Podcasts Archive

On the Road Less Traveled: An Unlikely Journey from the Orphanage to the Boardroom

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Podcast Conversations You May Like

Live Life in Crescendo – Cynthia Covey Haller

How to Live a Values Based Life – Harry Kraemer

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There are many podcasts on retirement, often hosted by financial advisors with their own financial motives, that cover the money side of the street. This podcast is different. You’ll get smarter about the investment decisions you’ll make about the most important asset you’ll have in retirement: your time.

About Retirement Wisdom

I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident.

Schedule a call today to discuss how The Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one – on your own terms.

About Your Podcast Host

Joe Casey is an executive coach who also helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a twenty-six-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking. Today, in addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, which thanks to his guests and loyal listeners, ranks in the top 1 % globally in popularity by Listen Notes, with over 1.6 million downloads. Business Insider has recognized Joe as one of 23 innovative coaches who are making a difference. He’s the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy.

Stop People Pleasing and Find Your Power

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Wise Quotes

On Reviewing Your Interests

“Go back and look at your passions. If you left some passions behind, did you really want to paint or play the piano? Or had you always wanted to find out about France or Belgium or Argentina? Well, the passions you left behind, and now you have to really have the time and the energy to pursue them. One of my passions, as you’ll see in my book, is to help people do better than they thought. And that’s a lifelong passion because no matter what you’re involved in, if you can pursue that, you’ll get a great response. So you have to go back and look at your passion and maybe in an athletic experience. And I do believe this concept of taking time to reflect. I like to take the holidays at the end of the year and sit down and spend time to do a really deep dive and ask questions. Now, passions are not only my interests, my likes, my dislikes, my talents, and also contextual. You may be in a situation where I don’t know how long it’s going to take California to come back, but you can commit yourself to getting involved with the problems there. That could take five years of your life if that’s what excites you.”

On Testing Your Pursuits

“Start writing early as possible, write things down and look at them monitor them. Sit down and write down here’s what I want to do. And then I think every once a year, do a very simple dive, to say that I accomplished it. And every three years, do a real deep dive, maybe I’m on the wrong path. I wouldn’t question every year where I’m at. I mean, it takes you by mind three years to see whether this thing is good enough, but write it down, but also spend time in what I call contextual sense. Think about what the world, where the world is going, like AI or biotech. You don’t have to be really knowledgeable, you just get interested in them. What are the trends in Alzheimer’s? A friend of mine runs it, has been involved in Alzheimer’s. And he’s got a foundation, which he’s now working to solve the problem. But write it down, write it down. Go back to some of the old things you did once. There are a lot of places, or finding another organization that fits something you’re really interested in.”

On Purpose

“Well, finding the new purpose is more difficult. You go through life and your first purpose will be to be financially independent and my second purpose was to have a family that I could support. The third purpose was to be successful in business and so forth. Older people in my mind, you have to reach back and find a purpose that you want. The fourth part of life is community, giving back. It’s pretty easy to find a purpose in giving back. The other purposes are material, and they’re ephemeral by the way, too.”

Retirement Wisdom · Mar 17, 2025 ·

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Will your next phase be your time? If you’re a people-pleaser, or know someone who is, you’ll want to hear from Hailey Magee, author of Stop People Pleasing and Find Your Power. It’s time to set better boundaries, advocate for your needs and priorities and start living the life you’ve imagined.

Hailey Magee joins us from Seattle.

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Bio

Hailey Magee is a certified coach who helps people around the world break the people-pleasing pattern and master the art of self-advocacy. Holding a credential from the International Coaching Federation and certified by Erickson Coaching International, Hailey has worked with over 500 private clients, helping recovering people-pleasers rediscover not only their power and agency, but their pleasure, joy, and sense of wonder. Her debut book, Stop People Pleasing and Find Your Power, was released by Simon & Schuster in 2024.

Hailey’s refreshingly nuanced perspectives on boundary-setting and self-advocacy have captured the attention of millions on social media. Her work has been featured in The New York Times, The Gottman Institute, Business Insider, and Newsweek, and she has facilitated workshops in partnership with WeWork, Women In Music, and a variety of other companies and organizations.

