167 Jann Freed 167 Jann Freed
Podcast 167

167: Your Breadcrumb Legacy and Sage-ing with Dr. Jann Freed

Today’s guest is Jann Freed. Jann is a leadership development consultant and speaker who helps organizations improve employee engagement, navigate change, and develop leadership skills at all ages and career stages. She specializes in helping employees over the age of 50 find meaning and purpose beyond careers. She uses a concept called the Breadcrumb Legacy, in which people create new meaning for themselves and others, to achieve this. She is the co-author of five books, a professor, blogger, and podcaster, as well as a very active member of her community. Jann joins the podcast to talk about her experiences coaching individuals from leadership into retirement, finding purpose in life as retirees’ full-time careers come to an end, and what she has learned from interviewing hundreds of the world’s foremost leaders on life and business.

In this podcast interview, you’ll learn:

  • How Jann defines leadership.
  • Why leaving a career or a position is not retiring from life – and why people are so bad at planning the phase of life that comes after a career.
  • Why Jann wants to retire the idea of retirement as we know it.
  • Why certain retirees spiral when they overthink the search for purpose and meaning in life – and the simple steps Jann recommends retirees take to sage, not age.

Inspiring Quote

  • “If you are what you do, and you don’t do it anymore, then who are you?” — Jann Freed
  • When you learn how to die, you learn how to live.” — Mitch Albom
  • What’s your reason for getting up in the morning?” — Richard Leider

Interview Resources


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Read Full Transcript


Casey Weade: Jann, welcome to the podcast.

Jan Freed: Thank you, Casey. I’m honored to be here.

Casey Weade: Well, it’s a pleasure to have you here with us. And before we get started, I know we’ve got a Facebook Live audience that’s watching right now. This is going to end up, your video is going to be on our YouTube page as well, in addition to TV, etc. And I don’t think there’s probably a soul out there that’s not wondering why you have a body hanging on your wall.

Jan Freed: Actually, there’s an artist in town, a really well-known kind of ceramicist, and she makes these lifelike little bodies. And so, this one is holding a book. And so, since I’m surrounded by books, I love that little body hanging there.

Casey Weade: Yes. So, is that an expression of your perpetual learning that you’ve done throughout life?

Jan Freed: That’s a good way to look at it. I look at that and I think, okay, it’s time for me to continue reading. That’s true.

Casey Weade: Yeah, well, I love what you’ve done. You’ve continued to grow and learn throughout every stage of your life and where you find yourself today. You continue to learn and grow and I think that’s one of the most powerful things that we can do in our lives, especially as we step into retirement. Quite often, we miss out on that. And on that note, we didn’t reach out to you for this interview, you had reached out to us. What was it that made you want to reach out to me for this interview?

Jan Freed: Well, we have a mutual friend. You were on, I forget what Marianne calls it, Transition to Retirement or her program. And I just feel like my work, and it complements the financial services work. And so, I was very intrigued with your interest in purpose and how it relates with wealth and money. And then I’m here today to share how I see it all going together because I think there’s just a natural link between legacy and money, and we can talk more about that.

Casey Weade: Yeah, well and also leadership. I think your primary role historically has been in leadership development. You’ve got a PhD in leadership development and consulting there. You’ve consulted with many major universities. You’ve consulted with many major firms as well. How does leadership play a role in retirement planning?

Jan Freed: I always say the most important person to lead is yourself. And I had a leadership book come out in 2013 called Leading With Wisdom: Sage Advice From 100 Experts. So, I actually interviewed more than 100 thought leaders in the field of leadership— authors, some of the top executive coaches, Marshall Goldsmith being one, Warren Bennis. I mean, some of these people have now passed on. And what I learned is it’s hard to be a good leader if you’re not a good person. And so, I’m kind of continuing on in that work, but the most important person to lead is yourself. And I also developed a definition of leadership that if you’re in a position to influence the lives of others, then you’re a leader so that includes parents, teachers, coaches, pastors, anyone who’s in that leadership role. Sometimes people don’t see themselves as a leader, but if you’re in a position to influence the lives of others, and that influence can be positive or negative. Well, that’s why we have to kind of think about what influence are we having. So, to me, that just kind of drills it down to a personal level.

Casey Weade: Well, I find that sometimes we have these leadership qualities we don’t know they’re there. They’re hidden within us. But once we find this financial freedom, now we have the ability to leverage all those talents and strengths because we don’t have to worry about gaining any more money. It’s not about the money anymore. We don’t have all these shoulds, you should fill out that TPS report. We have the ability to focus on where we can make the biggest impact. Now you said something there, but I have to drill down deeper into, you said that you can’t be a good leader without being a good person first. So, we have to define, and I’m sure you have your own definition, what makes a good person?

