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Most of us think of questions as something we ask other people. Dr. Marilee Adams has spent years showing the opposite: the most consequential questions we ask are the ones we ask ourselves. Adams, founder of the Inquiry Institute and author of the half-million-copy bestseller Change Your Questions, Change Your Life, (a new 5th edition has just been published) joins us to make us smarter about our internal questioning. She introduces us to two mindsets that live inside all of us — Judger and Lea...
What’s in your backyard that you haven’t explored yet? And what if you decided to treat your own state like a foreign country? Beth Sobiloff and Marcia Rothwell, the co-hosts of Two Grannies on the Road , have set out to visit all 351 cities and towns in Massachusetts. They’re 121 towns in. Along the way, they’ve met second-act bakers, retired leaders turned magicians, mayors, alpaca farmers, and a man with the world’s largest collection of Back to the Future memorabilia. In this conversation, B...
There’s a challenge that comes with being known for what you do. When you move on you now have to figure out who you truly are. Deborah Santana spent more than three decades inside one of the most recognizable partnerships in American music as COO of the New Santana Band, co-architect of the Milagro Foundation, and the steady, contemplative presence behind a global touring life with her ex-husband, the legendary musician Carlos Santana. At an age when most people are quietly winding down, she di...
Most of us were trained to win at the game of life, deliver the results and get the promotion. Then one day, we arrive at retirement and discover that the game we were trained for isn’t the one that actually produces a flourishing life. New York Times best-selling author Daniel Coyle , joins us to discuss his new book Flourish: The Art of Building Meaning, Joy, and Fulfillment . He unpacks what five years of studying thriving communities (a Michigan deli, a major league baseball team, and a Verm...
Registration for the September Designing Your New Life in Retirement is now open ________________________ Caregiving is one of the most common, and least discussed, forces that can completely reshape retirement. If you’re in your 50s or 60s, there’s a good chance you’ll either be a caregiver, or already are one. And yet, most people haven’t had the conversations, made the plans, or even considered what happens when a parent needs significant care. What starts as helping out… can quickly turn int...
Part Two is a solo conversation with Richard Eyre about the most personal project of his grandparenting work: the body of distilled life wisdom he has spent years developing for his 34 grandchildren — now published in the second half of The Grandparenting Blueprint . This conversation moves from the framework to the practice of how to translate a lifetime of learning into something children can actually carry with them. ( Part One is here ). This second part of the conversation opens with Richar...
Part Two is here What does it mean to grandparent on purpose? For Richard and Linda Eyre, the answer has been decades in the making. The bestselling authors of Teaching Your Children Values have evolved with their family, from nine children to 34 grandchildren, and along the way have developed a philosophy of proactive grandparenting that mirrors what good leadership looks like at any stage of life. In this 1st of 2 conversations about Richard Eyre’s new book, The Grandparenting Blueprint: How t...
The wellness industry has a problem, and Ezekiel Emanuel is one of the few people willing to call it out. In his new book, Eat Your Ice Cream: A Contrarian’s Guide to Living Longer, Healthier, and Happier , the bioethicist, oncologist, and former White House health advisor challenges both the influencers selling unproven supplements and the culture of wellness-as-self-punishment. In this episode, Emanuel makes a compelling research-backed case that the single most powerful determinant of health,...
What if cognitive decline in your 60s, 70s, and 80s is not inevitable — but largely a function of choices you’re making right now? What can you do to stay sharp in retirement? Dr. Majid Fotuhi is a neurologist, who teaches at Johns Hopkins University, and the author of The Invincible Brain: The Clinically Proven Plan to Age-Proof Your Brain and Stay Sharp for Life . He has spent decades studying the most malleable structure in the human brain, the hippocampus, and what he’s found challenges almo...
Retirement triggers one of the most profound re-evaluations many people will ever face. A career ends. Structure disappears. Identity shifts. And suddenly a question that could be put off — What do I really want out of life? — becomes more urgent and unavoidable. Valerie Tiberius has spent her career building a useful framework for exactly that question. Her insights offer you something much more valuable than advice on life from your Financial Advisor – a way of thinking about your values, goal...
