Ep 100 - What 100 Episodes Taught Me About Retirement... And About Being Human

After 100 episodes of diving into the messy, hilarious, emotional and utterly human world of retirement, I return with the rawest and most powerful episode yet. This milestone isn't a celebration; it's a challenge. A wake-up call. A bold invitation to stop drifting, stop delaying, stop hiding behind old identities… and finally step into the second half of life with honesty, courage, and intention. This episode strips retirement down to what it really is: not money, not timing, not spreadsheets, but the ongoing evolution of you. Who you are when the job title disappears. Who do you dare to become next? And what you're no longer willing to tolerate in the life you have left. What You'll Learn The biggest insight 100 episodes have revealed about human beings and retirement Why retirement isn't actually about retirement, it's about identity The hidden question sitting under nearly every conversation I have ever had Why most people drift through the second half of life instead of designing it How self-honesty becomes the true starting line of retirement Why courage, not money, is the single biggest predictor of a fulfilling future What it really means to write the next chapter of your life on purpose Challenge of the Week 👉 Answer the only question that truly matters: What are you no longer willing to tolerate in the second half of your life? Write it down. Say it out loud. Let it change something. Because that answer is your starting line, your compass, your invitation to evolve. Next Episode Season 7 begins soon — with a fresh blend of interviews, solo episodes, and deeper dives into the emotional, behavioural, and wildly human side of retirement. Expect honesty, humour, science, challenge… and more than a few loving kicks up the backside.

If you want to retire well in 2026, you don't need a ten-year spreadsheet, a suitcase full of pensions, or a perfectly colour-coded life plan. You need five human foundations: clarity around your money, health that actually supports your freedom, purpose that wakes you up in the morning, people you want in your corner, and the courage to take action. In this episode, I strip away the fluff and break down what actually moves the needle... the things your future self will thank you for getting right now, not "one day." What You'll Learn Why your "vibes-based" retirement plan needs to become a real plan How financial clarity — not wealth — creates confidence and choice Why health is the core engine of your next chapter (not a side quest) How to explore purpose without pretending golf is a personality The huge role relationships play in your retirement experience Why courage — not spreadsheets — is the final unlock The 5 Things That Matter 1️⃣ The Money Plan (not the one in your head) You don't retire on vibes — you retire on numbers, clarity, and confidence. Know what you've got, how it's structured, and what it can actually do. 2️⃣ Your Health (so you can enjoy the freedom you've worked for) No point having time and money if you're exhausted, aching, or stuck on the sofa. Small, consistent actions → big retirement quality. 3️⃣ Purpose (you need something to wake up for) Work gave you identity, rhythm, and direction. Retirement requires you to create it — not wait for it to appear. 4️⃣ Relationships (your real retirement portfolio) Remove work, and the room gets quiet fast. Build connection intentionally: tribes, friendships, laughter, people who energise you. 5️⃣ Courage (the part no one likes to talk about) Fear keeps people in holding patterns: waiting for "readiness," waiting for a sign. Confidence doesn't precede action — it comes from it. Challenge of the Week 👉 Pick one of the five pillars and make a visible move. Book the financial planning call Start a consistent walk routine Try a new hobby or project you've always avoided Message someone you miss and reconnect Commit to one brave retirement decision you've been postponing Don't wait for certainty. Do the human thing that moves life forward.