Jan Freed: That’s an excellent question. But I think a good person is someone who, especially in the workplace, creates a healthy environment. But really, again, it goes back to that if you’re in a position to influence the lives of others, that the environment, maybe it’s the home environment, it’s a healthy place where people can thrive and not just survive but kind of thrive which is a lot of it revolves around meaning and purpose again, and I think this is going to become very critical as organizations come back together after COVID-19. So, this whole idea of culture and so, becoming a good person, it really has to do with understanding, I think the power of the ego because oftentimes it’s the ego that ends up causing us many problems.

Casey Weade: Do you find in that realm that you have individuals that have these big egos, and that the best leaders aren’t the ones that think they’re the best leaders. Are they the ones that think, Oh, I’ve got horrible leadership qualities, and that’s what actually makes them such great leaders?

Jan Freed: Yeah, I mean, I would agree more with the first that some people who think they’re really good are not good. And again, humility has a lot to do with being a good leader. So being humble and right now, what we’re seeing is compassion and empathy. Those were actually themes in my book. But now during COVID-19, everyone’s talking about how you need to demonstrate compassion and empathy and forgiveness and really understand pain and loss and healing, and all of those are in my book. I mean, I really think my book is kind of timeless. Actually, it was before all this happened, but those are characteristics that are not necessarily top of list. These are skills that business schools don’t teach. For the most part, they don’t teach them. Now, I do because it’s my passion but most schools don’t teach about how to lead and manage a crisis. And so, that’s why I think all of this is important right now.

Casey Weade: You do a lot of one-on-one coaching and correct me if I’m wrong, but you’ve done a lot of one-on-one coaching with leaders in the corporate world and in their transition, as you’ve coached some of these individuals from leadership positions into retirement, how does leadership show up for them, and retirement?

Jan Freed: That’s a good point. I would say that one of the taglines that I often use is, “If you are what you do, and you don’t do it anymore, then who are you?” And so, I often say that people need to really think about the next phase because we may be leaving a career or a position but we’re not retiring from life. If you just look at the word retire, what does it mean, like retire bonds? It kind of means put away, put on a shelf. The time is expired. Well, we’re not retiring from life.

And so, every other phase of our life, another example I often use is I say, “If you’ve got kids, you don’t plan for where they’re going to go to college, their senior year in high school.” Or even little kids. I’ve got a son in San Francisco and his main mentor, she’s now trying to get her son into preschool, I think it was preschool. No, it was an elementary school. And she went to Stanford for her MBA, and she said it was harder to get her kid into the preschool that she wanted than for her to get into Stanford for an MBA.

My point is, we’re so used to planning every phase of our life but few people put that much thought into the next phase after career. Now it could be an encore career or whatever, but people, they think vacation, they think, I’m going to be golfing every day. That research says that doesn’t fulfill. It may for a while but it’s not about meaning and purpose, golfing every day or sitting on a beach every day. It might be great for a while but it’s not really fulfilling long term.

Casey Weade: If it is true that we define ourselves by who we are as connected to what we do, that makes it feel like we do need to reinvent ourselves as we step into retirement. But there’s differing opinions on that. Is reinvention the right word?

Jan Freed: Well, one of the things that I often say, Casey, is if you really like what you’re doing and you can continue doing it, then there’s no reason to stop. And that’s why some people who’ve been self-employed for a long time and what I mean by that is— writers, artists, people who we think of them in the creative industries— they’re painting forever or they’re writing books forever. No one’s telling them they have to stop.

This whole idea of retirement was created at a time when people didn’t live to be 70. So, the whole idea of retiring at 65 or whatever, 62, that’s just a man-made, person-made created timeline. And now people are living well into their 80s. My father is going to be 95 next month and my mom lived to be 93 and died two years ago. So, again, these are kind of man-made constructs that really don’t make sense anymore. So, I always say, if you can continue doing what you want to do and no one’s going to tell you to stop and you like it, then you keep doing it. If it’s one of these things where you can’t wait until it ends, then it’s really good to think about what’s next. Now what’s next? It could be volunteer, it could be part time, or it could be another encore career.

So, I actually retired, I don’t like that word really, because I’m out to retire retirement. But I retired after 30 years of college teaching so that I could launch my own business. And so, I would say that I’m in an encore career and having a ball because it is about going and learning and growing.

Casey Weade: I’m wondering what it means to define yourself, especially around defining yourself around what you do. How do you define yourself?