Hailey is dedicated to offering her clients clear, research-supported strategies for change. She resides in Seattle, WA.

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For More on Hailey Magee

The Power of Saying No – Vanessa Patrick, PhD

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Podcast Episodes You May Like

The Joy of Saying No – Natalie Lue

Edit Your Life – Elisabeth Sharp McKetta

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About Retirement Wisdom

I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident.

Schedule a call today to discuss how The Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one – on your own terms.

About Your Podcast Host

Read Talk: The Science of Conversation and the Art of Being Ourselves

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Wise Quotes

On People Pleasing

“It’s really just the act of putting other people first at our own detriment, chronically. So unlike regular generosity, which can feel really great and benefit our relationships, people pleasing tends to be a chronic pattern of behavior that really negatively affects us over time. And the costs are high. First of all, because we’re always centering other people and putting them first, we become really disconnected from ourselves. So we struggle to access our own dreams, our own desires, our own needs, and that can lead to life feeling kind of hollow and one dimensional. On top of that, our emotional health can suffer because we’re often over committed, burned out, resentful and disconnected.”

On Boundaries

“I think of these as the growing pains of strengthening a new muscle of learning how to prioritize ourselves. Like with any new workout, there’s some soreness after. But what we can do is we can find some reasons that might make that guilt or selfish feeling feel a little bit worth it. And for me, the best way to flip the script and really become more confident prioritizing yourself is really just to remember that over commitment and lead to resentment in our relationships and really harm them over time. So if you’re over-committed spending too many hours watching your grandkids, you might begin to resent your kids for asking so often. And if you’re over-committed to a certain volunteer organization, you might slowly begin to resent the people at the organization, because you’re so burnt out and taxed from all your giving. So what I like to remind us is that our boundaries, learning how to prioritize ourselves, are not anti-relationship. They’re pro-relationship because they create the distance at which you can really love and appreciate a person or an organization without resenting them. And I say in my book, research actually shows, which I found this so, so reaffirming, that people who practice healthy selfishness, quote unquote, which basically means those who have a healthy respect for their own needs and health, actually report having more positive relationships and more loving attitudes toward others, because they’re not constantly fatigued and burned out. So this really helps us flip the script.”

On Fear

“…the common thread is there’s fear. I’m doing this because I have to and I’m afraid. And that’s so different from kindness, which is really just, I’m doing this because I want to. I’m doing this because I want to help. And if you’re listening to this and you’re like, I’m still not sure, which one is it? The simplest little question you can ask yourself to discern which one is happening is just ask right now, do my insides match my outsides? Because when we’re being kind, they match our outside, smiling and giving and generosity is matched by an inner sense of just goodwill and contentment. But when we’re people pleasing outside, we’re smiling and happy and giving, but inside we’re shut down or resentful or frustrated or overwhelmed. And so that dissonance is what you want to watch out for.”

Retirement Wisdom · Mar 10, 2025 ·

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We spend a lot of time each day in conversation. What if you could get better at it? Alison Wood Brooks, author of the new book, Talk: The Science of Conversation and the Art of Being Ourselves, shares her research and tips on how to master conversation, become a better listener, navigate difficult discussions – and what makes an effective apology.

Alison Wood Brooks joins us from Massachusetts.

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Bio

Dr. Alison Wood Brooks is the O’Brien Associate Professor of Business Administration and Hellman Faculty Fellow at the Harvard Business School, where she created and teaches a course called TALK. As a behavioral scientist, she is a leading expert on the science of conversation. Her award-winning research has been published in top academic journals and is regularly cited in media outlets such as The New York Times, The Wall Street Journal, Harvard Business Review, and NPR. Her research was referenced in two of the top ten most-viewed TED talks of all time and depicted in Pixar’s Inside Out 2. In 2021, she was named a Best 40 Under 40 Business School Professor by Poets & Quants. “TALK: The Science of Conversation and the Art of Being Ourselves” is her first book.

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For More on Alison Woods Brooks

Our New Social Life – Natalie Kerr & Jaime Kurtz

Workbook

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Podcast Episodes You May Like

Retiring: Creating a Life That Works for You – Teresa Amabile

Big Goals – Caroline Adams Miller

The Ritual Effect – Michael Norton

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What Will Your Next Story Be?

