Kerry hannon new world of work Kerry hannon new world of work
Podcast 318

318: How to Succeed in the New World of Work with Kerry Hannon

Today, I’m talking to Kerry Hannon. Kerry is a senior columnist at Yahoo! Finance and has been writing for decades about women’s finance, the changing nature of retirement, and what the workplace will look like in the future.

She is a workplace futurist and strategist on career transitions, entrepreneurship, personal finance, and retirement. You’ve likely seen her writing in the New York Times, MarketWatch, and Forbes, and she has appeared as a career and financial expert on all the major TV networks.

In her newest book, In Control at 50+: How to Succeed in the New World of Work, Kerry gives her readers a guide to help them navigate the post-pandemic workplace and take an active role in their careers and financial future.

In our conversation, Kerry and I explore how the pandemic has profoundly changed the workplace for people of all ages, how to conquer your fears and find work you love at any age, and the critical differences between how men and women manage their money.


Here's all you have to do...

  • Step 1.) Subscribe to the podcast and leave an honest rating & review over on iTunes.
  • Step 2.) Text BOOK, that’s B-O-O-K to 866-482-9559 for a link to our book request page, complete the form and we will ship you the book for free. It’s that simple!

In this podcast interview, you’ll learn:
  • How an aging population and fewer younger workers are creating a better workplace for people over 50.
  • Why it’s so easy to get stuck in a professional rut as you get older–and how to get the confidence you need to regain control of your working life.
  • How to get the skills and education you need to make a career transition.
  • How the COVID pandemic uniquely affected how women work.
  • The best ways to navigate issues around money in long-term partnerships and marriages.
Inspiring Quote
  • "Work is not a four-letter word. It gives us financial empowerment, social network, and mental stimulation." - @KerryHannon
  • "Net worth is not a game. It’s not a competition. It’s really an individual pursuit." - @KerryHannon
Interview Resources
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Read the Transcript

Casey Weade: Kerry, welcome to the podcast.

Kerry Hannon: Casey, it’s an honor to be here. So, thank you so much for the invitation.

Casey Weade: I’m excited to have you here. I got to say, when I was doing my research, I ended up with about six or eight pages of notes. I’ve distilled those down to a couple of pages here, but it really was a challenge because you’ve written for decades and you’ve written on so many different topics that there’s a wealth of information that we could cover today with you. I’d love to just get in there and pull out as much as I possibly could, but I said, today, I really want to focus on two main topics, that being the workplace, Second Acts, entrepreneurship and retirement, but also with your background and one of your passions being women’s finance.

I want to bring an element of that into the conversation as well. And as reviewing your bio, I noticed that you were a workplace futurist, and as a workplace futurist, I bet that’s a new term to quite a few individuals out there. I know it’s a relatively new term to myself. I’ve seen it a few times now just because I spend so much time in this arena. But for those who don’t know, what exactly is a workplace futurist?

Kerry Hannon: Yeah, well, Casey, that’s a great question. It’s really taking a look. I’ve spent so long studying the workplace and how it’s shifting and all the things, all the various elements that go into what we consider our working lives in the workplace. And I’ve also studied extensively longevity, the aging population globally, and sort of how did this impact what is going on? And then this new book really takes a look at the five big trends that are coming out of the pandemic, which have profoundly changed the workplace going forward.

So, how can we look forward and prepare ourselves? So, yeah, so we’re in control of our working lives and really make the most of some of these really important changes that did start pre-pandemic but have really just lit up after. Of course, we’re sort of still in the pandemic but coming out of the pandemic, let’s say, that are going to be with us for decades moving forward. So, I think the whole point is, as a workplace futurist, it’s really having an eye into sighting the trends and giving people advice on how do we take control of these today.

Casey Weade: With so many books and writings that you’ve done around aging and starting a second act, a new career, entrepreneurship, and retirement, do you see that as the biggest, most impactful trend right now and going into the future? Is it going to be demographics that’s driving the workforce more than anything else?

Kerry Hannon: Yeah, the thing is that’s very true. I mean, population aging is really profoundly changing because there are just not as many younger workers coming up, and older workers want to stay on the job longer. And frankly, they need to in many cases in order, can you imagine if you retired at 65 and you’re living too if, say, the lifespan is 85 to 90? Seriously, how many people have saved enough to really finance three decades of not working?

And so, when I look at work, I think of work as not a four-letter word. This is something that gives us financial empowerment, it gives us social network, it gives us mental stimulation. There are so many great things about it, but it is this idea that there’s a shift here on where the workers are coming from.

But Casey, coming out of the pandemic, all of these trends, I think, are really beneficial to the worker over 50. But the younger workers need to pay attention to this stuff, too, because they’re impacted very much by these as well. And I’ll take them up quickly, and then as you go forward, if we want to dig into each of them, the five big trends I see are remote work is here to stay. The genie is out of the bottle. Yes, it started prior to the pandemic, but it’s no longer a perk, a must-have.

Number two, contract work has taken off, so employers to understand that, yeah, they can cherry-pick people to come in for projects for assignments. This can be fabulous for workers who want to continue to work in retirement in some fashion. Entrepreneurship has just boomed for people midlife, and younger entrepreneurs as well, but it’s really coming out of the pandemic.

People had this time to do that inner MRI, that soul searching about, hey, you know, what really matters to me? What do I want to do with my life? What are my priorities? How can I take control of that? And entrepreneurship is certainly one way that many people are saying, I’ve always wanted to do that. Let me give it a shot.

