37 years in one business...and then what?
In this energising episode, I sit down with the ever-curious and inspiring Mike Chesworth, who spent 37 years at Westpac before stepping boldly into a new life chapter.
In this energising episode, I sit down with the ever-curious and inspiring Mike Chesworth, who spent 37 years at Westpac—finishing his career as Head of Financial Advice—before stepping boldly into a new life chapter, his epic retirement. Since then? Banjo lessons, photojournalism, bike-building for kids with disabilities, gravel cycling adventures, and a big dose of bush travel.
We talk about planning early, resisting the identity trap of corporate life, and why curiosity and nimbleness might just be the two most important skills in retirement. It’s honest, wise, and a whole lot of fun.
LISTEN TO THIS EPISODE OF THE PODCAST HERE:
Highlights of the conversation:
How Mike planned his retirement from age 45 – including the goal that kept him focused: following the Tour de France at 50
His honest take on leaving work at 57 – from corporate grind to creative freedom
Why the banjo beat the guitar as his epic pursuit– and what his wife thought of the decision
Reinvention after retirement – studying photojournalism at uni, being the oldest in the room, and chasing high distinctions just for fun
Volunteering with heart and skill – building bikes for kids with disabilities through Freedom Solutions
Letting go of your old identity – and becoming known as ‘the bike guy’ instead of ‘the banker’
The golden value of a good financial planner – even when you’ve worked in financial advice for decades
Retirement without a roadmap – what happens to people who don’t plan ahead
Why simplicity and frugality in early life gave Mike freedom later
Redundancy vs. retrenchment – and the surprising truth behind 13 restructures
The loneliness of retirement in the workplace – “people don’t retire anymore… they just disappear”
Why curiosity and nimbleness matter more than ever – especially as AI reshapes our world
Mike’s take on the future of financial advice – and why he’s cautiously optimistic about AI’s role
Grassroots retirement travel – from outback pubs to wildflower-covered deserts
Finding your people in retirement – and why some friends come from work, others from a shared trail
Trying and quitting without guilt – boards, projects, and roles that weren’t the right fit
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My new book Prime Time is now available for pre-order!
I wrote Prime Time – 27 Lessons for the New Midlife for anyone navigating that space between “not done yet” and “what’s next?” It’s for all of us in our 40s, 50s and 60s who want to make this next chapter the best one yet — with more purpose, more clarity, more momentum.
This book brings together everything I’ve learned (and lived) about money, work, health, relationships, identity and ageing better — in 27 real, practical, powerful lessons.
It’s now available for pre-order, and I’d be so grateful if you grabbed a copy. Pre-orders make a huge difference in getting the book into more hands and onto more shelves.
Order your copy on Booktopia here.
Or Amazon here.
I'll be signing all the pre-orders from Booktopia before they hit the mail!
Let’s make your Prime Time count.