{"id":193948,"date":"2026-06-23T10:19:08","date_gmt":"2026-06-23T15:19:08","guid":{"rendered":"https:\/\/www.artofmanliness.com\/?p=193948"},"modified":"2026-07-15T06:54:03","modified_gmt":"2026-07-15T11:54:03","slug":"podcast-1122-the-retirement-trap-should-you-really-stop-working-at-65","status":"publish","type":"post","link":"https:\/\/www.artofmanliness.com\/finance\/money\/podcast-1122-the-retirement-trap-should-you-really-stop-working-at-65\/","title":{"rendered":"Podcast #1,122: The Retirement Trap \u2014 Should You Really Stop Working at 65?"},"content":{"rendered":"<div class=\"art19-web-player awp-medium awp-theme-dark-blue\" data-episode-id=\"e829f9c9-2d98-4a89-8195-6f29948a1589\">&nbsp;<\/div>\n<p>The modern idea of retirement was built on a bet that turned out to be wrong. It assumed people would spend most of their lives working and only a relatively short period of time retired. Instead, many Americans now reach 65 healthy, active, and with an entire third of their life ahead of them. Yet we&#8217;re still using a retirement model designed for a world in which old age was shorter and fewer people expected decades of life after leaving the workforce.<\/p>\n<p>My guest says that outdated assumption creates some unfortunate unintended consequences. It causes people to stress excessively about money, postpone meaningful experiences with family and friends, and sometimes sacrifice the very things that make life worth living in the first place. He argues that by rethinking retirement \u2014 not necessarily eliminating it, but reimagining it \u2014 we can enjoy more of our lives now while actually feeling more secure about the future.<\/p>\n<p>His name is Derek Coburn, and he&#8217;s a financial advisor and the author of <a href=\"https:\/\/amzn.to\/3QESSMK\"><em>Let&#8217;s Retire Retirement<\/em><\/a>. Today on the show, Derek explains why the traditional retirement model came about, why it may no longer make sense for many people, and how working even a few years past 65 can dramatically change the math of retirement planning. We also discuss the surprising psychological challenges many people face after they stop working, why purpose matters more than leisure, and how thinking differently about retirement can free you up to spend more time on what matters most right now \u2014 whether that&#8217;s traveling, strengthening your marriage, or making the most of the limited summers you have left with your kids.<\/p>\n<h3><b>Connect With Derek Coburn<\/b><\/h3>\n<div>\n<ul>\n<li><a href=\"https:\/\/www.derekcoburn.com\/\" target=\"_blank\" rel=\"noopener\" data-saferedirecturl=\"https:\/\/www.google.com\/url?q=https:\/\/www.derekcoburn.com\/&amp;source=gmail&amp;ust=1782136980142000&amp;usg=AOvVaw0DUDvKpaOZDtSh01BPesn6\">Derek&#8217;s website<\/a>&nbsp;(including his&nbsp;<a href=\"https:\/\/www.derekcoburn.com\/neverretire\" target=\"_blank\" rel=\"noopener\" data-saferedirecturl=\"https:\/\/www.google.com\/url?q=https:\/\/www.derekcoburn.com\/neverretire&amp;source=gmail&amp;ust=1782136980142000&amp;usg=AOvVaw1H50X8ff45aqwrd297K_au\">retirement calculator<\/a>)<\/li>\n<li><a href=\"https:\/\/www.instagram.com\/cadredc\/\" target=\"_blank\" rel=\"noopener\" data-saferedirecturl=\"https:\/\/www.google.com\/url?q=https:\/\/www.instagram.com\/cadredc\/&amp;source=gmail&amp;ust=1782136980142000&amp;usg=AOvVaw0apmhH7JJkihtKIegVGq1v\">Derek on IG<\/a><\/li>\n<\/ul>\n<p><a href=\"https:\/\/amzn.to\/3QESSMK\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-193950\" src=\"https:\/\/content.artofmanliness.com\/uploads\/2026\/06\/71WUTjpbnL._SL1500_.jpg\" alt=\"\" width=\"325\" height=\"502\" srcset=\"https:\/\/content.artofmanliness.com\/uploads\/2026\/06\/71WUTjpbnL._SL1500_.jpg 325w, https:\/\/content.artofmanliness.com\/uploads\/2026\/06\/71WUTjpbnL._SL1500_-320x494.jpg 320w\" sizes=\"auto, (max-width: 325px) 100vw, 325px\" \/><\/a><\/p>\n<h3>Listen to the Podcast! (And don\u2019t forget to leave us a review!)<\/h3>\n<p><a href=\"https:\/\/podcasts.apple.com\/us\/podcast\/the-art-of-manliness\/id332516054?mt=2\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-111440 size-full\" src=\"https:\/\/content.artofmanliness.com\/uploads\/2020\/02\/listen-apple-podcasts.jpg\" alt=\"Apple Podcast.\" width=\"300\" height=\"77\"\/><\/a><\/p>\n<p><a href=\"https:\/\/overcast.fm\/itunes332516054\/the-art-of-manliness\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-111443 size-full\" src=\"https:\/\/content.artofmanliness.com\/uploads\/2020\/02\/overcast-1.png\" alt=\"Overcast.\" width=\"300\" height=\"79\"\/><\/a><\/p>\n<p><a href=\"https:\/\/open.spotify.com\/show\/2vJHmWhhcMQRXtTruuFWTJ\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-111444 size-full\" src=\"https:\/\/content.artofmanliness.com\/uploads\/2020\/02\/spotify.png\" alt=\"Spotify.\" width=\"300\" height=\"109\"\/><\/a><\/p>\n<p><a href=\"https:\/\/castro.fm\/podcast\/3c765314-b44c-410d-91c5-a36600abcca3\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-191297\" src=\"https:\/\/content.artofmanliness.com\/uploads\/2020\/08\/podcastcastro_orig.png\" alt=\"Listen on Castro button.\" width=\"300\" height=\"100\"\/><\/a><\/p>\n<p><a href=\"https:\/\/art19.com\/shows\/the-art-of-manliness\/episodes\/e829f9c9-2d98-4a89-8195-6f29948a1589\">Listen to the episode on a separate page.<\/a><\/p>\n<p><a href=\"https:\/\/rss.art19.com\/episodes\/e829f9c9-2d98-4a89-8195-6f29948a1589.mp3\">Download this episode.<\/a><\/p>\n<p><a href=\"https:\/\/www.omnycontent.com\/d\/playlist\/aaea4e69-af51-495e-afc9-a9760146922b\/6081eee7-c459-4e12-a1ab-aadc000fc4a7\/413a6904-4d72-4be8-9421-aadc000fc4ba\/podcast.rss\">Subscribe to the podcast in the media player of your choice.