Jan Freed: Well, it’s interesting because I do kind of have a personal mission statement, and my mission is I want to continue to learn and share what I’m learning with others. So, for me, it is about learning. And so, I’ve written five books, I’m working on another one now. I have a monthly podcast, I write, I’m going to have a regular column in training magazine. I’ve been writing for them last few years and now I’m going to have a column, and being invited on your podcast and then I invite others on mine and I just had a leadership summit where I interviewed 20 plus leaders— Bill George being one of them, former CEO of Medtronic. And so, again, to me, it is invigorating to just keep learning.

Casey Weade: And I have talked to some of our past guests around the way we define ourselves, and Marianne Oehser talked about your happiness portfolio. And what’s the danger in defining yourself by what you do? You define yourself by the way that you learn. You continue to learn and share that information as life changes. Is there a danger of getting too narrow with the way we define ourselves?

Jan Freed: Well, I think once a person is out of a structured workplace situation, then it’s about really discovery and exploring. So, I tell my clients who are approaching the next phase of life, try things out, you don’t have to like it. If you don’t like it, you stop doing it, but it does give you the freedom and flexibility to try some things out.

Several people get into painting or ceramics or kind of creative photography. And so, that’s one way, it’s a time to kind of follow maybe what you loved when you were younger that you haven’t had time to do. And really, you can learn in many things. We have a friend who was a very successful banker and actually kind of retired early and he’s taking golf lessons because he said, “I always wanted to be a better golfer.”

And so, it doesn’t matter what it is you want to learn, whether it’s a language. I do think that we’re living in interesting times, though, because several of my friends, they’re radiologists, and two of them are in the same firm and they are just now and I mean, just now, like they’re both done this weekend after 40 years of working and high on their list was, really they have the freedom to travel wherever they wanted. Well, who knows what’s happening to the travel industry right now. So, people are having to think about other things for the time being, but I think it’s a time of discovery and exploration. And if something doesn’t work, you don’t have to do it. You can try something else.

Casey Weade: I think that’s the key. We have to continue to try things. We have to get out there and actually just try it. Sometimes we have spent too much time contemplating whether we’re actually going to enjoy it or not. And Dean Niewolny, CEO of the Halftime Institute on previous interview, he called these low-cost probes. You don’t have to commit your entire life to something, just go out and try these things. Now you mentioned passion, purpose, and meaning several times and I sometimes wonder how people define the difference between passion, purpose, meaning. Do each of those mean something different to you? Are they all the same? Is there an order to this?

Jan Freed: That’s an excellent question because sometimes those words are used interchangeably. I’m not going to necessarily answer the question in a sense, but go a different direction. What I find people are struggling with— I don’t have a passion or I feel like I don’t have a purpose. And what I say is, again, sometimes you have to grow into that. It kind of goes what you just said about exploration and discovery and sometimes the purpose or passion, maybe it’s not a big P. I’ve heard people describe it as a little, meaning it could change. Maybe your passion is, let’s just say, helping others. Well, you could help others in lots of different ways. So, I don’t think it has to be so narrow.

One of my role models in this work is Richard Leider and he’s out of Minneapolis. He’s written great books on this whole topic. But he’s really known as the purpose guy, The Power of Purpose, his classic book but I like some of the others just as well. And Richard says, “What’s your reason for getting up in the morning?” I had a client, a very successful lawyer, but because of some serious health issues was having to definitely stop being a lawyer much earlier than he wanted to but needed something to do.

And so, I was talking to him about all these options. And he says, “Well, you know, I don’t want to work,” and I wasn’t really describing work. But all he could think about was work and I was trying to give him options and he said, “I am tired of working,” and I said, “No, you’re going to be doing something. What’s going to get you up in the morning? You’re going to be doing something,” and so I use the definition of work as contribution. To what do you want to contribute? So, it might be, like I said, a volunteer basis, it might be part time, it might be a whole new career but what is going to be your contribution or why bother to get out of that?

Casey Weade: I think we framed it wrong in our minds. We think about work as something, nobody wants to work. Nobody wants to do these things. And we’ve been homeschooling our kids ever since we’ve been confined with COVID. We decided we’re going to do this forever. And one of the ways we’ve framed this is, it’s not homework, it’s fun work. So, the kids have never heard the word homework before but they cannot wait to do their fun work. And that’s kind of like retirement. Right now, it’s your opportunity to do that fun work.