Friendship is one of the most powerful forces shaping our lives—and our health. Friendships become harder to maintain as life evolves, especially during major transitions like retirement. Losing work friends is normal, yet few realize how new connections can be cultivated. Our guest today highlights why identity shifts can, perhaps counterintuitively, create oppotunities to build new friendships. My guest today is Janice McCabe , is a sociologist at Dartmouth and author of Making, Keeping, and L...
________________________ Get started in April on your most important project. Learn more here _________________________ Retirement planning focuses heavily on finances — investments, Social Security, and risks. But there’s another question that often sneaks up on people once the career chapter closes: Do I still matter? Our guest today has spent years researching one of the most powerful psychological needs we have as human beings — the need to feel valued and to add value. Jennifer Breheny Wall...
Discern what you’ll retire to. Join our group program starting in April. Learn more here _________________________ What if the secret to happiness isn’t success or achievement — but simply feeling loved? In this episode, one of the world’s top researchers on happiness and well-being Sonja Lyubomirsky explains why connection, curiosity, and listening may be the most powerful ingredients for a fulfilling life — and a meaningful retirement. Her new book, co-authored with relationship scientist Dr. ...
What’s next? Don’t drift. Design. Our next small group coaching program starts in April. Learn more here . ________________________ Most retirement planning conversations start and end with money. Rod Yancy, founder of Oath Planning, challenges that assumption head-on — arguing that mindset, emotional health, and identity matter more than any portfolio balance when it comes to actually thriving in retirement. In this conversation, Rod shares data from Oath’s latest client survey, their Q1 2026 M...
What’s next? Don’t drift. Design. Our next small group coaching program starts in April. Learn more here . _________________________ Who are you when you’re no longer your title? For many high-performing professionals, that question can feel destabilizing — even frightening. Michael Kay is a CFP, a financial life planner, the author of the new book How To Craft Your Chapter X: A Guide For High-Performing Men to Discover Meaning (and Joy) In Retirement . He’s been through it himself—the excitemen...
What if the biggest risk in retirement isn’t the market — but misunderstanding your own goals? As you approach retirement, the questions shift. It’s no longer just “How much have I saved?” It becomes, “When do I want the freedom to retire?” “How much risk do I really need to take?” And perhaps most importantly — “What is my money for?” Today, I’m joined by financial planner Zach Morris for a candid conversation about risk tolerance versus risk capacity, sequence of return risk, working one more ...
Don’t drift into retirement. Design yours. Learn more about our next small group coaching program starting in September here . Sign up here . Very Early Registration Discount ends on June 21st. _______________________ What happens when you finally get everything you worked for…and realize something is missing? In this powerful and deeply honest conversation, Darrow Kirkpatrick shares what early retirement can really feel like — beyond the spreadsheets and freedom headlines. After leaving his sof...
Will you retire with purpose? Don’t leave it to chance. Design Your New Life after you leave full-time work. Learn more about our next small group coaching program starting in September- and sign up here . __________________________ What if the word retirement is setting us up for the wrong life? After years in senior leadership roles, Cesar Aguirre discovered something most of us miss about retirement: the word itself matters more than we think. In English, we “retire” – we withdraw. In Portugu...
Sign up for our next Designing Your Life small group coaching program starting in September here __________________________ What happens when you’ve done everything “right” — built a successful career, made a difference, checked the boxes — and yet something still is missing? Today I’m joined by Dave Evans, co-author of How to Live a Meaningful Life: Using Design Thinking to Unlock Purpose, Joy, and Flow Every Day and the #1 New York Times Bestseller Designing Your Life, and a longtime Stanford ...
What if creativity works like medicine? New research shows that regular engagement with the arts can slow biological aging, protect the brain, reduce stress, and promote a new sense of purpose, identity and meaning—especially in retirement. This episode reframes art as one of the most powerful, underused tools for healthy aging. Our guest today, Dr. Daisy Fancourt, is a leading researcher on the health impacts of arts engagement and the author of the new book Art Cure:The Science of How the Arts...
