Tom McCaffery: Leaving the Safe Path to Figure Out Who You Really Are

Tom has built a life around work ethic, stability, and solving big problems. But in recent years, he started asking harder questions about what he actually wanted—and whether the safe path was still the right one. In this episode, we talk about what it means to walk away from structure, how creativity shows up in business, and why being second-in-command can be a strength. Tom opens up about the cost of doing things you're good at but don’t love, the pull to make art later in life, and the tension between building stability and chasing truth. We also get into imposter syndrome, abstract art in Calgary, and how AI might shape the future of leadership. How To Connect: Jeff Humphreys - ⁠⁠⁠⁠⁠https://www.jeffhumphreys.ca Tom McCaffery - https://tworiver.ca Podcast Location - ⁠⁠⁠⁠⁠https://www.modelmilk.ca Podcast Production - ⁠⁠⁠⁠⁠https://www.shortlinecreative.com