The Retirement Trap — Should You Really Stop Working at 65?

A

One of the things I've learned after running AOM for nearly two decades is that the fun part is creating, writing articles, recording podcasts, designing products, things like that. The less fun part is all the operational stuff that comes with selling those products online. And that's one reason we've used Shopify for the AOM Store. Shopify is the commerce platform behind millions of businesses around the world and 10% of all e commerce in the US. It handles all the stuff you don't want to spend your day worrying about. Inventory, payments, analytics, shipping, returns, all all in one place. What I like is that it scales with you. Whether you're selling your first product or managing an established store, Shopify gives you the tools to keep things running smoothly. They've even built in AI tools that can help with product descriptions, page headlines, and product photography. Plus, as a customer, you've probably seen that purple Shop pay button. There's a reason why it's everywhere. It makes checkout incredibly easy, which means fewer abandoned carts and more completed sales. It's time to turn those what ifs into reality with Shopify today. Sign up for your $1 per month trial today at shopify.commanliness that's shopify.commanliness that'S shopify.commanliness Ever notice how life's best stories don't happen in your living room? They happen on the open road, out on the water, or parked under the stars. At Progressive, they get that you want to focus on the experience, not worry about the what ifs. That's why they offer quality insurance designed for your ride, whether that's a boat or RV or motorcycle adventure with confidence. Visit progressive.com and see how easy it is to protect your favorite way to get away. Progressive Casualty Insurance Company and affiliates not available in DC. Prices vary based on how you buy. Brett McKay here. And welcome to another edition of the AOM podcast, which since 2008 has featured conversations with the world's best authors, thinkers and leaders that glean their edifying life, improving insights without the fluff and filler. The AOM Podcast is just one part of the McKay mission to help individuals practice timeless virtues through thought, word and deed. Also, be sure to explore our articles in artofmanliness.com, read the deeper dives we do in our substack newsletter@dyingbreed.net and turn our content into real world action by joining the Strenuous Life program@strenuouslife.com now on to the show. 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'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 reimagining it, we can enjoy more of our lives now while actually feeling more secure about the future. His name is Derek Coburn, and he's a financial advisor and the author of let's Retire Retirement. 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's traveling, strengthening your marriage, or making the most of the limited summers you have left with your kids. After the show's over, check out our show notes at AWIM is retirement. All right? Derek Cockburn, welcome to the show.

B

Hey, Brett, thanks for having me.

A

So you are a financial advisor and you got a book out called let's Retire Retirement, which you're making the case we need to retire. This idea of retirement that we have. Let'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's like a fixture in our culture, and it seems like it's always exist. You've seen your grandparents retire, you've seen your parents retire. But this idea of stopping work completely at age 65 to go on cruises and putts around the house, this is a relatively new idea. It's like maybe just a little over a century old. And what'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?

B

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 van Bismarck, picked the age of 70 as the age for them to start receiving benefits because, quote, that is the age at which people are expected to die, end quote. And literally pick the age because they didn't think they would have to pay anyone because they were going to pass away shortly thereafter. And then like 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 70s. So back then, even if retirement did exist, it'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 80s. If you make it to 75 or 80 can be even longer than that. Yet we've never updated this age of 65 to keep up with how much longer we're living.

A

Okay, so late 19th century, some old people couldn't support themselves anymore because most of the jobs back then were physical and they couldn't do them anymore because they're just old and beat down. In Germany, they set the retirement age at 65 because, you know, most people didn't live longer than that. So relatively few people would actually collect benefits 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're office jobs. So we're not beating ourselves too much up anymore. And you can do that, you know, for a long time. But we still kept this idea that, okay, at age 65, that's when you should stop working completely. And so now people have to amass a ton of money, enough money to live on, you know, one decade, two decades, maybe three decades past 65. 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 to retire, 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, you know, roughly it's like 25 times your annual retirement spending. So if you plan on spend spending something like $75,000 a year in retirement, you'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'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 30s, 40s, 50s. They don't spend money on having fun or time having fun. They just figure, I've got to work, work, work, save, save, save, and I got to wait until retirement to finally enjoy my life.

