The author and ‘workplace futurist’ discusses how people born between 1965-80 can improve their retirement wherewithal, the viability of Social Security for this generation, and the benefits and limitations of working longer.
Our guest on the podcast today is Kerry Hannon. Kerry is a senior columnist and on-air expert for Yahoo Finance and writes about retirement, jobs, career transitions, entrepreneurship, leadership, and personal finance. She has written 14 books about retirement, careers, and personal finance and is co-author of a new book, Retirement Bites: A Gen X Guide to Securing Your Financial Future. Kerry is a former columnist and contributor for The New York Times, MarketWatch, Forbes, PBS, and AARP. She graduated from Duke University.
Retirement Bites: A Gen X Guide to Securing Your Financial Future, by Kerry Hannon and Janna Herron
“401(k) Savers Stayed Strong Through Market Volatility, Fidelity Found,” Video interview with Kerry Hannon, kerryhannon.com, June 15, 2025.
“Experts Caution Adding Private Assets Like Crypto to 401(k)s,” Video interview with Kerry Hannon, kerryhannon.com, Aug. 17, 2025.
“Retirement Savers Are Eager to Invest in Private Assets, New Survey Finds,” by Kerry Hannon, yahoofinance.com, Aug. 25, 2025.
“Robust Returns and Steady Saving Yield Record Number of 401(k) Millionaires,” by Kerry Hannon, yahoofinance.com, Sept. 13, 2025.
“401(k) Savers Play It Safe, Even as Demand for Private Assets Surge,” by Kerry Hannon, yahoofinance.com, Sept. 9, 2025.
“An Increasing Number of Americans Are Claiming Social Security Early This Year. What’s Up?” Video interview with Kerry Hannon, kerryhannon.com, May 14, 2025.
“Some Retirees Will See Bump in Social Security Benefits in April,” Video interview with Kerry Hannon, kerryhannon.com, March 26, 2025.
“Social Security Benefits Will Rise 2.5% in 2025,” by Kerry Hannon, yahoofinance.com, Oct. 13, 2024.
“How to Build Your Own Target-Date Retirement Fund,” by Kerry Hannon, yahoofinance.com, Feb. 15, 2025.
“2025 Target-Date Fund Investment Strategy,” Morningstar.com.
“Americans’ Retirement Vehicle of Choice Just Topped $4 Trillion,” Video interview with Kerry Hannon, kerryhannon.com, May 21, 2025.
“More Men Are Returning to the Office. Here’s Why That Matters to Women,” by Kerry Hannon, yahoofinance.com, July 20, 2025.
“Author: Getting Employees Back to the Office Is at an “Inflection Point,'” by Kerry Hannon, yahoofinance.com, Aug. 24, 2025.
“Changing Jobs Can Shake-Up Saving for Retirement. Here’s How to Avoid That,” Video interview with Kerry Hannon, kerryhannon.com, May 3, 2025.
Reality Bites (1994 movie)
“Beyond the Status Quo: A Critical Assessment of Lifecycle Investment Advice,” by Scott Cederburg, Aizhan Anarkulova, and Michael S. O’Doherty, papers.ssrn.com, July 10, 2025 (revised).
“How Americans View Their Jobs,” by Juliana Menasce Horowitz and Kim Parker, pewresearch.org, March 30, 2023.
“Kerry Hannon: Remote Work Trend Benefits Older Workers,” The Long View podcast, Morningstar.com, Oct. 21, 2020.
(Please stay tuned for important disclosure information at the conclusion of this episode.)
Amy Arnott: Hi and welcome to The Long View. I’m Amy Arnott, portfolio strategist for Morningstar.
Christine Benz: And I’m Christine Benz, director of personal finance and retirement planning for Morningstar.
Arnott: Our guest on the podcast today is Kerry Hannon. Kerry is a senior columnist and on-air expert for Yahoo Finance and writes about retirement, jobs, career transitions, entrepreneurship, leadership, and personal finance. She has written 14 books about retirement, careers, and personal finance and is co-author of a new book, Retirement Bites: A Gen X Guide to Securing Your Financial Future. Kerry is a former columnist and contributor for The New York Times, MarketWatch, Forbes, PBS, and AARP. She graduated from Duke University.
Kerry, welcome to The Long View.
Hannon: Oh, terrific to be here. Thanks for the invitation.
Arnott: Well, we’re glad you could join us. You’re a very prolific writer and you’ve written 14 other books in addition to your regular job at Yahoo Finance. Why did you decide to write a book focusing on retirement issues for Gen X? And I guess we should specify at the beginning that that spans the range of people born between 1965 and 1980.