Jan Freed: I like to, actually, this is unrelated but kind of related to what you just said. Years ago, we had a friend and every time his young son wanted ice cream, he would give him kind of cheese. So, he thought that—

Casey Weade: It’s all about framing and maybe that’s one of your biggest values. Can you share with the audience, and I know you help the employees find meaning and purpose beyond their careers, 50 plus, where is your biggest and highest value? What do you think you’ve made the biggest impact in a client’s life?

Jan Freed: I created these workshops and I call them Beyond the Money. Again, that’s why I think what I do and what you do is very complementary because the money part is very important. But once people have enough money, now enough, if defined by them not me, but once you have enough money for your lifestyle, then what else is it you’re going to do with life? And it might be 30 years.

And so, what else are you going to do? And so, I created these workshops called Beyond the Money. And in the workshops, we talk about meaning and purpose, we talk about legacy work. And it’s the legacy part that I think has added the most value because most people don’t think about legacy. So, what I do in workshops, Casey, is I ask people, “When do we leave a legacy?”

And people will say, “Well, when we leave,” and I’ll say, “Okay, well, what do you mean?” “Well, when we leave our career, when we retire, when we leave a position, when we die.” And I say, “Okay, what about when we leave here or when we leave the room, we leave the meeting, we leave the interaction, I’m leaving.”

So, I created this concept called Breadcrumb Legacy, and I’m leaving some bread crumbs with your audience today. So, they’re going to be thinking something about me based on our conversation. And so, I believe that when leaders understand this, when people in general understand this, we live our lives differently. So, for instance, we’re in a traffic jam and we’re on the freeway. If we really thought about what bread crumbs were leaving, we would say, “Oh, you know what, I’m really upset. I’m going to lay on my horn or road rage,” but no, I’m not going to do that because it would not be good.

Again, a current example is— I don’t know if you’ve been reading about how some leaders have been laying off people using Zoom calls— and two leaders in particular and these are well-known companies and people can Google this if they want to find out the details. But two CEOs said, “Well, we intentionally turned off the video because we thought it would be easier to hear the message if it was just audio.”

I mean, again, those are bread crumbs that people will remember. Meanwhile, what’s gone viral is the letter that Brian Chesky, the CEO of Airbnb, he had to lay off people, and the letter that he wrote to all of these employees— and I would encourage your listeners to go Google that, just put Airbnb CEO letter, Brian Chesky.

The letter is full of compassion and empathy and it’s transparent and he talks about the decisions and how they came to the decisions and why they have to make these decisions. Even in the letter has the people who did not get laid off— I forget what he calls it— but they’ve created like an alumni network meaning if you’re still an employee, he wants the current employees to help the employees who are laid off find jobs.

So, he says, “We will do everything we can to help you find another position.” Who’s going to remember? His letter has gone viral. Why is that? Well, it’s because it really resonates because it was very meaningful. And somebody who lays people off using Zoom audio because they don’t want to see faces and expressions.

In fact, I think what else? There was another company I was reading about where they said, “We will only do this one on one. There has to be a one-on-one discussion,” so that you really feel like it’s a more humane approach. So, all of these are bread crumbs. All of these are part of someone’s legacy and how they will be remembered.

Casey Weade: The Breadcrumb Legacy, it reminds me of The Compound Effect by Darren Hardy. Darren Hardy is a longtime mentor of mine and it’s all these little things that ultimately create the legacy but, in our planning, we’re working with a financial advisor. Quite often, we’re talking about legacy is this one big thing that we’re doing at the end of life. We’re just talking about this one point in time that has yet to occur. But in every single moment of every single day, right now, I think this is the most impactful thing that we could share, maybe in our entire conversation is just shifting our mindset. I know I’m already thinking about this, Oh, well, I better be careful. This is my legacy right here, right now.

Jan Freed: Yes, I like that. I’m making a note here. I like that. And the other thing, Casey, is we don’t know when life ends. That’s why we create it all the time. We often think, we’re going to have this long life and all of these things that we’ve done add up. It’s true, they do add up but life could end it— 18 life could end it, 23, 35. So, again, it’s all along the way.

I call it forward thinking because when people really have this, aha, I mean you cannot believe when I do these workshops, I always collect a feedback at the end in terms of an evaluation form. It’s the legacy part that people are like, I never thought of this. A lot of people think it’s just for important, rich. I don’t have the money to leave a legacy.

It’s not about money. It’s really about how you live your life. And because life could end at any time, it’s really important for everyone at every age and I’ve been teaching these concepts to undergraduates, traditionally age undergraduates, 20 to 22-year-olds, and they just eat it up. They just eat it up. In fact, millennials are being called the purpose generation.