In the season finale, I tear up the traditional retirement rulebook and replace it with a bold, human, and rebellious manifesto for the second half of life. The old rules — work 40 years, aim for "enough," play it safe, slow down — were never designed for modern retirees who want meaning, energy, experiences, connection, and agency. This episode lays out The New Rules of Retirement — ten powerful principles for anyone who refuses to drift through retirement and instead wants to design it boldly, live it fully, and leave a legacy that's felt as much as it's funded. This is your encore… so make it loud. What You'll Learn Why the old retirement rules are outdated, limiting, and designed for a different era Ten modern, human-first principles for living boldly after work Why retirement isn't the end — it's the starting line How to prioritise time, meaning, purpose, and memory dividends over fear and preservation Why confidence comes before clarity, and flexibility beats perfection The truth about retirement as an emotional journey, not just a financial event How to shape a legacy through impact, stories, and how you live — not just what you leave Challenge of the Week 👉 Write your own new retirement rule. Just one. Something that becomes a north star for how you want to live the next chapter. Examples: "I spend without guilt when it brings me joy." "My time is my greatest asset." "I will not shrink my life to fit someone else's expectations." "I choose connection over busyness." "The second half of my life will be better than the first." Write it. Repeat it. Live it. Resources & Mentions The New Rules of Retirement — Dan's Season 6 manifesto Episode references: Episode 4: Time Isn't What You Think It Is Episode 9: The Retirement Reinvention Curve Episode 10: Modern Software, Ancient Hardware Episode 11: The Retirement Focus Ratio My sketches, book, and newsletter Final Note This episode wraps Season 6, a season dedicated to human-first retirement, emotional truth, and challenging the defaults. If these conversations have sparked anything in you, share them with someone who needs a more rebellious, honest, and liberating view of retirement.

Most financial planning conversations in retirement are 90% about money, but most retirees spend 90% of their time thinking about life. That's the Retirement Focus Ratio, and it's completely out of sync. In this episode, I challenge the industry obsession with spreadsheets and show why the real success of retirement isn't built in Excel, but in how you live, spend, and find meaning after work. You'll discover how to rebalance your focus from money to life, and why the best retirement plans aren't about preserving wealth; they're about unleashing it to create joy, connection, and purpose. What You'll Learn Why retirement planning often solves the wrong problem The disconnect between financial advice and emotional reality How to flip your Retirement Focus Ratio from 90% money / 10% life to 50/50 (or better) The key steps to building a life-led retirement plan How money becomes more meaningful when it supports purpose Why you can't measure joy in basis points, but you can design for it Challenge of the Week 👉 Audit your own Retirement Focus Ratio. Ask yourself: How much of my energy is focused on money vs life? What would go in my "Retirement Life Plan"? What's one step I could take to shift the balance? Then take action: Book a call to talk about legacy Write your ideal week Start a "Life List" — not a bucket list The goal isn't to ignore THE money. It's to elevate THE life. Next Episode Coming up in Episode 12 — the grand finale of Season 6: The New Rules of Retirement (For Rebels Only) A bold manifesto for those who refuse to drift through retirement, and want to design, live, and leave a legacy on their own terms.

Retirement is a modern invention, but your brain didn't get the upgrade. In this episode, I unpack why so many retirees feel restless, guilty, or underwhelmed, even when life looks "perfect on paper." It's not because something is wrong with you, it's because you're trying to run a 21st-century life on Stone Age wiring. I explore the mismatch between modern retirement and ancient survival instincts, why you struggle to relax, why doing nothing feels uncomfortable, why spending feels risky, and why your brain craves purpose, progress and tribe. Most importantly, I share how to retrain your mind for this new chapter, without fighting your biology. What You'll Learn Why retirement feels unsettling (and why it's not your fault) The clash between modern freedom and caveman brain wiring How dopamine, productivity and survival instincts mess with your retirement mindset Why your brain resists rest, spending and stillness Five ways to "upgrade the software" — from micro-missions to novelty, contribution and healthy discomfort How to feel useful, alive and excited again in retirement Challenge of the Week 👉 Pick one "Brain Upgrade" and try it for 7 days: Set a Micro Mission (e.g. walk 10k steps daily, plan a trip, finish a book) Add Novelty — try something new for 30 minutes a day Create Contribution — teach, help, give or mentor someone Introduce Healthy Discomfort — cold shower, tech-free evening, social challenge At the end of the week ask: How did it feel? What did it teach me about what my brain needs? Resources & Mentions Micro Missions, Contribution Loops & Novelty Windows — My behavioural retirement tools Next Episode Episode 11 — The Retirement Focus Ratio: Are You Solving the Wrong Problem? Why most retirement plans are 90% about money… but most retiree worries are 90% about life. And how to fix the imbalance.

