Outward Bound and Me

In this thought provoking episode of Outward Bound and Me, Dylan Carroll sits down with alumnus Matt Gupwell to explore the lasting impact of a three-week Outward Bound residential course in Aberdyfi back in 1989. Matt explains how, after 35 jobs (of which he was dismissed from 30 of them), a late diagnosis of neurodiversity led to a better understanding of self, and a career as a neurodiversity speaker, trainer and mentor with blue-chip companies and the NHS.
 
Matt shares vivid memories of his time at Aberdyfi, where instructors recognised strengths in him that he couldn’t yet see in himself. Years later, after navigating anxiety and insecurity, Matt now understands how those early experiences outdoors laid the foundations for his future career in education, coaching, and neurodiversity advocacy: “I think it was the first time that I remember feeling safe. We use the term psychologically safe. I felt like I could go to my instructor on that course at any point and say, ‘I’m struggling. This isn't fair. I don't understand’, and I was never made to feel small or stupid. That was the first time I felt ‘I'm being treated like an adult here’”.
 
Matt reflects on growing up in the Midlands, discovering climbing as a teenager, and how the outdoors became a vital source of regulation and belonging long before his later-life ADHD diagnosis. Together, Dylan and Matt discuss masking, mental health, identity, and why outdoor education can change and offer young people something traditional systems often cannot. This is a powerful episode about self-discovery, compassion, and the life-changing value of feeling truly seen.

Creators and Guests

Host
Dylan Carroll
Dylan Carroll is the Head of Partnerships at The Outward Bound Trust, leading the Corporate, Trusts & Foundations, Alumni and Legacy teams. Following a career in sales and marketing working across Europe, he now has 20 years fundraising leadership experience, working previously at Barnardo’s, as a consultant, and chairing the Institute of Fundraising. Dylan believes in the power of storytelling to showcase the impact an Outward Bound experience can have on individuals at a pivotal time in their lives, and how Outward Bound pedagogy has influenced countless futures, career, and life choices. He hopes that through this podcast, individual stories of resilience, failure and success, adventure and fun, will be shared with a wider audience, so that people will think on their own connection to the charity, the outdoors and nature, and possibly their own lives and autobiography, and the impact they have on others. The stories in this podcast are individual, but contribute to a collective 85 year tapestry of a charity that has had a lasting impact on many lives.
Guest
Matt Gupwell
Late diagnosed at 46 with ADHD, Matt Gupwell has turned his own personal journey with neurodiversity into a career supporting and mentoring individuals and organisations, who want to move beyond good intentions and oversimplistic labels, to build lives and workplaces where people are genuinely understood and supported. Drawing on his own lived experience of ADHD, autism, dyslexia, addiction, and anxiety disorders, alongside research and frontline practice, Matt is a respected mental health and neurodiversity advocate, keynote speaker, consultant, and podcast host, who helps organisations build psychologically safe, high-performing cultures. He established ‘Think Neurodiversity’ in 2021, to focus on mental health, performance, and inclusive organisational design. Matt began his professional journey with neurodiversity with one simple aim, to help build a future where his neurodivergent sons, and others like them, would be understood, supported, and valued in education and at work. Following in his older brother’s footsteps, Matt undertook a 3 week residential course at the Outward Bound Centre in Aberdyfi in the summer of 1989. A full on adventure, where Matt began to understand himself and others, guided by instructors who focussed on his needs to build rapport and enable him to use Outward Bound as a springboard to success. Outward Bound came at a time in Matt’s life that challenged his way of thinking, as his brain and psyche was challenging his.

What is Outward Bound and Me?

Outward Bound & Me is a fortnightly podcast where host Dylan Carroll speaks with Outward Bound alumni from across the decades. Each episode delves into powerful stories of life before, during, and after their time on course—from personal breakthroughs to hilarious moments in the wild. Whether you’re a former participant, outdoor enthusiast, or simply curious about how adventure shapes lives, this podcast offers inspiration, reflection, and a deeper look into the legacy of Outward Bound since 1941.