Monique Rhodes discusses how to navigate challenging life transitions, particularly retirement, by embracing mindfulness and understanding that happiness is an internal job. She shares practical strategies for getting unstuck, rediscovering purpose, and managing the emotional shifts that come with change, emphasizing self-compassion and overcoming the fear of the unknown. The episode also explores how Type A personalities can benefit from mindfulness and the importance of allowing oneself to receive support.
This episode features Anna Rappaport, an actuary and expert, who explores phased retirement not as an HR policy but as a holistic life strategy. She introduces her "Life Portfolio" framework, highlighting the critical importance of Health, People, Pursuits, and Places alongside financial security. Rappaport also discusses the "Reboot, Rewire, Retire" concept for redefining life after full-time work, examining the benefits for both employees and employers, and practical steps for navigating this transition to a more fulfilling later life.
Don’t just retire. Design. Join us in our group program. Two new groups starting in September. Don’t put off planning for your life in retirement. Take the first step today. _________________________ What does it truly mean to age well in a world where longevity is increasing, but health spans vary wildly? In this episode, we meet with Dr. Arnold Gilberg, author of The Myth of Aging: A Prescription for Emotional and Physical Well-Being . Dr. Gilberg challenges the traditional definition of retir...
Financial planner Dan Haylett discusses the paradox of retirement, where financial independence often masks deeper psychological challenges like loss of identity and structure. He introduces five human pillars for well-being—purpose, identity, relationships, structure, and health—and offers guidance on building new rhythms, redefining self-worth beyond work, and navigating couple dynamics. The episode reframes retirement as a vital transition requiring intentional planning for a fulfilling life.
This "Best of 2025" episode offers a rich collection of wisdom for designing a fulfilling life after work. Experts share advice on navigating emotional transitions, embracing freedom, fostering a growth mindset, and building mindful habits. The discussion also covers the importance of intergenerational relationships, holistic preparation using the SHELF framework, finding liberation in minimalism, understanding our intrinsic drive for growth, and prioritizing what truly matters based on end-of-life reflections.
What if the most creative chapter of your life hasn’t happened yet? Today’s conversation is about second acts that arrive not quietly—but boldly. Kim Gottlieb-Walker published her debut novel at age 78 after a 50-year career as a photographer. She also leads the Vintage Writers, a lively weekly Zoom group of women authors over 70. Joining her is Roselyn Teukolsky, a former math and computer science educator who retired and now writes fiction. This conversation explores creative courage, identity...
Start the new year right with new habits. FREE 3 session program – 3 Fridays in January at Noon Eastern. Sign up here . __________________________ Are you ready to graduate from the grind? Then here’s your most important project: Future You. Learn more . ______________________ You’ve spent decades building a career, mastering a craft, and maybe even raising a family. But what happens when the ‘work’ stops? Do you stop creating? Or do you finally have the freedom to chase the ideas that used to v...
“You are what you repeatedly do.” Start the New Year strong. Join my FREE 3 session Tiny Habits program. Register here _________________________ What’s your most important project in 2026? Future You. Don’t wing it. Design it. Learn more here . _________________________ What happens when a financial columnist and CFP® professional suddenly becomes her mother’s caregiver? Beth Pinsker discovered that her expertise couldn’t prepare her for the relentless tenacity required to navigate Medicare maze...
Don’t retire. Redesign . Join our small group program beginning in January. Learn more . ___________________________ Will your retirement life look like the glossy images you see in the brochures? Wise up. There’s a real transition that happens when the paychecks stop and you move into your new life. But here’s the thing: it presents an opportunity for rewarding personal growth, or even transformation, that may not be apparent to you at first. Tom Marks spent decades defining himself by his prof...
Two New Designing Your Life groups kicking off in January 2026 is coming soon. Is It Time to Design What’s Next? . Learn more and sign up today Early registration discount ends 12/15 “Now I know what I’m retiring to.” _________________________ What if everything you’ve been chasing in your full-time working years—the promotion, the bigger paycheck—hasn’t been leading you toward the life you really want? Today’s guest, Jon Rosemberg, knows this tension firsthand. After 25 years of climbing the co...
