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Are you looking for the best deal on a new home? Discover the Dr. Horton home of the Week. With new construction homes now selling in ellensburg from the mid-3002, Dr. Horton has the right home at the best value for you, offering one and two story homes near Central Washington University. Your new home is within reach. So what are you waiting for? Learn more about the Dr. Horton Home of the Week. Tap your screen now or visit Dr. Horton.com and schedule a tour today. Dr. Horton, America's builder and equal Housing opportunity Builder.
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This is all of it. I'm Alison Stewart live from the WNYC studios in soho. Thank you for spending part of your day with us. I'm really grateful that you're here. On today's show, Josh Groban joins us to talk about his new album of classic movie song covers. We'll hear from the stars of the Tony Award winning musical the Lost Boys. And WNY NYC host Tiffany Hansen talks about her debut novel my Name Was Jerry Sass. Plus, we'll head to Staten island to learn about its glorious and abundant parkland as well as the new exhibit at the Staten Island Museum that looks at the role the borough played in American history. That's the plan. So let's get this started with how you'll spend your time, not necessarily your money, in retirement. For most of us, we think about retirement, the primary question is can I afford it? Not what am I going to do with my time when I get there. But now that many people who are retiring from their nine to five jobs are living for decades afterwards, it's something we should start thinking about. Here. Now to talk about it is Brian o'. Connor. He's a writer who covers personal finance. He wrote a piece for the New York Times called you're about to retire when what are you doing for the next 20 or 30 years? Hey, Brian.
C
Hey, Alison. Thank you for having me on.
B
So what made you focus on spending our time versus money?
C
Well, I've been covering personal finance for quite a while. And so I've talked to a lot of financial advisors, a lot of retirement planners. And it was just in this last year or two, as the silver tsunami, as it's called, baby boomers started to retire, planners started mentioning that lifestyle had become the most important question. They were asking people who are getting to retire. I had never heard that before, but it kind of makes sense. If you're going to spend 30 years in retirement, you're going to need to do something in that time and it's going to have a big effect on what you can afford to do and all of the other plans, financial and everything else just need to flow from that.
B
So are we talking about life expectancy changing?
C
Life expectancy is going up for wealthier people and especially whiter people. People in low wage jobs and many minorities do not get that benefit. So, you know, we're not talking about everybody in the United States, all 4 million people who will retire this year. But it is a factor. You can spend easily 20 years in retirement now, whereas maybe in the 70s, maybe you were going to get 15 years.
D
Listeners, we want to hear from you if you're retired, how do you like to spend your time?
B
How did you handle the transition from working to retirement?
D
Retirement Call or text us now at 2124-3396-9221-2433. WNYC. Did you get a part time job? Did you volunteer? What advice would you give someone who's planning for retirement about how they should organize their time, take it day by day, travel, see family? Give us a call or text us now at 2124-3396-9221-2433. WNYC. Joining me is Brian O'. Connor. He wrote a piece for the New York Times called you' what are you going to do for the next 20 to 30 years? As you said, this is a piece for people who can retire either financially or they have their family to live with, people who are really blessed in that way. What surprises people about retiring?
C
Mostly that there are a lot of assumptions that people are making. The stories that I've been doing the last few years for, the times have been we have spent 30 years pretty much just focused on the accumulation, the financial accumulation, investing and setting up that nest egg. And now when people retire, you know, it's not like an E.F. hutton ad on the, you know, Sunday golf tournament. It's there's a lot of decisions to make. There's a lot of financial decisions. You don't just start plucking money out. You have to figure out how you're going to take the money out of which accounts. When are you going to collect Social Security? What's your tax situation going to be? Where do you want to live? And like you said, especially if you're going to work part time, a lot of people, not many, but a significant portion of people who have their dream retirement location will sell the big home, move down there, buy the condo on the beach and then realize, hey, I don't really like it down here or one section of Florida. I was Talking to people who were saying, I can't get a doctor. There's, there's, you know, just nobody taking Medicare patients. I have to drive 90 minutes to find a doctor, you know, and so the same kind of thing can apply financially. If you decide to go back to work, it can be difficult to unwind some of the financial decisions that you've made that can now be effective because you're going to be earning a salary. I think the number one surprise that a lot of people talk about when they retire is that they don't know that their Social Security benefits will most likely be taxable. And this is sort of the gap between what people who grew up and saw their grandparents retire or their parents retirement and what people who retired now. It's not going to be necessarily the, the same thing. And so you've really got to look forward, like, you know, what am I going to do? How am I going to spend my time and make those choices and then make sure that you can support that financially.