<\/a><\/p>\n<h3>Transcript&nbsp;<\/h3>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>Brett McKay here and welcome to another edition of the AoM podcast. The modern idea of retirement was built on a bet that turned out to be wrong. It assumed people would spend most of their lives working and only a relatively short period of time retired. Instead, many Americans now reach 65, healthy, active, and with an entire third of their life ahead of them.<\/p>\n<p>Yet we&#8217;re still using a retirement model designed for a world in which old age was shorter and fewer people expected decades of life after leaving the workforce. My guest says that outdated assumption creates some unfortunate unintended consequences. It causes people to stress excessively about money, postpone meaningful experiences with family and friends, and sometimes sacrifice the very things that make life worth living in the first place. He argues that by rethinking retirement, not necessarily eliminating it, but re-imagining it, we can enjoy more of our lives now while actually feeling more secure about the future. His name is Derek Coburn. He&#8217;s a financial advisor and the author of <i>Let&#8217;s Retire Retirement.<\/i> Today on the show, Derek explains why the traditional retirement model came about, why it may no longer make sense for many people and how working even a few years past 65 can dramatically change the math of retirement planning. We also discussed the surprising psychological challenges many people face after they stop working, why purpose matters more than leisure and how thinking differently about retirement can free you up to spend more time on what matters most right now, whether that&#8217;s traveling, strengthening your marriage, or making the most of the limited summers you have left with your kids. After the show is over, check out our show notes at aom.is\/retirement.<\/p>\n<p>All right, Derek Coburn, welcome to the show.<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Hey, Brett, thanks for having me.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>So you are a financial advisor and you got a book out called <i>Let&#8217;s Retire Retirement<\/i>, which you&#8217;re making the case that we need to retire this idea of retirement that we have. Let&#8217;s talk about retirement in general. First, when people think of retirement, they think about stopping work around age 65 and then never working again. It&#8217;s like a fixture in our culture, and it seems like it&#8217;s always existed if you&#8217;ve seen your grandparents retire, you&#8217;ve seen your parents retire. But this idea of stopping work completely at age 65 to go on cruises and puts around the house, this is a relatively new idea. It&#8217;s like maybe just a little over a century old. And what&#8217;s interesting, you talk about this in the book, it was created in conditions that no longer exist today. So can you give us a short history lesson on the origins of our modern idea of retirement?<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Essentially, back in 1889, Germany was putting together the first ever social insurance plan to take care of their older workers who were phasing out of their jobs. And the chancellor at the time, Otto Von Bismarck picked the age of 70 as the age for them to start receiving benefits because that is the age at which people are expected to die and literally picked the age because they didn&#8217;t think they would have to pay anyone because they were going to pass away shortly thereafter. And then 27 years later, they lowered the age to 65 finally. But this was at a time when life expectancy, if you made it that far, would only get you into your late seventies. So back then, even if retirement did exist, it&#8217;s like you would only have to come up with a third of your income because you were getting some government subsidy to go along with everything else. And so now fast forward to today, if you make it to 65, your life expectancy is going to be in the mid to high eighties. If you make it to 75 or 80, it can be even longer than that. Yet we&#8217;ve never updated this age of 65 to keep up with how much longer we&#8217;re living.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>Okay, so late 19th century, some old people couldn&#8217;t support themselves anymore because most of the jobs back then were physical and they couldn&#8217;t do them anymore because they&#8217;re just old and beat down. In Germany, they set the retirement age at 65 because most people didn&#8217;t live longer than that. So relatively few people would actually collect benefits for very long, which that made the system financially manageable. And then other countries like the US adopted similar systems for retirement. But today, people are living a lot longer. A lot of jobs are knowledge work, jobs these days they&#8217;re office jobs, so we&#8217;re not beating ourselves too much up anymore, and you can do that for a long time. But we still kept this idea that, okay, at age 65, that&#8217;s when you should stop working completely. And so now people have to amass a ton of money, enough money to live on one decade, two decades, maybe three decades past 65.<\/p>\n<p>And so they go to financial advisor, their financial advisor is going to give them a number, and this is the number they need to get to retire and never work again. And it varies, but I think the general rule is to save and invest enough that you can safely withdraw about 4% of your portfolio each year in retirement, which means accumulating roughly, it&#8217;s like 25 times your annual retirement spending. So if you plan on spending something like $75,000 a year in retirement, you&#8217;ll need to have almost 2 million saved by age 65. And a lot of people struggle to reach those kind of numbers. And you argue that there are several problems that arise out of this. And one is that just people have a lot of stress and anxiety about the retirement, and they&#8217;re trying to save enough to stop working at 65 and never work again. And so they just put their nose to the grindstone in their thirties, forties, fifties. They don&#8217;t spend money on having fun or time having fun. They just figure, I&#8217;ve got to work, work, work, save, save, save, and I got to wait until retirement to finally enjoy my life.