And lifetime learning, the ability to learn online, virtual learning opportunities absolutely exploded. So, you’ve got those four things. And the fifth one is truly career transition, which you mentioned at the top. Career transition used to be only for the outliers for, oh, my gosh, you’re such a risk taker. Do you really have enough runway ahead of you if you’re over 50 to really make a turn?

But in fact, people in their 20s, 30s, 40s, 50s, everyone’s going, hey, yeah, right, I want to be doing work I love, and that’s meaningful to me. And I can make this transition. But what I’m doing is I’m not reinventing myself, I’m redeploying the skills I already have, moving in a new direction, and yeah, grabbing hold of some of that new learning to add to my skill set.

Casey Weade: So, those five things – remote work, contract work, entrepreneurship, lifetime learning, career transition, those things don’t sound unique to the 50-plus demographic. These elements are going to benefit the whole workforce. And do you see this as maybe one of the number one drivers today to the reason that we have the lowest unemployment rate since World War II?

Kerry Hannon: I mean, there really are still even with the latest job numbers, we’ve got almost two jobs open for everyone looking for a job. I mean, it’s a tight labor market, and employers are looking for people who can do the job right now, someone they really don’t want to spend a lot of time training. So, that’s why that virtual learning piece is important to remember. But they want someone who can step in and do the job now.

And I think there’s this real demand for talent. And if you’ve got a baby, you’ve got some opportunities out there. So, I think that ability to look for how you want to shift your work life and make it fit into some of these patterns because employers are seeking out that sort of enthusiasm, that curiosity, someone who’s willing to try new ways of doing things.

Casey Weade: Well, it’s good to report on the good news. And I would say that is really good news. This is something, those five things could be something that are massive drivers for economic growth over the coming decades. And it seems like everything’s so darn negative out there. That seems pretty darn positive. So, it’s great to hear that from you.

Looking at your book, you said In Control at 50+, that was something that hit me with the title In Control at 50+: How to Succeed in the New World of Work. We talked about the new world of work. I just want to say In Control of 50+, that title, are you implying that those 50-plus usually aren’t in control? Is this something that you struggle with?

Kerry Hannon: A trick question. No. I think what happens is that when you reach this certain age, you’ve been in the workplace for two decades or more, three decades almost. And often, people get stuck in a rut. They get stuck in a moment as the U2 song says, they stay in their lane, they’re afraid to step out of it. They often feel that they don’t want to raise their hand for new assignments to push the edge a little bit, which is absolutely what they have to do to ramp up their love of their work and their engagement in their work.

But what happens is people, they stay in their lane because they’re afraid of failure. They don’t want to get noticed. They want to just keep doing what they’ve always been doing. And employers start seeing that as, hey, they’re trying to switch a little bit. They’re not as engaged. They’re not as involved as they once were. And they don’t offer them those new assignments. They don’t offer them workplace training. They get overlooked for promotions and so forth.

And so, you see the tunnel slowly narrowing for someone as they get older if they get complacent. So, the importance is you can’t be complacent. You have to constantly be challenging yourself because, as we said, with longevity, chances are good you’re going to stay in the workplace in some respect as you age. And it’s not just this magic age of 65, you step away because that’s an old way of thinking. It’s truly an old way of thinking. And you understand the financial realities of so many people out there that when you’re earning money, it is so empowering and your ability to build financial security for yourself, and also for those that you might be leaving behind for.

Casey Weade: So, could we say that there’s a lack of confidence in some ways in that 50-plus worker in many aspects of the way that they’re working, and that is resulting in a lack of control, and what you’re trying to give that 50-plus worker is more confidence, which will result in more control?

Kerry Hannon: Exactly. I want them to own it, like really, do that inner soul searching and say to yourself, what is my mission? Why do I care about in the world? Don’t be afraid if you start peeling things back, you’re going to find nothing because the truth of the matter is you will. There’s a core to you. And if it’s not, sit quietly with it. Think about these things. What is it that really matters to you? Often, people think it’s an employer coming to tap you and say, oh, I’d like you to work for me, but really you should be saying, hey, I want to be part of your organization because I believe in who you are, I believe in your mission.

And you want them to see. If you’re wearing that on your sleeve, how much you really want to work someplace because they’re true to who you are, then you’re taking control because you’re making a difference in your own way. And I just think people tend to sort of feel like they’re victims or they’re powerless in some way when the reality is we have a great deal of power and a great deal of experience to bring to the workplace, but it’s a matter of shifting that mindset.

Casey Weade: When you look at the great resignation that kicked off in 2020, so over the last couple of years, we’ve had this great resignation, has that shown up in every demographic? Or are we seeing that great resignation not show up in certain demographics, such as the 50-plus group?

Kerry Hannon: Well, I like to call it the great reimagination because I do think that...

Casey Weade: I love the way you put a positive spin on everything.

Kerry Hannon: I do think it’s people saying, you know what? Forget it. Life’s too short. We all lost people we love during COVID, the early days when we didn’t know what, we were afraid. It was scary, right? And you’re like, what it matters. What really matters? And so, I think people did take that time to sit with that and say, no, I want to reimagine where I want to be going with my time. And work is a lot of what we do with our time. So, that’s important.