Hannon: So, I have a backstory of this is that I wrote a series of columns about Gen X being woefully behind in their retirement savings based on variety of reports and surveys I had been eyeballing, and you just cannot imagine the response I got. We had millions of views on Yahoo Finance globally on this and thousands and thousands of comments, and I said to my editor, I said, “You know, guess what? We’ve got a book here.” And so, my agent of course was like, well, who else has written about Gen X and retirement? And when I did a search, absolutely nobody had written a book about Gen X and retirement. And so, there was this opportunity to kind of explore what was going on with this specific generation of mostly Americans that I focused on but individuals who everyone thinks of them as this sandwich generation, between the massive boomer generation and the millennials, and this is a crew that had certain economic headwinds. And so, it was an opportunity to jump into this and really say, hey guys, we got your back.
Benz: So, before we get into the substance of that, Kerry, we noticed that the book sprinkles in a lot of pop culture references that Gen Xers can relate to from the 1980s and ‘90s. In fact, the title I think relates to that movie, Reality Bites, right? I remember the soundtrack with Lisa Loeb. I loved it. I had it on CD. Did you always envision that this book would have a humorous, kind of more accessible tone?
Hannon: Yes. And I think that’s what this generation looks for. This is a generation that has just done it themselves. They are the kids that their moms and dads are at work, they kind of made up their own way, and they always had an attitude of some sort. Maybe the buzzword was slackers, but I’m not saying slackers. It’s just pretty independent thinkers and we wanted to have some fun with it. There was a lot of great cultural references we could go to from music to movies to books. And so, yeah, I think that’s an opportunity because you both know that sitting down and reading a book about personal finance and retirement is not really a go-to for most people. So, let’s try to make it a little fun. It’s not paint by numbers, but we can make it kind of fun by just touching into how they can relate to why they’re at this juncture in their life and what they can do in sort of a proactive way.
Arnott: Yeah. I love the fact that it’s a pretty fun read, but you also get across a lot of really helpful and practical information. So that’s a nice combination. What makes retirement especially challenging for this generation and why are people in Gen X so much less confident about their retirement prospects than other generations?
Hannon: Those are really great questions, and it takes some understanding about for this group of individuals when they entered the job market 401(k) were really just starting. It was very, very new and now we know not everyone had traditional pensions in America, but it was sort of the stepping down of that opportunity for saving for retirement that maybe their previous generation or their parents had available to them, to really a do-it-yourself retirement operation and nobody had the tools to figure out how to do that. Or even given much financial education about what they needed to do, starting quite early to sock away money for that time way down the road that was called retirement.
So, as 401(k)s inched onto the scene, we didn’t understand what they were. There weren’t a lot of investment options and there wasn’t a lot of money you could even put aside in them at that time. And so, there was that issue. So, for the first generation that truly has to own the 401(k) as their method of retirement savings, this has been pretty daunting. And if you didn’t start in your 20s, the statistics show that Gen X started somewhere like in their early 30s to save for retirement where we have millennials in Gen Z starting much, much earlier because of auto-enrollment that a lot of employers now enable people to jump into retirement savings without having to actually make that conscious decision. They can opt out of course. So, I think they had that happening.
There were several economic shifts and jolts along the way. There was the tech boom and bust. There was the recession. There were lots of times where any assets they did have invested really took a slam. And then there’s a generation that is caught between right now dealing with aging parents and kids and so they’re torn by where their loyalties should be. Where should I be putting my money? These are very hard decisions that you need to sit down and talk to your kids and talk to your parents about, but it’s hard to have those kinds of discussions. And as a result, this generation tended, and does today, have very high credit card debt and high student loans, and these are issues that are pretty tough to tackle, and they need to pay attention to it. So, when you’re struggling with debt and not knowing how to be paying down debt or saving for retirement, well, this can be quite hard for people to deal with. So, there’s a lot of issues along the way that make people a little less confident. It’s something that retirement just seems so far away and now with the first Gen Xer—or the oldest Gen Xer, I should say—turning 60 in 2025, the time is here. The youngest is still in their 40s and so there’s plenty of time and runway ahead, but the pedal to the metal is here.
Benz: Kerry, are there any areas where Gen X is actually doing all right because they have had a pretty good market environment at least since the global financial crisis? Are there any metrics where Gen X is thriving?
Hannon: I do love that. And anytime we talk about retirement—you both know this—it’s such an individual thing. It’s hard to be general. So, when we look at Gen X, we often say, “in general,” or “on average,” or “the median,” and all those things. So, there are pockets of folks that really did get ahead of the game. They really have stayed invested in equities. They have ridden the growth in the market. They’ve been stuck to their knitting as the market jumped around a bit. So, some people really have had some success doing that and that’s really quite good.
One other really positive thing I should note is home equity. The thing is, Gen X really has quite—as a generation and we look at it as a whole—have quite a bit of equity built up in their housing and in their homes. This is a really good thing we hope moving forward because to have that ability to tap that asset, so whether they got it started a bit late with their retirement planning, whether they didn’t quite always understand the importance of socking away as much as they possibly could, take advantage of the employer match and so forth, they were buying homes. And so, this, I think, will serve many of them in good stead moving forward.