<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Yeah, it&#8217;s going to allow me to finally live the life I want to live one day. So if I sacrifice and I put off things like my health, the relationship that I have with my spouse and my kids, my travel, me having a good time, if I just put my head down and don&#8217;t focus on those things for 30 years, then maybe one day I&#8217;ll be able to do all of those things.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>But the sad thing is by the time you get to 65, you might not have the vim and vigor to do those things you&#8217;ve always wanted to do. You&#8217;re no longer 30 or 40 anymore. Now you&#8217;re 65.<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Yeah, my dad came down with dementia at the age of 62. He had it for 10 years before he passed away. Nothing is promised. And so a lot of people think like, well, what if I get injured? What if I get hurt? What if I lose my job? Well, if we&#8217;re sitting here at 75 and those things happen, all of the research, all the data shows us that the things that people regret are not, I didn&#8217;t work more was I didn&#8217;t spend more time with the people and things that were most important to me.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>How have you seen that play out in the clients you&#8217;ve served? Have you seen people who they got to 65, 70 and they retired and sure they got enough for retirement, but they look back in their life like, boy, I really regret not taking more advantage of the time I had when I was younger.<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>My book has been pretty triggering for some people in their sixties and seventies because they sort of wish somebody would&#8217;ve made them aware that they could have done things differently. And you have a lot of people that have put off and they have, it&#8217;s essentially the ultimate form of a rival fallacy. People felt like they were going to have this amazing life being able to do all of these things, and when they get there, it&#8217;s not what they thought it was going to be. I&#8217;ve had clients come into my office over the years and very few ever came in before the book with their hand raised knowing that they didn&#8217;t want to retire. So I would humor them and I would say, what do you want to do when you stop working? And the couple would say, we want to travel the world together. And I would say, great, me too. When was the last time the two of you went out on a date? And more than 50% of the time, they would just look at each other and not have a great answer. I have other clients who have said that when they retire, they want to play golf five days a week. And I ask them how often they&#8217;re playing golf now, and the majority of them say that they&#8217;re not playing golf. And it&#8217;s like, look, if we&#8217;re not working the muscles, if we&#8217;re not developing the relationships to have the physical skills and the relationships to play golf 20 years from now, I think it&#8217;s going to be hard for us to all of a sudden start to make it happen once we get there.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>All right. So this idea of a hard stop retirement at 65, it can cause a lot of stress and it can cause you to put off things for the future just like I got to work more and save more and not take the vacation now with my family, I got to save that for retirement. Another interesting point about the hard stop retirement that people don&#8217;t think about, it&#8217;s like, oh, it&#8217;d be so great to never have to work again, not wake up early, not have to go to meetings. But a lot of people, once they hit that and they&#8217;re not working anymore, they have this period where they almost have an existential crisis. They don&#8217;t know, okay, what do I do with myself now? That&#8217;s another problem of this hard stop retirement.<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Yeah, there was some good research done in 2013 by Barbara Fredrickson where she was looking at people who were prioritizing personal happiness and people that were prioritizing purpose. So personal happiness was more of a selfish for purposes of this study. It was people that were saying, \u201cWhat can I do to make myself happy?\u201d That was their reason for waking up in the morning. And the other group of people were solving for \u201cWhat can I do to make this world a better place?\u201d And when they looked at them, they hooked them up to brain monitors and heart monitors, and the people that were solving for happiness had the same response in their body that our body has when it&#8217;s dealing with a chronic adversity. So something like losing a job, losing a loved one, their inflammation was going higher, their immunity was going down, they were more likely to get sick and pass away. Whereas the group that was prioritizing purpose, they felt like there was a bigger reason for them to wake up every morning. It had just the opposite effect. Their inflammation markers were much lower, their immunity was better, they were less likely to get sick to get a disease. So there is actually a real scientific reason in backing here that says, Hey, maybe we should never want to arrive at a place where we&#8217;re fully checked out in terms of the role that we&#8217;re playing to make this world a better place.