And so, yeah, what demographic? I think I saw it across the board in many ways, but I think women, particularly women who were raising families, did step away because it became almost untenable, or if you were caregiving for an aging adult. I mean, Casey, I had my 91-year-old mom living with me and she had dementia and I was hanging by a thread. And it was so hard to continue to work and to care for mom. And I had to get up at four in the morning and do as much work as I could before she woke up because once she was up, I was on duty. So, I can really empathize with the women who said, and it is mostly women, although some men who did choose to resign rather than try to make it all work.

Now, remote work has helped, contract work has helped, but I think that this is changing. And I’m going to diverge just quickly, but I think this whole thing about everyone’s got to return to the office. The office is great when you’re in your 20s. I think it’s fabulous for networking. But as you get older, truthfully, it was designed for in many ways men going off to work and women staying home and taking care of the family. People have found through remote work that people are more productive and performance is better because you get the work done. You’re not wasting time commuting and sitting around the water cooler. So, there are two sides of that argument. But I think for women, remote work is a really great thing if you’re caregiving.

Casey Weade: And I see it as a great thing. As an employer, what happened? We ended up losing some team members. Sure. We lost those that weren’t passionate about what they were doing here at our team. The ones that we attracted were passionate. So, there was a shuffling that created, I think, a better organization and probably a better economy, hopefully, over the long run, because I have more people that are more passionate about what they’re doing today.

Now, when you look at that 50-plus group, you talk about this lack of confidence and concerns about being too loud or seen. And you talked a little bit about this on Dr. Phil as well, just the risk of age discrimination as well. And maybe you don’t know the statistics, but it does seem to me that that 50-plus demographic did not make the great resignation to the degree. We didn’t see the big transitions as much in that older population of workers that we saw and those that are in their 20s, 30s, maybe 40s as well. And part of that, if that’s the case due to this fear of, well, am I going to be able to get another job due to my age?

Kerry Hannon: Yeah, good point. I do think that there was quite a bit of shuffling in that 50-plus set. Some of that was because people took early retirements or they were laid off.

Casey Weade: And as an advisor, we saw a lot of that. Big shift to accelerating retirement.

Kerry Hannon: So, that was in the early days, particularly that first year was really a time where real shockwaves went through the workplace, and a lot of older workers for fear of their health as well, did step out. But what we’re seeing is people since January of this year have come back into the workplace. There are more people who unretired, who are back and maybe not full steam ahead. They may be doing contract work, part-time, seasonal work, but they’re back in the workforce again.

And I see that as a super positive thing because again, like you said, it adds to the economic base. It’s really important for our economy and it’s important from a health perspective, too, because I think people who are working are generally healthier. They’re immensely engaged. It’s good physically. Their minds stay, use it or lose it. So, it’s important to understand that, yeah, I think the younger workers were more nimble about making these changes, but we’re definitely seeing the rolling back into the workplace again of people who stepped out.

Casey Weade: Well, you and I both want to deliver confidence to this demographic, these individuals that may not love what they’re doing, they want to make a career transition. And instead, many times what we see them doing is they just retire. They say, ah, and I don’t want to do it. I’m not going to go look for another job.

When they do love working, they just don’t like certain elements of their work, but there’s this fear or maybe lack of confidence about going out and getting another job at that age. So, talk to me a little bit about age discrimination. Do you see that still as a massive issue today? Is that something that is a myth and a fear that maybe this generation retirees shouldn’t be as concerned about?

Kerry Hannon: I don’t think it’s a myth. I think ageism is alive and well in the workplace. Without question, it is present. And it’s so deep in our culture, Casey, that it’s not just the workplace, it’s everywhere. So, it’s hard, too. And even we often say people in this demographic are their own worst enemies because we sabotage ourselves by saying the language, the way we say things. I’ve been doing this for decades now or I have to catch myself saying stuff that someone will say, how long have you known so-and-so? Oh, I’ve known him for about three decades or 30 years. Whoa, don’t say that. Not in the workplace, you don’t want to bring attention that you’ve been sometimes.

But what I’m saying is, yes, it’s still alive and well. What I love about remote work in this instance is it goes a long way to fighting ageism because you’re not side by side with somebody who’s a couple of decades younger than you. It’s subliminal. But when you’re being judged on your performance, your productivity, and it’s just, just a much better gauge to your sort of value as an employee and as a team member when you don’t have that subtlety of being in the workplace and having that sort of judged by your outside, by how you look.

And also, for remote work, if somebody has trouble with a lot of people retire early for health issues. And they say they’re going to work longer, but health thing keeps them from doing that. And if you can work remotely and virtually, you don’t have that long commute, you don’t have to worry. If that’s a problem for mobility issues or if your employer doesn’t have a workplace that’s ergonomically correct for whatever your issue might be, this can be a real life-saving opportunity to work remotely and really kind of beat back at ageism.

The other quick thing I’m going to say about ageism, which is I have this thing called Kerry’s fitness program. So, it’s like my three-part program. It’s really not that hard to do, but it’s essential for almost anything in your life, but the number one thing is to get physically fit. And I got to say, when I give speeches, people come up to me, a lot of times, it’s women and they’ll say, should I dye my hair? Should I get Botox? And I’m like, gosh, if you really want to, by all means, go do that if it’s going to make you feel great about yourself.

