How to Reinvent Yourself After 50: A Conversation with Jann Freed

Reading: How to Make the Rest of Your Life the Best of Your Life

Covey Podcast

How to Make the Rest of Your Life the Best of Your Life

Finding support when you’re looking to reinvent yourself can be scary. Jann Freed has the tips to help you thrive.

with Jann Freed

“This whole idea of 50+ and reinvention – it’s real. It’s important,” says author Jann Freed. “Because we’re active, we’re healthier, and we really want to continue to contribute.” Freed spent 30 years teaching  before shifting into entrepreneurship as a leadership development consultant. Here she shares her research from her books to answer the most-asked questions about reinventing yourself.  Learn how grief plays a role in transition, how reinvention is easier for women, and the steps you can take to build relationships to support you. Get Freed’s reading list for personal growth and the #1 trick you need to focus on when you’re in transition.

Jann Freed, PhD, is an author, professor, speaker, and consultant who focuses on change management and leadership development at all ages and career stages. Dr. Freed is the author or co-author of five books, including Leading with Wisdom: Sage Advice from 100 Experts. She is Professor of Business Management Emerita and the former Mark and Kay De Cook Endowed Chair in Leadership and Character Development at Central College in Pella, Iowa. After 30 years of college teaching and administrative responsibilities, she left to become a senior consultant with the organizational development firm the Genysys Group.

LJS: So let’s talk a little bit about your personal reinvention. I always like to start there because I think once you’ve lived it you really have better bona fides for understanding what to do and how hard it is. It’s not so easy, as we know. So talk a little bit about what you’ve done in your career and what your major transition was that was fairly recent into your coaching and your writing.

JF: Okay, sure. That’s a great place to start. Well, I taught for 30 years – I say only 30 years – at a small liberal arts college. I taught business management leadership, and I loved it. I loved what I was doing. But my professional mentor, who was at the University of Illinois, Chicago, sent me a book called From Aging to Saging: A Revolutionary Approach to Growing Older. And he said, “Jann, Baby Boomers are not going to know what to do with their lives.” And yes, we talk about a life extension, but it’s not just at the end of life. It’s more in the middle. And so this whole idea of 50+ and reinvention, it’s real, it’s important. Because we’re active, we’re healthier, and we really want to continue to contribute. So it took me about five years to really transition out of my full-time teaching career. I was tenured, I held an endowed chair. I could have stayed there forever, but I thought, you know, I’m really antsy. I want to do something else. I want to actually practice what I’ve been teaching for decades.

And so, my colleagues who were my age, they’re like, “We can’t believe you’re doing this.” And I call it – I was in this transition. Like, I wanted to go from something to something else and do it at an age when I was young enough to do it. So I do leadership coaching. I coach clients, and my focus is really on helping people make the rest of life the best of life. So I talk about what’s next, because this is really uncharted territory. I mean, we’re really still new at this. And as your podcast points out, people are still trying to figure it out. And it isn’t all so easy. It took me five years. I tell my clients, while you’re still working there are certain things that you should or could be doing now to prepare for what’s next.

How do we get women, especially, prepared for career changes?

LJS: Let’s talk about that. Oh, my goodness. This is my biggest rant or whatever. How do we get women, especially, to be prepared and think about being prepared? I guess it’s human nature. I see an awful lot of heads in the sand. Even when things are going badly, people are afraid to look up; they’re afraid to admit what’s happening in their personal career or in their sector. I see a lot of denial, and a lot of times I get people calling me for help at CoveyClub and they’re like, “Oh, I’m about to be fired. I’m standing in the bathroom. What do I do?” And it’s like, it’s a little late, but we can still help you. But how do we get people? Do you have thoughts on that? You must. On how to think ahead and plan ahead.

JF: I know your audience is primarily women, but what I will say is women really are better at this than men, because so much of your career is your platform, your identity. And that’s true for men or women. But I often say society allows women more freedom. So we can go to wine clubs or wine groups, book groups, women can socialize in groups easier than men. Men can play golf, tennis. They might have power lunches, but they don’t feel as comfortable going out to movies with two or three guys.

LJS: Oh, God forbid.

JF: Yeah, I know. Exactly. And so really what’s interesting is [for] women…it is still hard, but it’s much harder for men, I think. And one of the things that I point out is that the statistics are not good. Suicide for white males 50+ higher than average. Drug and alcohol use and abuse for people 50+ is increasing. Divorce rates.

