A “Happy Mistake” on Mount Katahdin and Leadership Lessons in ADHD Education — John Willson

My guest for Episode #305 of the My Favorite Mistake podcast is John Willson, Executive Director of SOAR, the world’s premier outdoor adventure program serving youth with ADHD and learning disabilities.

Episode page with video and more

With over 30 years of experience, John is a passionate advocate for experiential education and life skills development through structured, strengths-based environments. SOAR, which stands for Success Oriented Achievements Realized, supports young people ages 8 to 25 through summer camps, boarding schools, and gap year programs focused on building confidence and resilience.

John’s favorite mistake took place on Mount Katahdin, the northern end of the Appalachian Trail, where he unknowingly summited a false peak in poor weather conditions. Faced with a difficult decision—turn back through a dangerous route he already knew or forge ahead into unknown terrain—he pressed on despite worsening conditions. Although it was arguably the “wrong” decision in the moment, it led to a powerful sense of accomplishment and a safer descent than expected. John describes this as a “happy mistake” that taught him about risk, perseverance, and the sometimes unexpected rewards of pressing forward.

In our conversation, John shares how this philosophy of “failing forward” underpins SOAR’s mission. He explains how their structured programs help kids with ADHD and learning differences build critical life skills, develop self-awareness, and form friendships—often for the first time. We also explore the importance of creating environments where neurodiverse individuals are supported, understood, and encouraged to take safe risks, with a strong network behind them.

John and I also discuss the evolving understanding of ADHD, the challenges of diagnosis, and how labels matter less than building strategies that work. He shares practical advice for parents and adults alike, emphasizing the role of support systems, coaching, and compassion. Whether you’re a parent, educator, or someone navigating your own neurodiversity, this episode offers insights into how mistakes—when supported by reflection and community—can lead to breakthroughs.

Questions and Topics:

• What’s your favorite mistake?
• Is it true that one of your most common mistakes is people misspelling your last name?
• Did you go back and climb Mount Katahdin again on a clearer day?
• What do you mean by “summit fever”?
• If that decision had led to a bad outcome, would it change how you reflect on it?
• What lessons did you take away from that pattern of decision-making?
• What are some ways the SOAR summer camp is tailored for kids with ADHD or learning disabilities?
• How much of the benefit comes from being with other kids who share similar strengths and challenges?
• How does being in that kind of environment help kids feel more accepted?
• How does SOAR help kids who struggle to make friends build relationships?
• When were you diagnosed with ADHD?
• How did that diagnosis shape your connection to SOAR and the work you do?
• How many SOAR staff members also have ADHD, versus being trained to support it?
• What kind of person tends to thrive on your staff?
• What’s your take on people wondering if they have ADHD or if it’s anxiety or something else?
• What matters more—getting a diagnosis or developing the right coping strategies?
• What advice would you give someone recently diagnosed with ADHD—or who suspects they might have it?
• Can you talk about the role of support systems in success for neurodiverse individuals?
• What’s your view on younger people being more open about neurodiversity in the workplace?
• Can you share some practical first steps after receiving an ADHD diagnosis?
• Why is identifying your support network such a crucial part of success?