Hi Reader

Welcome to edition #50 of The Super Sunday Retirement Roundup.

In this weeks all action newsletter I share with you:

• The 5 big retirement problems money won't solve
• My thoughts on why we shouldn't worry about the latest (and not last) stock market wobble
• How retirement could ruin you!
• Why 'pure independence' could be the key to a fulfilling life
• How to shift your mindset in for and in retirement
• What the happiest retirees all have in common

As always, grab your favourite beverage, something to jot some notes on and enjoy my latest thoughts and findings.

And... Please do let me know if any of this resonates (or equally if you think I'm talking rubbish!).

I love to hear your feedback and thoughts.

My Latest Thoughts

The Problems Money Can't Fix

Retirement’s Biggest Challenges

Retirement is sold and marketed as a lifelong dream, a golden era (I hate this phrase!) of leisure, travel, and finally, enough time to binge-watch every TV show you missed while working.

But here’s the catch: while money can fund your retirement, it can’t help you find fulfilment in it.

Yes, having financial security is crucial (no one enjoys stress-testing their budget at the supermarket), but if you think a hefty pension pot alone will guarantee happiness, purpose, and a strong sense of identity...

...you might be in for a surprise.

Retirement isn’t just about having the means to stop working, it’s about knowing what you’re working toward once the job titles and deadlines disappear.

Here are five big challenges money won’t solve in retirement... and what you can do about them.

1. The “Who Am I Now?” Crisis (a.k.a. The Identity Gap)

For decades, your job wasn’t just what you did; it was who you were.

Whether you were a CEO, teacher, or accountant, work gave you a role, a reputation, and a reason to wake up in the morning.

Then, suddenly… poof.

Retirement can feel like an identity crisis in disguise.

Researchers at the University of Florida found that people who closely tie their identity to work often struggle with self-worth in retirement.

Without a clear sense of who you are beyond your career, that newfound freedom can feel less like a holiday and more like an existential void.

The Fix:

👉 Instead of asking, What do I do now? start with Who do I want to be?

👉 Explore new roles: mentor, volunteer, artist, student, adventurer—whatever excites you.

👉 Give yourself permission to experiment. Your new identity isn’t set in stone; it’s a work in progress.

2. The “Too Much Free Time” Paradox

Ever spent months dreaming of a holiday, only to get there and think, Now what?

Retirement can be like that, except it’s decades long.

Sure, money can buy you free time, but it can’t tell you how to fill it meaningfully.

A study in the Journal of Applied Psychology found that retirees who replaced work with structured, engaging activities reported higher life satisfaction than those who simply “took it easy.”

The Fix:

👉 Plan your time with as much care as you planned your finances.

👉 Structure your days - morning walks, creative hobbies, social meet-ups, even part-time work.

👉 Try “time-blocking” retirement: Instead of staring at blank days, fill your calendar with activities that excite and challenge you.

(And yes, Netflix marathons are fine, but maybe don’t let them be the main event!)

3. The Loneliness Trap

One thing you don’t realise while working? Your job was secretly your social life in disguise.

Meetings, chats by the coffee machine, after-work drinks, they all disappear overnight in retirement.

And if you don’t proactively nurture relationships, loneliness can sneak up on you faster than a bad investment decision.

Harvard’s famous Study of Adult Development (which has tracked people for over 80 years) found that the biggest predictor of long-term happiness isn’t wealth or career success... it’s relationships.

The Fix:

👉 Be intentional about friendships: Schedule catch-ups, join clubs, stay involved.

👉 Consider community volunteering - it gives you purpose and people.

👉 Keep learning! Retirement is the perfect time to take a class or join a group that connects you with like-minded people.

(Also, if you needed an excuse to get a dog, this is it... built-in companionship and an easy way to meet people at the park.)

4. The “Happiness Plateau” Dilemma

Research shows that happiness tends to dip after the initial honeymoon phase of retirement. Why? Because the thrill of endless free time wears off when there’s no deeper meaning attached to it.

Studies from the London School of Economics suggest that people feel happiest when they’re engaged, whether that’s through learning, contributing, or pursuing passions.

In other words, retirement happiness isn’t about escaping work; it’s about replacing it with something that matters.

The Fix:

👉 Find a passion project, something that challenges and fulfils you.

👉 Set personal growth goals: Learn a new language, write a book, or train for a marathon.

