If You Can't Answer This Question, You May Not Be Ready To Retire - Edition #52 of The Super Sunday Retirement Roundup


Hi Reader

Welcome to edition #52 of The Super Sunday Retirement Roundup.

WOW! This is edition 52... Which means (give or take a few missed weeks here and there) I've somehow produced a whole years worth of weekly newsletters... where has that time gone? And yes it does appear to fly when your having fun.

I've had a blast writing and sharing my thoughts with you, and my biggest hope is that you have had a equally great time reading them!

With that in mind, this episode feels like the right time to take a little mini break and recharge the batteries a bit. I'm taking a few weeks off over the Easter holidays and need to get my head down and have pin point focus on a few things over the next month or so.

That means I'm going to give my self a month off from writing this newsletter, but don't panic, I will be back first week in May!

With that in mind, I wanted to leave you on a big high this week, so please find below...

  • A question that you need to answer to be 100% ready to retire
  • A FREE workbook to help you answer the question
  • How retirement can often feel more like a void than a victory
  • How Ikigai can help uncover your purpose
  • Creating new identities should be exciting and rewarding

As always, grab that drink, notepad, pen and open mind and sit down to enjoy my latest thoughts.

Take care and see you in a few weeks time...


My Latest Thoughts

If You Can’t Answer This Question, You Might Not Be Ready to Retire Yet…

Let’s play a little thought experiment.

Imagine you walk into a room full of strangers, no name tags, no business cards, no introductions.

Someone turns to you and says:

“So, what do you do?”

But there’s a catch.

You can’t mention your job.

Not your title, not your industry, not even a humble “I used to be in [insert impressive career here].”

What do you say?

Seriously, pause and try to answer that.

If you feel the uncomfortable swirl of silence rushing in, you’re not alone. Most of us have been so wrapped up in what we do that we’ve forgotten how to talk about who we are.

And that, my friend, is why this question might be the biggest test of your retirement readiness.


The Great Identity Swap

Most people picture retirement as a never-ending holiday... like school’s out forever, but with a better wine budget.

Sleep in, travel more, no alarm clocks, no Zoom calls.

Cue the beach sunsets and stock photos of couples laughing over salad.

But here’s the truth they don’t put in the brochure:

Retirement isn’t just a lifestyle change, it’s an identity shift.

For 30 or 40 years, your name has likely been followed by a title. You mattered because of the problems you solved, the people you led, the results you delivered. You were “the go-to,” “the decision maker,” “the one who gets it done.”

But then one day, poof, it’s gone.

The email signature vanishes.

The calendar clears.

And suddenly, nobody’s asking for your input on the quarterly report.

What now?


The Retirement Hangover

A few ago I started to work with a man, let’s call him Dave, who had an illustrious career as a CFO. Sharp guy. Excel wizard. Walked into retirement with confidence and a spreadsheet.

Three months in, he was miserable.

“I thought I’d feel free,” he told me. “But I just feel invisible.”

No one needed his opinion on profit margins anymore. No one cared that he streamlined operations in six different countries. His LinkedIn was pristine, but his days were empty.

He came to me after he realised what a lot of people discover too late: retirement without purpose isn’t freedom, it’s drift.


You’re Not Done...You’re Evolving

Here’s the shift: Retirement isn’t about stepping away from meaning. It’s about stepping into a new kind of meaning.

But to do that, you have to start asking better questions before you exit the workforce.

Instead of:

“Can I afford to retire?”

Also ask:

“Who am I without my work?”

“What drives me if I’m not being paid?”

“How do I want to contribute, connect, and grow?”

These aren’t soft questions. They’re hard. And they’re necessary.

Because you’re not done yet, you’re just in transition.

And that transition can be incredible, if you’ve got something beyond work pulling you forward.


The Real Retirement Planning

Yes, money matters. But meaning matters more.

If you’ve been defining yourself by your productivity, your position, or your salary, retirement can feel like a void.

But if you start building a sense of self that isn’t attached to your title, a self rooted in curiosity, contribution, creativity, or community, then retirement doesn’t have to be an ending. It becomes a launchpad.

Maybe you’re a mentor, an artist, a volunteer, a coach, a storyteller, a traveler, a grandparent, a student of life. Maybe you build something new. Maybe you finally write that book, start that garden, or teach others what you’ve spent decades learning.

The possibilities are endless.

But only if you’ve done the work to see yourself beyond the CV.


So, Back to the Question…

"If your career ended tomorrow and you had no title, no business card, no company behind your name… how would you describe who you are and why you matter"?

If the answer comes easily, that’s a good sign.

If it doesn’t? Don’t panic. Just start exploring.

Because your second half can be your best half, but only if you’re willing to redefine what “success” looks like when there’s no longer a job to define it for you.


Your Free Gift! - 10 Ways To Explore Who You Are Before You Retire

I've put together a workbook for you! One for you to use to help tackle the above. I know, I know... I'm very generous, but there is no need to thank me, just make sure you use it because it really will help!

👉 10_Ways_to_Explore_Who_You_Are.pdf


Read These Articles

👉 Why Retirement Can Feel More Like a Void Than a Victory - By ME!

Is Retirement Really Freedom, or Just a Void in Disguise? We’re sold the dream that retirement is life’s ultimate reward, but what if all that free time feels more like an empty hole than a holiday? In my latest blog, I explore why so many retirees find themselves stuck in the “busy trap” and how true fulfilment in retirement isn’t about filling time, but about filling it with purpose. Click the link above to discover how to turn the void into your greatest canvas.


The Humans vs Retirement Podcast

👉 Episode 77 - The Ikigai Way: How to Uncover Your Purpose with David Marlow

Episode Summary

In this inspiring and heartfelt episode, I sit down with David Marlow, veteran leader, coach, and author of The Ikigai Way to explore how the ancient Japanese concept of Ikigai can powerfully guide us into a more fulfilling and purposeful retirement. From personal stories of career transitions to uncovering identity after work, David shares how aligning our inner essence with what we do can transform our experience of aging, retirement, and meaning in life.

What You’ll Learn in This Episode

  • What Ikigai really means (beyond the Instagram-friendly Venn diagram)
  • How to align your essence and purpose with daily life, before and after retirement
  • The power of experimenting, curiosity, and continuous self-discovery
  • How to reframe retirement from “ending” to “uncovering”
  • Practical tools and reflections to help you discover your own Ikigai

Listen in via:

👉 Apple Podcasts

👉 Spotify

👉 Youtube Podcasts

👉 Youtube Video



The Super Sunday Retirement Roundup

Each week I bring you…👉 Some exclusive thoughts about a modern day retirement 👉 Six key lessons from the latest episode of The Humans vs Retirement Podcast 👉 A blog 👉 A sketch

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