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>Okay, so the big argument in your book is that instead of thinking, alright, when I hit 65, I&#8217;m going to quit working completely, you&#8217;re advocating that people might consider continuing to work past 65 and that could involve a different job or fewer hours. But you highlight that by working past 65, the retirement math becomes less anxiety inducing. So if a listeners right now in their thirties, forties, and fifties and they&#8217;re thinking, oh my gosh, I don&#8217;t have enough safer retirement, how can working an additional five to 10 years, how can that change your retirement savings plan so that it might not be as stressful for you and you can enjoy the present more?<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>So I tell this story in my book, it&#8217;s called A Tale of Two Tony&#8217;s \u2014 about a guy named Tony who&#8217;s 45 years old. He makes $150,000 a year and he has $150,000 saved for retirement. And he meets with his advisor, has a conversation like the one we&#8217;ve already talked about, and without giving it much thought, agrees to 65 as his retirement age. The advisor comes back and tells him that he&#8217;ll have to save $2,400 a month every month adjusted for inflation for the next 20 years in order to stop working. That&#8217;s $30,000 a year. That&#8217;s 20% of what he&#8217;s making. And that&#8217;s a non-starter for most people. So he immediately starts feeling the stress and the anxiety of already being behind, feeling like he can&#8217;t catch up, he&#8217;s working longer at the office, he&#8217;s not going to the gym, he&#8217;s getting less sleep, he&#8217;s canceling family vacations.<\/p>\n<p>And then I introduced an alternate reality similar to this movie Sliding Doors from a long time ago where it was a movie with Gwyneth Paltrow where her life could go in one of two directions based on whether she caught a train or not. So I have this alternate reality take place where after that initial meeting, he comes home and he is talking more about it with his wife, and his wife says, why do you want to retire at 65? You like what you do, you like the people you do it with, and even if you&#8217;re not doing this, I can&#8217;t imagine you sitting around not doing anything at all. He&#8217;s like, you know what? You&#8217;re right. So he calls the advisor back up and he says, before we meet again, can you update my plan to show me retiring at 75 instead of 65? And the amount that he has to save goes down from $2,400 a month to $110 a month, it goes down by 96%. And even if Tony were to say, I&#8217;ll go tell him 70 instead of 65, it&#8217;s a 75% reduction in the amount that he has to save, it goes down to $600. So by recognizing and planning that, Hey, I&#8217;m willing to do this right now, what I&#8217;m doing or something else for a little bit longer, it opens up an incredible amount of financial flexibility in the short term and lets people lean into spending more of their time and money on the people and things that are most important to them right now.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>I think when I saw that math, I was like, that&#8217;s crazy. Hopefully people see that and it gives &#8217;em some hope. If they think they&#8217;re behind on retirement, they&#8217;re like, I&#8217;m never going to have a comfortable retirement. It&#8217;s like, well, if you just worked five or 10 more years past 65, you&#8217;re probably going to be okay. So I think it can reduce that anxiety and that stress. But then the big point you&#8217;re trying to make with this book is that by extending your working life a few years, you free up time. You would&#8217;ve spent working extra hours and money, you would&#8217;ve been siphoning off to your retirement account so you can use it to enjoy life when you&#8217;re young and vibrant. That&#8217;s the big case you&#8217;re making.<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Exactly.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>Yeah. And you talk about, you&#8217;ve got kids in their teens, and you talk about this in the book, you were very conscious about this and deliberate that when my kids are teenagers, I want to be able to spend more time with them and do more with them when they&#8217;re teenagers. What was it about the teen years that made you think, I really want to maximize this stage of life?<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Yeah. Well, I mean it&#8217;s been more of an evolved way of thinking for me. So I would say that when I became really mindful about it was when my dad got dementia, and Brett, when my kids were 10 and seven respectively, my wife and I had this nighttime routine where we would take turns tucking our kids into bed each night, and I found myself with my oldest son one night wishing it would hurry up. And God, I&#8217;m not saying this out loud, but I&#8217;m thinking to myself, hurry up and fall asleep so I can go and hang out with your mom or respond to this email or watch this show on Netflix. And then it occurred to me that he&#8217;s probably not going to want to be doing this with me for very much longer. So I tried to really force myself to be present, and that worked a little bit, but not the way that I wanted it to work.