👉 Look for ways to contribute: Many retirees find immense joy in mentoring, coaching, or supporting causes they care about.

Retirement isn’t a finish line; it’s a blank canvas. The question is: What will you paint?

5. The “Chasing the Wrong Goals” Trap

Picture this: You’ve retired, you’re financially secure, and you’ve ticked off a couple of big trips that you always wanted to do. But something still feels… missing.

That’s because experiences matter more than stuff.

The University of Texas found that people who prioritise experiences over material wealth report higher levels of life satisfaction.

Buying a fancy new car? A short dopamine hit.

Spending time learning, growing, and connecting with loved ones? Long-term fulfilment.

The Fix:

👉 Shift from acquiring to experiencing.

👉 Invest in memories over possessions.

👉 Ask yourself: “What will I be glad I spent time on when I’m 90?”

Because at the end of the day, the most valuable things in retirement can’t be bought... only built.

Final Thoughts: Money is the Means, Not the Meaning

Yes, money matters. No one is suggesting you throw your retirement savings plan out the window and go full “Eat, Pray, Love” without a financial safety net.

But remember: Money can fund purpose, but it can’t find it for you. That’s your job.

Retirement isn’t just about having the resources to stop working, it’s about having the reason to keep living fully.

So, if you’re planning for retirement, don’t just ask, How much do I need? Ask, Who do I want to become?

Because while money can help you buy back your time, only you can decide how to spend it wisely.

And that, my friend, is the real retirement jackpot.

I would love to hear... what’s your vision for a meaningful retirement? Let’s talk!

Read These Articles

👉 Riding The Market Rollercoaster: Why a Wobble is No Reason to Worry - by Me

In my latest blog post I explore the natural fluctuations of financial markets and emphasise the importance of maintaining a long-term perspective. Market volatility is an inherent aspect of investing, and short-term downturns shouldn't deter you from your financial goals. By understanding the cyclical nature of markets and focusing on your long-term objectives, you can navigate these 'wobbles' with confidence and avoid making impulsive decisions that could hinder your retirement plans. Discover strategies to stay the course and ensure your retirement remains on track, despite the market's ups and downs.

👉 How Retirement Can Ruin Your Health, Happiness & Purpose - By Paul Long

Now this isn't strictly something for you read... Paul has provided a summary in his latest substack post and then included a brilliant video on this subject. Click on the link above, read the summary and then click on his video to find out more.

👉 Pure Independence - by Morgan Housel

In his recent article, "Pure Independence," Morgan Housel presents a straightforward formula for a fulfilling life: combining independence with purpose. While purpose varies individually, encompassing elements like family, community, or work, independence is a universal aspiration. Housel illustrates this through a personal anecdote about his son's journey from shyness to confidently ordering ice cream alone, highlighting the profound satisfaction derived from self-reliance. He emphasises that achieving true independence requires financial stability, which in turn allows individuals to make choices aligned with their genuine desires, free from external pressures. This autonomy not only enhances personal well-being but also fosters a deeper sense of fulfilment.

The Humans vs Retirement Podcast

👉 Episode 76 - The Retirement Mindset Shift with Lindsay Troxell

Episode Summary

Retirement isn’t just a financial transition, it’s a psychological and emotional one, too. In this episode of Humans vs. Retirement, I sit down with Lindsay Troxell, a coach and life planner who has been at the forefront of shifting the financial industry’s focus toward a more human-first approach.

Lindsay shares powerful insights on mindset, identity, and habits, and why most people unknowingly experience an identity crisis in retirement. Lindsay and I explore how to reshape your beliefs, redefine purpose, and build new habits for a fulfilling second half of life.

If you’ve ever asked yourself: Who am I without my job title? How do I retire with meaning? or Why does retirement feel like a letdown?, this episode is for you.

What You’ll Learn in This Episode

• Why retirement isn’t just about money—and why financial security alone won’t make you happy.
• How habits and mindset shape your retirement experience (and how to rewire them).
• The common identity crisis retirees face—and how to navigate it with confidence.
• Why traditional financial planning treats retirement as a math problem, when it’s actually a human challenge.
• How to develop purpose, fulfilment, and structure in retirement.
• The importance of coaching and why having a financial plan isn’t enough.

Listen in via:

👉 Apple Podcasts​

👉 Spotify​

👉 Youtube Podcasts​

👉 Youtube Video​

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