Michael F. Kay spent decades as a CPA and financial professional before transitioning into life coaching focused on the emotional and identity side of retirement. In this conversation, he explains the origin of “Chapter X” (solve for X) and why many high-performing men reach retirement without a clear picture of what comes next.  

Together, Jacquie and Michael unpack the universal fears that show up in retirement—relevance, vitality, identity—and why the solution is never one-size-fits-all. Michael shares practical ways to reclaim curiosity, experiment without pressure, and let go of ego-driven competition that no longer serves you.  They also talk about the value of remembering past transitions (your first day at work, your first promotion) as proof you already have the tools to navigate change. Michael describes exercises from his book—including writing a multi-perspective eulogy—to clarify values and live intentionally now. The episode closes with a powerful reminder: retirement is your chance to curate your days around meaning and joy, not “shoulds,” deadlines, or status.  

Key topics discussed 

 * Michael’s path: musician → CPA → financial life planner → life coach 
 * Why retirement questions start with: “What does that mean to you?” • The origin of “Chapter X” and the idea of “solve for X” 
 * What “X” really is: what gets you out of bed, meaning, purpose, curiosity 
 * Why high-performing men often struggle more with the transition 
 * Identity beyond the job title: “Who are you when you’re no longer your job?” 
 * The danger of “waiting to die” and the sadness of purposeless later years 
 * Depression in seniors and the pull of living in the past 
 * Retirement as a new transition: reclaiming a beginner’s mind 
 * No one dies from being uncomfortable: normalizing transition anxiety 
 * Unlearning: ego, competition, ladder-climbing, and “should” 
 * Go-go / slow-go / no-go stages and using vitality wisely 
 * Contribution doesn’t have to be big: small acts that lift others
 *  Joy as a filter: if it isn’t joyful, don’t do it 
 * Curating your day: energy, sleep, priorities, and flexibility 
 * The book’s process: progressive exercises + expert chapters (gerontology, psychology, exercise, couples) 
 * The eulogy exercise: clarifying values and living them now  

Action steps: 

 1. Define your X: Write down what you want to get out of bed for in this season of life. 
 2. Try a beginner’s mind experiment: Pick one new activity and commit to 3 tries—no pressure to “be good.” 
 3. Audit your “shoulds”: List the things you do out of obligation; cross out one this week. 
 4. Recall a past transition: Write about your first day at your first real job—what did you learn about adapting? 
 5. Create a 2–3 item day: Put only 2–3 priorities on your calendar, leaving space for joy.  

Connect with Michael:  https://michaelfkay.com

Grab Michael's book on Amazon [https://www.amazon.com/stores/Michael-F-Kay/author/B00EYNSE6Q?ref=sr_ntt_srch_lnk_1&qid=1768959132&sr=1-1&shoppingPortalEnabled=true&ccs_id=973a263c-face-4029-9197-9eca2ba9baad]

Solve for X: Finding Purpose and Joy After a High-Performing Career - with Michael Kay

In this solo follow-up, Jacquie reflects on her conversation with Jermaine Ee (founder of HeirLight) from Episode 294. She distills Jermaine’s wisdom on living intentionally, defining “enough,” and designing ordinary days that feel truly meaningful. Listeners get practical prompts and small experiments to bring more clarity, gratitude, and purpose into their daily retirement life.

Why this matters

Retirement isn’t just about filling a calendar—it’s about creating days that genuinely satisfy. Jacquie explores how to step out of comparison, focus on what matters, and design a “perfect average day” that brings joy, not just busyness.

What we covered

 * The power of asking: “What would I do every day if money and recognition didn’t matter?”
 * Living with clarity: identifying what truly matters now
 * Defining “enough” and escaping the comparison trap
 * Jermaine’s “tiny list” strategy for whose opinions matter
 * Designing your “perfect average day” (and why it’s more important than big dreams)
 * Meaning vs. busyness: how to choose fulfillment over a packed schedule
 * Legacy, conversations, and not waiting for the “perfect” moment
 * Bonus tips: new communities, prioritizing health, staying curious, capturing memories

Key takeaways

 * Clarity is love in practical form.
 * Comparison is the thief of joy.
 * Designing small, meaningful days matters more than chasing big achievements.
 * Don’t wait to have important conversations or experiences.
 * Retirement is richer when you choose relationships, activities, and routines that energize you.

READY TO RAMP UP YOUR RETIREMENT JOURNEY?

Have a chat with Jacquie: https://calendly.com/jacquiedoucette/discovery

New to Beyond Retirement? Start Here: https://beyondretirement.ca/start-here/

Check out the Beyond Retirement Library: https://placeforbooks.com/

Intentional Living, Clarity, and the Perfect Average Day

What if the goal of retirement isn’t just “more free time”… but a life you’re not trying to escape from?  