D
It's really interesting because in your article, there were some people who, they didn't stop working. They just picked another job or picked a job that they had in their soul they dreamed of doing one day. So is it helpful to think of retirement for some people as sort of like a comma versus the end of working a period?
C
Yeah, yeah, the best. One of the people I talked to said she had had a life coach that she'd worked with in her job who said, you know, you need to plan U 2.0. And so that's really the way to think of it. You know, you might have seen your grandparents, your aunts and uncles. People, you know, would work and then they would start to get kind of run down or they would have a medical condition or something like that. And then, you know, retirement was really kind of a finite experience for them. My own father and grandfather basically just retired when they got got sick. And that's not the case now. Most of people who are retiring are probably arriving at 65 or 67 with some kind of managed medical condition, but it's well under control. So they're not retiring necessarily for health issues. And they're going to have a pretty active segment in that first 10, even 15 years in retirement. In fact, another big surprise is that a lot of people, their first several years of retirement, they actually spend more than when they were working. Really, they think they'll spend less because, well, I don't have to go out to lunch and I don't have to go to the dry cleaner and I don't have to commute and park and all that kind of stuff. But this activity phase has been described as every day is Saturday and that's the day of the week when you spend the most money. You know, they're gonn to get the fancy golf clubs, they're going to take the kids on the Disney cruise, they're you know, whatever it's going to be, there's usually some pent up demand and financial planners really encourage that because you know your health is a wild card. So it's better to do that stuff early on, you know, when you're physically able and quite honestly you're going to have the enthusiasm for it because you know you've been cooped up at work or you know, in the warehouse or wherever it's going to be. You need a reward. You should bust out and have a little fun.
B
Let's read a couple of texts. I retired last year at 71. 30 years, not likely given my family 10 to 15. I'm quite happy with what I'm doing now. Reading, doing puzzles, walking my dog, spending time with my family and friends once in a while travel. I am never bored and do not miss my work life one iota. This says looking forward to retirement. On one one will be in some international travel while enjoying cycling, kayaking at the Jersey shore. The third says I do all the things I enjoyed as a child. Theater, going theater, gardening, hiking, baking. I also volunteer at my Brooklyn Library branch and teach gardening classes for children and adults there. Let's talk to Rita who's calling from New York. Hi Rita, thanks for calling all of it.
E
Well hello, I retired at 57. Not by choice but my job moved to another state state and my husband and I actually did not want to go. So what I did first was rest a liberal collect that unemployment and after that I just took a small part time job. I worked for Meals on Wheel Senior center. We have that in Rockland county or had at the time senior centers. After that when my husband retired we were able to just enjoy life and you know, do local things and a little traveling, a cruise and some of the traveling. But then he passed away six years after he retired. So there I was. What do I do? I actually started a support group through my neighbor website and I'm friends with four women now that we started almost 10 years ago. The the friendship, the support group and I volunteer at my church's thrift shop. That keeps me pretty busy but I'm enjoying myself in terms of keeping very busy I miss my husband more than you can know. But thank God that I do continue to keep very active reading, socializing, have more friends now than I ever did in my life.
D
Thank you so much for calling. She brought up two interesting things, Brian. The first was your social life, because we've heard all of these examples where people say, I'm by myself. I used to see people all the time. And loneliness is really bad for your health.
