Living a 'soft retirement' and test driving jobs

Andrew hit his late 50s and realised the world of work wasn’t quite calling his name anymore. So instead of retiring outright, he started experimenting, calling it his “I’m not done yet” era.

In this episode, I chat with Andrew Middleton, a thoughtful, quietly funny voice out of the UK who’s navigating what he calls “soft retirement.” After a long career in leadership roles, Andrew hit his late 50s and realised the world of work wasn’t quite calling his name anymore. So instead of retiring outright, he started experimenting, calling it his “I’m not done yet” era.

Since then, he’s worked as a wedding registrar, learned to film videos, shared his journey on LinkedIn, and quietly built a life that works for him - one with freedom, flexibility, and purpose.

We talk about what really changes in your 50s, the invisible shift in how the world sees you, and how to design a life that lets you keep showing up on your own terms. If you’re feeling the itch for something new - but don’t want to throw away everything you’ve learned so far - this one’s for you.

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Highlights of the conversation:

• Redefining retirement, gently – Andrew talks about “soft retirement” as an easing-in, not a dropping-out, and why keeping some structure (and income) matters more than people think.

• Discovering joy in unexpected places – How becoming a wedding registrar brought meaning, public speaking practice, and the kind of community feeling that no corporate boardroom ever could.

• “I’m not done yet” and neither are you – Andrew’s mantra reflects a wider shift happening among midlifers who are resisting the old ‘sit still and slow down’ model. You’re not broken - the midlife and retirement template is.

• The quiet hit of ageism in your 50s – We explore how the world subtly changes how it sees you, and the choice you have: shrink, or shape something new.

• Learning as a life strategy – From mastering videography to facilitating Zoom workshops during lockdown, Andrew shares how staying curious kept him feeling valuable.

• Life as a portfolio, not a job title – We talk about test-driving roles, mixing paid and unpaid work, and why sometimes “just enough” income can unlock a whole lot of freedom.

• Ageing well isn’t just about health, it’s about attitude – From Reformer Pilates to spontaneous travel, Andrew shares how staying open (even when awkward or out of your depth) keeps life interesting.

• Community, connection, and the long game – The people you’ll need most later in life might not be your current friends, and building those relationships now matters more than you think.

• The ‘Oh sh*t’ moment – We dive into those unexpected wake-up calls - a health scare, redundancy, an identity shake - and how they can become turning points if you let them.

• What matters most, really – Andrew wraps it all with a gentle reflection: have fun, do some good, and if you can, make a little money along the way.

Tell us in the comments what you're loving (or hating) about this stage.

From Bec’s Desk

Andrew is a voice of truth about ageism and reshaping your life, work and purpose. And he’s someone I really enjoyed chatting with. His open mind to exploring everything, trying new things and looking for ways to make a difference is refreshing and so clearly aligned with the lessons I share on midlife here on Prime Time.

Speaking of lessons…

Anyone who follows me on Facebook knows I’m having a Prime-Time adventure with my family. We’re relishing the European Summer. It’s been 27 years since I last saw this part of the world and so far, it’s everything we dreamed of and more. But being away means I haven’t been at home to receive my first printed copy of Prime Time:27 Lessons for the New Midlife. But, my publisher Sophie got her copy from the printers yesterday and sent me some real life action photos. I couldn’t resist sharing them with you.

It’s here! The first print edition has been spotted in Sydney this week in my publisher’s office.

The book itself is bigger than How to Have an Epic Retirement is today, with a spine of 33mm. It’s jam packed with financial and lifestyle education for midlifers and pre-retirees. I’m excited to see it in stores on the 30^th July.

You can pre-order your copy now via Amazon Australia so you get it in your hot little hands as soon as it’s released.

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Prime Time: Live Book Launch Event

OK, we’re doing it. I’m holding a free live online event for the book launch on launch day… and my publisher from Hachette, Sophie Hamley, will be my cohost. If you’d like to attend, please register your interest below. It’s a free event, and I’ll do my best to pack it with valuable information.

Register here for the Prime Time: 27 Lessons for the New Midlife live online book launch.

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