Meet Jessie Henderson | Systems Change Consultant, Facilitator, Peer, Wonderer and Wanderer

We had the good fortune of connecting with Jessie Henderson and we’ve shared our conversation below.

Hi Jessie, we’d love to hear about how you approach risk and risk-taking.
My relationship with risk has evolved significantly over the years. In my youth, I often took uncalculated risks that led to challenging situations. As I matured, I learned to channel that risk taking spirit into opportunities for growth and positive outcomes.

Personally and professionally, I’ve embraced risk as a pathway to growth. I don’t let gaps in my knowledge stop me from exploring new opportunities or adding skills to my repertoire. Whether it’s diving into a new business venture or learning an entirely new field, I’m willing to take that initial leap and figure things out along the way.

I used to say, self deprecatingly, “There is nothing special about me, Im just too stupid to know what I can’t do.” However, a good friend, Jason Gold, helped me reframe this perspective in a powerful way. Now I say, “I’m not necessarily unique or brave, I’m simply someone who chooses not to be constrained by perceived limitations.” This mindset has been transformative in my career, allowing me to take risks that others might shy away from.

When you approach new challenges with this perspective, risk becomes less about potential failure and more about potential discovery. It’s about being open to possibilities rather than being limited by preconceptions. I’ve found that risks become much more comfortable and manageable when I’m clear about my intentions. When I know exactly what I’m trying to achieve, taking the leap feels natural, and the outcome – whatever it may be – tends to be worthwhile.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
I don’t think anything truly sets me apart from the rest of the world. If anything, my experiences have shown me that we are all the same—we just navigate life with different circumstances, choices, and influences.

How did I get to where I am professionally? Through the kindness and compassion of others, but also through my own tenacity and commitment to approaching life with intention and kindness. I got here by separating myself from the people, places, and things that could have pulled me away from where I wanted to be. It wasn’t easy. There was a time in my life when I felt completely alone, in a dark place, surrounded by others who felt the same. And yet, even in that darkness, those people helped me see the light. Many of them don’t even know the impact they had on me, but I carry that gratitude with me every day.

How did I overcome challenges? Through good intentions, good deeds, and kindness. Challenges never stop coming, but somewhere along the way, I learned to laugh at myself—even in failure. That perspective has helped me appreciate both success and struggle as part of the process.

What lessons have I learned? Too many to list, but one of the biggest is that there is always a reason to be kind. There is always room to forgive. And there is always space to include love in what we do. Things won’t always go perfectly, but as long as we move forward with intention, we’re making progress—and that’s what matters.

What do I want the world to know about me, my brand, and my story? That change is always possible. No one is stuck. Change starts with self, and it happens one small step at a time. What we do and who we are has a ripple effect on the world. But the key is sacrifice. A lot of people want change but aren’t willing to endure discomfort in the present to find peace and stability in the future. Growth comes from experiencing difficulty, not avoiding it.

As for my brand, I want people to know that the status quo isn’t fixed. There’s a place for people who look like me and come from my background in every space. And I also believe we don’t have to be overly sensitive—we grow by stepping into difficult situations and facing them head-on. That’s where real transformation happens.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
If my best friend were visiting for a week, the first thing we’d do is grab a great meal at Jack’s on Pearl—it’s a steakhouse I’m absolutely addicted to. Nothing sets the tone for a great trip like a perfectly cooked steak.

Hopefully, it’d be spring or summer because we’d definitely go paddleboarding at Chatfield Reservoir. It’s one of my happy places—there’s something about being on the water, just flowing, especially with good company.

After that, we’d head to Garden of the Gods. No matter how many times I visit, I’m always in awe of its beauty. It’s one of those places that reminds you just how close nature and the city really are.

To really experience the city, we’d go on a bike ride through Denver. The city has come a long way in improving its bike lanes, so you can get pretty much anywhere safely while taking in that unique mix of urban energy and nature that makes Denver stand out.

For something fun and interactive, we’d check out the Museum of Illusions—it’s a great place to explore and get lost in a little bit of wonder. Then, we’d wind down at Goldfinch, one of my favorite lounges, where we could relax and enjoy good drinks in a laid-back atmosphere.

Of course, I’d have to take them to Mach 983 for a workout. It’s more than just a gym—it’s my community, and I’d want them to experience that energy firsthand.

At some point, we’d take a drive through the Eisenhower Tunnel. No matter where you’re headed on the other side, the view is breathtaking, and it’s a reminder of how much beauty surrounds us.

That’s just a start—there’s so much more, but this mix of food, nature, culture, and movement would make for an unforgettable week.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I owe immense gratitude to Mike Sanchez. He not only introduced me to peer support but demonstrated a profound level of kindness that transformed my perspective. Mike provided both the inspiration and practical skills that set me on my current path.

Megan Robins deserves special recognition for her unwavering belief in my potential and her patience in helping cultivate my professional growth. She and the entire WORTH team have played, and continue to play, an integral role in keeping me grounded and reminding me that there are people doing good work with the right intentions.

Fred Dayton and the MACH983 CrossFit Gym family showed me the power of community in a way I’d never experienced before. Fred’s willingness to embrace me and help me utilize my diverse background to support others was truly life-changing. He believed in me in ways I never knew I needed, and this encouraging family has become part of who I am today.

I have to give a special shout out to Andy Yost. He showed me that you can be both a consummate professional and deeply down-to-earth. He’s the kind of guy who can seamlessly transition from discussing deep philosophy to eating that questionable Skyline Chili. The ENTIRE Yostfish family has been incredible, especially Shannon Patterson, who has been instrumental in my growth. They’ve challenged and guided me in all the right ways, helping me realize my potential and showing me that changing systems, while not easy, is possible when people have the right intentions and skills. The experiences they’ve shared with me – from traveling to facilitating to being part of a group of professionals with good intentions and great skills – have been truly transformative. They’ve shown me what it looks like when dedication to systems change combines with genuine humanity.

Finally, I believe every person I’ve ever met has sparked something in me and contributed to my journey in some way. I’m deeply appreciative of all these connections, both big and small, that have shaped who I am today.

Website: https://Peersupportco.org

Linkedin: https://www.linkedin.com/in/jessie-henderson-5661a2282