Introduction
Midlife identity is something most successful men never question until the job, the title or the kids’ need for them quietly falls away. Steve Pratt spent decades in television and podcasting, co-founding the world’s first branded podcast agency while playing the part his children nicknamed the “Lego businessman”.
After selling the company he set out to fix midlife the way he’d fixed everything else. It didn’t work. So he spent a year running midlife experiments on himself instead, and in this episode of Don’t Let The Old Man In he tells Pod O’Sullivan what he found underneath the costume.
Why this conversation matters
Steve wrote a whole chapter of his book, Earn It, about embracing your weirdness and being the only one in the room. Yet he’d spent his life fitting in: first as the perpetual new kid at school, then in the corporate rooms where selling unusual television meant looking the part and staying likeable and conflict averse. He only noticed the contradiction in midlife.
When he left Pacific Content four years ago, he read William Bridges’s Transitions and took one idea to heart. Stories run beginning, middle, end. Transitions run end, middle, beginning, and most of us try to skip the middle. Steve swore he wouldn’t. Then he spent a year in his basement reading, journaling and trying to crush the liminal state. “In hindsight, I was like, you idiot,” he says.
What followed was cheaper and far more useful: a run of small experiments, written up with his friend Geoff Siskind on their Substack, The Midlife Field Guide. Most cost nothing but time.
What we discuss
- Growing his first and only beard at 53, and what it taught him about identity and the costumes we wear
- What fitting in cost him, and why the second half of life is when you finally get to choose
- The messy middle: why trying to win at a transition is the surest way to miss it
- Ditching the Apple Watch, Oura ring and Strava, and the morning he ran in circles to hit exactly 5 km
- A chance meeting with Dr Gabor Maté in a ferry queue that led to clinically supervised ketamine-assisted therapy, and the counsellor who told him, “You’re done”
- Doing a stand-up comedy course with his daughter, Cedar, and watching her bring the house down first
- Leaving the family Wordle chat for a month, his dad’s verdict on his return, and what writing publicly has done for their relationship
- Why telling people what you’re going to do (the internet, a mate, your partner) keeps you honest
Why midlife men should listen
Most of us carry scoreboards and expectations we never chose. Steve’s challenge for tomorrow is simple: look at the apps and devices you check every day that hand you a number or a streak, and ask who designed them, why, and whether they’re built for your benefit or theirs. Then break the streak for a week and see what happens.
As he puts it, the hard stuff is mostly free. The expensive part is not doing it. By the end of the conversation Pod has one word for him: free.
Guest info
Steve Pratt
Steve Pratt is a Vancouver-based writer, speaker and creative strategist. He started out producing television across music, children’s programming, entertainment journalism and local news, then led digital audio at the CBC, where he launched one of the world’s first legal music podcasts in 2005 and helped build the CBC Radio 3 community. He went on to co-found Pacific Content, the world’s first branded podcast agency, making shows for clients including Ford, Audible, BMW, Slack, Shopify and Adobe; Entrepreneur named it one of its 100 Brilliant Companies.
He is the author of Earn It: Unconventional Strategies for Brave Marketers and founder of The Creativity Business, which offers speaking, workshops and consulting on creative marketing. With his friend Geoff Siskind, he writes The Midlife Field Guide on Substack, documenting their experiments in search of meaning in middle age.
Steve lives in Vancouver with his wife, Debbie, and their three children.