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Wisdom Notes keeps ideas coming your way once a month to help you create it.

Best Books for Retirement

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Wise Quotes

On Boomerasking

“Asking questions is magical. It’s why there’s a whole part of the acronym is about asking. But Boomerasking, which is named after the outgoing and incoming returning arc of a boomerang, is sort of a boundary condition on the power of question asking, because it’s like this. It would be like, I say to you, Joe, have you ever been to Nepal? And you say no, and I’m like, let me tell you about the time I went to Nepal. It’s almost like you’re thinly veiling your egocentrism and sort of self-centeredness, your desire to disclose about yourself. You’re kind of masking it with this insincere question. And you hear it all the time. And what we find in our research is that when I say, have you ever been to Nepal, first of all, that question is so specific, you’re already on high alert. You’re like, oh, God, here comes a story about Nepal. But even if I were to ask you, like, how was your weekend, and then I let you answer, and even if you were excited to answer that, and then I bring it right back to myself immediately without following up on your answer, it makes you feel like I wasn’t interested to begin with. And that’s a really bad feeling. In the end, conversation needs to be sort of ping pongy back and forth, where both people are sharing about themselves, but also feeling affirmed and validated and listened to as we’re playing this ping pong game. And so if you bring it right back to yourself in boomerask, it undermines the healthy ping ponginess of a conversation. Thank you. Follow ups and callbacks do exactly the opposite. So whereas Boomer asks are a villain and you’re doing, you’re bringing it too much back to yourself, which people do all the time. Follow up questions, keep the focus on the other person. So anytime someone gives you this great gift of a disclosure, you share anything about your weekend. Or if I say, have you been to Nepal and you say, no, but I’ve been to Tibet or whatever.If they’re giving you any sort of sharing, some disclosure, some information about their perspective, that is such an amazing gift. That is the greatest gift that humans can really give to each other. And so a follow up question shows, hey, I value the gift you just gave me. I want to hear about your time in Tibet. I want to hear about your weekend. I actually care about your perspective and I want to learn from you. So follow up questions are superheroes.”

On Listening – and Mind Wandering

“The idea of listening seems so simple on its surface. It’s sort of deceptively simple. The human mind, unfortunately, and fortunately, was not built to focus on one person and one idea at a time. Our brains are amazing. And so they were more built to wander, right? They’re we’re constantly drawing connections between adjacent and unrelated ideas. We’re thinking so much, you know, even while I’m talking to you, I might for a fleeting moment, remember, oh, I got to pick up my kid in like an hour and a half, right? That’s not bad, per se, doesn’t mean that I’m a bad listener. But it is bad if I’m pretending to listen to you, and I’m actually thinking about something else. And it means that we aren’t actually exchanging the information that we believe we are exchanging. If we’re constantly pretending to listen to each other, and we’re not actually hearing each other, that will become a problem. You know, if you disclose something important about yourself to me, and I don’t hear it, but I pretend to hear it, that’s not going to go well. So we studied we studied this tendency by having hundreds of people come together and have conversations. And we interrupted them every five minutes. And we said, Okay, were you just listening to your partner? 24% of the time, people self reported that they were not listening to their partner, that their mind was wandering elsewhere. And we suspect that is a pretty massive underestimate because we all know that it’s embarrassing to admit that you weren’t listening. There’s this very high social expectation that you listen attentively. So we suspect that our minds are wandering even more frequently than that, and that’s already a very high number. This isn’t a bad thing. It’s not a criticism about the human mind, but what can be helpful about it is realizing, oh, my mind is wandering a lot of the time, your mind is wandering a lot of the time. What can we do to make sure that we actually are hearing each other, that we’re actually exchanging the information we think we are, that we’re making each other not only feel heard, but making sure that we actually are heard. I want to allow your mind to wander and also have a successful conversation. And so I think that’s a very helpful thought experiment of what can we do? First of all, we can give people more grace, when they don’t hear something, like it’s not because they’re not interested all the time, often it’s because they’re doing, they’re so interested that they’re probably elaborating on something you already said earlier. And being a little bit more direct and overt about admitting when we haven’t heard someone, right? Like, oh, I missed that thing. Did you mean this or this? Can you repeat that? These little repair strategies can be very, very helpful.”