Jermaine Ee is a storyteller based in Los Angeles and the founder of HeirLight, a fast, modern, emotionally intelligent way to create a legally binding will, health care directive, and durable power of attorney.  

In this episode, Jermaine talks about the pressure to postpone life for a promised future—and how clarity often arrives quickly once avoidance ends. You’ll hear Jermaine’s perspective on defining what is enough (and whose voices shape that definition), why the best days aren’t always the big adventures, and how one conversation with his mom led to a dream trip that changed everything.  We also touch on estate planning in a refreshingly human way: not as a fear-based task, but as a way to reduce confusion, protect dignity, and care for the people you love.  

Key Topics: 

 * Why so many people trade their present for a promised future 
 * How culture shapes our definition of “enough” 
 * Living for the weekend vs. designing a good Tuesday 
 * The “small paper” exercise: whose opinions actually matter 
 * Choosing relationships that add energy (and reducing time with draining ones) 
 * Busy vs. meaningful: saying no more often 
 * A powerful reminder: ask your parents about their dreams 
 * Estate planning as clarity (not fear): will, health care directive, power of attorney  

Thoughts to ponder 

 * Whose voices are shaping your definition of “enough” right now? 
 * What’s one thing you could do on a random Tuesday that would make it a good day? 
 * What conversation are you avoiding that would bring clarity to your family? 
 * If you asked your parents (or kids) about their dreams today, what might you learn?  

Action steps (try this in 7 days) 

 1. Design your “good Tuesday.” Write down 3 small things that would make an ordinary day feel like a win. 
 2. Do the small-paper exercise. List the 5–7 people whose opinions truly matter—and stop outsourcing your self-worth to everyone else. 
 3. Start one clarity conversation. Pick one topic you’ve been avoiding (health wishes, finances, family expectations, legacy) and take the first step.  

Connect with Jermaine:  

 * HeirLight: https://heirlight.com [https://heirlight.com/] 
 * Jermaine: https://eejermaine.com  [https://eejermaine.com/]
 * LinkedIn: https://www.linkedin.com/in/eejermaine

HeirLight is launching in Texas, Florida, Oklahoma, Pennsylvania, and Illinois by March 15, 2026.

For 50% off the HeirLight service, use: www.heirlight.com/en/podcast  [http://www.heirlight.com/en/podcast]



What Is “Enough”? Culture, Comparison, and a Life Well-Designed - with Jermaine Ee

In this solo episode, Jacquie dives into the essential—yet often avoided—topic of long-term care, sparked by key takeaways from her interview with Raymond Lavine. She explores why long-term care planning matters, what can happen when caregiving needs arise unexpectedly, and how listeners can take practical steps now to protect their choices, finances, and family relationships.

Why this matters

Retirement dreams often focus on freedom and independence, but the reality is that many retirees will eventually need some form of care—sometimes suddenly. Planning ahead can mean the difference between empowered choices and stressful crisis management.

What we covered

 * How caregiving needs can disrupt retirement plans—often without warning
 * The hidden ripple effects: finances, family roles, and household dynamics
 * The true cost of care—money, time, energy, and emotional bandwidth
 * Raymond Lavine’s three core planning questions: Where? Who? How?
 * The importance of starting conversations early, before a crisis
 * Organizing vital documents and communicating your wishes
 * Understanding care costs in your area
 * Exploring long-term care insurance and why earlier is better
 * Making your home safer, one simple change at a time
 * Proactive steps for those who can’t or don’t want insurance

Key takeaways

 * Don’t wait for a crisis. Planning ahead preserves dignity, options, and family harmony.
 * Start small. Even simple conversations and small home changes make a difference.
 * Know your options. Research care costs, insurance, and local resources early.
 * Empower your family. Clear documents and communication prevent confusion and conflict.
 * Self-care matters. Healthy habits and a safe home reduce future risks.

READY TO RAMP UP YOUR RETIREMENT JOURNEY?

Have a chat with Jacquie: https://calendly.com/jacquiedoucette/discovery

New to Beyond Retirement? Start Here: https://beyondretirement.ca/start-here/

Check out the Beyond Retirement Library: https://placeforbooks.com/

Planning for the Unexpected: Is Long-term Care on Your Radar?

Retirement is supposed to feel like freedom… until caregiving enters the picture.  

Raymond Lavine is a caregiving planning advocate who helps families prepare for long-term care realities before a crisis hits. He’s the host of the podcast Planning with Purpose: The Caregiver’s Blueprint and co-author of the Amazon bestseller Empathy and Understanding in Business.  

Raymond shares how his parents’ experiences shaped his work, why even affluent families can get squeezed by care costs, and what changes—logistically, emotionally, and financially—when one person needs ongoing support.  You’ll also hear practical ways to reduce stress even if you’re not ready to buy a plan today: decluttering, home modifications, organizing documents, and building habits that make aging at home safer.  

