The Art of Manliness - June 23, 2026


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


Episode Stats


Length

39 minutes

Words per minute

206.65

Word count

8,250

Sentence count

430

Harmful content

Misogyny

1

sentences flagged

Hate speech

2

sentences flagged


Summary

Summaries generated with gmurro/bart-large-finetuned-filtered-spotify-podcast-summ .

The modern idea of retirement was built on a bet that turned out to be wrong. Derek Coburn 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.

Transcript

Transcript generated with Whisper (turbo).
Misogyny classifications generated with MilaNLProc/bert-base-uncased-ear-misogyny .
Hate speech classifications generated with facebook/roberta-hate-speech-dynabench-r4-target .
00:00:00.000 One of the things I've learned after running AOM for nearly two decades is that the fun part is
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00:01:52.240 Brett McKay here, and welcome to another edition of the AOM Podcast, which since 2008 has featured
00:01:57.100 conversations with the world's best authors, thinkers, and leaders that glean their edifying,
00:02:02.040 life-improving insights without the fluff and filler. The AOM Podcast is just one part of the
00:02:06.440 McKay mission to help individuals practice timeless virtues through thought, word, and deed.
00:02:10.980 Also, be sure to explore our articles in ArtOfManliness.com, read the deeper dives we do in our sub-stack newsletter at DyingBreed.net, and turn our content into real-world action by joining the Strenuous Life program at StrenuousLife.com.
00:02:22.660 Now on to the show.
00:02:31.680 The modern idea of retirement was built on a bet that turned out to be wrong.
00:02:35.200 It assumed people would spend most of their lives working and only a relatively short period of time retired.
00:02:39.620 Instead, many Americans now reach 65 healthy, active, and with an entire third of their life
00:02:44.280 ahead of them. Yet we're still using a retirement model designed for a world in which old age was
00:02:48.460 shorter and fewer people expected decades of life after leaving the workforce. My guest says that
00:02:53.600 outdated assumption creates some unfortunate, unintended consequences. It causes people to
00:02:57.940 stress excessively about money, postpone meaningful experiences with family and friends,
00:03:02.200 and sometimes sacrifice the very things that make life worth living in the first place.
00:03:05.620 He argues that by rethinking retirement, not necessarily eliminating it, but reimagining
00:03:10.100 it, we can enjoy more of our lives now while actually feeling more secure about the future.
00:03:14.820 His name is Derek Coburn, and he's a financial advisor and the author of Let's Retire Retirement.
00:03:19.780 Today on the show, Derek explains why the traditional retirement model came about,
00:03:23.180 why it may no longer make sense for many people, and how working even a few years past 65 can
00:03:27.440 dramatically change the math of retirement planning. We also discuss the surprising
00:03:31.380 psychological challenges many people face after they stop working, why purpose matters more
00:03:35.560 than leisure, and how thinking differently about retirement can free you up to spend
00:03:38.880 more time on what matters most right now, whether that's traveling, strengthening your
00:03:42.840 marriage, or making the most of the limited summers you have left with your kids. After
00:03:46.840 the show's over, check out our show notes at awim.is slash retirement. All right, Derek
00:04:02.980 Coburn. Welcome to the show. Hey, Brett. Thanks for having me. So you are a financial advisor
00:04:07.780 and you got a book out called Let's Retire Retirement, which you're making the case we
00:04:12.900 need to retire this idea of retirement that we have. Let's talk about retirement in general
00:04:18.240 first. When people think of retirement, they think about stopping work around age 65 and then never
00:04:24.740 working again. It's like a fixture in our culture. And it seems like it's always existed. You've seen
00:04:29.580 your grandparents retire, you've seen your parents retire. But this idea of stopping work completely
00:04:35.060 at age 65 to go on cruises and putz around the house, this is a relatively new idea. It's like
00:04:40.360 maybe just a little over a century old. And what's interesting, you talk about this in the book,
00:04:45.360 it was created in conditions that no longer exist today. So can you give us a short history lesson
00:04:51.100 on the origins of our modern idea of retirement? Essentially back in 1889, Germany was putting
00:04:58.780 together the first ever social insurance plan to take care of their older workers who were
00:05:05.400 phasing out of their jobs. And the chancellor at the time, Otto van Bismarck, picked the age of