On Difficult Conversations

“So my teaching and research on conversation has been incredibly empowering for me and for anyone who is nervous or conflict averse, because it made me realize that first of all, as we were talking about earlier, whole conversations aren’t hard and bad and scary and hostile. It’s just like little moments. And that’s what we talk about in the book. It’s called, it’s not like difficult conversations. It’s moments of difficulty. And moments of difficulty can crop up even in conversations that are supposed to be fun, right? Like you think about gathering with your family at Thanksgiving or going out on a date or having a gathering with friends. You never know when a little moment of a little rift is going to happen. A little moment of difficulty crops up that was unexpected. And even more sort of troublingly, I worry that we often sort of poke barbs into each other in ways that we never even know that that moment of difficulty has come and gone. That someone that you’re talking to might ruminate about later and you didn’t even know that you said something hurtful. But let’s set that aside. In the moments when you do know that things have gotten difficult, these moments of difficulty can occur for any, for any number of reasons. And in the book, we talk about a model, like layers of the earth. And above the surface, these are the words and gestures that you can see during the conversation. We might simply be using the same word to mean different things, or we might use different words to mean the same thing, or we’re just sort of talking past each other, we misunderstand each other. Those sorts of coordination problems can cause all kinds of moments of difficulty during a conversation. Just below that at the sort of surface of the earth are our emotions. So let’s say you’re feeling really calm, but I’m like stressed out. And I need you to like be there for me more intensely that can cause conflict, or I’m really excited and want to have a good time and you’re feeling sort of sleepy and want to be peaceful. We’re going to have a bit of a emotional clash there. Beneath that are our beliefs. So I believe the truth about something, I believe some data about vaccines, you believe different data about vaccines. We disagree and are we going to confront that and discuss it? Are we going to avoid it? It’s up to us beneath that we have differences in motives.”

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About Retirement Wisdom

I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident.

Schedule a call today to discuss how The Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one – on your own terms.

About Your Podcast Host

Tiny Experiments: How to Live Freely in a Goal-Obsessed World

Retirement Wisdom · Mar 3, 2025 ·

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Can an experimental mindset help you navigate your transition to retirement? Anne-Laure Le Cunff, author of the new book Tiny Experiments, discusses how to become a scientist of your own life and unlock new habits, interests, and behaviors for your next phase of life.

Anne-Laure Le Cunff joins us from Austin.

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Bio

Anne-Laure Le Cunff is the author of Tiny Experiments: How to Live Freely in a Goal-Obsessed World. She’s a neuroscientist, entrepreneur, and writer. A former Google executive, she went back to university to earn a Ph.D. in Psychology & Neuroscience from King’s College London. As the founder of Ness Labs and author of its widely read newsletter, she writes about evidence-based ways for people to make the most of their minds, navigate uncertainty, and practice lifelong learning. Her work has been featured in peer-reviewed academic journals and mainstream publications such as WIRED, Forbes, Rolling Stone, Fortune, Entrepreneur, and more.

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For More on Anne-Laure Le Cunff

Ness Labs

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Best Books for Retirement

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Podcast Episodes You May Like

Tiny Habits Can Lead to Big Changes – BJ Fogg

Design Your Life and Get Unstuck – Dave Evans

Growing Old, Staying Rad – Steven Kotler

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About Retirement Wisdom

I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident.

Schedule a call today to discuss how The Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one – on your own terms.

About Your Podcast Host

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Wise Quotes

On Becoming a Scientist of Your Own Life

“An experimental mindset is one where we have both high ambition and high curiosity. This is really embracing the fact that you need both if you want to grow in life. And if you want to achieve more than what you think is currently possible, if you want to achieve more than what is within the realm of your imagination with what you know today, you need hard work, sure, but you need to keep some doors open for exploration, surprises, serendipity, and those kinds of collaborations that we can’t really plan for. And an experimental mindset is really about becoming the scientist of your own life, treating everything, every challenge and uncertainty in general as an opportunity to experiment and to learn something new.”

