What does it really mean to be strong? And how much of the way we think about masculinity is something we’ve consciously chosen — rather than simply inherited?

Harry Garside is an Olympic boxing medallist who has also done ballet, and happens to paint his nails. Two typically juxtaposed traits that saw him both criticised and celebrated when he was thrust into the spotlight at the 2018 Commonwealth Games. In 2024, he joined me for a powerful conversation about masculinity, vulnerability, confidence and the transformative power of discomfort.

Harry reflects on how boxing gave him a deeper understanding of what his body was capable of, helping him develop self-confidence and a sense of security. He also shares what he has learned from working with young people, particularly the boys who appear the loudest or toughest in the room but may be carrying stories that nobody has taken the time to hear.

We explore Harry’s fascination with deliberately stepping outside his comfort zone. For more than five years, he has undertaken monthly “uncomfortable challenges” — from going without speaking to improv, makeup and asking strangers for money — using discomfort as a way to learn, grow and challenge himself.

We also discuss the traditional rules we inherit about what it means to be a man, and whether some of those rules still serve us.

LINKS 

• Listen to the full episode with Harry here
• Follow Harry (@harry_garside) on Instagram
• Sign up to the Better Than Yesterday newsletter
• Watch episodes of Better Than Yesterday on YouTube
• Watch full stories recorded live at  Story Club on YouTube
• Get tickets for our next Story Club show
• Get Osher's latest book "So What? Now What?" here
• Send a pic of what you're looking at to sendosheremail@gmail.com