About Me and Why I Started Progression.
Jackson May
I first got into mountain biking in the summer of 2014—and I’ve been hooked ever since. Around that time, I also discovered a love for education, which led me to study Child and Adolescent Development at SF State. Since then, I’ve spent over a decade teaching and coaching youth. Today, I’m a full-time middle school history teacher with 13 years in education and 10 years of coaching experience.
I started Progression Bike Coaching because I know what it’s like to pick up mountain biking as an adult and wish there was a program that made it easier to learn. When I started riding in my 20s, I had a hard time finding the kind of coaching that matched my needs—so I decided to create it myself.
Mountain biking has completely changed my life. It’s boosted my confidence, helped me manage ADHD, and shown me the mental and physical benefits of riding. Over the years, I’ve ridden just about every major trail and bike park on the West Coast, across all types of riding—from cross-country to enduro to freeride. I never imagined I’d be hitting big features, but with practice and a growth mindset, I’ve surprised myself.
That’s the mindset I bring to every rider I coach. I’ve worked with hundreds of people—ages 6 to 60, beginners to experts—and nothing makes me happier than helping others build confidence, have fun, and discover what they’re capable of on the bike. I truly believe, If I can do it, anyone can.