But the most important thing you could do is to get physically fit because, and I don’t mean bench pressing or running fast miles, but if you swim or walk, I walk my dog a couple of miles a day, whatever you do to stay physically fit, you exude this positivity, this kind of energy. And a potential employer or a client, they don’t know what they’re looking at, but they want you on their team. They want to be around you. And it’s this positivity that comes from physical fitness. So, number one thing to fight ageism, get out there and do something to eat healthy and exercise. I know that may seem like nothing to do with work, but it has everything to do with it.

Casey Weade: Yeah, well, I listened to one of those speeches, a speech that you delivered to employers, and you were talking about the benefits of having older employees. You shared five benefits of employing older jobseekers. And as you were saying that, I’m going, wouldn’t it be great if someone that was in that demographic looking for a new job could describe those things during a job interview or leverage those five benefits in some way? And I think you would want to be very tactful in the way that you did this during a job interview. But in your opinion, I mean, how can someone, in this demographic, in an interview situation or maybe just seeking a job, how can they leverage those benefits to really impart that on the employer?

Kerry Hannon: One of my favorite things to tell people to do, Casey, and truthfully, I do this myself, too, is, one of the big stumbling blocks of employers think that workers over 50 or “older” workers, which I hate that term, are stuck in their ways. They’re stuck in a moment. They don’t want to try new ways of doing things. They are sort of not interested in working with someone who’s younger than them as much. They’re in, as we talked earlier, in their lane. They just want to keep doing it the way they’ve always done it.

If you can slip in the word curious, I’m curious about how your company does this. So, I’m curious about don’t overdo it. But the word curious is very special because if used with some discretion, it’s a word that indicates you want to learn new things, that you’re open-minded, that you’re engaged in the world, that you’ve thought a little bit about what this employer does or what their mission is, and you want to know more. So, it’s an eagerness that the word curious really seems to encapsulate in a fabulous way.

Casey Weade: Oh, I can see that. Yeah, we want to leverage that heavily.

Kerry Hannon: Yeah. And there’s other less sort of subtle things in terms of talking about teams that you’ve worked on. And when you’ve paired up with somebody younger and how that partnership was so successful to both of you in achieving results because what an employer is looking for is what I call that car story, your challenge, your action, your result. So, you need to give examples about when you had a workplace challenge, what the action you took was, and what the result was. And the result needs to be something qualitatively, like sales were up 15% or I brought in a job two months ahead of time or whatever it is, but some number that qualifies it.

But if you can use an example where it was a team thing, where it wasn’t just I, I, I, me, me, me, but it was what, I was working with John who was in his late 30s and we really put together this great initiative and this happened and just showed the excitement of working with someone younger. I got to say, I took a full-time position at the beginning of this year in January with Yahoo! Finance. I wasn’t looking for this position. I have had run my own business for 20 years, but they found me on LinkedIn and the recruiter called me and I’m like, I don’t know.

But what happened is I ended up, I work for somebody who is in fact a couple of decades younger than me now and I love it and you know what I love so much, Casey, is I get so energized by her. She’s so smart and she has great ideas and she respects me. Oh, my gosh, that’s the two-way street, right? She comes right back at me and values me in a way that I’m like, yeah, yeah, thanks, but I value her just as much. So, it’s that reciprocity, that respect of each other that I found amazing. And if you can find ways to put those kinds of stories together about what you love about working with somebody from a different generation, employers like that, because it’s all about the multigenerational workforce moving forward.

Casey Weade: And then the question is, what do you want to impart on the employers? And I want to say this from the standpoint of you testified before Congress not long ago about the importance of older workers or 50-pluses. And what did you really hope to impart on Congress, but what did you hope to accomplish with that talk, that address that you gave them?

Kerry Hannon: Yeah. One of the big, big, big stumbling blocks is this education piece, this reskilling, this upskilling. Everything is changing so quickly in the workplace in terms of technology and the way projects are done, the way teams work together, the way the different metrics are very different than they once were. And the speed of changes is just faster than we’ve ever seen before. We can’t find employees that have the right skill set. Well, let’s find out what that skill set is. What are you looking for? When you can identify what it is you want, there needs to be this way of reskilling and upskilling to keep workers on the job as they age.

And a lot of this can happen. I was talking about because the Department of Labor has a jobs site that’s really quite good, but it’s very aimed at these career centers, these job centers, but it’s aimed at younger workers. So, people need help redoing their resumes. If they haven’t done one in a couple of decades, they need to know what skills they need to add. And you can do these online now. You don’t have to enroll in a big program. But I do think the community college system in America is so fabulous. If employers can pair up with community colleges and the government can help out a little bit, we can have a way of retraining that is a natural. So, you don’t just go to college or maybe go into trade school and you’re done. You’re constantly adding.

And just to go quickly further, I wrote a story for The New York Times not that long ago about a wonderful initiative in Ohio that a company had teamed up with a community college. And what they had done, the college had bought these semi-trailers, the trailer units, and they bring them to the company and they’ve retrofitted them with school, like computers, like little workstations. So, instead of a worker having to go reskill and upskill by going after work to a program, they bring the education right to the parking lot. They can come out and they can do their– so it keeps your skill set sharp. And that kind of initiative, I think, could be replicated in lots of different areas.