<\/p>\n<p>And then I had this crazy thought one day, which was, if I woke up 30 years from now and a company invented a time machine that allowed me to go back in time to have one more nighttime routine with the 10-year-old version of my son, how much money would I pay for that? And the number that came into my mind was $50,000. And it&#8217;s all relative, right? It&#8217;s going to be a different amount for different people. But the point I&#8217;m trying to make is that there are these small moments that not they don&#8217;t seem like a big deal. We&#8217;re taking them to an amusement park or on a great vacation, but just laying there with him and knowing this is a fleeting moment in time and that I&#8217;m going to really miss it and I&#8217;d be willing to pay a lot of money to revisit it at some point in the future to allow myself to be really present for them when this happens.<\/p>\n<p>And then another thing I&#8217;ll add is fast forward to when my oldest was about 13. There was a day, it was around four or five o&#8217;clock in the evening and I was getting ready to work out, and he asked me if I would play Legos with him. And I was like, gosh, buddy, I&#8217;m getting ready to work out. I haven&#8217;t done this in a couple of days. I really want to make it happen. And while I was working out, I was thinking, I want to organize my day and my life in a way that I never say no to my kid again. I want to make sure that I&#8217;m available, I&#8217;ve done everything that needs to get done by three o&#8217;clock, and then I&#8217;m around if they want to hang out with me. And a lot of days they don&#8217;t want to hang out with me.<\/p>\n<p>And if that happens, then I can get back to the things that didn&#8217;t have to get done but are nice for me to do. But the more I&#8217;m around, the more that they&#8217;re asking, the more that I&#8217;m saying yes, the more they come back and say, let&#8217;s do it again. And so now I&#8217;ve got this great rhythm with both of my boys where we&#8217;re working out together four days a week, we share a lot of music in common, we&#8217;re playing golf and just really have carved out a lot of similar and shared hobbies and interests that we can take in together.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>So you&#8217;re prioritizing enjoying your kids while they&#8217;re still around rather than prioritizing, okay, I&#8217;ve got to do everything I can now to build up my retirement account.<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>If my macro idea is that by recognizing that I&#8217;ll probably work longer in my seventies, freezing me up to spend a lot more of my time and money differently now, then I&#8217;m really, I&#8217;ve got that under the microscope with how I&#8217;m parenting right now. So I&#8217;ve got two and four years respectively before my boys go off for college. And it&#8217;s almost like I&#8217;m saying no to a lot of speaking gigs right now. I&#8217;m saying no to coaching. It&#8217;s something I thought about, but I&#8217;m not going to do because what I&#8217;m solving for on a daily basis is maxing out the time that I&#8217;m going to have with them. And it&#8217;s almost like the version of me five years from now is writing a sponsorship check to free me to lean into this time with them because I know once they&#8217;re gone, I&#8217;m going to be ready to ramp up my activity, ramp up the hours I&#8217;m working, ramp up the contribution that I&#8217;m making<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>This is really useful for me because I&#8217;m a neurotic saver. I love to squirrel away money because it makes me feel safe. And so there&#8217;s been times in my own working life I&#8217;m like, well, we can&#8217;t take the time off to do the vacation because I got to get this thing done so we can make the money and save it for retirement. After reading this book, I&#8217;m thinking, oh my gosh, my son, he&#8217;s 15. I got maybe three summers left with him, maybe four. I want to be able to do stuff with him. I need to take my foot off the gas a little bit and realize it&#8217;s going to be okay. I can work an additional five to 10 years in my seventies when I&#8217;ve got a lot more time because I&#8217;m going to be by myself with just my wife, but I can&#8217;t get back that time with my son now. So take the vacation.<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>And I think all of these things, whether it&#8217;s the dating example or the golf example, or the time with our kids, the <i>18 Summers<\/i> with Jim and Jamie Shields, that&#8217;s in their book, family board meetings is the first time I heard of this. But there&#8217;s a lot of people that need to hear that, that need to be reminded that you only have this limited time with your kids. The main thing that I&#8217;m solving for in my life right now, having a 16 and a 13-year-old at my house, is I&#8217;m trying to do as many things as possible to increase the likelihood that they&#8217;re going to want to spend time with me when they&#8217;re adults. So I&#8217;m very confident that because I&#8217;m making the most of my time with my kids now that I&#8217;m going to have 20, 30, 40 additional summers with them as well, because the more we&#8217;re leaning into something now, these relationships are going to compound the same way that your money&#8217;s going to compound in your portfolio.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>Alright, so working five to 10 years after age 65, it means you have to save less for retirement now, which means in your thirties, forties, and fifties, you can spend more of your money and time doing stuff that you enjoy with the people you love now. And as we talked about earlier, some people would just like to keep working, they wouldn&#8217;t be happy not doing anything they like working, it gives their life meaning. So stopping work at 65 wouldn&#8217;t be desirable for them anyway. But let&#8217;s say someone is not in that camp, their job doesn&#8217;t bring them any meaning they hate their job and they can&#8217;t wait until they&#8217;re 65 so they can quit their crappy job and stop working. What do you tell those people?