B

Yeah, it'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't focus on those things for 30 years, then maybe one day I'll be able to do all of those things.

A

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've always wanted to do because you're no longer 30 or 40 anymore. Now you're. You're 65.

B

Yeah. My dad came down with dementia at the age of 62. He had it for 10 years before he. 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're sitting here at 75 and those things happen, like, all of the research, all the data shows us that the things that people regret are not, you know, I didn't work more. It was. I didn't spend more time with the people and things that were most important to me.

A

How have you seen that play out in the clients you've served? Have you seen people who, you know, they got to 65, 70, and they retired and, you know, 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.

B

Yeah, my book has been pretty triggering for some people in their 60s and 70s because they sort of wish somebody would have 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's essentially like 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's not what they thought it was going to be like. I'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't want to retire. So I would humor them, and I would say, what do you want to do when you, you know, 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're playing golf now, and the majority of them say that they're not playing golf. And it's like, look, if we're not, you know, working the muscles, if we're not developing the relationships to have the physical skills and the relationships to play golf 20 years from now, I think it's going to be hard for us to all of a sudden start to make it happen once we get there.

A

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 because you're just like, I got to work more and save more and not take the vacation now with my family because I got to save that for retirement. Another interesting point about the hard stop retirement that people don't think about. It's like, oh, it'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're not working anymore, they have this period where they almost have, like, an existential crisis. They don't know, what do I do with myself now? That's another problem of this Hard stop retirement.

B

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, what can I do to make myself happy? That was their reason for waking up in the morning. And the other group of people were solving for what can I do to make this world a better place? 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'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, there is actually a real scientific reason and backing here that, that says, hey, maybe we should never want to arrive at a place where we're fully checked out in terms of the role that we're playing to make this world a better place.

A

Okay, so the big argument in your book is that instead of thinking, all right, when I hit 65, I'm going to quit working completely, you're advocating that people might consider continuing to work past 65. And, 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 you know listeners right now in their 30s, 40s, and 50s, and they're thinking, oh my gosh, I don't have enough save for 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, and you can enjoy the present more?

B

So I tell this story in my book. It's called a tale of two Tonys, about a guy named Tony who'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'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'll have to save $2,400 a month, every month, adjusted for inflation, for the next 20 years in order to stop working. That's $30,000 a year. That's 20% of what he's making, and that'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't catch up. He's working longer at the office, he's not going to the gym, he's getting less sleep, he's canceling family vacations. And then I introduce an alternate reality, similar to this movie Sliding Doors from a long time ago, where it was a movie with Gwyneth Paltrow where her. 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's 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're not doing this, I can't imagine you sitting around not doing anything at all. He's like, you know what? You'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'll go tell him 70 instead of 65, it's a 75% reduction in the amount that he has to save. It goes down to $600. So by recognizing and planning that, that, hey, I'm willing to do this right now, what I'm doing, or something else for a little bit longer, it opens up an incredible amount of. 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.

A

I think when I saw that math, I was like, that's crazy. Hopefully people see that, and it's like, it gives them some hope. If they think they're behind on retirement, they're like, I'm never going to have a comfortable retirement. It's like, well, if you just worked five or 10 more years past 65, you're probably going to be okay. So I think it can reduce that anxiety and that stress. But then the big point you're trying to make with this book is that by extending your working life a few years, you free up time you would have spent working extra hours and money you would have been siphoning off to your retirement account so you can use it to enjoy life when you're young and vibrant. That's the big case you're making.

B

Exactly, yeah.

A

I mean, and you talk about you've got kids in. In their teens, and you talk about this in the book. You were very conscious about this and deliberate that, okay, when my kids are teenagers, I want to be able to spend more time with them and do more with them when they're teenagers. What was it about the teen years that made you think, I really want to maximize this stage of life?