Benz: Kerry, you mentioned auto-enrollment as a benevolent force, especially for the younger age cohorts. When you think about Gen X, are there any regulatory changes you’d like to see related to 401(k) plans, for example, an increase in the contribution limit, any other sort of additions that you would like to see to how we deal with retirement plan contributions?
Hannon: Yeah, I do think, Christine, I think it would be amazing to be able, and Amy, to have a little more in terms of oomph, of what we can contribute to these accounts. Yes, it is—if you’re in an employer-provided plan, they can be fairly generous. But employer matches depending on how the economy is going—of late employers have been trimming back some of their matching contributions, and it would be nice to see a little bit more that people could set aside in these plans. And perhaps—and I don’t know, this is a tricky one—make it a little bit harder for people to use it as a piggy bank, because it has gotten pretty easy to take a loan from your 401(k) or to make a withdrawal for various hardships, and I do think that should be an avenue for people, but you don’t want it so easy that it becomes just an emergency fund instead of what it’s intended to be, which is a long-range investment.
Benz: Right. With people changing jobs so frequently, and it seems like as you look down the age bands, you see that more and more among younger savers. But as people change jobs more and more, it seems like there’s more opportunity for that kind of leakage from the 401(k) plans.
Hannon: I think definitely as people move around and even at this generation we’re going to see with people tending—and we can get into this a little bit later—but stretching out their working years while they may step away from a primary employer where they built up a 401(k), they may move elsewhere where they start another 401(k) or they roll this over into an individual retirement account. And one thing that I think people don’t understand and need more education is when you do roll over your 401(k) when you change jobs or you step away from the workplace into an individual retirement account, you need to then make some investment decisions. It’s not going to roll over in exactly those same investments that you had in your 401(k). And a lot of people get stuck with that money put into maybe cash accounts and that sort of stuff without the realization that they need to take some action here and really set up a plan for themselves. So, I think that we have an issue with leakage. It’s getting better. People have started to pay attention to how this works and making sure when people shift jobs that they know they can perhaps leave it right there at that former employer, they can maybe even take it to the new employer, roll it over to that plan, which isn’t as likely or shift to putting it into their own individual retirement account. But I do think there needs to be some more clarity for many, especially Gen Xers who may be facing this sooner rather than later.
Benz: And it’s usually kind of a multistep process as far as I understand it. When you roll over, you have to wait for the transfer of funds before you can make any allocations and so then the money often lingers in cash.
Arnott: We also wanted to talk a bit about Social Security and how that relates to retirement spending. You mentioned in the book that about 55% of Gen Xers aren’t convinced that Social Security will be there when they need it. Is that kind of concern overblown in your opinion?
Hannon: Oh gosh, I know Social Security is such a hot-button issue. It has been for many years now because we know that the pending time when the funds are going to be depleted and Social Security, the trustees’ report says, unless something gets done its benefits will be trimmed back to 70% to 80% of what the full benefit should be. It’s so hard to know whether Congress is going to act and what changes may come down with Social Security. But I have to say in my heart and maybe I’m just an upbeat kind of gal, but I tend to think that Social Security is going to be there.
Is there a concern? Yeah, because there’s not as many younger workers coming up to pay into the system and more older individual seniors needing to tap that benefit now. So, it’s a quite clear economic challenge that the Social Security Administration is facing in terms of how these benefits are going to get paid out because of the way the system is set up. But I would find it super hard to believe that it’s going to go away. And I would love to hear what you two think about this, but it is really something that people—in fact it’s good advice maybe not to even plan for it if that’s how you want to deal with it, but I do think it will be there for people. Potentially it may be a slightly reduced benefit they may tweak when you have access to it, which is of the cut in itself, but we’ll see.
Benz: I have a financial planner friend who said that younger clients especially would often ask him to remove Social Security from his planning calculations, and then when they would see the implications for their savings rate, they’re like, OK, put it back in because they didn’t like the implications of the heroic savings that they need to do between then and retirement. But I do tend to agree with you, Kerry, in terms of the people at this life stage, they’re not that young anymore. They’re pretty close to, or getting close to, being eligible to take benefits and it seems hard to believe that the rules would change for them, but I guess never say never.
Arnott: Yeah, it seems kind of politically untenable for major changes to the benefit program, but I guess we’ll see.
Benz: Right. Kerry, we wanted to ask about delaying Social Security because in financial-planning circles you hear that if you can, you should try to delay Social Security even up until age 70. Can you talk about the implications if you need to withdraw from your portfolio during that period while you’re waiting to take Social Security? How should people think about that?
Hannon: Again, this is an individual choice. It’s hard to say what’s right for everyone. But in general, if you have the ability and you have the savings, let’s start with savings outside of your retirement accounts, which many people do have built up substantial amounts or at least enough that could tie them over for as long as they can, certainly you can start your Social Security benefit at 62. But the numbers just bear out. If you can wait till age 70, that’s the biggest check you’ll get for the rest of your life, and the fact it’s with longevity—and again, that is again not across the board people living longer lives—but it is definitely a movement up that people could have.