C
It really is. I mean, Rita just really hit all the points, the positive things that you can do in your planning, which is you want to have a purpose, you want to feel like you contribute, you want to be interacting with people, you want to be learning something new. Those are all things that are going to definitely help your health. They're definitely going to keep you mentally sharper. And, you know, it's great volunteering if you had something you always wanted to do, right? Like if you were going to get a degree in library science, but, you know, you took chemistry to make your parents happy or became a lawyer or whatever. Now you can be a librarian. You can be a theater person with your community theater. You can play in a community orchestra. You know, you can learn to play the banjo. You know, not that anybody should do that, but, I mean, you know, some things can't be helped.
B
I'm gonna read a text to you that's gonna make you laugh. It says, omg, I don't know any men who retired with a plan, and it's pathetic. Women often do community and volunteer work through their lives and have hobbies. The men work and maybe play golf, and there's only so much pickleball and golf a guy can play. The men are bored and boring. They should learn to cook and clean and relieve their wives of 40 years of invisible labor. Sort of a funny text, but I was curious, did you find a gender divide when you were reporting this story?
C
I didn't really report that out. You can sort of think that men are a little bit more under the gun because their tendency is to not live as long as. As the women do. But, yeah, you know, I mean, take it. Take up cooking, for crying out loud. You know, I mean, you got. What are you gonna do all day? And it's. It's really, really all the. All the experts. It's really not healthy to just not have any kind of focus to not be learning anything, you know, I mean, learn French, Come on. You know, it's on YouTube. But, you know, you're not gonna just. You're not just gonna sit around and watch Law and Order reruns and, you know, and be dead in five years. You know, on the other hand, you know, all that volunteering, all that traveling, all that working with support groups and all that wonderful stuff that she's discussed, you know, you will have a point. People think, oh, a 30 year retirement, well, it's not going to be what you have at 65 is not going to, you know, be where you are when you're 95. Sometime between 80 and 85, people start to slow down. You've done all the things, you know, you can't play golf every day. And then, you know, people tend to settle into a little more established lifestyle, which is where having all those new social connections is going to be really important to keep you involved with your community. And then, you know, the other thing that Peter brought up is, you know, a lot of times, one, if you're married, there's only one way that story ends. Yeah, somebody, somebody goes first. And part of the planning is, you know, what will you do? First off, there's a big impact financially that people don't consider. You may lose some Social Security income, you may lose a pension for the people who still have them. And you may not want to, want to stay there. When I was a young reporter in Fort Lauderdale, you know, it always happened that, you know, the husband passed away. They would have a lovely little two bedroom stucco bungalow. The wife would move home, the widow would move home to be near the grandkids, and. And they'd be stuck with this house that nobody kind of really wanted except another retiree. Nobody wants to raise a family in a little house like that. So that's some the planning, but it's also defining these kinds of parts of your life.
D
Let's take a couple more calls. Let's talk to Brenda. Hi, Brenda, thank you so much for calling all of it. We're talking about what you should do when you retire.
E
Hi. I retired in 2002 from Verizon. I had worked for 38 years immediately out of high school, from a clerk to where I was a manager, was divorced, and my son had just graduated from college. So what first thing I decided to do when I retired was I took swimming lessons because I didn't know how to swim at the Y. I also joined Toastmasters because it was something I wanted to do, prove my speaking skills. And I traveled extensively. I've been to Australia, to Africa, to China, blah, blah, blah, blah, blah. And I also, about five years after I was retired, my sister said to me, who was a teacher she said, did you ever think of maybe substituting? So I substituted at a middle school, which was about six blocks from my house until Covid. And I also volunteered at a museum. And I belong to a book club. And when I get off the phone, I'm meeting some friends for lunch.
D
You're living my kind of life. Thanks for calling. Let's talk to Alan. Alan is a regular caller.
C
Yeah, I gotta say, Brenda's a hardy survivor. If she retired and was subbing in middle school, there's probably nothing she can't do.
D
Let's talk to Alan. Alan is a regular caller to this show and he called us from a cruise. He's back in Chelsea. Hi, Alan. It's nice to speak with you.