B

Yeah, well, I mean, it's more of, it's been more of an evolved way of thinking for me. So I would say that when I became really mindful about it was A, when my dad got dementia and B, when my kids were 10 and 7 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'm not saying this out loud, but I'm thinking to myself, like, 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's probably not going to want to be doing this with me for very much longer. So I tried to like really force myself to be present. And that worked a little bit, but not the way that I wanted it to work. And then I had this crazy thought one day which was, you know, 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's all relative, right? It's going to be a different amount for different people. But the point I'm trying to make is that there are these like small moments that are not like they don't, they don't seem like a big deal, like we'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'm going to really miss it, and I'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. And then another, another thing I'll add is fast forward to when my oldest was about 13. There was a day, it was around 4 or 5 o' 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'm getting ready to work out. I haven't done this in a couple of days. I really want to, I really want to make it happen. And while I was working out, I was thinking, you know, 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'm available, I'm done, everything that needs to get done by 3 o' clock, and then I'm around if they want to hang out with me. And a lot of days they don't want to hang out with me. And if that happens, then I can get back to the things that didn't have to get done but are nice for me to do. But the more I'm around, the more that they're asking, the more that I'm saying yes, the more they come back and say, let's do it again. And so now I've got this great rhythm with both of my boys where we're working out together four days a week. We share a lot of music in common, we're playing golf, and just really have carved out a lot of similar and shared hobbies and interests that we can take in together.

A

Yeah. So you're prioritizing, enjoying your kids while they're still around rather than prioritizing. Okay, I've got to do everything I can now to build up my retirement account.

B

Yeah. If my, like, macro idea is that by recognizing that I'll probably work longer in my 70s, freezing up to spend a lot more of my time and money differently now, then I'm really. I've got that under the microscope with how I'm parenting right now. So I've got two and four years respectively before my boys go off for college. And it's almost like I'm saying no to a lot of speaking gigs right now. I'm saying no to. To coaching. Like, it's something I thought about, but I'm not going to do because what I'm solving for on a daily basis is maxing out the time that I'm going to have with them. And it'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're gone, I'm going to be ready to ramp up my activity, ramp up the hours I'm working, ramp up the contribution that I'm making.

A

Yeah, I'm this book, this is really useful for me because I'm a neurotic saver. I just, I love to squirrel away money because it makes me feel safe. And so there's been times in my own working life from like, well, we can't take the time off to do the vacation because I got to get this thing done. So we make the money and save it for retirement. After reading this book, I'm thinking, oh, my gosh, my son, he'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's going to be okay. I can work an additional five to 10 years in my 70s when I've got a lot more time, because I'm going to be by myself with just my wife. But I can't get back that time with my son now. So take the vacation.

B

Yeah. And I think all of these things, whether it's the dating example or the golf example or the time with our kids. Right. Like the 18 summers. Jim and Jamie Shields that's in their book Family board meetings is the first time I heard of this. But, like, there'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. Like, the main thing that I'm solving for in my life right now, having a 16 and a 13 year old at my house, is I'm trying to do as many things as possible to increase the likelihood that they're going to want to spend time with me when they're adults. So I'm very confident that because I'm making the most of my time with my kids now, that I'm going to have, you know, 20, 30, 40 additional summers with them as well. Because the more we're leaning into something now, these relationships are going to compound the same way that your money is going to compound in your portfolio.