Casey Weade: I could see how this could be a little dangerous as well. It’s focusing a little too much on that, Well, this is my legacy. This is my legacy. And lately for me, it has long been purpose. And Brian Portnoy in a past interview, he said, “You know, there’s a lot of danger. We should think about purpose. We should think about meaning. But if we do it too much, too often, they can really put us in a bad place.” And I’ve been one of those people always thinking about purpose and meaning and—

Jan Freed: Tell me more about. What’s the bad place? Let’s talk about that.

Casey Weade: You can feel a little discouraged. I think it’s the same thing with time. With time we go, Oh, well, this moment is gone. That moment is gone. It can be a little depressing if we focus too much on finding our meaning, finding our purpose, or maximizing every single second of every single day. It can be really exhausting.

Jan Freed: I see where you’re going. I was thinking, I had someone asked me in a workshop, “Well, don’t you think it’s self-centered to be thinking about yourself all the time?” And I said, “No. I don’t think it’s self-centered if you’re always trying to be your best person.” If you’re always—

Casey Weade: Are you thinking about yourself, though? When you’re thinking about legacy, isn’t that about somebody else? Or do we have that definition wrong?

Jan Freed: To me, it’s about how you want to be remembered. To me, I define it as living a life in a way that you want to be remembered. A lot of people think legacy is others’ perception of us, but I kind of use it as, how do you want to be perceived?

Casey Weade: It’s good. What are some simple actions that we could take each day to carry out that legacy? Are there some things you do every single day, some daily practices you might have to make sure you’re leaving the right bread crumbs?

Jan Freed: That’s a good idea. I’m certified as a sage-ing leader. Now sage-ing is a fancy word for positive aging, conscious aging, and I went through certification through an organization called Sage-ing. It’s S-A-G-E dash I-N-G. They copyrighted that word, Sage-ing International. So, the website is sage-ing.org. And, again, it’s S-A-G-E dash I-N-G.

One thing that’s interesting is since I write a lot about sage-ing, the computer will come back and tell me, “Well, you mean sagging?” I always laugh. I think, well, there might be some of that too, but no, I really mean sage-ing.

And so, I wanted to share with you— this is something I share in my workshops, in terms of my top 10 tips for becoming a sage and then we can go into more if you want. I think, again, the whole idea is don’t age, sage. In these workshops, I will often say, “Well, what’s the difference between someone who’s aging and someone who’s sage-ing?” How would you answer that question, Casey?

Casey Weade: This was one of my key questions for you. We’re talking about aging. I heard conscious aging, aging, sage-ing, positive aging. It’s all getting a little muddy for me across all these different things. Is there really a difference? It sounds like maybe, there’s not really a difference between all these different things when it comes to conscious sage-ing and positive aging. But if we’re just aging, we’re just getting old. We’re not focusing on our impact on a daily basis, like going through life intentionally. I think intentionality is the word that comes to mind when I think about positive, conscious or sage-ing.

Jan Freed: That’s a good word. That’s very good. So, when I say sage-ing or I just use the word sage, think of someone who’s getting older and someone who’s becoming an elder. Now elder, not elderly but when you hear the word elder or sage, what’s the difference between older and age? So, if somebody in your mind is a sage, what characteristics come to mind?

Casey Weade: Wisdom. That’s the main characteristic. A lot of the value I get from my seat— I’ve been a financial advisor and actually sitting in financial advisor’s position following my dad around since I was a teenager and I’ve always learned so much from the families that we work with, because they’ve always been substantially older than me. There’s a lot of wisdom to be gained. And I’ve always actively searched for, where’s the wisdom in this? What can I learn from this individual? Because I think as we age, there’s just so much wisdom that’s created that we don’t even know is there, just need someone to kind of pull it out of us.

Jan Freed: I would say you definitely are wise beyond your years, Casey. So, wisdom and sage-ing but, again, just getting older does not make someone a sage. It really is about processing your life experience and distilling the wisdom and then passing that wisdom on. One example I often use because people will say in workshops, I weave all these things together beyond the money, aging. In legacy, I weave all this together in my workshops and coaching, and I had someone asked me once, Well, do you have to be old to be a sage?” Because I had just said, being old doesn’t make you a sage. And I said, “No, no.” An example I often use, now, this is a few years ago, but did you see the movie Slumdog Millionaire?

Casey Weade: Long time ago. Yes.

Jan Freed: It got an Oscar for the best movie. Basically, it’s about a quiz show in India. So, he has to answer these questions and he’s a young guy, 20. How does he answer those questions? He answers those questions by thinking about his life experience. So, you don’t have to be old to be a sage.