<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Yeah, I changed the language in my book after the first couple of passes. I was using language like \u201cFind a job you love\u201d and I changed it to \u201cfind a job you don&#8217;t hate\u201d because I don&#8217;t think that everyone needs to find their purpose and have that be the time that they spend with work. And so for me, I want people, if they don&#8217;t like what they do, yeah, let&#8217;s figure out a plan to not have to do that any longer. Then you have to, and I&#8217;m sure if somebody hates what they do, not having to do that anymore for a period of time is going to be better when you compare it to what you&#8217;re doing now. But I don&#8217;t think that not doing anything at all is going to provide lasting happiness for many people. And so I think that the goal should be find a job that you don&#8217;t hate, find a job where maybe you like the people, you like the work, you don&#8217;t mind it, and it allows you to have the lifestyle to lean in more to these other things that we&#8217;ve been talking about.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>Alright, so if you don&#8217;t like your job, try to find a job in which you wouldn&#8217;t mind continuing to work after 65. And it&#8217;s probably a good idea to make that pivot long before you reach 65, since it does get harder to get hired as you get older. Another thing you do is you could pivot to something where you work fewer hours in your later years. You don&#8217;t necessarily have to work as many hours or you just want to have some income continuing to come in. Something people might think about is starting something on the side before they get older, so as they get older, they can maybe pivot into something they&#8217;re more interested in and that they would like to do more of.<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Yeah, look, I can share, my own personal experience was around 2010, 2011, I had about 350 wealth management clients and I was qualifying for these fancy trips that made me about 10 to 15 years younger than most of the other advisors who were there. And I was asking them a lot of questions and almost to a person, they all had like 2000 clients and they only enjoyed working with about 20% of them. And in our industry, especially back then, you couldn&#8217;t use social media, you couldn&#8217;t use word of mouth marketing very much. You couldn&#8217;t get testimonials, so you just had to take whatever fell into your lap. And I recognized that there were a lot of people that I was working with that I didn&#8217;t love working with for one reason or another. And so I shifted my practice. I went from 350 clients down to about 75, and then my wife and I started an organization together called Cadre, which is still around today.<\/p>\n<p>We&#8217;ve a community for CEOs and entrepreneurs and find ways to bring people together. But what was fascinating about that is the ancillary benefit that really popped was by me having two things going side by side at the same time. It allowed me to really have the courage and the ability to stick to my guns in terms of who do I want to work with and who do I want to support? And Adam Grant and his book Originals I think talked a little bit about looking at entrepreneurs and people that were starting businesses and the success rate that they had with their new business based on whether they had some steady stream of income coming in from another source at the time. So essentially it was two groups of people starting businesses. One group had a job and they were doing this new business on the side to build it up, and the second group just went all in on the new business.<\/p>\n<p>And the first group was far more likely to succeed with their business because they had this income coming in that allowed them to be a little bit more mindful and a little bit more deliberate with the way they were building it. And the takeaway is that entrepreneurs are often considered big risk takers, but really the good ones are great risk mitigators. And so I think that there&#8217;s an opportunity for a lot of people that maybe you start some kind of a side hustle while you add the thing that you have now and allow yourself to get a few clients to get a little bit of momentum, and maybe you keep both going at the same time, but maybe it provides an on-ramp for you to leave the job that you don&#8217;t love right now and start leaning into something that you enjoy much more.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>What about someone who&#8217;s got a job that involves a physical capacity that degrades with age and necessitates an early retirement? I&#8217;m thinking maybe you&#8217;re in a physically demanding job, you&#8217;re an HVAC installer, or I mean even surgeons, it requires a lot of fine motor skills or whatever. And maybe as you get into your seventies and eighties that sort of degrades, what do they do? They&#8217;ve trained their whole life to do this thing and they can no longer do it. What about them?<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Yeah, I think that there&#8217;s other opportunities in their fields. I think you see a lot of doctors, a lot of surgeons who take jobs as professors at universities or they sit on boards and contribute their knowledge that way. You&#8217;ve got auto mechanics that end up in more of a managerial type role, so hopefully there&#8217;s going to be some opportunities for them to pivot doing something else.