Podcast Episode Tom McCaffery: Leaving the Safe Path to Figure Out Who You Really Are The Calgary Sessions with Jeff Humphreys

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 Al might shape the
future of leadership.