If you step out of the workplace at 65, or you start your benefit at 62, or you’re at your full retirement age, you could have three decades living that you need to support your living costs for and if you can get the biggest check at age 70 moving forward you’re going to really come out ahead. That really does truly depend on—and again, if you go to the Social Security website, your my Social Security account, they very clearly show you what your check would be based on your earnings to date, what your check would be at 62, at your full retirement age say 67, and at age 70. And it’s a good example. They show it in a chart that makes it quite eye-popping the difference in those checks.
Yes, so the key is, if you have out savings outside of retirement account, preferably that you can start so that you don’t tap into your retirement portfolio too early. And the other thing that’s possible here is if you can shift into a second act, which we might talk about if you’re earning—if you continue to earn even if you step away from your primary employer, that can be your safety net. Those can be the funds you use for living that you don’t necessarily need to put into a retirement account and you can let that ride for a bit longer until those required minimum distributions kick in and then you have to go for it.
Arnott: So, we’re taping this in early August, and the budget and spending bill was just passed a few weeks ago in July. One of the things we heard a lot of discussion about leading up to the passage of that bill was the notion that Social Security benefits wouldn’t be taxed. Can you clarify if that’s really the case?
Hannon: So, the Social Security Administration sent out emails to everyone saying promises made, promises kept. Social Security we’ve made this so that seniors aren’t going to be taxed on their benefits. But the truth is, that’s not exactly what happened. And what happened was that the bill—which is wonderful on some levels—but what happened is that it enabled seniors to get a tax break, and it’s only temporary. The president signed into law in July that was, it’s a $6,000 boost to senior citizens, your standard deduction from 2025 to 2028, so a new temporary tax break and it’s for filers who are age 65 or older and then it phases out for those who earn over $75,000, $150,000 for couples. So, for a low-income senior, they’re not going to benefit from that. It’s sort of a benefit for upper middle-class seniors. Sure, I mean, that’s lovely. It’s a good thing if you qualify for that to have. But it is a temporary tax deduction. It is not a Social Security tax cut. So, I think that’s where the confusion came into being and I think we need to be clear about that.
Benz: We wanted to shift over to discuss portfolios and asset allocation. We’ve seen some academic papers recently, Scott Cederburg at the University of Arizona, for example, that have concluded that investors should keep 100% of their assets in stocks, both before and even during retirement. What’s your take on that, that more aggressive asset allocation relative to maybe the standard advice that people have gotten used to hearing?
Hannon: Well, I’d say, oh my gosh. I think that’s a pretty heady thing to think about. I do believe that assets in stocks and equities before and after retirement, it needs to be a significant part of your portfolio and it used to be people would think as you shifted more toward your retirement years or into retirement, you really need to ratchet it down. Yes, you need to stay invested. There’s no question equities are the oomph. You’re going to have some volatility. But over time, and as we talked about, you could have three decades to live in that retirement. You need to continue to have growth. But you also need to have some cash positions. You need to have assets that have liquidity that if there is a market turn down, if there’s extreme volatility in some way, that you’re not staying up at night, that you can have your living costs covered for a chunk of time. Some people might say you should have a year. I would say you should have more than that set aside in CDs, money markets, stuff that’s easy to get to and then go for—keep your portfolio balanced, skewed a little more heavily toward stocks than you may have thought you would need to, and so don’t jump out of them entirely, but I think 100% is really risky. And I don’t know, what do you two think?
Benz: I’m more in your camp, Kerry, more of a balanced allocation.
Arnott: Yeah, I think a lot of it depends on the time period you’re looking at and I do worry about hindsight bias that, as Christine mentioned, the market has been so strong for the most part ever since the global financial crisis, and I worry that that might be clouding people’s views a bit and making them overly optimistic on stocks.
Target-date funds get a lot of criticism for either having costs that are too high or being one-size-fits-all and not being customized enough. What’s your take on that, and why do you think target-date funds can still be a good option for people saving for retirement?
Hannon: I absolutely love target-date funds. I think they are the greatest thing going for most investors. They just make it simple. Target-date funds, the fees have come down for them. They’re not as costly as they once were, and I think particularly if they’re in target-date retirement funds that indexed. It is like the retirement vehicle of choice, these target-date funds. I think Morningstar’s numbers show that it is massive. I mean, they’ve just become absolutely massive because most employers—I should say many—but I know like when you talk to the Vanguards of the world, a huge percentage of their retirement savers are in target-date funds because this is what employers tend to default people into if they’re automatically enrolling somebody and if they’re doing an automatic escalation. And target-date funds, they really are set up to kind of do the risk balance that’s going to be suitable for you as you age, and most people have trouble doing this math, figuring it out. It’s a nice way to just have a solid investment portfolio that’s going to age with you so that it will shift from equities to the fixed income as you age. But if you if you are pretty risk tolerant and you’re like, “Hey, yeah, I’m up for having a little more risk in my portfolio. I think I’m going to live a nice long life and I’m really interested in getting as much oomph as I can,” you don’t have to pick a target-date fund that is dated to the year you turn 67, which is what most people do.