But I think it’s really understanding how to really understand what skills are needed and how to train people for them. I guess that was my biggest message, but also to understand the true value of having that experienced worker on the job who has done these things and has that ballast and that maturity. We found during the pandemic that older workers actually were less mentally, sort of emotional challenges faced during this period because you know what? They were calmer about everything. They’ve seen things. Yeah, we’d never seen this before, but we’ve seen big crises in our lifetime and we say, okay, we’re going to get through this, let’s take it today and move forward. And not this emotional roller coaster that someone younger really was pretty frightened in a different way.

Casey Weade: Well, that was something. I love that you said during that talk that I listen to anyway. This was how older workers are an insurance policy against volatile times. And that’s exactly what you said, you shared there. And I think that is wholeheartedly true. You share also that the government needs to be more focused on not just younger workers and actually provide resources for older workers, but I see that same thing in colleges and high schools. Most of the career counseling that we see out there today is aimed at 20-something or teenagers, for that matter.

And with all of the options, let’s say, can’t find a career counselor, and I’m 55 and I really want to make a transition, you share all these great opportunities from remote work, contract work, entrepreneurship, lifetime learning, career transition. But how do I figure out where to start? Because I find most of the individuals that we’re meeting with, they want to do something. They just have no idea. And they’re coming to us saying, what should I do? What’s that next thing for me? What do you think I should do? If someone’s in that situation, where do they begin and how do they really narrow it down to what’s going to be right for them?

Kerry Hannon: Yeah, I love that. And I got to say, Casey, I love that you’re doing this work with your clients because one of the big questions that people need to ask themselves is how do their finances fit into this? If they’re making a transition, how much do they need to earn right now? How much do they want to earn? What does their investment portfolio look like right now in terms of long longevity and kind of really that up? Because when you understand what you need in terms of monetary pay from an employer, that helps you figure out what you’re looking for, whether it’s a full-time position, a contract position, whether you have the wherewithal to start your own business.

I mean, if you’re financially fit and that’s second piece of my fitness program, if you’re financially fit, you’re nimble, you have the ability to try things out, maybe see if this is going to work. If this isn’t going to work, it gives you the chance to explore a little bit and try some things. You’re not stuck in having to earn a certain amount of money in order to pay the mortgage or whatever, pay off credit card debts. So, if you can really get lean and mean before you make a transition, whether it’s starting your own business or moving to a new field, you’re way ahead of the game.

And so, that means, really looking at that balance sheet, looking at your budget, where can you cut back? Where can you pay down some debt? Can you relocate to where the cost of living is a little bit less? It depends on your age and your circumstances, but can you pay down some of those big debts? And this takes times, it’s a process. Career transition and entrepreneurship are a process. It doesn’t happen overnight. It’s a period of exploration and really doing your time.

But I think having someone like you on their team is important because people need to know, what am I working with here? I mean, because to start your own business, you may need startup capital, most of it is self-funded. And you may not be able to pay yourself for about a year or so until the business because you’re reinvesting back in your business. And again, starting a business is a lot easier today because you don’t need bricks and mortar. You can do it virtually on your computer. You can hire virtual those contract workers. You don’t need a full-time staff.

So, the opportunities are tremendous, but really having that financial eyes wide open is critical to go into this. So, I do think that’s probably one of the most important things that people can do when you’re looking at making these career transitions. But it’s also, you come in and they say they don’t know whether– okay, you’re not a career coach. They need to find a career coach. And I do think career coaching is fabulous, and it doesn’t have to cost a lot of money. Again, these job centers that I mentioned, the Department of Labor has often offered career coaching. Sometimes, employers if you’ve been laid off or you took an early retirement package, also link you up with a career coach.

But if you can find somebody who’s unbiased, who does not know you, who can look at what you’ve done and kind of talk to you and get to kind of tease out the things that you love and let you explore a little bit, it gives you that chance to kind of go, oh yeah, I forgot that I’m good at that because a lot of these things we take for granted that we do that were really exceptional at, but we think, ehh, I’ve always done that, but in fact, you can pull that out and push it in a new direction, but you often need that cheerleader or that person to look at you. Your friends and family are going to do this. Trust me. Maybe they’ll help a little bit, but it’s good to have somebody who can come at it from a clear-eyed perspective.

Casey Weade: Well, there are a couple of big takeaways there. I mean, the one thing that I love is just try things, I heard you say, just try things. And that’s the beauty of this stage of your life. If you have the finances, if you have those first two steps that you talked about, your health and your finances nailed down, then that opens up the opportunity for something that one of our past podcast guests, Dean Niewolny, from the Halftime Institute called low-cost probes. You have the opportunity to do some probing.

The second thing you said there was work with somebody on this that doesn’t know you. I don’t think that would be what most would do. Your first stop is usually your friends and loved ones, the ones that know you the most. And even in some of the past guests we’ve had, I recently did this with a bunch of my closest friends. I sent an email out and I said, “Hey, what do you think my calling is?” And now, I hear you say, I probably should have emailed that to a bunch of random people.

Kerry Hannon: No, no, no, that’s okay. I mean, I think it’s fine that you do your friends because they will be thoughtful about it and they will recognize things in you that you take for granted, without question. But I think when you want somebody to kind of look down at everything, looking at your resume, looking at your past experience, the whole thing, it’s good to have somebody who can kind of help you walk through some of that and talk about that financial piece as well with you. How important is that? How much time do you want to devote to what you’re going to do next and really pull it all apart?