A

We're going to take a quick break for your word from our sponsors. I've been using Caldera Lab for over a year now, and I think that's probably the strongest endorsement I can give it. Most grooming products come into your life, sit on the bathroom counter for a couple of weeks, and then they just disappear. Caldera Lab has stuck. Part of the reason is that it's just so easy to use. The whole routine takes less than a minute in the morning, so there's never a reason to skip it. I've gotten to my 40s and I've started paying more attention to my skin. What surprised me about Caldera Lab is that the changes were subtle but noticeable. My skin just looks healthier. My favorite product is the great. It's their lightweight serum. It absorbs in seconds, doesn't feel greasy, and it's the product I notice the most when I use it consistently. It's clinically proven to help firm, brighten and reduce the appearance of fine lines. And after using it this long, I can see why. It's their hero product. I also use the hydrolayer moisturizer and the eye serum. Together they make for a simple routine that actually works A small habit with big results. Go to calderalab.com manliness and use code manliness for 20% off your first order. That's Caldera Lab that's spelled C A L D E R a l a b.com manliness and use code manliness for 20% off your first order. Check out the great so I know I've told this story before, but when I was first out on my own, I made a lot of boneheaded money mistakes. I wasn't blowing my money on anything exciting either. I'd buy a burger, forget how much is in my checking account, and then get hit with an overdraft fee that cost almost as much as the meal itself. When you're young and trying to get ahead, that stuff adds up fast. That's one reason Chime caught my attention. Chime is changing the way people bank with more rewarding fee free banking that's built for regular people, not the banks. Unlike a lot of traditional banks, Chime offers fee free overdraft coverage with Spotme and members can benefit from up to $1,150 in annual rewards. Fee free. You can also get savings that grow faster with a 3.75% APY that's nine times higher than the national average. And get 5% cash back on Chime Card purchases in a category of your choice like gas or groceries. And Chime is rated five stars by USA TODAY for customer service with real humans available 24.7chime is not just smarter banking, it is the most rewarding way to bank join the millions who are already banking fee free today. Head to chime.commanliness that's chime.commanliness it only takes a few minutes to sign up. Chime is a fintech, not a bank. Banking services for MyPay and Chime card provided by Chime's bank partners. Optional products and services may have fees or charges.

B

Stated annual percentage yield and cash back

A

for Chime prime only. No minimum balance required. Checking account rank based on a J.D. power survey published October 20, 2025. For more information on APY rates, my Pay Spot Me and travel perks go to Chime.com disclosures if you track your workouts, pay attention to your sleep and try to eat well, but you've never looked at your gut microbiome, you might be missing an important piece of the health puzzle. Last year I had microbiologist Brett Findlay on the podcast to talk about the microbiome and one thing that caught my attention was that you can actually test your gut at home and get a snapshot of what's going on in there. That intrigued me, so I wanted to try it out. That's why I decided to try out Tiny Health. Tiny Health is an at home gut health test that gives you a detailed breakdown of what's actually happening inside your body. Unlike a lot of gut tests that just give you a basic list of good and bad bacteria, Tiny Health use metagenomic sequencing, the same technology used in clinical research, to analyze your full gut ecosystem. I just did my sample today. It was really easy to do the process simple. You test at home, you send it in and you get a personalized action plan with diet, lifestyle and supplement recommendations based on your results and clinical evidence, not generic advice. Start improving your health with real data from Tiny Health. Tiny Health is offering my listeners their most aggressive offer yet. $50 off your first at home test kit@tinyhealth.com AOM that's tinyhealth.com AOM for $50 off your first at home Test. Check it out today. So I've got a few friends who run businesses where they have to hire a lot and one thing they all say is hiring is one of the hardest parts. Not just finding someone, but finding the right person. Because when you get the wrong hire, it creates more problems than it solves. And when you need the right person fast. This is a job for Sponsored Jobs with Indeed. What I like about Indeed Sponsored Jobs is that it helps you reach candidates who actually match what you're looking for and people are finding quality hires on Indeed right now in the minute I've been talking to you. Companies like yours made 27 hires on Indeed according to Indeed Data Worldwide. Sponsor Jobs boost your post and search results so you can connect with candidates who can actually move your business forward and you only pay for results. Spend less time searching and more time actually interviewing candidates who check all your boxes. Less stress, less time, more results. When you need the right person to cut through the chaos, this is a job for Indeed Sponsored Jobs and listeners of the show will get a $75 sponsored job credit to help get your job the premium status it deserves@ Indeed.com podcast just go to Indeed.com podcast right now and support our show by saying you heard about Indeed on this podcast. Again it's indeed dot com, so it's I N-E-E-D.com podcast. Terms and conditions apply. Need the right hire fast. This is a job for indeed sponsored jobs. And now back to the show. All right, so working five to 10 years after age 65, it means you have to save less for retirement now, which means in your 30s, 40s, and 50s, you can spend more of your money and time doing stuff that you enjoy with the. With the people you love now. And as we talked about earlier, some people would just like to keep working. They wouldn't be happy not doing anything. They like working. It gives their life meaning. So stopping work at 65 wouldn't be desirable for them anyway. But let's say someone is not in that camp. Their job doesn't bring them any meaning. They hate their job, and they just. They can't wait until they're 65 so they can quit their crappy job and stop working. What do you tell those people?