&nbsp;<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>Yeah maybe they got to think like an athlete, like a football player. They have to retire in their thirties and then they end up doing something that&#8217;s related to the field. They become a coach or something like that, or an agent. My dad, he was a federal game warden for the Fish and Wildlife Service for his entire career. They had mandatory retirement, I think it was like a 55 sometime in the fifties because a demanding, physically demanding job, but he kept working even though he didn&#8217;t have to. He had a pretty good pension with his job, but he got a contract job with the EPA checking oil rig compliance regulation stuff. He&#8217;s been doing that. He just turned 79. He&#8217;s still doing that. And I don&#8217;t think he loves it, but he doesn&#8217;t hate it. It&#8217;s just something to do and he really enjoys working. And I think that&#8217;s an example of doing something related to what you&#8217;re doing, but in a different capacity.<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>That&#8217;s a great example.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>Alright so if we&#8217;re shifting from a hard stop retirement to a continuous income or phased model where maybe we make less and less as we get closer to 75, how should our investment strategy change? What does the portfolio look like when you aren&#8217;t planning to completely drain it starting at age 65?<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Well, one of the nice advantages of working longer is that you can allow your money to potentially have more exposure to risk for a longer period of time. So somebody that is planning to retire at 65 is going to want to shift, in my opinion, more of their money to some conservative investments. That&#8217;s not going to be subject to a potential stock market decline of 20%. And if you&#8217;re still working and thereby you&#8217;re using your income primarily to live on and not drawing down from your investments, you can leave your money invested a little bit more aggressively for a little bit longer. That would be one thing. I think another thing is just the idea of getting more and more people comfortable spending their money. Earlier you mentioned you&#8217;re a great saver, and I will tell you that most of my clients now are in their sixties and seventies, and they all have probably eight figures plus of net worth.<\/p>\n<p>And the recurring theme in all of these conversations with my clients is just begging them to spend more of their money. Because the problem is, if you&#8217;ve been a great saver your entire life and you&#8217;ve played that game really well, it&#8217;s incredibly difficult to just flip the switch and all of a sudden lean into spending your money more. And if I have different groups of clients, let&#8217;s say in one bucket, I have clients that have enough money, they&#8217;re probably never going to run out of it, and they&#8217;re still earning an income, even if it&#8217;s like $50,000 a year or a hundred thousand dollars a year, those clients spend their money in much more of a carefree way than the ones who are completely out. The ones who are no longer doing anything at all have a really difficult time transitioning from this. My portfolio has gone up only for the past 40 years, and now I&#8217;m taking money out of it. And psychologically, it&#8217;s been interesting to see how many people have such a difficult time overcoming this.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>Yeah, I can see that happening because you spend your entire adult life saving and now it&#8217;s like, okay, now you got to spend it. You&#8217;re like, wait a minute, that&#8217;s not right. So that can be tough, but by having that job in your 70, 75, like you said, it releases some of that psychological pressure to not spend. You&#8217;re like, well, I still have money coming in. My retirement&#8217;s going to be okay. I can spin and I&#8217;ll be okay. Okay. So the argument you&#8217;re making is that people could stress out less and enjoy their lives in their younger years more if they plan to work past 65. And this is something that&#8217;s very doable now because most jobs aren&#8217;t physically demanding and people are living a lot longer. I mean, even if you stop working at 75, you could still have 20 years, two decades of not working at all.<\/p>\n<p>I think there are some people out there who truly don&#8217;t want to work any longer than they have to. And there&#8217;s some careers where it makes a lot of sense to maximize your earnings in your younger years where maybe it&#8217;s a physical job and you don&#8217;t see yourself pivoting to something else later. Or maybe you want to devote yourself to volunteer work after 65. But for a lot of people, this is a path that could allow them to make more of their lives now. And as part of that, you&#8217;re a huge advocate for continuing to invest in yourself as you age. What does that look like?<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Yeah, so the last chapter of my book is called just that \u2014 Investing in You. And I think that sometimes when we&#8217;re too focused on hitting our number, we do it at the expense of going to the gym. We do it at the expense of the quality of our sleep, hanging out with friends, having a good time. And I think that our society really over-indexes for the long-term benefits of doing these things that are healthy for us and good for us and undersells the short-term benefits. So yes, you should get a good night&#8217;s sleep tonight because you might feel better 20 years from now, but in my experience, you should really get a good night&#8217;s sleep tonight because of how you&#8217;re going to feel 20 hours from now. And I think that the idea that I&#8217;m trying to promote here is that I think that if you&#8217;re currently working, let&#8217;s say nine hours a day and you feel like you don&#8217;t have time to go to the gym, you don&#8217;t have time to see your best friend, you don&#8217;t have time to take your wife out on a date, that by actually making time to do those things, you&#8217;re going to be filling up your cup, you&#8217;re going to be giving yourself more energy, you&#8217;re going to be giving yourself more clarity.