Retirement isn't a finish line; it's an emotional rollercoaster. In this episode, I break the myth of the "happily ever after" retirement and introduce The Retirement Reinvention Curve — an honest, human map of what really happens when the work stops and life after work begins. From the initial shock and elation to the frustration, doubt, and eventual flourishing, I unpack the eight emotional stages we all go through when redefining identity, purpose, and meaning beyond the job title. This isn't about pensions or spreadsheets, it's about becoming who you are next. What You'll Learn Why retirement isn't a single event but a psychological transformation The 3 phases and 8 stages of The Retirement Reinvention Curve How to recognise where you are, and why nothing is "wrong" with you The real reason traditional retirement advice skips the emotional work Practical ways to move through frustration and doubt toward purpose and joy Why rebuilding your identity takes time, curiosity, and compassion Challenge of the Week 👉 Draw your own Retirement Reinvention Curve. Sketch a simple line from left to right — no artistic skills required. Then mark: Where you've been Where you are now Where you want to go next Write one sentence for each stage you've experienced: "What did it feel like? What did it teach me?" Then ask: "What does my next phase need from me?" Because awareness is the first step to reinvention. Resources & Mentions The Retirement Reinvention Curve — My framework for navigating the emotional journey after work. Next Episode Coming up in Episode 10: Modern Software, Ancient Hardware Why your brain wasn't built for retirement, and how to trick it into thriving in a world without structure, deadlines, or dopamine hits from work.

Tax. Death. Legacy. Three words that make most people squirm, but avoiding them doesn't make them go away. In this unapologetically bold and surprisingly uplifting episode, I turn the "taboo trifecta" into a conversation about freedom, meaning, and going out with style. You'll learn how to make tax and inheritance planning feel less like a funeral march and more like an encore. Because facing the end isn't morbid, it's empowering. And when you deal with your legacy intentionally, you stop hoarding, start living, and find your encore energy. What You'll Learn Why avoiding tax and death planning just creates chaos for the people you love Smart, simple ways to reduce tax without making life smaller Why trying to pay zero tax can actually limit your freedom The five essentials of facing mortality like a grown-up (and a rockstar) Why legacy is about memories, not just money How to turn your final chapter into something worth celebrating Challenge of the Week 👉 Complete one "Rock 'n' Roll Legacy Task." Pick one: Update your will Create or add to your Death File (accounts, wishes, passwords, etc.) Book a review of your tax and inheritance plan Write a letter to your future heirs Plan a Memory Dividend event — a trip, gathering, or moment you'll fund with joy You don't have to finish everything. Just start.  Because the ultimate act of love isn't what you leave behind, it's the clarity you leave people with. Resources & Mentions The Death File — Dan's "love on paper" concept for legacy admin Memory Dividends — Inspired by Bill Perkins' Die With Zero Next Episode Coming up in Episode 9: The Retirement Reinvention Curve: The Emotional Sh*tstorm You Didn't See Coming We'll unpack the real emotional rollercoaster of retirement, from the initial high to the inevitable dip, and explore how to rebuild and reignite your sense of purpose, identity, and joy.