Key Topics: 

 * Why families delay long-term care planning until a crisis 
 * How caregiving reshapes retirement for everyone involved 
 * The hidden logistics: meds, appointments, finances, bathing, transfers, and constant worry 
 * Why “having enough money” still doesn’t mean care won’t disrupt your life 
 * Planning choices: where you want care, who will manage it, and how you’ll pay 
 * Using care support to stay social, travel, and avoid getting “stuck” 
 * What people underestimate most: caregiving is “invisible” until it’s not 
 * Simple stress-reducers: declutter, improve lighting, add grab bars, swap knobs for levers
 * Keep documents and passwords in one place (digital + paper)  

Thoughts to ponder 

 * If caregiving started tomorrow, what would change first in your life? 
 * Who would coordinate care in your family—and do they know that? 
 * What would you want to protect most: dignity, independence, relationships, finances? 
 * What’s one small home change you could make this month to reduce risk?  

Action steps (try this in 7 days) 

1) Answer the “3 Care Questions.”      

 1. Where would I want care?      
 2. Who would manage it?      
 3. How would we pay? 

2) Create a “one place” folder.      

 * Health card/insurance info, key contacts, legal documents, medication list, passwords (securely stored). 

3) Do one safety upgrade.      

 * Add a grab bar, improve lighting, remove a rug, or swap a doorknob for a lever.  

Connect with Raymond: 

Website: https://lavineltcins.com

When Caregiving Changes Retirement: Planning Before the Crisis - with Raymond Lavine

In this solo episode, Jacquie draws inspiration from her conversation with Henry Quinlan—a publisher, memoirist, and passionate advocate for purposeful living in retirement. The episode explores how telling your story, reflecting on life’s turning points, and embracing new “second acts” can help you find meaning, connection, and fulfillment after the traditional working years.

What you’ll hear in this episode

 * Why retirement isn’t just about stopping work, but about moving toward something meaningful
 * The power of memoir and storytelling for self-discovery and legacy
 * How reflecting on your life’s “plot twists” can reveal hidden strengths and new opportunities
 * The value of curiosity, creativity, and staying engaged at any age
 * Practical ways to start writing your story—even if you don’t consider yourself a writer
 * Henry Quinlan’s approach to living with optimism, humor, and purpose in later life

Key takeaways

 * Retirement is a new beginning. It’s a chance to design a life that excites you, not just a time to wind down.
 * Everyone has a story worth telling. Memoir writing can clarify your values, celebrate your journey, and leave a legacy for loved ones.
 * Reflection brings meaning. Looking back at challenges and turning points can help you see how far you’ve come—and what you still want to do.
 * Curiosity keeps you young. Stay open to new interests, skills, and connections, no matter your age or background.
 * You don’t have to be a professional writer. Start with small stories, favorite memories, or lessons learned—what matters is capturing your unique perspective.

Beyond the Finish Line: Memoir, Meaning, and New Beginnings After Work

What really happens after the retirement celebration ends?   

Henry Quinlan is the founder and CEO of Omni Publishing Company and a lifelong publishing professional who found renewed purpose after retirement. He now focuses on helping seniors tell their stories, publish memoirs, and rethink happiness and fulfillment in later life. A Senior Achiever at the MIT AgeLab, Henry also speaks widely on retirement, relationships, and artificial intelligence for seniors.  

In this episode, Henry Quinlan shares decades of insight into why happiness doesn’t automatically arrive with retirement and how meaning, connection, and curiosity shape a fulfilling next chapter.  

Key Topics Covered 

 * The emotional transition into retirement 
 * Why men often struggle more than women after leaving work 
 * Memoir writing as a therapeutic and legacy-building tool 
 * The myth that retirement guarantees happiness 
 * Giving, contribution, and relationships as sources of fulfillment 
 * Artificial intelligence and its impact on seniors and society  

Connect with Henry: https://www.goldenyearslibrary.com/

Happiness is Not Guaranteed in Retirement - with Henry Quinlan

In this solo episode, Jacquie reflects on insights from her conversation with Dr. Denise Taylor and explores a quieter, more sustainable approach to intentional living in retirement. Instead of asking, “What should I do now?”, Jacquie invites listeners to consider, “How do I want to live now?” The episode focuses on creating rhythm (not busyness), choosing curiosity over striving, and finding meaning that isn’t tied to productivity.

