Hi Reader

It’s November. That time of year when we all glance at the calendar, realise it’s just over 50 days until Christmas and mutter, “Oh brilliant… where the hell did that year go?”

Time is a sarcastic little gremlin. When you’re young, it crawls along like double maths on a Monday. When you’re older, it vanishes quicker than my willpower when someone unveils a cheeseboard. One minute it’s spring, the next Michael Bublé is warming up and your diary is full of social events you don’t even remember agreeing to.

So today I’m talking about time, specifically, how we spend it (and our money) without really noticing it slip through our fingers. Not in a dramatic “find your purpose or die” way, but in a practical “maybe we should pay attention before another year disappears into mince pies and Mariah Carey” kind of way.

Grab a coffee, take five minutes, and let’s get into it... before time sprints off again.

FEATURED ARTICLE

The Psychological Battleground of Retirement

Where your brain, your wallet, and your watch go to war.

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Congratulations! You’ve finally escaped the meetings, the targets, the “urgent-but-not-actually-urgent” emails. You’ve made it to retirement — that magical land of freedom, leisure, and the promise of finally doing all the things you said you’d do when you had time.

Except now you do have time. And money. And you feel… weird.

You can’t quite relax. You’re unsure what to do next. You feel guilty for spending. You feel anxious when you’re not doing anything.

Welcome to retirement’s psychological battleground — the messy, emotional no-man’s-land between spending time and spending money.

In the middle of it all sits a nasty cocktail of fear, guilt, uncertainty, courage, doubt, and that lovely old classic — permission.

This, my friends, is where retirement gets real.

The Problem: Your Brain Wasn’t Built for This

Let’s start with the basics.
When you retire, you suddenly have more of one currency (time) and enough of another (money). But instead of feeling rich, many people feel… itchy. Unsettled. Almost guilty.

We’ve been trained since childhood to save, work hard, and delay gratification. That conditioning runs deep. So when the system suddenly switches to spend, your brain throws a tantrum.

And it’s not just money.
With time, we go from “I wish I had more of it” to “Dear God, what am I supposed to do with all of it?”
The result? Paralysis by abundance.

You’re financially free but psychologically shackled. You’ve mastered saving, but you’re terrible at spending, especially on yourself.

It’s not that you can’t enjoy retirement. It’s that your brain thinks enjoying it might get you killed.

Why You Feel So Bloody Awkward

Here’s what’s really going on:

• Fear – “What if I run out?” (You won’t. But fear doesn’t care about spreadsheets.)
• Guilt – “Should I really buy that car/trip/tennis membership when there are starving children, market crashes, and grandkids with iPads to fund?”
• Permission – “Who said I’m allowed to relax?” (Spoiler: You are.)
• Uncertainty – “What if the markets crash? What if I live to 112? What if Greg from the golf club is right about inflation?”
• Courage – “It actually takes balls to spend your own money and own your own time.”
• Doubt – “What if this isn’t what retirement’s supposed to feel like?”

This is the real frontline of retirement.
Not your withdrawal rate. Not your asset allocation.
It’s the battle between your head and your heart — between your logical self that says “I’ll be fine” and your emotional self that still whispers “Yeah, but what if…”

The Stats (Because Logic Likes to Pretend It Helps)

Half of retirees are scared to use their savings. Yes, half. Despite having plenty, they’d rather hoard it like emotional doomsday preppers.

Behavioural economists call it “loss aversion.” I call it “the voice in your head that still thinks you’re one bad splurge away from bankruptcy.”

Meanwhile, research shows retirees spend less than they can afford, even though they have no real reason not to. Translation: we save our whole lives, then die with too much money and not enough stories.

And on the time side? We crave freedom until we get it, then panic because there’s no structure.

You wanted “no more Mondays.” But after a few months, every day starts to feel like a slightly disappointing Sunday.

So, How Do You Win the War?

Here are three battlefield tactics to reclaim your sanity (and maybe enjoy your life while you’re at it):

1. Give Yourself Permission Slips

Literally, write them out.

“I hereby grant myself permission to go to Italy, order the wine I actually want, and not feel bad about it.”

You spent 40 years earning this moment. The least you can do is enjoy it.

2. Pair Your Time and Money

Stop treating them as separate.

Spend money to create time (like outsourcing boring crap), and spend time to enjoy your money (like actually using that campervan instead of polishing it).

When your time and money are aligned, life feels purposeful, not like a never-ending Sunday afternoon.

3. Plan for the Wobble Zone

That weird transition phase after you stop working? Totally normal. You’re rewiring your identity.

You’re not lazy, broken, or lost, you’re just unpractised at freedom. Build structure slowly. Try things. Say yes, screw up, recalibrate. It’s not a midlife crisis. It’s a midlife reprogramming.

The Real Script You Should Follow

The one we’re taught:

Save → Stop working → Panic → Underspend → Die wondering.

The one that actually works:

Save → Stop working → Relearn how to live → Spend bravely → Die empty but fulfilled.

The Brutal Truth (With a Hug)

You don’t have a spending problem. You have a permission problem.

Your financial plan probably works just fine. But your psychology? That’s still on probation.

Retirement isn’t the end of something. It’s the messy middle of becoming someone new.

So go ahead, spend your time like it matters and your money like it’s meant to be enjoyed. Because the scariest sentence you’ll ever say in hindsight is:

Now go live. And if anyone gives you grief for ordering the nice bottle, tell them you’re doing behavioural therapy.

PODCAST

Ep 95 - The Emotional Whirlwind of Retirement (And How to Survive it)

Retirement was supposed to feel like a permanent holiday… so why does it sometimes feel more like an emotional hangover? This week, I unpack the Retirement Reinvention Curve — the real 8-stage journey no glossy pension brochure warned you about. From “Yesss, no more emails!” to “Who even am I without a job title?” to eventually finding your groove again — it’s messy, it’s human, and you’re not the only one Googling “Is it normal to be bored in retirement?”. Listen in now ​​​​

SKETCH OF THE WEEK

The Identity Sweetspot

Retirement doesn’t just take away your payslip, it steals your identity lanyard too. One day you’re “someone important,” the next you’re Googling whether feeding squirrels counts as a hobby. This sketch is your roadmap out of the identity crisis: who you are, what gets you out of bed, and where you spend your time and energy. Nail the overlap, and you’ve got a new purpose. Miss it, and you’ll be stuck alphabetising the spice rack wondering where it all went wrong.

IN OTHER NEWS

What I've Read This Week

• A Way to Boost Longevity Knowledge for Better Retirement Planning - ThinkAdvisor
• Dr. Peter Attia says enjoying a longer, healthier life requires serious training: "Life is a sport" - CBS News
• You Don't Need a Reason to Do Something For Yourself - A Year of Mental Health

Spreading The Message

• I was interviewed by the brilliant Rory Henry for his podcast AFO|Wealth Management Forward, where I talked all about the human side of retirement, listen in via Apple or Spotify