Go for one that’s out a little bit further. Or you can shift that number around. There’s not a specific science to this. But I do think that the onset of the target-date fund has made retirement savings really manageable for so many people and it gives them the opportunity to really grow their accounts in a very manageable way and with an eye to volatility and when things get rocky, they automatically adjust over time to make up for, whether one if the equities get way out of whack in relationship to the fixed income, you don’t have to be making those decisions yourself.
Benz: We’re hearing a lot of buzz about adding private capital investment options to 401(k)-plan investment menus. In fact, just today, I think President Trump is signing something that will enable providers to make greater use of crypto, private equity, and so forth. What’s your take on that phenomenon?
Hannon: Yeah. So, right on. The president is expected to sign that executive order today. That’s smoothing the way for 401(k) administrators to include private assets in their plan offerings. Now, these have been allowed in retirement plans before—I mean, currently—and also pension funds have done this for years. But the question is, and what the directive is telling specifically is instructing the Department of Labor and the Securities and Exchange Commission to draft guidance for these defined-contribution plans or 401(k) plans to add these private market investments. So, this could be venture capital, it could be hedge funds, it could be real estate, possibly gold and crypto. And they’ve been able to do it, but nobody really wanted to do it because they don’t understand exactly how to do it. And the big concern is the red flags, as you just mentioned, to retirement savers. It’s a shift really from—and the idea is, oh, this is going to create diversification for people who, due to this longevity and so forth, that to get you one extra oomph away from the plain-vanilla stocks and bonds and really juice up your returns over time. They look at numbers like over a 30-year period.
But they come in lots of different flavors, with lots of different returns and risks. So, an individual investor, if this is in your retirement account, they need to understand those differences, and it’s pretty hard to do. I think we all recall the legendary Fidelity fund manager, Peter Lynch, who used to say, “you need to own what you know.” Well, I can guarantee you most people aren’t going to own what they know if they have private assets in their accounts. And so, unlike stocks and bonds, they’re going to be less liquid. You can’t easily sell those if you need cash over a shorter time horizon. And so, it depends on where you are on that retirement scale. If you’re getting close or you’re going to want to roll your 401(k) over into an IRA, when you change jobs, this liquidity can be a problem for you.
And so, I also think, maybe for some people, 5% if you really want to try this out. But private assets, in many ways, you have the liquidity. Traditionally, they’ve come with pretty high fees. That doesn’t mean they may work to bring those down. But for now, they are expensive. And where mutual fund fees have been coming down dramatically over the last several years. And as we know, fees, most people don’t even think about what fees they’re paying in their mutual fund accounts. And that over time can really, really take a big hit on your ultimate size of your portfolio when you retire because it chips away at it over time. And so, if you aren’t aware of these fees, if they are historically much higher than mutual funds, that can be a problem.
So, I just think it needs to be something pretty—I don’t know. In my opinion, I hate to stumble over this because it’s getting a lot of buzz right now. But I do think that fees are going to really reduce your net returns. And I think not understanding what you’re investing in, I think the possible volatility of these kinds of investments that you’re locked up in, I’m not sure they’re right for an individual investor. And it seems to me that they’re pretty, pretty risky. If you’re sophisticated, why not? Sophisticated investors with higher net worth have been investing in these things for years, and they do have potential to give you some returns. But it really is over a long haul. So, those are my concerns. I’d love to hear what you two think about that as well.
Arnott: I think both of us would kind of fall in the more skeptical camp.
Hannon: Yeah, it’s a bit of an unknown. There is kind of a reason why they haven’t been there before. And I don’t know, I hate to be cynical, but you’ll have to question what’s behind the push.
Arnott: Another section in the book is about managing your career and making career transitions as you get older. And this is a topic you’ve written about extensively in your other books as well. I thought it was interesting that the book mentions a study from the Pew Research Center, indicating that a greater percentage of workers aged 65 and older are actually highly satisfied with their jobs. Why do you think that is?
Hannon: I think older workers—workers over 65—yeah, I’m not the least bit surprised that they’re highly satisfied with their jobs because this is like an amazing time in your career. If you’re extending your working years and you have a job that you really enjoy and that you love, a lot of those major striving moments are behind you. You’re not as caught up in when is the next promotion? And when am I getting that big raise? And a lot of those sort of competitive things that pushed you, pushed you, pushed you as you were a younger worker, it’s quite liberating to be at a point where you go, you know what, I love what I’m doing. I’m valued for my expertise and my experience, and I’m just going for it here. And you have a chance to really focus on what you give to your job and what value added you have instead of worrying about all the stuff around the edges.
