What being the executor of a will ACTUALLY looks like
Today's guest, Mike Chesworth, was recently the executor of his fathers' will. He was generous enough to share his story and the things he learned along the way.
What really happens when you're named the executor of a loved one's will?
In this thoughtful and candid episode, I’m joined once again by the always generous and wise Mike Chesworth. After decades in financial services, Mike recently stepped into a new role — not in the boardroom, but in the deeply personal process of executing his late father’s estate.
From paperwork and probate to family dynamics and difficult conversations, Mike shares what he learned, what surprised him, and what he’d urge others to prepare for now — before the time comes.
Whether you’ve been named as an executor, are planning your own estate, or simply want to better support ageing parents — this one’s full of practical guidance and real insight.
LISTEN TO THIS EPISODE OF THE PODCAST HERE:
Highlights of the conversation:
What being named an executor actually involves — and why it’s far more emotional, time-consuming and detailed than most people expect
Why the real work begins almost immediately — and how tough that is when you’re still deep in grief
The pressure to “get it right” — and the invisible responsibility of honouring someone else’s wishes
Why fairness and practicality aren’t always the same — especially in modern families with multiple marriages and blended dynamics
The importance of open conversations, while everyone is still alive and well, can prevent tension, confusion or even legal fallout later
What legacy really means — and how it goes far beyond money
How an inheritance can unexpectedly impact aged pension entitlements — and why it’s worth understanding the implications
Why a will is only part of the picture — and what else matters, from funeral planning to bank accounts, passwords and bills
The “one folder” method used to stay on top of everything — and why it’s recommends for every family
Why you're better off resolving things within the family — before lawyers or resentment step in
The biggest lessons Mike took from this chapter of life — and what he’d want others to know before they go through it themselves
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From Bec’s Desk
We’re absolutely abuzz this week with so much excitement I hardly know where to start. First, our podcast - yes this podcast, just rose up the Australian Triton Podcast Ranker again. It’s sitting in #200 Australian Made podcast in the country!!
I started the week on the ABC Radio’s Nationwide Nightlife Program with Phillip Clark - a whole hour of talkback about Prime Time! And the callers and feedback afterwards was awesome! I didn’t realise SOOO many people listened to late night radio!
Then, over the past two days I’ve been in Sydney signing big piles of books at Dymocks, Kinokuniya and Abbey’s Bookstore. So if you’re wandering through the city and spot a signed copy, you’ll know I’ve been there with my pen! Later this week I’ll be in Melbourne — popping into both central and suburban stores to sign copies as well. I’ll share the details on my Facebook feed so you can track me down if you’re keen to grab one.
In between the bookshop visits, I also stopped by the set of Today Extra for another great conversation. We spoke at length about Prime Time — and why so many of us are choosing a slower, more considered path into retirement rather than rushing towards a “full stop” finish. It’s a topic that always sparks lively discussion, and it was wonderful to see how much it resonated.
And perhaps most exciting of all — this week we officially launched the criteria for the new benchmark, The Epic Retirement Tick (powerd by Chant West). This is something I’m incredibly proud of. It’s designed to help people cut through the confusion and see, at a glance, which funds and providers are really delivering quality outcomes for pre and post retirees. It’s the kind of tool I wish had existed years ago, and I’m thrilled we can finally share the framework with the world.
So yes — it’s been a big, buzzing week. Radio, books, TV, benchmarks, and plenty of conversations about how we can all make the second half of life not just longer, but better. And truly, this is only the beginning.
I hope you enjoyed this terrific show with Mike Chesworth. And if you haven’t got yourself a copy of Prime Time: 27 Lessons for the New Midlife yet — you can buy it here or in any bookseller in Australia.
Until next week - Make your Prime Time count!
Finally - check out this segment on Weekender about Prime Time - 😍 🏝️
Hi Bec, I listened to Mike and your podcast today and found it interesting. However, Mike has only seen half of the work involved as his mother is still alive making the transition from a combined estate to single estate reasonably straightforward. Having acted as a third party ( i.e. non family) Enduring Power of Attorney and Will Executor, I learnt one has to be careful after the death certificate has been issued. The temptation is to scan the QR code so all interested parties are notified. However, it is much better to identify each item of the estate that has to be processed and systematically transfer control from Enduring Power of Attorney ( which ceases on the death of the individual) to Will Executor. Also, even if the person has a prepaid funeral there are still costs involved so keeping the estate bank account alive until all expenses have been paid avoids any interested parties thinking monies have been paid to the Executor for the wrong reason. My advice would be to identify all the changes to be made, tick them off one by one and keep detailed records of everything you do so you maintain control through the whole process. At the end of the processthe Will beneficiaries are paid out and there are no disputes.
Ian Kilpatrick
That’s the spirit. Longer, better, and bolder — that’s how the second half should be lived