I just want to share my top 10, and we can go from there. So, I share with people. I kind of use this as a summary in my working with the clients. Number one, make intentional choices and decisions. So, again, we’re not just drifting along in life and you use the word, intentionality which is true so use time while still working to seek out role models, make connections and explore.

So, if people are still working, I say, “Don’t just work and then stop and fall off a cliff,” but while you’re still working, and I think it takes about five years to really think about what’s next and make those connections.

Casey Weade: What if we don’t find today that, I mean, I’ve met countless people that say, “Well, I don’t have a purpose,” or “I don’t know what my purpose is,” or “I don’t feel like I’m all that smart. I don’t know that I’ve got that many great life experiences to bestow on somebody else.” How do you coach someone into becoming a sage? Is it something that you have to be doing your entire life? Or can you go through life, 40 years later and go, Okay, now I’m going to be a sage and if so, what do we do?

Jan Freed: I don’t think it’s too late. I think that’s an excellent question. I’ve never been asked that. But it’s never too late to kind of have an awakening. Again, this whole idea of purpose, I would say, just go back to that exploring, discover and grow into it. Learn by growing, I think.

Number three is I have, be wise about how you spend your time and with whom and there’s all kinds of research about… You really want to spend your time around positive people, that this whole idea of negativity and bitterness. Whoever you surround yourself with and really, I think this is true for teenagers. You still have growing children. I have three grown sons. Their peer group, I was always very aware of who they were hanging out with. And I think that’s true throughout life. But again, we kind of forget that as we get older. I think it still matters who you’re hanging out with.

Number four, choose to be around positive people and people of all ages, so not just positive people but intergenerational, and that’s why, churches, I think, are so good because you get intergenerational mix in the congregation, or whether it’s art classes or just intergenerational, I think is very important.

Number five, discover your purpose, you can live with meaning and on purpose. You notice I use the word discover. It may not be something that you know automatically.

Casey Weade: Dr. Jann, what we’re going to do is, probably, we’ll go through all of them but we’re going to put a link in the show notes to that particular article so people can go through the whole list, see how it applies to their life. But I bet there’s something in there about mortality. You talk about mortality in your classes. You talk about the importance of mortality in your coaching and how we need to embrace our mortality. How uncomfortable is that to embrace our mortality? And where’s the benefit?

Jan Freed: It’s interesting because as I said, I’ve been teaching this with undergraduates for a long time and that is probably the biggest aha. One of the four books I use is a little book called Tuesdays with Morrie. Are you familiar with that book?

Casey Weade: No.

Jan Freed: It was a very popular book when it came out. And it’s based on a true story. And Mitch Albom is your author. Now he’s written several books since then, like The Five People You Meet in Heaven. There’s some spirituality integrated in this. He finds out his favorite professor from Brandeis University is dying of ALS. And so, he decides to go visit him every Tuesday. And then he writes the book, Tuesdays with Morrie. And the whole book is about sage-ing. It doesn’t use the word but the whole book is about sage-ing.

And my favorite line is, “When you learn how to die, you learn how to live.” Some motivational speakers will call it NDE, near-death experience. If you can imagine you’re having a near-death experience, you really embrace life more. If you’ve known anyone who had a near-death experience, they just approach life differently. Every day is a gift. And to me, I say the younger you understand this, the better off you are. I’m really big into this. My students would call me Dr. Death. So, I do talk about it a lot.

Casey Weade: What’s the biggest impact? And what does it mean to recognize your mortality? Just to recognize that you could die any day, we focusing on life expectancy and how much time we have left, what does it mean to focus on our mortality?

Jan Freed: Well, let me just tell you that I have an assignment where, either workshop participants or my students, whoever I’m doing it, the assignment is they have to write their own eulogy. Not obituary, but eulogy. Now when I started this, Casey, in about 2008, there was a bigger difference between obituaries and eulogy. Now in your mind, what’s the difference?

Casey Weade: A eulogy would be something that would be more touching and sentimental versus an obituary kind of stating the facts.

Jan Freed: Yeah, that’s good. Right. Obituaries, they used to tend to emphasize what someone has done, kind of the doing. And eulogy is kind of focused on who the person is.

Casey Weade: Deeper.