No, I don’t think you did the wrong thing there at all. I’m just saying you need kind of the combo of the two. Another exercise I love to do with people is this is kind of fun, you get them to talk about what their first job was, maybe just inevitably, they’ll start laughing. Like, right now, I’m thinking of my first job, real job was I sold Avon. Okay, so hilarious. I was super shy. And here I am going door to door. I mean, people don’t do that anymore, but believe me, we did do that and I was terrified. But whenever I made that human connection with somebody, I was like high off of it. It was fantastic. It wasn’t the sale, I didn’t care about that. It was the meeting of the person. And so, when I tease out what was it about that first job that really pushed me to get me out of my comfort zone, that’s something to remember when you’re looking for a job.

Secondly, I discovered something that really makes me happy. It’s a human connection and throughout my career that I’ve held dear to, I mean, I love to interview people. I love sitting here talking to you and being interviewed because it’s making a connection. I wish we were in person together because there’s something magical that happens when two human beings start engaging together in some sort of intellectual discussion or whatever it might be or fun. But truthfully, I love telling people stories. I love to hear about a guy who was with the Navy for his whole career and when he retired, he ran away with the circus. Oh, my gosh. Can you imagine how much fun is that?

Someone who was a botany teacher and then she became a chocolatier and I’m like, whoa, how did you go about doing that? And then, there are more serious ones perhaps, but of course, running a circus and being the circus manager was actually a very big job for this guy. But I just think, I don’t know. And I laughed with him. I remember asking, his name is Dan Covington, he took over as the company manager for the Big Apple Circus going up and down the East Coast. His wife was a nurse. She became the wardrobe manager there.

And I said, “Dan, this has nothing to do with the military.” And he’s like, “Oh, yes, it does.” He goes, “I redeployed a lot of those skills about the logistics of moving people from A to B, and how do I organize this?” And a lot of this is leadership skills he took from his military career, really played out nicely in something for a kid. He loved the circus since he’s a little kid in Baltimore, and everywhere he was deployed, he went to the circus. So, now, he’s doing circus stuff. So, I just got to say, open up, and when you tease out what about your first job or something you love the most and find out, can I find ways to replicate that? And what I’m going to do next?

Casey Weade: Well, what I often find when I’m having conversations with new individuals that don’t really know me that well, they might ask me some of those questions that can lead me down that path when everyone else already knows what you did when you were a little kid. They don’t really put as much emphasis on the importance of what that is and how to bring that forward into your life. And talking to someone that doesn’t have some of those biases, they might lead you down a path of asking some questions that you might just gloss over if it was someone you really knew well, such as joining the circus, might have been missed by someone else. I think we’d be remiss if we didn’t make a segue into women’s finances. And in order to make that, I think a good transition could be women’s careers and how women’s careers have been uniquely affected over the last couple of years since the COVID pandemic.

Kerry Hannon: Yeah, it’s been enormous, right? The number of women who did step out of the workplace and as you mentioned, the great resignation, but it was because it was untenable, really. And this is huge. And women had begun to make very big strides in the workplace. And this stepping back is sort of concerning. But what I do see is employers reaching out and finding ways. And again, I do think remote work, once again, it’s not remote exactly. Flexibility is what people want. It’s not necessarily that they don’t want to go to the office. Going to the office is fine, and there is a lot of great benefits to doing that.

But having flexible hours, the ability to, if you’re caregiving for somebody, an aging parent, a relative, or a child, that you can flex your time around to work in hours that really suit being able to do both. And I think employers are really getting much more, I think, coming out of the pandemic, they’re more empathetic to that, and also the need in order to create those situations for women to be in the workplace. But what has happened is, I am stating the obvious, but women’s pay has really not changed that much. In certain levels, certain positions, there’s equity. And I think a lot of my nieces and nephews in their 20s and early 30s, they say they think pay equity is just dandy. But I’ll wait to see what happens as they move up into the work world.

When women step out of the workplace as traditionally they did to raise families or what have you, they’d be out five or six years, they lost their way in many times. And it was hard, too. So, this pay gap of what is it, 80 cents on the dollar, but I think it’s much worse for different ethnicities, what we’re seeing there. So, that’s something you combat because not only are you making less, but you’re setting aside less for retirement because you’re making less.

And also, women tend to work in small businesses or nonprofits that might not have robust employer-provided retirement plans and having to save or doing contract work, which again, I’m a big fan of, but it’s also not great if you’re trying to set aside money for your future. And I often say it’s not saving for retirement, it’s saving for your life. And the fact is, if you don’t have an employer automatically investing you in something, directing your money in some place, you often don’t do it. So, I get very concerned that women still need to be extra proactive about these things and taking control of that. So, I think those are some of the big issues.

But also, there’s still longevity. Women still tend to live longer than men. I do think that is narrowing a bit. And then there’s sort of this other theme that women often will marry somebody older than them or their partner is older than them. And at the end of life, they may be widowed or they may be alone in some way. And a lot of the medical expenses taken up by an older partner suck away the financial wherewithal of a family so women can be left in a bad situation.

Casey Weade: You might give us one challenge. Are you going to give us another one here?

Kerry Hannon: I’m sorry, no, the other thing I was going to say. And we can talk more about that is ageism for women. It’s ageism and it’s lookism, right? So, it’s a lot to do with the– when I mentioned that Botox and gray hair and women, yeah, that’s a real thing.

Casey Weade: I just see pay gap, child-rearing type of role, older partners, aging, longevity. There’s a lot of stuff there. There’s a lot of things that are big risks for women’s finances.

