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.

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.

Retirement isn’t about how much time you have; it’s about how much time you feel. In this episode, I dive into one of the most misunderstood aspects of life after work: time perception. From brain science to everyday challenges, I uncover why retirement can sometimes feel like a blur and how you can make the most of your time, stretch it, and truly enrich it. What You’ll Learn Why your brain experiences time differently once work ends The science of time compression (and why some days vanish while others feel full) How “Memory Dividends” can transform your retirement years The three biggest retirement time traps, and how to avoid them Why time isn’t linear but psychological, and how that changes everything How to redefine what “a good use of time” really means in retirement Challenge of the Week 👉 Design your Ideal Day Grab a notepad (or open Notes on your phone) Write out your perfect Tuesday in retirement: when you wake, who you’re with, what you do, what you eat, where you are Then bring one small part of that ideal day into your life this week Resources & Mentions Dr. David Eagleman – Neuroscientist and author on time perception Bill Perkins, Die With Zero – Explore the idea of “Memory Dividends” Previous episodes of Humans vs Retirement on purpose, identity, and designing life after work Next Episode Stay tuned for Episode 5: The Skill No One Taught You — Spending Money. I’ll explore why retirees struggle to permit themselves to spend, how scarcity creeps in even when you have “enough,” and what it takes to break free and truly enjoy your wealth.

Most people retire with a solid income plan but no plan for a life they actually want to live. In this episode, I discuss the five human pillars that make retirement feel meaningful, not just financially viable: Purpose, Identity, Relationships, Structure, and Well-being. Expect punchy stories, research-backed insights, and practical prompts to start building a life worth funding. What you’ll learn Why money ≠ meaning in retirement, and how outcomes beat incomes. The Five Pillars framework (Purpose, Identity, Relationships, Structure, Well-being) and how each one stabilises your next chapter. The hidden risk of identity loss after the job title disappears, and two better questions to ask yourself now. Why too much unstructured time can feel like freedom that turns to fog, and simple ways to add rhythm without losing flexibility. The science bits (in plain English): Only 27% of retirees report feeling very fulfilled day-to-day (Stanford Center on Longevity). A strong sense of purpose links to a 15% lower risk of death (JAMA Psychiatry). The Harvard Adult Development Study shows close relationships are the biggest predictor of long-term happiness. 1 in 4 experience mild to moderate depression post-retirement—often due to lost meaning, routine, and social contact (NHS). Challenge of the Week Score yourself 1–10 on each pillar: Purpose, Identity, Relationships, Structure, Well-being. Pick the lowest score and do one tiny action this week to move it up by one point (e.g., book coffee with a friend, start a 15-minute morning walk, schedule a creative hour, message someone to mentor). Small moves → big momentum. Resources & links Mentioned research (as cited in the episode): Stanford Center on Longevity — fulfilment in retirement JAMA Psychiatry (2020) — purpose & mortality risk Harvard Study of Adult Development — relationships & happiness NHS guidance/statistics — mental health in later life Want more? Connect with me on LinkedIn and share your Challenge of the Week answers. Buy my book The Retirement You Didn't See Coming Book a time for us to chat about your retirement plans Next episode “The Skill No One Taught You: Spending Money.” We’ll get into guilt, scarcity, freedom, joy, and why many retirees have more than enough yet still struggle to spend with confidence.

In this episode of The Humans vs. Retirement Podcast, I delve into one of the most disorienting aspects of life after work: identity. For decades, we’ve answered the question “Who are you?” with a job title. Director. Manager. Teacher. Lawyer. And then retirement hits — and suddenly, the title is gone. What’s left is often a quiet identity crisis no one warned us about. This episode, The Past Built You. Your Future Needs You explores why losing a role feels like losing yourself and how to begin rebuilding an identity that’s deeper, freer, and far more authentic than anything you had before. What You’ll Learn in This Episode Why so many retirees experience role-based identity collapse. The hidden danger of achievement addiction, and why productivity isn’t the same as value. How identity is not fixed, but a story you tell yourself (and why that’s good news). Three powerful shifts to rebuild identity in retirement: From Role → Values From Productivity → Contribution From Legacy → Aliveness Why staying stuck in nostalgia is one of the biggest risks in retirement. How to introduce yourself without your past job title — and why this simple exercise is so transformative. Challenge of the Week 👉 Introduce yourself without using your past job title. Try it out loud. Then create an “I am” list: I am someone who makes people laugh. I am someone who listens deeply. I am someone who’s figuring it out, and that’s okay. This is how identity is rebuilt: one sentence at a time. Resources & Links 📖 Dr. Bruce Feiler — Life Is in the Transitions (on identity as fluid, not fixed). 📚 Research: Journal of Gerontological Psychology (2021) — 50% of retirees feel identity loss within the first 12 months. 👉 Share your “I am” list with me on LinkedIn or in your journal, whichever feels right. 👉 Want more? Connect with me on LinkedIn and share your Challenge of the Week answers. 👉 Buy my book The Retirement You Didn't See Coming 👉 Book a time for us to chat about your retirement plans Next Episode Up next: The Five Pillars of Retirement Well-Being (That No One Told You About) — unpacking purpose, identity, relationships, structure, and well-being, and why most people accidentally neglect all five after they retire.

