About Me and Why I Started Progression.
Jackson May
I first got into mountain biking in the summer of 2014 and have been hooked ever since.
Around that time, I also discovered my love for teaching and went on to earn a degree in Child and Adolescent Development from San Francisco State. I later earned a Master’s in Education and a History–Social Science teaching credential.
I’ve spent over 13 years in education and more than 10 years coaching riders of all ages and skill levels.
With over 20,000 hours of direct instruction experience, I’ve helped hundreds of students and athletes reach their goals.
I’m CPR and Wilderness First Aid certified and a Level 1 USA Cycling Instructor.
I started Progression Bike Coaching because I know how hard it can be to learn mountain biking as an adult and wanted to make it easier for others. My coaching focuses on confidence, safety, skill-building, and a growth mindset on and off the bike.
Mountain biking has helped me manage ADHD, gain confidence, and push my limits in ways I never imagined.
I love helping riders—whether they’re 6 or 60—discover what they’re capable of and find joy in the ride.