LJS: The suicide numbers for women 40+ are horrible.

JF: Yeah, no, it’s horrible. And divorce for people 50+ higher than average. And so they call it – what do they call it? The gray divorce. So the statistics are not good, which shows that people, men and women, are struggling with this change, as you’re saying.

So one of the things that I say to people is, while you’re still working – and I did this, actually, I did this – while you’re still working, start exploring, start discovering. Set up informational meetings, coffee dates. Try to figure it out. I joined a women’s executive group, so that gave me kind of an anchor. So when I let go of teaching, I was in an executive group already, so I already had a network. So try to make those connections because they aren’t so easy to make. And then if you don’t have a paycheck coming in, you even have that higher level of stress. So while you’re still on a regular paycheck, start doing some of this investigating. And one point that I often make in my workshops is, I say, if you are exploring this – I just got done taking this, it was called “Mastering Midlife” course, because even though this is my passion, I still want to grow and learn, so I can share this information. And I often say, if women are growing, you need to have this conversation with your significant other. Because when I was younger, I didn’t understand when people would say, well, they grew apart. What do you mean, they grew apart? Well, now I get it. If you’re not really growing and not having these conversations, then I think that’s where people really – the marriage or the commitment – whatever the relationship – breaks down. So I think it’s really important. I was doing a workshop where a man came up to me afterwards. He said, “Jann, the most important thing I learned is my wife and I have never talked about what’s next.” And I said, “You need to.” And he said, “I’m 68. The only thing we talk about is visiting grandchildren.” But he said, “They’ll grow up.”

I said, “You need to have those conversations now. And so are you on the same page? How do you want to live your life?” And I also say, look for role models [who are] living a life that looks attractive to you, and what is it about that life that is attractive, and then just start exploring that? So those are just a few tips right now.

LJS: Yeah. The majority of CoveyClub members are still working, most of them still in corporate life. About 28 percent of them are entrepreneurs. And about 60-something percent are currently in regular corporate jobs. And they’re trying to navigate that transition and figure it out. With your experience and what you’ve done, you say it’s about five years, that whole transition?

JF: I think so, because, for one of my books, Leading with Wisdom: Sage Advice from 100 Experts, I had a chance to interview William Bridges. Now, he’s one of the real experts on transitions. And I don’t know if you’ve had other people talk about this before, Lesley, but –

LJS: No, not him.

JF: No. Okay, well, he is now deceased, but his name is William Bridges and he’s written all kinds of books. My favorite is The Way of Transition. But he talks about three major steps: endings, the neutral zone, and beginnings. And he basically says, you don’t begin something unless something else is ending. Now, that could be a marriage, it could be a job, it could be, you move to a different neighborhood, different city. Before you start something new you’re ending something. And so he really stresses [that] we as humans, we don’t like endings. So the neutral zone is where he says … you need to process – you might have grief involved, grief involved in the loss of marriage. So you need to process in that neutral zone, really, before you begin something else. But we don’t like – we, and I’m generalizing – we don’t like the neutral zone. So that’s why some people have affairs. They don’t want to leave one marriage until they have another relationship started. They don’t want to be in that neutral zone.

Now, a newer book, which is similar – he has a similar take on it, but something different. Bruce Feiler, and his book is called Life Transitions. And then there’s a subtitle. But … he calls the neutral zone the messy middle. And people don’t like to stay in the messy middle. But his take is, he says it’s not so linear. You know, William Bridges made it sound like you go from here to here to here. And he says, no, he says, we’re going to have these life quakes, and a life quake, he says, happens about every seven years, and it’s a major event that really throws your life. You get demoted, you lose your job, you get laid off, you get divorced, there’s a death in the family. Something major kind of shakes up your life. And so he says it’s not [as] linear as Bridges talks about, but he still says endings, and then he calls it the messy middle, and then beginnings. And so for me, leaving a full-time teaching job where I could have stayed forever. The last few years were very emotional because I was in that, I knew I was going to let go, but I wasn’t telling anybody. I don’t know if you remember the show, it was with Laura Linney, a few years ago called The Big C?

LJS: Oh, yes, I remember that.