F
It's great to talk to you too, Alison. This is a great subject for me because I've been retired exactly 10 years. And when I retired, it was from the business world. I was a senior executive. I started a blog. I called it hello Pension, goodbye tension. And it's about living an engaged life in retirement. Hardly anybody is ready for it. You know, they say things like have been said here, like, oh, I'm gonna start reading more or I'll catch up on my TV or something. Boy, you better have a whole bunch of things to do because days are long when you're working for yourself like that. So, for instance, I became an Uber driver. I wanted to see what work felt like from the other end of the work spectrum because I knew what it felt like from the C suite, but I wanted to see what it felt like from the driver's seat. So I did that for about three or four months. And I loved it. I learned. I learned how to do better at it. And then when I was done with that, I became a dasher for doordash. Once again, it's not for the money, it's for the activity. And, you know, what you learn about it. You know, there's many other things. I love cooking. I plan a meal every night. Whether I'm inviting people over or just cooking for myself. I try to make a three course meal. So, you know, it really does come down to the fact that you're working for yourself. And a lot of people never did work for. For themselves. They. They work for somebody else who pretty much told them what to do.
D
And Alan, thank you so much for calling in. Call anytime. This is interesting. It says, retirement has been the happiest phase of my life. I don't call it retirement. I call it rewirement. It took away the distress and I De patterned now I focus on my health. I work part time. I'm dedicated to returning to artwork after 50 years. My first show, solo show, is opening this Friday. This. It's so, yeah, congratulations to them as well. You know, when I was thinking about
B
this, the transition to retirement seems to be a bit hard.
C
Right, right. Because if you, if you haven't planned it, you know, then it's just suddenly one day, you know, hey, I'm not. I'm not going to the office anymore. I'm not talking to the folks anymore. And so, you know, it is going to take a little getting used to. I think one of the big adjustments that people have to make is, you know, it seems it's like, well, I can do anything now. I mean, if you, if you've. If you're one of the privileged people who has enough money, who still has some. Has decent, you know, mobility and everything else, it's kind of scary that you can do anything, you know, I mean, the pressure's off. If you want to take up, you know, I don't know, ballet, you don't have to figure out, how am I going to be a career ballerina. You don't even have to be good at it. You know, there's nobody going to grade you. There's nobody going to fire you. And so it can be a little daunting for people to figure that out. I don't doubt that people are a little bit lost. That's why I think volunteering is a great idea. A couple people have mentioned it, and it is certainly a great way to. To get your feet, to have a schedule, to have a reason to get up. And then, you know, you can start to sort of put together, well, you know, what am I feeling? What am I thinking? What if I. If I could do anything, which I can basically do, what's to stop me? And like I said, you're not going to get fired. And you don't even have to be good at it. You have the freedom to stink at it.
F
Let's talk to you.
C
Go be the world's worst pro bowler.
B
Let's talk to Joyce in Manhattan. Hi, Joyce, thanks for calling, all of it.
D
You're on the air.
E
Hi.
G
Thanks so much for taking the call and for the show. Very interesting. I've also made the transition and I share with younger friends that don't ever get settled because you're always having to reinvent us. We always have to reinvent ourselves. And my approach has been education. I think you've touched upon this. But I mean a deep dive. I think that there's a societal bias to treat seniors as sort of light, sort of light, kind of educator, educational interests, sort of, you know, going to the senior homes and they're playing bingo and things like that. My approach has been to do very find your passion. Find what really interests you. And mine is art, and fortunate to have that. And whether it's painting or the studying of art or making sure that I'm aware of what shows are around the world actually, and pursuing reading and surrounding
E
myself with artists as if I was,
G
you know, my second career as a painter, whereas I had been in finance before.
E
So it's.
G
And then I also find other interests in reading in Japanese. I live in Japan, so of Japanese bent. And I'm doing some very deep educational approaches towards reading in traditional Japanese fiction and such. So I think that kind of nourishment of pursuing significant learning gives us a goal, a pursuit and. And a purpose. So that's my two cents.
D
Thank you so much. Let's talk to James in Westchester. Hey, James, thanks for calling, all of it. We're talking retirement.
