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The Humans vs Retirement Podcast

Dan Haylett
The Humans vs Retirement Podcast
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5 of 97
  • S6 Ep 96 - Why Your Brain Isn't Built for Retirement: Modern Software, Ancient Hardware!
    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.
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  • The Emotional Whirlwind of Retirement (and How to Survive It)
    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.
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  • S6 Ep 94 - Tax, Death and Rock 'n' Roll
    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.
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  • S6 Ep 93 - Your Retirement Plan is a Lie (But You Still Need One)
    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.
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  • S6 Ep 92 - Retirement Income Isn't About Products... It's About Permission
    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.
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About The Humans vs Retirement Podcast

Humans vs Retirement is the podcast that proves retirement isn't just about money, it's about life. Hosted by me Dan Haylett, I dive into the real, human side of retirement: the emotions, the mindset shifts, and the messy, wonderful journey of reinventing yourself for the next chapter. Through honest conversations with experts and inspiring stories from retirees themselves, you'll get the tools, ideas, and encouragement you need to retire to something, not just from something. If you want to make your second half even better than your first, hit subscribe and join the Humans vs Retirement community.
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