JF: She had cancer, but she didn’t want anybody to know it, so she’s living with it. But she wanted to act like life – she wanted everybody to treat her normal. Okay. And that’s kind of the way I was  Here’s another aspect of retirement that I don’t like, because I also say, Lesley, I’m out to retire “retirement”. We’re not retiring, but we’re moving on. We’re moving on. I love how Serena Williams said she wasn’t retiring from tennis. She was evolving away from tennis.

LJS: Yes. Perfect.

JF: And that’s what we’re doing. We’re evolving. But people don’t like the word retirement. And so if you announce you’re leaving, honestly, I saw this, our college president, he retired, and we had a presidential search committee, which I was on, but people just treated [him] like he was already gone, and he wasn’t gone yet. And so I didn’t want people to treat me like I didn’t have any value because I’d been there 30 years. And, I had a lot of influence on things. So this whole idea of the transition, letting go, I was … kind of very emotional, particularly my last year. And so, it’s a process, and I think understanding the whole process, I would recommend either Bridges’ books and or Bruce Feiler’s Life Transitions or Life in the Transitions, something like that.

LJS: So what you’re saying is that we have to get comfortable in the transition and living there for a while before we’re going to find out what we want to do. I think a lot of people think that they’ve got to have the answer. And it’s funny, I think that’s what we learned with CoveyClub when I was trying to figure out what CoveyClub did. And it wasn’t until one of my members said, “You hold a space for us while we figure out what’s next.” And I realized that’s powerful. Right?

JF: That’s powerful. And change in itself is usually an external event. Something happened. Transition is an internal event.

LJS: Ah, very good.

JF: And so I help leaders understand this, because if you don’t, you can’t help your employees work through it. It’s really kind of a counseling role because the transition is internal. So if there’s a layoff, that’s one thing, but what’s going on inside of people is another thing, and that’s transition.

LJS: Yeah, that makes sense. How delayed are the two? Because I see people and I’m wondering, if I see people who lose a job, run out, grab another job in two months, and then that blows up, and it’s because they haven’t really gone through the transition. Right. They’re just grabbing.

JF: Exactly. They grab something maybe too soon, because particularly it’s important in the transition [to ask], Why didn’t that relationship work out? Why didn’t that job work out? Why didn’t we like that neighborhood or that community? Trying to figure that out so that you’re not just jumping into the same thing. How many times do you know a person who jumps right back into either a similar type of relationship or a similar type of job? And from the outside, we might be thinking the likelihood of that working is not good.

LJS: Well, also, where is the growth there? Right? Because I think each one of these transitions, whether it happens from you or from the outside, there’s got to be some processing of growth. No?

JF: Yes, that’s a very good point.

LJS: How do you know if you’re in that growth period and you should lie low and give yourself some time to see where you’re going? Like, do you have a sense from the people you’ve worked with, how long that transition should be?

JF: Yeah, I really don’t in terms of… But I think so much of it is about emotions. So, like I said earlier, working through the grief. And I’ve done a lot of grief work because there’s a lot of sadness and loss in organizations now, particularly after COVID.

LJS: I can see that.

JF: Yes. And so my latest book is called Breadcrumb Legacy, How Great Leaders Live a Life Worth Remembering. And I have a whole chapter on death, dying, grief. I actually did a TEDx talk called Embracing Death, which is kind of interesting. I was talking about death and dying to 22 year olds, and that could be a whole other topic, but there’s so much because of COVID. COVID brought death, loss, grief front and center. Most people don’t do a lot of grief work, so they don’t know how to process that. And if you don’t know how to process your own grief as a leader, you can’t help others. And so, I think that’s an important topic, too.

LJS: So how does grief play into transition? Do you feel that? Or have you seen that there’s grief with any transition?

JF: Oh, sure. I think there’s grief with every transition. Even if you say, like marriage, you’re getting married. Okay, well, in our country, most of the time, you’re choosing to get married. That’s a happy occasion. But yet you’re grieving, well, I’m not single anymore. I’m not going to be able to do exactly what I did before. Now I’m more accountable to someone. Or maybe you’re leaving some single friends behind or you had a single group, or now you’re moving because…and that’s a happy event. So even in happy events there are – graduating from college, it’s a happy event. But it’s scary because now you’re not going to have college life. You’re in the real world and you’re leaving a lot of your really good friends behind. So I think every change has a transition that often involves grief and loss. You’re leaving your best friend, you’re not going to have a roommate.

