Jan. 15, 2026

Lucy Kellaway: The Best Kind of Late Midlife Crisis (AKA Starting Again at 58)

Lucy Kellaway: The Best Kind of Late Midlife Crisis (AKA Starting Again at 58)

On this week’s episode, we’re joined by Lucy Kellaway, former Financial Times columnist who did something quietly radical at 58: she walked away from a high-status career and retrained as a secondary school teacher - and hasn’t looked back.


Lucy talks honestly (and hilariously) about what it’s really like going back to square one when you’re old enough to know better: the nerves, the mistakes, the teenagers, and the oddly thrilling feeling of being alive again. It’s never just about a job change either - it’s about identity, confidence, and what happens when the “successful life” stops feeling like your life.


With January still in full “fresh start” mode, this one lands perfectly if you’ve been quietly wondering: Is it too late to reinvent myself… or is this actually the ideal time?

Get in touch with your thoughts at podcast@htb60.com.


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