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 OBE, 64 — former Financial Times columnist who did something genuinely radical on the edge of 60: she left her job, her marriage, and her Highbury home to retrain as a secondary school teacher in an inner London school.

Lucy talks candidly (and with real humour) about what pushed her to jump. By 2013, her marriage was deteriorating, her father’s health was failing, and decades at the FT had tipped into burnout and career malaise. Teaching wasn’t a neat reinvention. It meant starting again at the bottom, navigating teenagers, parents, younger colleagues, and an education system that doesn’t bend easily - all while rebuilding identity and confidence in midlife. Later, she relocated again to teach in the north east.

That experience didn’t stop with her. Lucy went on to found Now Teach, the UK’s only dedicated career-change charity for teaching. Now Teach has helped over 1,300 people retrain - and crucially remain - as secondary school teachers. Their free service offers 1-to-1 guidance, wellbeing, subject and career coaching, plus access to a peer network to share problems and find practical solutions. To learn more or apply: info@noweteach.org.uk

With January still deep in “fresh start” territory, this episode is for anyone quietly asking a dangerous question: is it too late — or am I finally ready?

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

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