And another opportunity here is that the intergenerational workplace, it gets a lot of bad—oh, there’s generational warfare in the office. It’s simply not true. If you are 65 and you are working for a manager who is in their 40s, I can attest it is so much fun because if you respect them and they respect you, it’s a whole new way of looking at work. They see things and problems you may have faced in your previous years in a different light. It’s energizing to work with somebody who has a fresh outlook on things, and they value what you bring to it and there’s sort of this great synergy that comes from having all these generations in the workplace. So, I do think it’s a fantastic time for workers who can really dig in and stay at it. And again, it’s if you love what you do, and I do think that that’s part of that equation.
Benz: I love that, Kerry. And I sense that you really bring that positive attitude to your work. I wanted to ask about the darker side of this, that people might have the best intentions about working longer, they might need to work longer for financial reasons, but when we look at the data, we do see that people tend to retire earlier than they expected. And that happens because of health issues, layoffs, any number of things. What steps can people take to continue working in jobs they like during their 60s or later?
Hannon: Yeah, this is a big topic as we see the boomer generation and the younger boomers extending work lives. And I think the Gen Xers are going to be in the same category. Work is not going to be something that you just turn the key on. But in order to be able, and yes, health issues definitely get in the way of this big plan to keep working longer and layoffs as well. But I think if you start—the key is really to start thinking five years before would be considered a traditional retirement plan for you, what do you want to do next? What would you like to move forward to do and not like what are you moving away from? So this involves like continuing to stay relevant with your skills, staying up to date with your industry, raising your hand if you’re in a work situation where you really love your employer and their mission, raise your hand for workplace-training programs that often go to younger workers, show that you’re interested in trying new things, maybe crossing into another department, shake it up a little bit and look for ways that you can add value there. But the most important thing is keeping your skills up to date, not resting back on your laurels, seeking out to see—now companies aren’t going to do this phased retirement stuff in general blanket across the board. It’s too expensive for them to do that, but they do cherry-pick people. So, look for starting that conversation, within reason, of how you might be able to reduce your time in the office or what it might be.
Also look for what opportunities to work remotely, because coming out of the pandemic, yes, everyone is saying come back to the office, but remote work—the genie is out of the bottle. This is a reality. Workers love remote working; most of them do, and employers understand that it works. And so, as you age, the ability to work remotely does a huge amount to addressing health issues that may have made it difficult for you to go into an office environment, the commute, and so forth if the office isn’t set up for any ways to make your job more comfortable for you to do it. So, I think you need to start thinking about what it is you might want to do, what skills you need to keep sharp, what’s happening in your industry, and also really digging into how remote work can work for you with a variety of things. And be accepting—you know, layoffs are tricky. It’s really hard to—still ageism—to get back into the workplace after a certain age, but contract jobs are popular. So, if you can find a way to work on—it’s always been true, but it’s more so than ever now—to segue into doing contract work, keep your resume alive, doing things like that.
Arnott: I wanted to follow up on the remote work issue. And as you mentioned, remote work is incredibly popular with employees, but I think we have started to see the pendulum swing back in the other direction on the employer side. And some big companies like Starbucks, JPMorgan, and so on, have started pushing their people to come back into the office. And I’m curious to get your thoughts on how that could impact an older worker.
Hannon: I think hybrid is really the name of the game these days, being in the office a bit, having some remote flexibility. The key to really loving your job, for almost anyone, is having autonomy and feeling like you’re in control of your time and when you work and where you work. So, as employers have been asking workers, demanding workers to get back into the office, that’s understandable on one level, but we are still seeing quite a bit of pushback from workers saying, OK, we get that, but let’s see, can we find a way to work around the edges? So, I think we’re going to see more of that.
For an older worker, that’s not such a bad thing. I do think face time is good to a certain extent. It lets people know you’re there and you’re involved. But again, it often may come down to an individual working with your manager and making the case for why you are just as efficient and your performance is just or if not better, working remotely. So, again, it falls in your court to make that case to your employer and that’s just something that you’ll need to pay attention to.
Benz: We wanted to discuss people shifting into retirement. That’s supposed to be a happy life stage, but people often do feel sad and depressed because they’re giving up a key part of their identity. Maybe the term “retirement” too is flawed and that it means I’m going to step back. How can people work through that transition? And I guess a question is, do you have to let yourself kind of grieve the loss of identity before you can move forward? How would you think people should approach it?
Hannon: You’re so spot on there. It’s so true. I mean, retirement really is an outdated concept for many people. And heck, yeah, you’re going to grieve a little bit if you step away because that’s your identity. I mean, you’re relevant. And it happens, I dare say, still more for men than women, your friendships are there. That’s a lot of your network is at the office. And so, it’s really important to say, hey, recognize that there’s a process of letting go. But there’s also, if you have had the opportunity to kind of look forward to what it is that you’re transitioning to and focus more on the to rather than what you’re transitioning from as we sort of talked about, is that going to go.