Kerry Hannon: Yeah, and women have to be tougher negotiators. And we often don’t start from the very beginning in a job asking for more money. And that sets you up for the whole time, that sets you up for your next raises for how much you can set aside for retirement. So, truthfully, right from the beginning, women have to be fairly hard-nosed.

I used to, when I was younger, I would change jobs every five years because I knew I was making less than the guys and I would find a guy at it where I was headed and kind of somehow get him to tell me how much he was making, and I would go in and negotiate for that. Now, I don’t know how open people are today about talking about salaries, but I do think pay transparency is a big issue, and it can really be fabulous for women as we see more of this rolling out that the states are often taking a look at this in terms of hiring process. So, that’s important.

The other thing I got to say quickly, Casey, is that women tend to take on in the workplace a lot of non-promotable work. And there’s a great book out there right now by these Carnegie Mellon professors called The No Club. And it’s because women have to learn to say no because it’s not that their managers are so terrible and asking them to do this work that’s non-promotable, like planning the company picnic or something, but the fact is that women tend to end up doing that. It’s expected that they’ll get it done or doing the onboarding for a new employee, or even I got to say, being in charge of diversity efforts at a company, if it doesn’t apply to the bottom line, it might not be a promotable thing if it’s not a metric that can be measured.

So, what I’m saying is I love that book, by the way, but I do think that there’s something here that women need to really own in a way. And I’m very hopeful that the younger generations are doing this. But in my generation, it wasn’t. And so, that’s why I’m saying women over 50 tend to really be still butting up against some of these things.

Casey Weade: Well, I think I’m going to get a positive takeaway from you out of this next one here. And that is when I was looking at your bio, I saw that a key passion for Kerry is helping and advising women on how to take charge of their own financial planning. So, what trends are you seeing here? Are women taking more charge of their financial well-being than what we’ve seen in years past?

Kerry Hannon: Absolutely. And I’m not sure what is driving this, but I am seeing this for sure, and a lot of it, and I will just say younger women in particular seem to be getting a grip on this much sooner. And I still worry that younger workers, that there are still some roadblocks here, but in fact, I think there is a sort of reality that people need to take control of these things. And the message is getting through, I do think it is. And I hope you’re seeing this as well.

And I just think it’s imperative that it continues because it used to be this. And I’ll still meet women who do this and go, oh, I’m not good at math or it just bores me or, oh, stop it. It’s not that complicated and it doesn’t bore them. They just don’t understand the language. And right now, there are so many great ways to educate yourself online to learn about these things or some great websites that it’s really opening up the window for women to say, okay, yeah, I know I got to take control of this. And they are. And it’s so empowering. I just love seeing this.

Casey Weade: Well, now, we’re hearing and seeing more men say those things, ah, it’s not my thing. She takes care of that.

Kerry Hannon: Yeah, it’s okay. Okay, I’m all right with that.

Casey Weade: Which I love to see it. I love to see that, especially, I mean, more than anything, just taking in the longevity factors into consideration. We know who we’re going to be working with someday. I think it’s 85% of women or men, they married, I mean, someday.

Kerry Hannon: Women will be single, yeah.

Casey Weade: Someday, they’ll be taking over those finances.

Kerry Hannon: Yeah, no, without question. They need to understand where everything is. And this is not a great example, and I’m not being a downer here, but like when my younger brother passed away a couple of years ago, he was 55, his wife knew nothing about the finances. She didn’t even have a bank account. She didn’t in her name. She didn’t know how to use an ATM card. She didn’t know where the bills were. I mean, it was mind-boggling. I’m like, in my own family.

And so, I’ve done a lot in our family circle, have really worked to educate her, and she’s okay. But I’ve just oh, my gosh. So, I do think there are these pockets. So, if in your families, people, like I tell women join you, put together a little money circle of your friends, just a couple of them. And you keep yourself accountable to keeping, learning or staying involved. Women love to talk about some kinds of things that involve money. So, why don’t bring it into investing topics or insurance and those kinds of things that impact our day-to-day lives.

Casey Weade: Well, and you wrote an article not long ago sharing some of the statistics around women’s finances, particularly the advantages that women often have over men. Men don’t have all of the strengths that women have. Women don’t have all the strengths that men have. I mean, it goes both ways. But there has been some research, if you could share some of that with us around the advantages that women have when it comes to personal finance?

Kerry Hannon: Yeah. Thank you for asking that. I think it’s so true. And I love to tell women, come on. See, here’s the thing is, women are fabulous investors. And why they’re really good investors, and studies have shown that if you do, you show it to two. I think Vanguard get it, looking at two 401(k) plans, women’s and men’s. And they looked at them and the women outperformed the men because of this. Women do their homework. They go slow. They don’t make rash decisions. They don’t trade in and out of all the latest, greatest, hottest thing that they can invest in. They stay the course. They really have a way of, and they’re getting better at this. Women now say, I don’t know, and they’re not afraid to ask.

They used to be afraid to ask, maybe their advisor or whatever because they didn’t want to seem stupid or they didn’t want to be talked down to. But I think there’s been a real movement of advisors and maybe more women financial advisors have come in, and people like yourself are really sensitive to this. Let’s say, they listen. They say, no question is too dumb. Ask me, ask me.