B

Yeah, I changed the language in my book after the first couple of passes, I was using language like find a job you love, and I changed it to find a job you don't hate. Because I don't think that everyone needs to find their purpose and have that be, you know, the time that they spend with work. And so for me, I want people, like, if they don't like what they do, like, yeah, let's figure out a plan to not have to do that any longer than you have to. And I'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're doing now. But I don't think that, like, 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't hate, find a job where maybe you like the people, you like the work, you don't mind it, and it allows you to have the lifestyle to lean in more to these other things that we've been talking about.

A

All right, so if you don't like your job, try to find a job in which you wouldn't mind continuing to work after 65. And it'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 could do is you could pivot to something where you work fewer hours in your later years. You don't necessarily have to work as many hours you just want to have some income continuing to come in. Something people might think about is starting something on the side before they. Before they get older. So as they get older, they can maybe pivot into something they're more interested in and that they would like to do more of.

B

Yeah, look, I can share my own experience. 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. And almost to a person, they all had like 2,000 clients, and they only enjoyed working with about 20% of them. And in our industry, especially back then, you couldn't use social media, you couldn't use word of mouth marketing very much. You couldn'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'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, and which is still around today. We've got 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, in 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 kind of on the side to build it up. And the second group just went all in on the new business. 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, like, there'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't love right now and start leaning into something that you enjoy much more.

A

What about someone who's got a job that involves a physical capacity that degrades with age and necessitates an early retirement? Like, I'm thinking, you know, maybe you're in a physically demanding job, like you're an H VAC installer or I mean, even surgeons, you know, it requires a lot of fine, you know, motor skills or whatever. And maybe as you get into your 70s and 80s, like that sort of degrades. How, what do you tell. I mean, what do they do? They've trained their whole life to do this thing and they can no longer do it. What about them?

B

Yeah, you know, I think that there's other opportunities, like in their fields. You know, I think you see a lot of doctors, a lot of surgeons who, who take jobs as professors at universities or they sit on boards and contribute their knowledge. That way you've got auto mechanics that end up in more of a managerial type role. So hopefully there's going to be some opportunities for them to pivot doing something else.

A

Yeah, maybe. You got to think like an athlete, right? Like a football player. You know, they have to retire in their 30s and then they end up doing something that's related to the field. Like they become a coach or something like that, or for sure an agent. You know, 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 50s. It's a demanding, physically demanding job. But he kept working even though he didn'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.

B

Oh, cool.

A

He's been doing that. He just turned 79. He's still doing that. And I don't think he like, loves it, but he doesn't hate it. It's just something to do. And he, he really enjoys working. And I think that's an example of doing something related to what you're doing, but in a different capacity.

B

No, that's a great example.

A

All right, so if we'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? Like, what does a portfolio look like when you aren't planning to completely drain it starting at age 65?

B

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's not going to be subject to a potential stock market decline of 20%. And if you're still working and thereby you're. You'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. 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're a great saver. And I will tell you that most of my clients now are in their 60s and 70s, and they all have probably, you know, eight. Eight figures plus of net worth. 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've been a great saver your entire life and you played that game really well, it's incredibly difficult to just flip the switch and all of a sudden, like, lean into spending your money more. And if I have different groups of clients, let's say in one bucket, I have clients that have enough money, they're probably never going to run out of it, and they're still earning an income. Even if it's like $50,000 a year or $100,000 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. This. My portfolio has gone up only for the past 40 years, and now I'm taking money out of it. And psychologically, it's. It's been. It's been interesting to see how many people have such a difficult time overcoming this.

A

Yeah, I can see that happening because you spend your entire adult life saving, and now it's like, okay, now you got to spend it. You're like, wait a minute, that's not right. So that can be tough. But, like, by having that job in your 70s, you know, 70, 70, 75. Yeah, like you said, it released some of that psychological pressure to not spend. Like, well, you know, I still have money coming in, my retirement's going to be okay. I can spend and I'll be okay.