What you’ll hear in this episode

 * Why intentional living isn’t always about doing more
 * The shift from “What should I do?” to “How do I want to live?”
 * How many retirees leave the job—but keep the pace, pressure, and identity of work
 * Rhythm vs. routine: listening to your energy instead of living by urgency
 * Why stillness can feel uncomfortable (and why it’s often exactly what we need)
 * Curiosity as a key driver of well-being as we age
 * How “Back in my day…” thinking quietly closes doors—and how to keep them open
 * The identity question that can surface after retirement: “If I’m not that anymore… who am I?”
 * Why meaning doesn’t require output, metrics, or a new label
 * The difference between working longer because it’s joyful vs. working longer as avoidance

Key takeaways

 * Intention starts with rhythm, not goals. Your days don’t need to be packed to be purposeful.
 * Rhythm is energy-aware living. Notice when you feel alert, when you need rest, and when you’re simply done.
 * Curiosity keeps the future open. You don’t have to be good at something to explore it.
 * Meaning isn’t the same as productivity. Presence, listening, and care can be deeply meaningful.
 * Not every season calls for acceleration. Some seasons call for integration, simplification, and rest.

READY TO RAMP UP YOUR RETIREMENT JOURNEY?

Have a chat with Jacquie: https://calendly.com/jacquiedoucette/discovery

New to Beyond Retirement? Start Here: https://beyondretirement.ca/start-here/

Check out the Beyond Retirement Library: https://placeforbooks.com/

Living Intentionally: Choosing Curiosity, Rhythm, and Meaning

What if retirement wasn’t about filling your time — but about choosing how you want to live?  

 Dr. Denise Taylor is a chartered psychologist, later-life specialist, and author whose work focuses on meaning, wellbeing, and identity beyond full-time work. With over four decades of experience blending psychology, research, and lived experience, Denise challenges conventional narratives about retirement and aging.  

 In this conversation, Denise shares why curiosity, slowing down, and letting go of relentless productivity may be the keys to a more meaningful later life — and why it’s okay to choose a quieter, more intentional path.  

Key Topics Covered 

 * The evolution of retirement over time 
 * From physical rest to reinvention and choice 
 * Identity beyond professional titles 
 * Who we are when the job title falls away 
 * Being versus doing 
 * Learning to slow down without guilt 
 * Curiosity as a driver of healthy aging 
 * Staying mentally and emotionally engaged 
 * Conscious aging and alternative narratives 
 * Moving away from relentless striving  

Connect with Denise: 

Website: https://denisetaylor.co.uk/   [https://denisetaylor.co.uk/]

Substack: https://ageingreimagined.substack.com/

Letting Go of Striving in Retirement - with Dr Denise Taylor

In this solo episode, Jacquie reflects on a conversation that lingered long after the microphones were off: Scott Walker's retirement-fueled decision to reunite his college band, The Resisters, with help from Lutefish technology. The episode explores how rekindling old passions can restore connection, identity, and joyand why retirement is less about stopping and more about returning to the parts of ourselves that were always there.

What youll hear in this episode

 * Why Scott's line You can't make new old friends hits so deeply in retirement
 * How distance doesn't have to mean disconnectionand how technology can bridge the gap
 * The idea of a secret identity: the passions we set aside during the busy middle chapter of life
 * A simple reflection prompt: What did you get lost in before adulthood took over?
 * Why structure matters (and why motivation often follows action)
 * How shared purpose builds real connectionand why loneliness isnt solved by staying busy
 * Practical takeaways to help you reconnect with people and passions in your own retirement

Key takeaways

 * Old friendships are a unique kind of wealth. People who knew you before titles and responsibilities can help you reconnect with who you are.
 * Technology is a tool, not a threat. Used intentionally, it can support real human connections across distance.
 * Your early passions are clues. The things you loved before life got busy often point toward what will feel meaningful now.
 * Structure creates momentum. Weekly rituals and commitments make it easier to begin even when you feel rusty.
 * Connection is the reward. The activity may be the excuse, but the deeper outcome is belonging.

READY TO RAMP UP YOUR RETIREMENT JOURNEY?

Have a chat with Jacquie:  https://calendly.com/jacquiedoucette/discovery

New to Beyond Retirement? Start Here: https://beyondretirement.ca/start-here/

Check out the Beyond Retirement Library: https://placeforbooks.com/



Connection & Purpose in Retirement

Jacquie Doucette (@jacquied) · Zencastr

Jacquie Doucette (@jacquied)

What really happens after retirement?

If you’re approaching retirement—or already there—and wondering what now?, you’re not alone. The world is full of financial advice for retirement, but there’s far less about how to actually live a fulfilling life once the 9-to-5 ends.

Beyond Retirement is the podcast that explores what comes after the career chapter. Whether your retirement was planned or unexpected, joyful or jarring, you’ll find real stories, honest conversations, and practical inspiration here.

Join host Jacquie Doucette as she shares her own journey and speaks with people who’ve reimagined life after work—some fully retired, some shifting gears, and all discovering new meaning in this next stage. From finding purpose to building community, embracing play, and navigating change, we’ll explore how to create a life that truly fits.

Because retirement isn’t the end—it’s a new beginning.

Let’s figure out what comes next, together.