I am a big fan of working with a coach of some kind, if you can, who can kind of see it from the balcony, really look at you and your lifestyle and help you think about how you might balance your life moving forward to add some of those things that you had to set aside while you were working full speed ahead. But also, you might want to find ways that you can volunteer or continue working for pay on a different wavelength in a different way that really matters to you and allows you to give back or whether it’s traveling you want to do. But there’s a whole variety of buckets as people look at their retirement years. And so, it’s a making a plan. It’s not like going in with your eyes closed. And there’s so many ways that you can start jotting down what are the things that you love to do? What would you like to do more of? It’s a holistic way of looking at retirement. It’s not just about money.
I think work is part of a retirement plan. That’s for me. I think it’s having some way of earning money. If it’s volunteer, that’s great as well, because you’re adding to who you are and you’re feeling part of the world, and it builds your network again. So much in retirement we hear a lot about loneliness. Getting involved, being engaged in the world is critical.
So, yes, you may grieve that change. Often, we hate change in general, but if you look forward to what’s next and maybe have someone to guide you to start focusing on, OK, where do I want to go? And particularly if you might shift to a second act of some kind, following a passion or a dream. Take a little time before you step away to moonlight or volunteer. See if that’s something that’s as dreamy as you think it might be. And how much you might talk to a financial advisor about, you know, are you in a good shape, are you lean and mean, can you actually make a shift to do something where you might have to invest some of your own money and starting a small business if that’s what turns you on, or what are some ways you need to move somewhere where the cost of living is less? There are little ways but mostly paying down debt and getting a clean slate to start this next act with enthusiasm, I think is really important.
But I do, and I know I’m babbling, a gap year is always good. If you can take a gap year to kind of really suss out what it is you want to do. You don’t have to know the minute you step away from work what it is you’re going to do. It’s like a patchwork quilt. You might do something for a couple of years and turn and do something else for the next five years or do a couple of things at the same time. It’s not exclusive like your linear career might have been.
Arnott: I’m curious, is it common for retirees to have a certain vision about what they’d like to do in retirement but maybe find out that things look different after they actually retire and start doing the thing that they thought they wanted to do.
Hannon: I think you’re right. I think that people go, oh, I’m just going to love not having anything to do. Well, seriously, I don’t think that that works, especially if you’re a high energy sort of individual who has been quite successful. But you might get it out of your system, some of the traveling you’d wanted to do and spending time with family. But you’ll reach a point, I think, that you’ll say, OK, so what really is meaningful? And I hear people say that a lot of times, yeah, that first year I just needed to decompress. Everyone’s path is going to be different, but I just needed to go out and not have to do that grind. But then they start thinking, OK, where can I give back? What is it that I can do that’s going to add benefit to my life and hopefully to the world? We see a lot of these sort of encore movements of people getting focused in new directions, but they do tend to hit that pause button initially. And I will add, I recently saw a Gallup study that said that, you know, people are so stressed out about retirement, about having enough money and they’re going to outlive their money. But when they look, they followed a group of people, preretirement and postretirement. And actually, when they got postretirement, they were happier than they ever imagined they would be. So, I think it’s the fear of the unknown on some level of what it’s going to look like in retirement. But when you actually get there, it’s not as bad as you think.
Benz: We really like the idea, which came from the interview with retirement coach, Robert Laura, of making a list of 20 things that you’re curious about pursuing when you retire and taping that to the refrigerator. Is that something you’ve done in your own life, Kerry?
Hannon: I just love that. But see, oh, well, it’s a good question to ask me in my own life, but I don’t actually plan to retire.
Benz: That’s good. That’s good information
Hannon: But that’s because I’m a writer and I sell words for a living. So that’s whether speaking or writing books or columns. And so, I can’t imagine not being a writer and not sharing with the world in that way. And I don’t have to run at as fast a pace as I do today. I can definitely ratchet that down. And I just love it so much. But I do keep photos and images of things I want to spend more time doing or to remind me why I’m working so hard right now. That’s my end goal. So, I think Bob Laura’s look at, what are you curious about? Like what haven’t you had time to do? And having those images in front of you on a regular basis, it can really be inspiring and to help you start to get a little dreamy, but also practical and meet with your financial advisor, whatever, and say, how can I make this work, what do I need to do in order to do that?
I’m a real horse person. And I love the Virginia farmland. And so, I know I want to spend a lot of time doing horsey things and being out in the country and so forth. But that involves, that’s a commitment financially, and I need to make sure I’ve saved appropriately to be able to do that. And so, it gives you this, I think I call it sort of an emotional attachment to your goals. And so, what he is talking about is, when you see that, and you go, oh, yeah, how do I make that work in my life? And how do I connect the dots so that I’m able to do that? And some of it is financial, some of it’s personal. And you work it out. And those things can change over time. It’s not a set-in-stone kind of thing. But I find the dreamers are the ones that get the most out of their retirement years.
