Episode
Part 2: The loneliness of leadership no one warned you about, with Christian O'Connell
- Podcast
- How I Work
- Published
- Jul 29, 2026
- Duration seconds
- 2057
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Summary
There is a version of leadership that looks effortless from the outside. The one where the leader always has the answers, always holds the vision, always appears composed. And then there is the version that happens in private, at 5:00 AM, when your mind is rehearsing every possible failure and no one can see it. What surprises most people is how often those two versions belong to the same person. In part two of my conversation with Christian O'Connell, breakfast radio host heard by hundreds of thousands of Australians every morning, we get into the parts of leadership nobody talks about publicly. Christian opens up about the loneliness of leading a team, the night he finally put his thoughts on a whiteboard and told his people the truth about how he'd been feeling, and why he believes his next book will be about leadership because nobody warned him how hard it would be. If you have ever found yourself carrying something heavy at work and deciding the most responsible thing to do as a leader is keep it to yourself, this conversation will make you question whether that instinct is actually protecting your team or just protecting you. Christian and I discuss: Why confidence is the wrong thing to aim for before you speak in public What happened when Christian finally stopped pretending everything was fine with his team The one thing that does more for a team than any solution or action plan Why 5am is the worst possible time to trust your own thoughts The David Letterman line that changed how Christian thinks about taking risks Why Christian considers himself an accidental leader, and what he's doing about it Key quotes "Confidence is something that catches up. Momen…