Navigating 'the retirement you didn't see coming'

Dan Haylett joins me from the UK this week to break down the illusions of retirement — and why the real planning starts well before you stop working.

What if the first step to planning for retirement is unlearning what you thought you knew about it — and starting fresh? What if we planned for this stage of life purpose-first, then thought about the money.

In this week’s episode, I sit down with UK financial planner, retirement coach, and podcaster Dan Haylett, whose new book The Retirement You Didn’t See Coming unpacks the biggest illusions about retirement — and the uncomfortable truths we rarely talk about, but should.

From identity shifts to the “Tuesday blues,” Dan unpacks the raw, real and often surprising emotional curve that retirement brings — and why spreadsheets and numbers only get you so far.

Whether retirement is around the corner or still a few years away, this conversation is an honest and refreshing guide to preparing not just your finances — but your whole self — for what’s next.

LISTEN TO THIS EPISODE OF THE PODCAST HERE:

• LISTEN ON APPLE PODCASTS

• LISTEN ON SPOTIFY

Highlights of the conversation:

• Retirement is not the goal. Why we need to shift away from “the end point” mentality and treat retirement as a life phase, not a destination.

• The set of beliefs and illusions in retirement — From “Retirement is the goal”, to “The financial plan is the whole plan”, and “Retirement is the same for everyone”, we unpack the biggest myths we’ve inherited about retirement — and how to challenge them with clarity and intention.

• Why spreadsheets only get you so far. Dan shares why the real work lies in the human side of the journey.

• The blank canvas problem. Freedom sounds great… until it becomes aimless. Learn how structure and purpose make the difference.

• Day 182: the most dangerous day. Six months after retirement, many people feel adrift. Dan shares what this moment is — and how to avoid the slump.

• You’re not too early. Why starting the planning process in your 40s or 50s is one of the best things you can do — even if you don’t plan to retire yet.

---

---

From Bec’s Desk

So much of the second half of life comes down to our sense of purpose and identity, how closely those are tied to our work, and what happens before and after that link is broken.

For some, midlife brings an earlier disconnection from work than expected. Burnout or exhaustion can make retirement feel like the only way out. Others find themselves pushed out by circumstances beyond their control. In those moments, people respond in different ways: some give up and retire, some sigh with relief and step away, while others take time to reflect, look for different things from their work, and repackage themselves for the next phase.

It’s messy and complex. Confidence plays a role, so does ageism, so do skills, and of course, money.

This stage of life is rarely discussed, and yet it matters to more people than ever. Retirement can feel like something that just happens to you - whether that’s through burnout or circumstances beyond your control - but I want it to be something you choose. That means learning how to prepare, how to plan financially, and how to reshape your sense of purpose as life shifts and changes.

That’s why I want to talk about it more. Because retirement doesn’t have to be something that simply happens to you. Even if an ending or burnout arrives later in your working life, you can still choose what comes next - if you take time to set yourself up for this phase of life. That choice begins with preparation, financial planning, and the courage to reshape your sense of purpose as life changes. They’re the three critical markers of our Prime Time.

And as the world shifts - with AI creeping into workplaces and the risk of being left behind if we don’t adapt - we have to stop and ask: what really matters? For me, the science is clear: family, purpose, and passions matter most. And when your finances are in order, they give you the freedom to focus on those things without constant stress. That’s the real power of this stage of life - the ability to choose, to shape your Prime Time around what matters most to you, and to re-enter the world of work if it feels right, without feeling like you’ve been pushed out.

Retirement isn’t the ultimate goal anymore.” Dan titled a chapter in his book with that line. So did I. And we never discussed it until this show. Maybe that says something about where midlifers and pre-retirees are right now - realising retirement isn’t the finish line, but just another choice point in a life that’s long and keeps changing in priority and direction — longer and more twisty than it’s ever been before.

I want to hear where you’re at today…

And of course — if you haven’t picked up a copy of Prime Time: 27 Lessons for the New Midlife yet - what are you waiting for? You can’t learn if you’re not curious!

---

Prime Time: the juiciest stage of life

Prime Time: 27 Lessons for the New Midlife (the book) is the prequel to How to Have an Epic Retirement. It’s written for people in their late 40s, 50s and 60s who want to make the most of the juicy, potential-filled years leading up to retirement — and then step into an epic one.

The book debuted as the #1 bestselling self-help title by an Australian author, and it’s redefining how a generation thinks about midlife. You’ll find it wherever you buy books.

It works through six pillars of your Prime Time, years when you might be looking for more from life than just the grind of work:

• Power

• Money

• Work, Purpose & Happiness

• Health

• Family & Community

• Travel

It’s a modern, forward-thinking guidebook designed to open your mind, help you explore your choices in midlife and the years before retirement, and support your decisions — so you don’t have to make the mistakes to learn from them.

Order your copy now on Amazon. Or find it wherever you buy books.