Arnott: Another big question people grapple with as they transition into retirement is relocating. If they’ve been tied to a certain city or state because of their job or family, a lot of people start thinking about maybe moving to a different area after they retire. How can people think through that issue and decide if and when they might want to relocate?
Hannon: I think for many people relocating and retirement can be a great idea. But definitely it’s not something you take lightly. I know someone who, she and her husband decided they were going to retire from the Washington, D.C., area down to the Raleigh-Durham area. And they bought land, and they were starting to build a house, but they went down and spent a couple of months renting. And her allergies were just through the roof, and she was miserable. And so, they decided, you know, this is probably not a good place for us to move to. That’s just a real basic thing.
But when you look at where to relocate in retirement, there’s so many factors you need to consider. Yes, cost of living is going to be one, but you also need to know, are you going to be near healthcare, a good medical center? Are you going to be near friends and family in some way? You’re leaving a community you’ve perhaps lived in for some time. Are you going to have connections around you where you’re going to? What kind of transportation is there? How might the area be impacted by climate change? Coastal communities used to be dreamy, but I mean, really, what are your insurance costs likely to be when you live in a place like that? Looking at the tax situation, it’s not just about taxing retirement accounts or taxing income. There are all kinds of taxes, from sales tax on. So, you need to do a really good analysis of the tax situation. So, on and on.
I love college towns for many people because you have cultural—if you want to keep working, there’s often seasonal jobs there. There’s usually a good healthcare center. But again, there’s a pretty good checklist that you need to go through before you jump in. If you can check it out in advance, go and rent before you make these kind of big decisions. And in today’s market, maybe you can find a way that you can buy the next place with cash, and you don’t have a mortgage, and it really frees you up financially.
Benz: Kerry, we wanted to ask what’s next for you. It sounds like you have no plans to retire. You love what you do, but do you have things that are on your checklist that you’d like to accomplish during your professional life?
Hannon: You know, it’s so fun. I don’t know. I get so excited about meeting with people and speaking. I guess I’d like to have more opportunities to reach people in real time, in person. We’ve done so much virtual stuff lately coming out of the pandemic that for me, I get so high off of talking to groups and hearing people’s stories. I love people’s career stories and how they got where they are and so forth. So that would be interesting. So, I’d like to maybe do more public speaking in that way.
I tell you, I’ve written a lot of books, and I have one book, a fiction book. All my books that have been published have been nonfiction. When I was 12 years old, I wrote a fiction book about horses, and I have it all written in a spiral notebook. I have it. I haven’t shown it to anyone, but I tell you, maybe, maybe, maybe, I will write fiction. Who knows?
Arnott: Well, they always say, if you’re thinking about what you want to do later in life, you should look back to what you loved doing as a child. And it sounds like you had a huge passion in both horses and writing even back then.
Hannon: So, all good. But I hopefully will run out this path as long as I can and see where it goes. But it’s always adding to your skill set. I mean, you two both do this too. It’s always like, hey, I’m curious about that. Let me find out a little bit more there. And I think it’s so critical to always be learning new things that keeps you resilient and it keeps you being open to new opportunities. So, this is where you don’t know where you’re going to go¸ but if you stay curious and open, those invitations come to you.
Arnott: Toward the end of the book, you include a list of books and resources about retirement that people can refer to. Are there any resources that in terms of books, podcasts, or blogs that you think are particularly helpful that might not be as widely recognized?
Hannon: Oh my gosh, there really are so many, so many good ones. This podcast is pretty tremendous, obviously, The Long View. But it involves scoping around on what’s going to turn you on. I do think we’re getting more interesting. You think that everyone had tapped out writing about personal finance and retirement and careers, but there’s just a rich mine of new books coming out this year. And I know you’ve had some of the authors on your show as well. And it’s fun just to look at them. I hate to name names because there are just a lot of good ones out there. So, I guess I’d encourage people to pick up the book and look at that list.
Arnott: Well, thank you so much for joining us today, Kerry. We really enjoyed talking with you, and congratulations on the book.
Hannon: Thank you so much. This has been so much fun. I really enjoyed it.
Benz: Thanks so much, Kerry.
Arnott: Thank you for joining us on The Long View. If you could, please take a moment to subscribe to and rate the podcast on Apple, Spotify, or wherever you get your podcasts.
You can follow me on social media at Amy Arnott on LinkedIn.
Benz: And @Christine_Benz on X or Christine Benz on LinkedIn.
Arnott: George Castady is our engineer for the podcast and Kari Greczek produces the show notes each week.
Finally, we’d love to get your feedback. If you have a comment or a guest idea, please email us at TheLongView@Morningstar.com. Until next time, thanks for joining us.
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