And so, women are getting a lot more, and women like to ask questions because they want to know and they want to do their homework. So, these things really help women be very good investors. And they also tend to invest when they think about their finances for something, like they have something in mind, whether it’s a trip or something in the future. They visualize what they’re saving for. There’s something beautiful about that because when you can put an image on...

Casey Weade: You don’t see as many women, if I may, looking at their net worth as a scorecard. There’s more meaning...

Kerry Hannon: Yes. Oh, my God, you miss the big one. You were so right. Thank you, Casey. Bingo. That’s it. It’s not a game. It’s not a game, it’s not a competition. It’s really an individual pursuit.

Casey Weade: Yeah, it’s a beautiful thing. And I think a lot of the times, for these women that want to get involved in the personal finances, most of them are maybe in a situation where they’re married and they’ve had somebody else that’s been managing those finances for them. And now, they go, all right, well, I listen to Kerry. And she said I need to get involved in this. And I wonder if we could get into this by referencing an article you wrote for MarketWatch last year where you referenced the marriage as a business relationship.

Kerry Hannon: My husband always hates that one, but I think it’s true.

Casey Weade: I don’t know how many people are going to do it, though.

Kerry Hannon: But at the very core of it, that’s what marriage is. It’s a partnership. So, it’s a business partnership and you’re both accountable and there’s got to be transparency. And yeah, you’re each going to have different things you might want to spend on or save for or invest in, but it needs to be a respectful conversation and it’s got to be on the table. There can’t be any secrets, really. So, I do this thing, and a lot of women I know are doing this too, and men, we try to have money dates with our partners. And I tell you, I get a stomach ache over the whole thing. But every time I do it, I’m glad we do.

Casey Weade: I’m surprised.

Kerry Hannon: Well, because I have different hobbies than my husband does and mine are expensive. So, I sometimes don’t need to want to share all of that, but you need to sit down and say, okay, we got these things coming up in the next couple of months. We’ve got a wedding to go to. We got to buy presents. We got to travel. Everything, you don’t do lay out your Excel spreadsheet, but you need to be open about what expenses are ahead. With cash, even with investments, the markets have been pretty volatile, like talk about it. You have to sit in a vacuum to say should we be doing anything? How is this impacting us in any way?

Casey Weade: You’ve been focused on money over the last three decades, so you are in a unique position here. And I find that all the research I’ve done, all the articles that I read, all the people that I interview, sometimes those things are imparted on me, and I end up doing some strange things when it comes to money and finance. And I wonder for yourself, do you have any– I mean, doing a money date with your spouse is pretty unusual, right? Not a lot of folks are doing that. We’ve incorporated that into our marriage. And I wonder if you’ve found that you’ve picked up any other strange money habits over the year, unique money habits for yourself?

Kerry Hannon: Well, I do. And I don’t know if it’s unique, but I encourage women to have credit in their own names, obviously, your own credit card, your own bank account. I mean, we have joint accounts, but my retirement money’s in my name and I have my own checking and savings accounts. Now, true, I run my own business for 20 years. So, that’s important. But you need to have your own resources and have that sense of you’re in control of that part of your thing, and it’s imperative.

So, every dime I spend on, okay, I’ll admit, my passion is horses. So, that’s something that my husband doesn’t necessarily share in the same way. So, I don’t have to approve everything I spend with him. We have sort of this understanding. So, again, don’t hide things, but also respect each other’s. Yeah, I’m earning X, this is what I’m doing with this portion of this. And set some guardrails.

Casey Weade: Yeah, that’s great. Kerry. As we bring the conversation to the close, I want to ask you a very philosophical question. And you can integrate this with your own retirement or just your philosophy around retirement. You’re on the Retire With Purpose podcast. What does that mean to you? What does retire with purpose mean to Kerry?

Kerry Hannon: Well, here’s the thing. I’m not crazy about the word retire because I think that seems like you’re stepping backwards or you’re withdrawing. So, I don’t know what the proper word is, but I do think this is a period of life if you are stepping away from a primary career in which you stay engaged in the world in some way, whether it’s for money or not, although I think earning a little money is always great. But you can’t just step back and not be involved in the world, you need to stay engaged in doing something that matters. That’s what keeps us, that’s our humanity, and that’s what makes life special.

So, try to spend, be thoughtful about how you’re going to use this chapter of your life, whether it’s a mix of work and travel and giving back, whatever it is. But instead of retire, and I’m not going to say we fire, but think of it as a way of redirecting your energy. Instead of stepping away from the world, step into the world. Retire, one expression, I think maybe even Chris has used this, Chris Farrell with you, is retire to something, don’t retire from something.

Casey Weade: Sure. Well, that’s beautiful. And I hope that so many are really listening closely to that. You can check out Kerry at or you can also check out her YouTube channel. You got a new YouTube show, a new podcast show out right now, The Second Act Show. Great podcast, great conversations happening over there. So, if you want to dive deeper into that particular topic, that’s a great resource.

Also, we want to give away Kerry’s book, In Control at 50+: How to Succeed in the New World of Work. If you’re watching on YouTube, you see it right there over Kerry’s shoulder. And we’re going to be giving that away for those of you that write an honest rating and review the podcast over on iTunes. Just write us an honest rating and review over there and then shoot us an email at [email protected] with your iTunes username, and we’ll send the book out to you for free. Kerry, thank you so much for joining us here on the podcast. It’s been a true pleasure.

Kerry Hannon: Thank you, Casey. Loved it.