H
I'm from Westchester, but right now in Tobago, enjoying my retirement. I was a curator at the New York public library for 37 years of film, video and music at the Schomburg Center. And I retired in 2009. And I started doing some things that I always loved doing in connection with my work. One, I used to work at WO Radio in the back in the 70s, talk radio, as you know. But I started doing voice stuff. I joined. I was already a member of after, but I got to. That was around the time that they merged with sag, so I became a SAG AFTRA guy. And I started doing stuff in theaters, voiceover things, very creative stuff, and I loved it. And I also started singing at weddings. I got chances to sing it for selected weddings. And I sang one song at last just before they cut the cake. And man, I mean, I just loved all that. And now I travel a little more. So I'm in Tobago right now.
D
Would you sing a little bit of At Last for us? Can you pop it up?
H
At last My love has come along My lonely days are over and life
G
is like a song.
E
Thank you.
C
I don't know, James, if you're single and singing like that, you know, you could be very busy. I gotta tell you, I love this idea. A friend of mine said so if you're a retiree out there and you want to keep sharp and you want to make a little extra money on the side A friend of mine said, learn to play the bagpipes. You don't have to learn anything but Amazing Grace. And you can, you know, play funerals for, you know, 10 times a week if you want.
D
We have been talking about retirement. Brian o' Connor wrote a piece for the Times called you're about to retire. What are you doing for the next 20 or 30 years? Thanks to everybody who texted and called in. Thanks Brian.
C
You got a great audience. Thanks for having me.
A
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Podcast: All Of It with Alison Stewart
Host: Alison Stewart (WNYC)
Guest: Brian O’Connor (Personal Finance Writer)
Date: August 11, 2026
In this episode, host Alison Stewart explores the evolving concept of retirement, highlighting the increasing importance of planning how to spend your time—not just your money—during the post-career years. The show features personal finance journalist Brian O’Connor, who shares insights from his New York Times article and personal reporting, stressing that retirement is a new chapter requiring intentional design, purpose, and engagement. The episode includes vivid stories and reflections from callers who describe their own retirement transitions, challenges, and successes.
"Now that many people who are retiring from their nine to five jobs are living for decades afterwards, it's something we should start thinking about."
"Life expectancy is going up for wealthier people and especially whiter people. People in low wage jobs and many minorities do not get that benefit."
“You need to plan U 2.0. ... There's usually some pent up demand and financial planners really encourage that because your health is a wild card.”
"Omg, I don't know any men who retired with a plan, and it's pathetic. Women often do community and volunteer work... The men are bored and boring. They should learn to cook and clean and relieve their wives of 40 years of invisible labor."
“Don’t ever get settled because you’re always having to reinvent... nourishment of pursuing significant learning gives us a goal, a pursuit and a purpose.”
"But thank God that I do continue to keep very active... have more friends now than I ever did in my life." (11:56)
"The first thing I decided to do when I retired was I took swimming lessons... I also joined Toastmasters..." (16:53)
"Boy, you better have a whole bunch of things to do because days are long when you're working for yourself like that." (18:25)
"Find your passion. Find what really interests you.... nourishment of pursuing significant learning gives us a goal, a pursuit and a purpose." (23:47)
"I started doing stuff in theaters, voiceover things, very creative stuff, and I loved it. And I also started singing at weddings." (24:26)
Sings "At Last" live (25:29).
"If I could do anything, which I can basically do, what's to stop me? ... You have the freedom to stink at it."
Brian O’Connor:
"You have the freedom to stink at it." (21:38)
Alison Stewart (reading a listener text):
"Retirement has been the happiest phase of my life. I don't call it retirement. I call it rewirement." (20:07)
Caller James:
"At last, my love has come along, my lonely days are over and life is like a song." (Sings live, 25:29)
The episode blends warmth, humor, and realism, reflecting New York’s vibrant and diverse community. The message: Retirement isn’t just an ending, but an opportunity for reinvention, learning, community, and joy. Money matters, but how you use your time—and who you spend it with—matters even more.
For listeners and future retirees:
Start thinking now about what you want to do with your days, not just whether you can afford to stop working. Find purpose, try new things, connect with others, and keep learning—because the time you gain in retirement is as valuable a resource as money.