On Reframing Retirement

“I think retirement is such an amazing phase in life for experimentation. But unfortunately, because all of a sudden, everything we knew, all of the routines and the ways of working are changed for lots of people overnight, we find ourselves in that liminal space, that space of uncertainty. And so we might tend to have one of those three automatic responses. Because we might experience cynicism, escapism, perfectionism, instead of experimenting. Some of the key benefits of embracing this experimental mindset are really to use this phase to discover new things that you might want to do. To maybe reconnect with things that you were curious about and had to pause or put aside because you focused on your career or on your family or on any other projects. And it’s really considering that time as a time of possibility. All of a sudden, you don’t have someone else deciding what your calendar and schedule is supposed to look like. And you have this newfound freedom, which, yes, comes with a lot of uncertainty. We can also come with a lot of creativity.”

On Tiny Experiments

So tiny experiments, as I described them in my book, are inspired by the scientific method. But you don’t need a lab, you don’t need equipment. You certainly don’t need to apply for funding. You can just run your own tiny experiments by designing your protocol. And I call this protocol a pact because it’s a commitment to curiosity. The way you design a pact is by choosing an action, something you’re curious about, and committing to performing that action for a certain duration. And again, it’s inspired by the scientific method where when you conduct an experiment, you say, these are the number of trials we’re going to conduct, and this is how we’re going to collect data. And to choose on an action, it always starts with, again, with curiosity. So you can use this magic word, maybe. Maybe if I did that thing, I would feel more creative. Maybe if I did that thing, I would be more productive. Maybe if I did that thing, my garden would look better. Maybe if I did that thing, I would meet new friends. And so you start with maybe and you, that’s basically the hypothesis. That’s your hypothesis. And then you say, okay, what is the thing? So let’s say you kind of want to grow your professional network after you’re retired, you want to meet other people who maybe are retired and working on interesting projects and you want to connect with them. So you say, maybe if every Monday I reach out to someone I admire, someone whose work I enjoy on LinkedIn, I send them a message and I do that for six weeks. So that’s your pact. I will reach out to a new person every Monday for six weeks. That’s your data collection. That’s your pact. And the great thing is again, same as scientific experiments is that you withhold judgment until you’re done. A scientist doesn’t stop the experiment in the middle and say, I don’t quite like what I’m seeing here. Let’s stop. No, they collect the data and then the assess it. So you finish this, you send your six messages on LinkedIn over the next six weeks and at the end of the six weeks, you ask yourself, did that work? Was my hypothesis correct? Did that help me grow my professional network? Did I meet interesting people? And do I want to keep going? And if yes, that could even turn into a habit. Thank you. There’s a completely different definition of success and failure when you design experiments.”

Retirement Wisdom · Feb 24, 2025 ·

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Our guest today notes that “retirement is a little bit like life. It’s likely to be different than you think it’s going to be.” David Horton, MD shares the story of his life wife Dee Dee, and carrying on her mission and legacy. He discusses her book, Layer Upon Layer, which he helped complete.

David Horton joins us from Washington State.

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Bio

David Horton, a retired oncologist turned book editor, spent his career driven by a deep passion for science and genuine connection with his patients. After completing his residency, he moved to the Pacific Northwest, where he met his wife, DeeDee. Known for his patient-centered approach grounded in respect, empathy, and the art of deep listening, David founded RadiantCare Oncology, building a practice that aligned with his values as both a doctor and a person. David and DeeDee shared 32 years of love, self-growth, and adventure, creating a steadfast partnership.

Now retired, David is dedicated to honoring DeeDee’s mission by publishing her book, Layer Upon Layer, to continue her message and legacy

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For More on David Horton, MD

Layer Upon Layer book

The Well-Lived Life – Dr. Gladys McGarey

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Best Books on Retirement

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Podcast Episodes You May Like

Ride or Die – Jarie Bolander

On My Way Back to You – Sarah Cart

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About Retirement Wisdom

I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident.

Schedule a call today to discuss how The Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one – on your own terms.

About Your Podcast Host

Joe Casey is an executive coach who also helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a twenty-six-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking. Today, in addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, which thanks to his guests and loyal listeners, ranks in the top 1 % globally in popularity by Listen Notes, with over 1.5 million downloads. Business Insider has recognized Joe as one of 23 innovative coaches who are making a difference. He’s the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy.