From Microsoft to Middle School: Damon’s Unlikely Pivot

In this episode of Success Your Own Way, we sit down with Damon, a former Microsoft sales executive who made a dramatic career pivot leaving big tech behind to teach middle school social studies. Damon shares why he made the shift, what he learned from his students, and how his definition of success has evolved over time. From authenticity and leadership to personal fulfillment and redefining ambition, Damon’s story is honest, inspiring, and full of life lessons (with a few laughs along the way). Whether you're considering a big life change or just want to hear what it’s like to go from selling tech to wrangling 8th graders, this one's for you.