B

Yeah.

A

Okay, so the argument you'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's very doable now because, you know, most jobs aren'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. I think there are some people out there who truly don't want to work any longer than they have to. And there's some careers where it makes a lot of sense to maximize your earnings in your younger years, you know, where maybe it's a physical job and you don't see yourself pivoting to something else later or, you know, 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 a, you know, more of their lives now. And as part of that, you're a huge advocate for continuing to invest in yourself as you age. What does that look like?

B

Yeah. So the last chapter of my book is called Just that, Investing in youn. And you know, I think that sometimes when we'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, like, yes, you should get a good night's sleep tonight because you might feel better 20 years from now, but in my experience, you should really get a good night's sleep tonight because of how you're going to feel 20 hours from now. And I think that the idea that I'm trying to promote here is that I think that if you're currently working, let's say nine hours a day, and you feel like you don't have time to go to the gym, you don't have time to see your best friend, you don't have time to take your wife out on a date, that by actually making time to do those things, you're going to be filling up your cup, you're going to be, you're going to be giving yourself more energy, you're going to be giving yourself more clarity. 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're better rested, you don't have the brain fog, and you're showing up with more vigor than you were before.

A

For someone listening right now who'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?

B

So, look, I think, I think I'm selling. I'm not really selling anything, but I think I'm selling a lot of the same things that other people are selling, like, lean into these relationships that are important to you, take better care of yourself, have more fun. But I'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 derekcoburn.com neverretire where people can enter in like 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'm going to do this for a little bit longer. Like I gave the the tale of two Tony's example before, but even like working just one extra year, somebody were to say, I'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, so really think about, you know, how committed are you to your plan? How much of your plan right now is on autopilot? Did you pick 65 because that's really the age that, you know, you want to stop working, or did you pick 65 because that's typically what everyone else says to do?

A

Well, Derek, this has been a great conversation. Where can people go to learn more about the book and your work?

B

Yeah, I've loved our chat here, Brett. My website, Derek Coburn.com I've been writing a lot more just kind of piggyback on a lot of the ideas in my book around what I'm doing from a parenting and how I'm spending time with my wife, how I'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, so but yeah, it'd be great to keep in touch with some some of your folks.

A

All right. Well, Derek Corburn, thanks for time. It's been a pleasure.

B

Thanks so much Brett.

A

My guest today was Derek Coburn. He's the author of the book let's Retire Retirement. It's available on Amazon.com youm can learn more information about his work at his website derekcoburn.com also check out our shownotes at AOM is retirement where you find links to resources. We delve deeper into this topic. Well, that wraps up another edition of the awin podcast. If you haven't done so already, I'd appreciate it if you take one minute to give us Reviewing off a podcast or Spotify helps out a lot and if you've done that already, thank you. Please consider sharing the show with a friend or family member who you think was something out of it. As always, thank you for the continued support. Until next time is Brett McKay reminding you not listen to anyone podcast, but put what you've heard into action. You're listening to this podcast, so I know you've got a curious mind. Here's a helpful fact you might not know yet. Drivers who switch and save with Progressive save over $900 on average. Pop over to progressive.com, answer some questions and you'll get a quick quote with discounts that are easy to come by. In fact, 99% of their auto customers earn at least one discount. Visit progressive.com and see if you can enjoy a little cash back. Progressive Casualty Insurance Company and affiliates national average 12 month savings of $946 by new customers surveyed who saved with Progressive between June 2024 and May 2025. Potential savings will vary. My name is Shannon Maldonado. I'm the founder of Yaoi, a gift shop. From the lens of artists and handmade objects, I chose Shopify because when I was testing other platforms, it was definitely one of the most user friendly. It was important to me to think about where we would be in the future. All of the tools for reading your sales, like planning inventory, they're just right there on your dashboard. For anyone starting a small business, the biggest thing I can tell you is it doesn't have to be perfect. Shopify can help you build upon it. Start your free trial on shopify.com.