179: The Good Listening To Show with Chris Grimes - Episode 179

179: The Good Listening To Show with Chris Grimes - Episode 179

How do people find strength to completely change direction in midlife? This conversation between host Chris Grimes and guest Jon Kaye leans right into that question with humour, honesty and a lot of creative spark.

Jon is introduced as an “enigmatic free thinker”, co‑founder of Do Radio, presenter of the Tomorrow’s World show and author of the newsletter *Unmastered* – summed up as “think clearly, live deliberately and create without chasing applause.” He talks about spending years in private equity, grinding through 100‑hour weeks, missing weddings and holidays, and chasing money above everything else.

Then came the pivotal moments: first, leaving a secure job to co‑found a new firm after one influential investor “said yes” to backing them; and later, walking away from the successful company he’d built to prioritise family, connection and creativity. You’ll hear how Jon effectively “retired” at 40, took his young family out of school and travelled the world, then rebuilt his life around making music, writing and community projects.

His basement studio – full of cables, synths and flashing lights – becomes a metaphor for creative experimentation and friction. As Jon puts it, “Friction is important. Let’s not make things too easy,” because that’s often where the real beauty appears. The pair also talk about Do Radio’s deliberately old‑school format, where shows run on a schedule you can’t pause or download, to get people listening together again.

Jon’s small but loyal audience for *Unmastered* reflects his belief that “we don’t all need to be global superstars” – a refreshing message for anyone tired of chasing likes and metrics. If you’re questioning the role of work, money and creativity in your own life, this gentle, funny and reflective chat might nudge you to ask: what would deliberate living actually look like for you?