LJS: Right. So talk a little bit about the idea of legacy and talk a little bit about what a breadcrumb legacy is. What does that mean? Because legacy is very important to everybody who’s listening, and understanding what that means I think changes as you get a little bit older.

JF: Yes. Well, I was doing, out of my last book, Leading with Wisdom, I had a chapter, and these chapters all evolved from interviewing more than 100 what I called “sages” and some of the top thought gurus in the field. And one chapter was “Leaders Live their Legacy,” and that was a chapter that really resonated for keynotes and workshops. So then I decided to do a deep dive. And when I would do workshops into legacy, what I call legacy work, legacy thinking, and I would do a workshop and I’d say, well, when do we leave our legacy? And people would say, well, when we die, when we leave, we leave a job, we leave a community, when we leave the earth, I’d say, absolutely. But what about when I leave this workshop today? What am I leaving?

LJS: I love that.

JF: Yeah, we’re leaving our legacy in bite-sized pieces, which I call breadcrumbs, all the time. It could be positive, it could be negative. And when we think about this, I say, it can be like our true north, our moral compass. It can prevent us from road rage. It can really keep you on the right track. Now, I was doing a workshop recently, and a man said to me, “Don’t you find that self centered that you’re thinking about your legacy all the time?” He said, “I think that’s very self centered.” And I said, “Okay, let’s substitute the words influence or impact. How do you feel about thinking about the influence you’re having on others on a daily basis, or the impact you’re having on others?” And he goes, “Oh, now I get it.” Again, I think we think so much about… It’s kind of funny, Lesley, because about a year ago, I read this article […] and it was about Tom Jones, the singer. And if you remember, I can’t remember, What’s New Pussycat?

LJS: Yes.

JF: Title was, “I’m Turning 80: It’s Time to Think About My Legacy.” And I’m reading the article, and in the article, he even says, you know, I guess I probably already have one, but what if I’m not happy with it? Well, maybe I need to change it. So this idea of, if we think about how we want to be remembered, then we should try to live in that way. And so that’s kind of where my latest book is coming from.

LJS: And what do you see, since we’re talking specifically about women, 40, 50, 60+. What do you see women doing differently, good or bad, towards planning for change? You’ve interviewed a lot of people. What are the tips and tricks that you’ve learned that are helpful?

JF: Yeah, I think that’s very good. First of all, I think a support group, and it can be any kind. You know, women that you really trust, because the key is –  Robert Waldinger, he’s at Harvard, he just had a book come out called The Good Life: Lessons from the World’s Longest Scientific Study of Happiness. And he had a TEDx talk with the same title, The Good Life, and it went viral, I want to say over 40 million views. And he says in the book – and the book is quite thick – but in the first ten […] pages, he says, if I had to summarize the good life in one sentence, it’s about positive relationships. It’s all about relationships. And I think I’m generalizing, but I think women are better at relationships than men. “Better” meaning better at cultivating and sustaining them. And so I even helped my husband create a book group because he likes to read. And I said, you need more friends, and he’s a very nice guy, and it’s been very successful. And I talk about that in my Breadcrumb Legacy book. But this whole idea of relationships – I’m in a book group, actually. We have it tonight. So I’m in a women’s book group. I’m in a women’s executive group, as I mentioned. Men might … have a breakfast club, but do you really get together to share or ask for help even?

LJS: They can’t ask for directions. How are they going to ask for help, Jann?

JF: Very good point. But I think this Mastering Midlife, … there were 12 of us in it, I believe, and it was online, and it was taught by Pam Maxon, … a Duke professor. But one of the things that we all agreed on at the end of the course is the most valuable thing of the course was the conversation among each other and the network. So now I feel like I have 12 other people, we can talk a common language. And, I had mentioned that one of my sons is struggling with something, and one of the women in the group sent me an email and said, “Let’s talk. I have a similar issue.” I think it’s that support, the relationships, and, as we get older, it’s really important that people continue to cultivate relationships because our circle of friends shrinks, people die, people move away, and some people don’t stay in touch.

LJS: You’re talking about CoveyClub exactly. That’s one of my points. Exactly.

JF: And some relationships, Lesley, become unhealthy because of that – drinking, they can be unhealthy, unhealthy habits. And so we have to cultivate and pay attention to our relationships. And relationships take time and they’re messy. I’m actually writing a paper that I’m going to turn into a presentation called How to Make Friends After 50.

