Show Notes
This is the first episode in this two-part special, where Sarah sits down with Ciarán Casey, Director of My Learning Limited and author of Leadership in Tune.
In part one, Ciaran walks us through his career, from programming on IBM systems in the 1980s, through GE Capital, a startup venture with his brother, and back into corporate life at First Active.
Ciaran has moved across five or six industries over a three-decade career, a pattern most people avoid, choosing instead to build deep expertise in one lane. In this conversation, he unpacks what actually drove those moves: not ambition or a grand plan, but a restlessness with stability and a constant pull toward growth and challenge. Along the way, Ciaran shares the personal framework he uses for big decisions: weighing not which choice avoids regret, but which regret is easier to live with.
In this episode, you’ll discover: Why Ciaran believes stability doesn't equal fulfillment, and how boredom, not crisis, has driven most of his career moves The "exam question" he asks himself before any move: is there an opportunity for growth here? His end-of-year ritual of asking, "What did I learn this year?" Why the real danger isn't standing at a crossroads, it's staying too long on a comfortable road His most defining career pivot Introducing regret as a decision-making tool
In part 2, Sarah and Ciarán dig deeper into his decision-making framework around regret, and the leadership model behind his book Leadership in Tune. Meeting at the Crossroads is available on Apple Podcasts, Spotify, and wherever you get your podcasts.
If today's episode resonated with you, share it with a fellow business owner who might be standing at their own crossroads.
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Every business owner faces moments that stop them in their tracks. Meeting at the Crossroads is the podcast that meets you in those moments.