<\/p>\n<p>And even though you might be now working eight hours a day instead of nine hours a day, in my experience, you can be a lot more productive with those hours because you&#8217;re better rested. You don&#8217;t have the brain fog, and you&#8217;re showing up with more vigor than you were before.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>For someone listening right now who&#8217;s exhausted by the grind but feels trapped by this traditional retirement timeline, what is the very first step they can take today to start applying your framework?<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Lean into these relationships that are important to you, take better care of yourself, have more fun. But I&#8217;m hopefully solving the elephant in the room for a lot of these people, which is like, how can I afford to do this? So I have a calculator on my website, which you can link up hopefully derek coburn.com\/never retire, where people can enter in their income and the assets that they have and they can experiment with, well, what happens if I work two more years? Or what happens if I work four more years and be able to really embody the financial impact, the flexibility that will come from agreeing to say, I&#8217;m going to do this for a little bit longer.<\/p>\n<p>I gave the tale to Tony&#8217;s example before, but even working just one extra year, somebody were to say, I&#8217;ll go till 66 instead of 65. Typically correlates with about a 15 to 20% reduction in the amount of money that they have to save on an annual basis. So really think about how committed are you to your plan? How much of your plan right now is on autopilot? Did you pick 65 because that&#8217;s really the age that you know want to stop working? Or did you pick 65? Because that&#8217;s typically what everyone else says to do.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>Well, Derek, this has been a great conversation. Where can people go to learn more about the book and your work?<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Yeah, I&#8217;ve loved our chat here, Brett, my website, derekcoburn.com. I&#8217;ve been writing a lot more just kind of piggyback on a lot of the ideas in my book around what I&#8217;m doing from a parenting and how I&#8217;m spending time with my wife, how I&#8217;m spending time with my friends, and just really trying to tie all this together and keep building on what was in the book. So I encourage people to go there, sign up for my email newsletter. I hang out on Instagram a little bit too. But yeah, it&#8217;d be great to keep in touch with some of your folks.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>All right. Well, Derek Coburn, thanks for time. It&#8217;s been a pleasure.<\/p>\n<p><strong>Derek Coburn:<\/strong><\/p>\n<p>Thanks so much, Brett.<\/p>\n<p><strong>Brett McKay:<\/strong><\/p>\n<p>My guest today was Derek Coburn. He&#8217;s the author of the book <i>Let&#8217;s Retire Retirement<\/i>. It&#8217;s available on amazon.com. You can learn more information about his work at his website, derekcoburn.com. Until next time, this is Brett McKay reminding you to not only listen to the podcast, but to put what you&#8217;ve heard into action.<\/p>\n<\/div>\n","protected":false},"excerpt":{"rendered":"<p>&nbsp; The modern idea of retirement was built on a bet that turned out to be wrong. It assumed people would spend most of their lives working and only a relatively short period of time retired. Instead, many Americans now reach 65 healthy, active, and with an entire third of their life ahead of them. [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":193949,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[42377,42395,156],"tags":[],"class_list":["post-193948","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-finance","category-money","category-podcast"],"featured_image_urls":{"aom":"https:\/\/content.artofmanliness.com\/uploads\/2026\/06\/lrr-1-372x230.jpg","reactor-320":"https:\/\/content.artofmanliness.com\/uploads\/2026\/06\/lrr-1-320x167.jpg"},"yoast_head":"<!-- This site is optimized with the Yoast SEO Premium plugin v27.8 (Yoast SEO v27.8) - https:\/\/yoast.com\/product\/yoast-seo-premium-wordpress\/ -->\n<title>Podcast #1,122: The Retirement Trap \u2014 Should You Really Stop Working at 65? | The Art of Manliness<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.artofmanliness.com\/finance\/money\/podcast-1122-the-retirement-trap-should-you-really-stop-working-at-65\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Podcast #1,122: The Retirement Trap \u2014 Should You Really Stop Working at 65? | The Art of Manliness\" \/>\n<meta property=\"og:description\" content=\"&nbsp; The modern idea of retirement was built on a bet that turned out to be wrong. 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It assumed people would spend most of their lives working and only a relatively short period of time retired. Instead, many Americans now reach 65 healthy, active, and with an entire third of their life ahead of them. 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