The Learning To Lead Show with Mark J. Cundiff · 2026-06-18 · 54 min
What happens when a burned-out school teacher decides to bet on himself? In this episode, I sit down with my longtime mentor and friend, Jonathan Milligan - author, online business coach, and the very person who taught me how to build the blog and podcast you're listening to right now. Jonathan has spent over a decade helping creative professionals turn their story, message, and expertise into a business they love. We talk about his winding journey from teaching to flipping houses to recruiting and finally into coaching, the hardest leadership decision he ever made (cutting his team from 15 people down to two), and why he believes consistency - not talent - is the real secret to lasting influence. If you've ever struggled with self-doubt, shiny object syndrome, or wondering whether your story is even worth telling, this conversation is for you. About Jonathan Milligan Jonathan Milligan is an author, blogger, speaker, and online business coach who has spent the last decade guiding creative professionals toward meaningful work. Since 2009, he's run his own portable lifestyle business online, and he's the author of 17 books (with another on the way).
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