Welcome back to Humans vs Retirement! Season 6 kicks off with something brand new — no guests, no panels, just me, the mic, and the unfiltered truth about retirement. In this episode, I tackle one of the biggest myths of all: that retirement is the finish line. Spoiler alert — it’s not. Retirement is the starting line of an entirely new chapter, and one that comes with as many emotional and psychological hurdles as financial ones. From the collapse of structure and identity, to the massive gap between our healthspan and lifespan, I explore why retirement isn’t about winding down — it’s about gearing up for your next act. You’ll also get this week’s Challenge of the Week: a practical exercise to help you shift from “retiring from” to “retiring to.” What You’ll Learn in This Episode Why the glossy brochure version of retirement is a dangerous myth. The difference between lifespan and healthspan — and why it matters more than you think. How retirement strips away routine, identity, and purpose (and why no one warns you about it). The 4 phases of retirement (and why most people get stuck in the messy middle). The most important question you can ask yourself before — and after — retiring. A powerful reframe: retirement as a threshold, launchpad, and second mountain. This week’s Challenge of the Week: Write your new job description as CEO of Your Own Life. Resources & Links 📚 Dr. Riley Moynes — The 4 Phases of Retirement (featured in Episode 78). 💡 Bill Perkins (2020) — Die With Zero (on memory dividends). 👉 Want more? Connect with me on LinkedIn and share your Challenge of the Week answers. 👉 Buy my book The Retirement You Didn't See Coming 👉 Book a time for us to chat about your retirement plans Next Episode Up next: Past Built You. Future Needs You — exploring identity collapse in retirement and how to rebuild a stronger, truer self without your job title.

In this deeply insightful and refreshingly honest conversation, I sit down with retirement coach and former financial services executive Toni Petrillo, founder of Retire with Intention. We explore the emotional complexities and personal transformations that often define life after full-time work, diving into the hidden challenges retirees face, particularly around identity, relationships, and what Toni calls the “messy middle.” From evolving partnership dynamics to redefining self-worth and navigating the in-between, this episode offers both practical wisdom and warm reassurance for anyone feeling unsettled in retirement. What You’ll Learn Why a solid financial plan isn’t enough, and what you need instead The concept of “retiring with intention” and how to do it well How relationship dynamics shift after work ends (and how to prepare) The danger of rushing through retirement's “messy middle” Tools and exercises to rediscover identity, purpose, and self Why curiosity and honest self-reflection are underrated retirement superpowers The real reason so many retirees feel lost, even when everything looks great on paper Key Topics Toni’s journey from financial executive to retirement coach Letting go of your business card and your professional identity The new relationship rules for life post-career Setting boundaries with adult children and grandchildren Rebuilding your relationship with yourself in retirement Understanding and embracing the “messy middle” of post-work life Designing a retirement based on your individual AND shared vision The power of pausing, experimenting, and reflecting The underestimated emotional labour of retiring Why permission, especially to feel, pause, and evolve, is everything Resources & Mentions Retire with Intention — Toni Petrillo’s coaching practice Harvard Online Course: Managing Happiness (mentioned by Toni) Statistics on Grey Divorce in the UK  Stay Connected Want more thought-provoking conversations like this one? Subscribe to Humans vs Retirement on Apple, Spotify, or wherever you get your podcasts Visit humansvsretirement.com for tools, downloads, and insights Share this episode with someone who needs to hear it; you might just save them (and their family) from future chaos. Download for free my whitepaper - The Skill of Spending Money in Retirement Connect with me on LinkedIn for more insights and updates. Subscribe to my weekly newsletter - The Retirement Fix Leave us a ⭐⭐⭐⭐⭐ review if this episode helped shift your perspective! It helps spread the word.

In this powerful and entertaining episode, I'm delighted to be joined by podcasting legend Matt Halloran, co-founder of ProudMouth. Together, we explore why podcasting isn't just a tool for business; it’s a deeply human medium that offers purpose, connection, and even legacy in retirement. Whether you're a financial planner looking to build trust with your audience or you're approaching retirement and searching for a creative outlet to share your story, this episode is packed with insight, humour, and encouragement. From storytelling to encore careers, legacy creation to building an ecosystem around your voice, this one goes beyond the mic. What You’ll Learn Why podcasting is the perfect pursuit for your second half of life How telling your story can create a real connection and leave a lasting legacy The simple tools and mindset needed to launch a podcast, even in retirement How podcasting can transform how financial advisers build trust and attract clients Why “giving away your wisdom” isn’t bad business, it’s great business The 4-part formula for powerful content: storytelling, education, entertainment, and call-to-action Key Topics Covered My journey into podcasting and how Matt helped spark it The evolution of podcasting: from radio tapes to legacy libraries Podcasting as therapy, storytelling, and a vehicle for human connection How retirees can use podcasting to reinvent themselves post-career The magic of interviewing clients, friends, and family Building a podcast around your encore career or consultancy Using voice to build trust and deepen client relationships Pitfalls to avoid when starting and how to play the long game Why being proud of your voice is the first step to being heard Resources & Mentions ProudMouth – Matt’s podcasting and marketing company for financial professionals The PodRocket Academy – Free courses to help you launch your podcast Book: Influence by Dr. Robert Cialdini Podcast: Ologies by Alie Ward (Matt’s pick for top-tier podcast hosting) Stay Connected Want more thought-provoking conversations like this one? Subscribe to Humans vs Retirement on Apple, Spotify, or wherever you get your podcasts Visit humansvsretirement.com for tools, downloads, and insights Share this episode with someone who needs to hear it; you might just save them (and their family) from future chaos. Download for free my whitepaper - The Skill of Spending Money in Retirement Connect with me on LinkedIn for more insights and updates. Subscribe to my weekly newsletter - The Retirement Fix Leave us a ⭐⭐⭐⭐⭐ review if this episode helped shift your perspective! It helps spread the word.