundation of what a photo can be, but art, at its core, is an expression of passion and perspective, something that can never be artificially created.

Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. What is the story you hope people tell about you when you’re gone?
I hope people will remember me for my passion, creativity, and dedication. Photography has always been what I love most, even if it hasn’t always been easy. There were times I felt like giving up, but the drive to keep creating and sharing my perspective always brought me back.

Through High Ability Imagery, I want my story to be one of perseverance — of building something meaningful from the ground up and staying committed to quality, even when it would have been easier to cut corners. My hope is that people will say I not only captured images, but also inspired others to see the beauty in their own work, their spaces, and their communities.

At the end of the day, I’d like my legacy to be that I lived with creativity, worked with integrity, and built something that truly helped others.

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