LJS: Oh, love. Fabulous. 

JF: Could be a whole other podcast because I’ve done a lot of research.

LJS: Interesting.

JF: The Atlantic magazine had, they call them friendship files. They had a series of articles on how to make friends and what the value of friends is. So men and women need to continue to think about who are you hanging around? Because they say that the five people who you hang around with the most, you become kind of the average of them.

LJS: Oh, that’s interesting. Have you got any research on virtual friends versus live friends? Now that we’ve spent so much time getting to know people virtually.

JF: Yeah, a little bit. But I wouldn’t say necessarily research, but I mean, I’ve talked about this with other people in terms of like, I taught a graduate course and it was online for ten years, once a year since I left my full-time, graduate teaching. And so we were way ahead of Zoom. They used a different educational platform, but I was amazed at how well I got to know the students online, given the fact that I had 30 years. I was very resistant because 30 years of in-classroom teaching …, teaching a class of 25 to 30, and then I was teaching 20 or 25 online, and I was really amazed at how well I got to know them. And that’s ten years of experience there. So, I don’t think it matters so much. Face to face is still important, but I think Zoom does a nice job.

LJS: I have no problem with it, but I know some people feel it’s not the same. Actually, I have a lot of people in CoveyClub who I’ve been on Zoom with for four years and have yet to meet live, but I would consider them good friends.

JF: Yes, exactly.

LJS: Interesting. So what do you see as barriers that older women set up towards making these connections or towards moving into the next thing that they’re doing? Do you think most of the barriers are personally set up, accidentally, even? Culturally set up? Or do you think it’s just individual mentality, that we need to know ourselves really well and work through those situations?

JF: That’s an excellent question. And I think I would say that it’s mindset. And you’ve probably had people talk about the difference. Carol Dweck’s research on growth mindset versus fixed.

LJS: Love Carol. I think I mention her like every fifth.

JF: No, she’s … wonderful. And I kind of boil it down to that. A fixed mindset is about proving yourself. And so much of our culture and society reinforces proving yourself, proving yourself in school, proving yourself in the workplace, achievements. Where a growth mindset is on improving yourself and how can you grow and how can you learn from situations? And to me, that whole growth mindset would be involved with transitions. How can I learn from what just happened? So a growth mindset. And what I notice with some women, and again, this is not scientific, okay. It’s more anecdotal.

LJS: Sure.

JF: It goes back to mindset. Like, I have single friends, some divorced, some never married, and it’s their mindset. “I’m just fine. I’m independent. I don’t need anybody now.” Research says people who have companions live, I don’t know, I think it’s two to three years longer.

LJS: Okay.

JF: And I think it’s more enjoyable. I look at some of my friends and I think they could be doing some more adventure, but they’re alone. So then I share with them that we just got done with –  my husband and I went on a Backroads trip. Backroads is a tour company. They started out as a biking company, but we like the walking/hiking. And, they schlep all your stuff. Great food, great restaurants, or great hotels. But there were two women on our latest trip, two single women, not together. One was from Houston, one was from Arizona. They didn’t know each other, and they were just there enjoying everything. And I recommend that to my single friends, because when you want companionship, you have it, you feel safe. You’re traveling. Backroads, they have a tour anywhere in the world you want to go. Greece, whatever. But when you want to be by yourself, you can be by yourself. And if you want to eat alone, you can eat alone…. And so, there’s a company, we did a river cruise a few years ago and discovered that this company is called Grand Circle. Pretty sure that’s right. And that’s a river cruise. But they also own something called Outdoor Adventure Travel. OAT. And I’m mentioning this because I think your listeners… We met a woman there, she was single, she’d been divorced for quite a while. And she said she’s done many trips with this company and she loves that company. It’s the only company she knows of that will not charge you more for a single room. Single people tend to get penalized.

LJS: Yeah.

JF: Ah, again, I think it’s mindset. If you want adventure, there are ways to do it. And actually, I have a married friend whose husband doesn’t like to travel, so she goes on these trips by herself. And loves it. And doesn’t want to take a friend because she said, if I take a friend, then I’m compromising.

LJS: Right.

JF: I want to be totally independent. So, anyway, those are just some tips. I think it’s mindset.

LJS: Yes. I would say from the 200 people I’ve interviewed so far in this podcast, when people ask me, what’s the one thing that holds them all together? It’s mindset. It’s extraordinary.


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