Jan Freed: Yeah. Now I will say since 2008, obituaries, the tone, they’ve taken on more of a eulogy tone. I don’t know. I study obituaries. I read them in the New York Times. I read them in our local paper. So, the tone has changed. So, I have participants write their own eulogy and they have to come back and share it. And I tell them there’s no right or wrong, there’s no link, there’s no good or bad. It’s just whatever, it could be first person, it could be third person. But that has been an exercise that we laugh, we cry. Some people put it to music, some people put it to poetry. The point is, if that’s how you want to be remembered, then you need to start living your life like that right now. And I think it’s made a difference when I did this for years with college students.

Casey Weade: There’s always little things, little bread crumbs that you’re leaving behind that are really impactful if you’re paying close attention here. I know you’ve studied retirement for a long time. You’ve studied it around the world, not just here in the United States. In different cultures, how does retirement vary from culture to culture? What makes retirement unique here in, say North America?

Jan Freed: Well, I think one big aspect is how we tend to want to segregate older people, put them in a home or a different village or a different place where other cultures, particularly Latin American cultures, it’s just assumed that grandparents will move in with you and you’ll take care of them, and extended families. And I think that’s true in other cultures, as well. I’m just more familiar with Latin American cultures. So, I think that’s one big place and that’s why there’s a person named Dr. Bill Thomas, and he’s written several books. Right now, he’s on a mission. I think it’s called ChangingAging. And he really wants intergenerational communities where you’re not just segregating people who are older off on their own, again, because it kind of violates that whole intergenerational learning.

Casey Weade: When I hear that, and you’re not the first one to have this discussion about the importance of having intergenerational relationships. We tend to isolate ourselves in our own age demographic, especially when we get into that 60, 65, 75 age group. And it always makes me think about the villages in Florida, this retirement community. That’s just very concentrated in an age group where you’re probably not going to be spending nearly as much time around you and there is some truth that that relationship with someone that’s younger really does keep you young. What is it exactly about those intergenerational relationships that increases longevity and happiness in life?

Jan Freed: Well, there’s more opportunities to share wisdom.

Casey Weade: There’s more sage-ing opportunities.

Jan Freed: Well, and it goes both ways, though, because another person I follow and I’ve gotten to know is Chip Conley, and he’s created this Modern Elder Academy in Baja. And he talks about how elders have EQ, emotional intelligence, emotional quotient, and he says, younger people have more DQ, digital quotient, digital intelligence. And again, we can learn from them, they can learn from us and that intergenerational learning.

Casey Weade: I think there’s going to be a lot of value in that and just spending time as a sage, if we’re using sage as a noun, sage-ing being a verb, then we can use some of that wisdom and impart it on our youth, and that can really make us live much longer lives.

So, I’ve got a few more general questions and one has to do with all the interviews you’ve done. You’ve interviewed hundreds of individuals for your books to your podcast— Dan Payne, Jim Autry, and you’ve got some pretty interesting individuals that you’ve spoken to around the world. What is the one interview that you conducted that really stands out in your mind?

Jan Freed: That’s an excellent question.

Casey Weade: I’m not saying the best. It’s hard to define the best and then somebody gets offended. What’s the one that really just stands out to you right now?

Jan Freed: That’s a great question. Probably, my interview with William Bridges. William Bridges was like the authority on transition. He wrote books on career transition. He wrote a book called The Way of Transition. He really is the authority, William Bridges. And I was so intrigued because it was an aha for me because there’s a difference between change and transition. And I had never thought of that before.

We always say people don’t like change. He said, “It’s not that so much people don’t like transition.” Now the difference is transition is an internal process and changes an external process. Let’s say like during these times, so many people are getting laid off. Well, the laying off part is the change. Something happened to them, their jobs disappeared, but the transition is internal. Now what do I do with my life? How do I pay my rent? What’s going to happen? That’s that transition. And I was so intrigued by what he was sharing that I read his books, then I went back and interviewed him again.

Now unfortunately, he has passed away a couple years ago, but he was just kind and generous and smart. And really, if you Google him, William Bridges, I mean, communities use his framework on transition and what he says is, there are three main phases of transition. And you start with endings— endings, neutral zone, beginnings— and you start with endings because you don’t start something until something has ended.

You don’t start a new job unless another job ended. You don’t start a new marriage unless another marriage ended. Or maybe you got married, but your singlehood ended. But he says most people don’t like the neutral zone. They don’t want to stay. They don’t want to figure out what didn’t work. So, they want to jump to the next relationship or the next job. And that’s why he says a lot of things don’t work out. So, anyway, that just came to my mind.

Casey Weade: I think the quote that came to mind as you said that is, Soren Kierkegaard. I couldn’t remember the name or individual specifics but, “We live forward, but we understand backward. Life can only be understood backwards, but it must be lived forwards.”

