Career Pivots, Lifelong Learning, and Building a Business After an AI Layoff with Ryan Drumheller

In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Ryan Drumheller a self-described extroverted IT leader, fractional CIO, and founder of StellarHorn Group, where he helps businesses cut through the noise of technology and AI to drive real, measurable results. With over 20 years of experience in IT and leadership, Ryan is a relentless lifelong learner: two master's degrees, a bachelor's, more than 170 certifications, and doctoral ambitions still on the table. Outside of work, he's into music, sports, and video games and lately, golf. Ryan's path to all those credentials was anything but linear. He flamed out of community college after a year, landed an IT job quickly, and spent his twenties working hard without much of a plan. His parents young, with his dad a corrections officer steered him toward trade school, but Ryan was already taking apart PCs at night and quietly betting that IT was the future. The career epiphany didn't hit until his late twenties, when he looked at the hours he was putting in and thought, it can be different. That's when he went back for his bachelor's, then his master's, and never really stopped. In this conversation, Ryan challenges one of the most rigid beliefs in our culture: that there's one right path high school, straight to college, straight to career and that falling outside it means you won't amount to much. He's living proof otherwise. He and Kim get into how traditional education rewards a single narrow kind of intelligence, and how much talent gets boxed out because it doesn't fit. Ryan aced the technical classes he cared about even student-taught a programming course in high school while checking out of everything else. His bachelor's forced him through courses he found irrelevant; his master's, at a school built around relevant coursework, was night and day. Proof, as Kim puts it, that it can be done differently if we're open to it. Ryan and Kim also dig into the hard, honest math of going out on your own. Faced with a likely steady paycheck versus chasing the dream, Ryan landed on doing both taking the guarantee while building the product in the shadows. Along the way he learned something important about himself: he sells a product he believes in with total confidence, but selling himself as a service always felt like a stumble. The deeper realization is that he works better with people than as a solopreneur and instead of fighting his own nature, he's building something that fits it. Underneath it all, he's candid that imposter syndrome shows up in every phase, and that his answer is the same each time: look at the evidence, and remember that he's always figured it out before. This episode explores: Why the linear path — high school, college, career — isn't the only route to success How a community-college flameout became a 170-certification career Why traditional education rewards one narrow kind of intelligence Using what you're good at to help you learn what's hard The career epiphany: realizing "it can be different" Turning a job loss in the AI wave into a deliberate pivot How a hobby meant to escape technology became the work itself The honest math of a steady paycheck vs. chasing the dream — and doing both Why if you can't sell, you don't have a business Building around your nature instead of fighting it (team player vs. solopreneur) Using AI as a creative thought partner, not a human replacement Why imposter syndrome shows up at every stage — and how evidence pulls you out "You're not a victim, you're a survivor": owning your experience and doing the work Ryan's perspective is a powerful reminder that there's no single timeline for figuring it out — and that the disruptions we don't choose can point us toward the work we're actually built for. His journey from a checked-out high schooler to a credential-stacking CIO building a company around the game he loves shows that you can take the unconventional route and still arrive somewhere that feels like home. If you're a leader, technologist, career-changer, or anyone who took the long way around, this conversation offers practical perspective, hard-won honesty, and a refreshing case that you can pick yourself up, pivot, and keep moving — no cheat codes required. Connect with me here: Website: https://www.kimmillerhershon.com LinkedIn: https://www.linkedin.com/in/kmillerhershon Newsletter: https://link.kimmillerhershon.com/widget/form/aEdmdA1W5MhoMCMfy5O8 Webinar: https://webinar.kimmillerhershon.com/?utm_source=Podcast Guest Details: Guest: Ryan Drumheller Company: StellarHorn Group Focus: Fractional CIO services; building golf technology software Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.