Most people treat retirement planning like an Olympic sport, building spreadsheets, forecasting returns, and trying to engineer certainty in a world that's anything but certain. But here's the truth: no plan survives contact with real life. In this episode, I unpack why traditional retirement plans often do more harm than good,  creating false security, stifling adaptability, and ignoring the human side of money. You'll learn why the best retirement plan isn't a fixed prediction, but a living process that evolves with you. Because the plan isn't the point... You are. What You'll Learn Why most traditional retirement plans fail (and how they create false security) The difference between planning and plans, and why adaptability wins every time The 5 elements of a Living Plan that actually work in the real world How to balance numbers with meaning and flexibility with confidence The question every retiree should ask: "Is my plan protecting me, or preventing me from living?" Challenge of the Week 👉 Audit your plan — or your mindset about planning. Ask yourself: Is my plan giving me clarity, confidence, and control, or just false certainty? Where am I clinging to a version of the future that no longer fits? What's one thing I could loosen, update, or rethink to make my plan feel more alive and aligned with who I am today? You don't need to tear it up. Just tune it up, so it becomes a compass, not a cage. Resources & Mentions Quote: James Clear — "You don't rise to the level of your goals. You fall to the level of your systems." The Living Plan Framework: values-led, flexible, regularly refreshed, guardrails-based, emotionally supportive Next Episode Coming up in Episode 8: Tax, Death, and Rock 'n' Roll Yes, we're going there. I dive into tax planning, inheritance, and legacy design… but without the doom and gloom. Expect honesty, humour, and a fresh take on how to make your final chapter feel meaningful... not morbid.

Most retirees believe the key to a successful income strategy lies in the products — specifically, the right pension wrapper, withdrawal rate, or investment mix. But here's the truth: it's not about products at all. It's about permission. In this episode, I challenge the obsession with spreadsheets and simulations, revealing why confidence to spend doesn't come from perfect plans — it comes from understanding, repetition, and emotional safety. You'll discover the Permission Pyramid, the secret behind guardrails-based freedom, and why your financial plan should feel like permission to live, not a restriction on joy. What You'll Learn Why most retirees don't need better products — they need better permission The myth that spreadsheets create confidence The three levels of the Permission Pyramid: Numbers Clarity, Emotional Confidence, Behavioural Permission How guardrails create freedom (not restriction) in your income strategy The real role of a retirement plan — to give you permission to live well Three key questions to help you feel confident spending your income Challenge of the Week 👉 Write your own Retirement Spending Permission Slip. Literally. Write it down and make it visible. "I, [your name], give myself permission to spend money in retirement that: aligns with my values fits within my plan creates joy, meaning, and memories honours the work I did to earn it and supports the life I want now — not just a future I might never meet." Stick it on the fridge. Make it your phone background. Repeat it until it feels real. Resources & Mentions The Permission Pyramid — My 3-level model for income confidence Guardrails-Based Spending — freedom within boundaries Next Episode Coming up in Episode 7: Your Retirement Plan Is a Lie (But You Still Need One) We'll explore why traditional financial plans often give false security, what happens when life refuses to behave, and how to design a living, breathing plan that adapts as you do.

You've worked hard. Saved smart. Invested wisely. You've built a life where money is no longer the problem. But here's the awkward truth: spending it freely, without guilt, hesitation, or second-guessing, is the part no one prepared you for. In this episode, I unpack why so many retirees struggle to permit themselves to spend, where that scarcity mindset comes from, and how to start using money to create joy, connection, and memory dividends. Saving was your superpower. Spending is your next skill. What You'll Learn Why spending in retirement isn't a maths problem, it's a psychological one The "permission gap" and why most retirees hesitate to enjoy what they've saved How money guilt shows up (and why you're not alone in feeling it) The hidden costs of under-spending... memories, experiences, and lost joy What "good spending" really looks like: values, memory dividends, and well-being Practical tools, from guardrails to pre-spending permission slips, to help you spend with confidence Challenge of the Week 👉 Plan one guilt-free spend, and do it. Not research it. Not think about it. Not ask five friends if it's sensible. Just spend. Choose something that creates a memory, feels indulgent, and is true to you. Then, when that little voice says, "Should I really?" — answer, "Yes. Future Me will thank me." Resources & Mentions Schroders UK Retirement Study (2022): On retirees struggling to spend freely Bill Perkins, Die With Zero — The principle of converting money into meaningful life experiences Retirement planning tools like Guardrails, Bucket Planning, and Spending Statements Next Episode Coming up in Episode 6: Retirement Income Isn't About Products — It's About Permission We'll explore why true confidence to spend comes from psychology, not portfolio returns, and how your retirement income strategy should feel like freedom, not fear.