Jan Freed: Yes. So that’s processing. That’s a wisdom processing what didn’t work. And so, Bridges says, “If you don’t really realize why that job didn’t work out or what went wrong with that relationship, we tend to just jump in again.”

Casey Weade: That’s the value and being a younger individual, spending so much time with individuals that have had those experiences already so you can kind of go ahead and understand it, moving forward because you’re interviewing, you’re talking to other individuals that have already experienced that. What does Retire With Purpose mean to you?

Jan Freed: Now again, I’m trying to retire the word retirement.

Casey Weade: I want to say I went to your website and before I can even get through it, it says, “Don’t retire, reinspire.” So, I’m guessing you’re going to take us along those lines.

Jan Freed: Yeah, I mean, I think it’s now what? What’s next? And so, Retire With Purpose, I would reword that and say, “Continue to live with purpose” because again, retire in our mind, it usually means put away, expired, whatever. And we’re not retiring from life. So, I would say continue with purpose. And again, purpose isn’t something that you have to know or you can learn, you can discover, you explore, but like going back to Richard Leider, “What’s your reason for getting up in the morning?” And if you have no reason, it’s easy to get depressed. It’s easy to get depressed and feel, like, you don’t have value. It doesn’t have to be a big P in purpose. It can be a little P, and it can grow. The size of the P in purpose can grow. I think that would be my answer.

Casey Weade: I think that’s what’s really changing in retirement. It’s not that retirement is going away. I mean, we’re still retiring. It’s just that, again, our definition of retirement is changing. I think it’s truly just financial freedom today. We can talk about retirement as financial freedom, it’s that job optional position where you say, “Okay, where can I make the biggest impact? Where do I find the highest level of meaning and purpose? And now, I can focus on that because of the financial freedom.”

Jan Freed: Yes. And again, I always go back to, you have to have enough money for your lifestyle, whatever that is. But going back to one of my role models, Richard Leider, is he with MetLife Institute did all this research several years ago. I think you’d find this very interesting because the main conclusion is that as people get older meaning trumps money and significance trumps success. So, once people have enough money, then they’re looking for meaning and significance. And I think that’s really key.

I think my message, again, goes very well with financial advisors and my goal is to be a major speaker at one of these large conferences where they bring hundreds of like a rewards conference, rewards trip, all these advisors together because once people have enough money figured out it’s everything else they’re worried about. And so, advisors need to have that in mind, although, you’re one of the few, I think, Casey, advisors who are willing to spend that much time because time is money.

And so, a lot of people don’t want to get into the meaning and purpose because we want to focus on building your portfolio but what are people building their portfolio for? And that’s where the legacy work, I think, comes in.

Casey Weade: I think the definition of retirement plan is changing a little bit as well. It used to be, well, I go to see a financial advisor. I think most still have this picture in their mind, I go see a financial advisor, I walk out with some investments and maybe some investment strategies, maybe if I’m lucky, I’ll get some tax strategies. But now, there’s so much more being created out of that relationship— investments, insurance products, all that stuff, it’s kind of been commoditized. The value in working with someone is the coaching. I think that’s why you’re seeing so much retirement coaching come along, and people are going, yeah, you said you can do this real quick and be a quick meeting, you’re just going to send me a Fact Finder, I’ll send it back and get it done. But then I think there’s becoming a much larger demographic out there that’s looking to go deeper and get even more value out of relationship.

Jann Weade: I totally agree with you, even long-term insurance. Again, helping people think about that value, is that worth it? And yeah, very good.

Casey Weade: Well, Jann, it’s been a pleasure. I have no doubt you’re going to be on one of these major stages before too long. I’ll probably see you at a major conference here.

Jan Freed: That’s my goal, Casey. That’s what I want. I really think that.

Casey Weade: As individuals are listening right now and they want to go deeper with you, maybe they want to take advantage of some coaching, they want to read some of your works. Where can they go deeper with you?

Jan Freed: Probably, the best place to start is my website. It’s Jann with two N’s, Freed with two E’s, so jannfreed.com. I mentioned, I have a monthly podcast called, actually, I’m making it bimonthly now, “Becoming a Sage.” Those are probably the best places. I’m on LinkedIn, I’m on Twitter.

Casey Weade: We will put a link to your site right there in the show notes. You can check it out at RetireWithPurpose.com. Dr. Jann, thank you for joining us today.

Jan Freed: Well, thank you. And honestly, Casey, you are very wise. You are a sage in the making.

Casey Weade: Well, thank you. You’re flattering. I can’t wait to do this again.

Jan Freed: Thank you.