00:05:12.540 70 as the age for them to start receiving benefits because, quote, that is the age at which people
00:05:18.100 are expected to die, end quote. And literally picked the age because they didn't think they
00:05:23.280 would have to pay anyone because they were going to pass away shortly thereafter. And then like
00:05:26.900 27 years later, they lowered the age to 65 finally. But this was at a time when life
00:05:32.720 expectancy, if you made it that far, would only get you into your late 70s. So back then,
00:05:37.380 even if retirement did exist, it's like you would only have to come up with like a third of your
00:05:42.380 income because you were getting some government subsidy to go along with everything else. And so
00:05:47.120 now fast forward to today, if you make it to 65, your life expectancy is going to be in the mid
00:05:52.860 to high 80s. If you make it to 75 or 80, it can be even longer than that. Yet we've never updated
00:05:58.680 this age of 65 to keep up with how much longer we're living. Okay. So late 19th century, some
00:06:05.640 old people couldn't support themselves anymore because most of the jobs back then were physical 0.99
00:06:09.920 and they couldn't do them anymore because they're just old and beat down. In Germany, they set the 0.85
00:06:13.780 retirement age at 65 because most people didn't live longer than that. So relatively few people
00:06:19.340 would actually collect benefits for very long, which that made the system financially manageable.
00:06:24.980 And then other countries like the US adopted similar systems for retirement. But today,
00:06:30.900 people are living a lot longer. A lot of jobs are knowledge work jobs these days. They're
00:06:35.660 office jobs. So we're not beating ourselves too much up anymore. And you can do that for a long
00:06:41.300 time. But we still kept this idea that, okay, at age 65, that's when you should stop working
00:06:46.980 completely. And so now people have to amass a ton of money, enough money to live on one decade,
00:06:54.820 two decades, maybe three decades past 65. And so they go to the financial advisor,
00:07:00.360 their financial advisor is going to give them a number. And this is the number they need to get to
00:07:04.440 to retire and never work again. And it varies, but I think the general rule is to save and invest
00:07:11.280 enough that you can safely withdraw about 4% of your portfolio each year in retirement.
00:07:16.980 which means accumulating, you know, roughly it's like 25 times your annual retirement spending.
00:07:23.740 So if you plan on spending something like $75,000 a year in retirement, you'll need to have almost
00:07:30.640 2 million saved by age 65. And a lot of people struggle to reach those kinds of numbers.
00:07:36.460 And you argue that there are several problems that arise out of this. And one is that just
00:07:41.920 people have a lot of stress and anxiety about the retirement and they're trying to save enough to
00:07:46.100 stop working at 65 and never work again. And so they just put their nose to the grindstone
00:07:50.680 in their 30s, 40s, 50s. They don't spend money on having fun or time having fun. They just figure
00:07:57.480 I've got to work, work, work, save, save, save. And I got to wait until retirement to finally
00:08:02.060 enjoy my life. Yeah, it's going to allow me to finally live the life I want to live one day.
00:08:08.220 So if I sacrifice and I put off things like my health, the relationship that I have with my
00:08:13.220 spouse and my kids, my travel, me having a good time. If I just put my head down and don't focus
00:08:19.400 on those things for 30 years, then maybe one day I'll be able to do all of those things.
00:08:24.640 But the sad thing is by the time you get to 65, you might not have the vim and vigor to do those
00:08:31.380 things you've always wanted to do because you're no longer 30 or 40 anymore. Now you're 65.
00:08:36.400 Yeah. My dad came down with dementia at the age of 62. He had it for 10 years before he
00:08:41.700 he passed away. Nothing is promised. And so a lot of people think like, well, what if I get
00:08:46.760 injured? What if I get hurt? What if I lose my job? Well, if we're sitting here at 75 and those
00:08:51.900 things happen, like all of the research, all the data shows us that the things that people regret
00:08:57.460 are not, you know, I didn't work more. It was, I didn't spend more time with the people and things
00:09:02.540 that were most important to me. How have you seen that play out in the clients you've served? Have
00:09:07.260 you seen people who, you know, they got to 65, 70 and they retired and, you know, sure they
00:09:13.720 got enough for retirement, but they look back in their life like, boy, I really regret not taking
00:09:19.760 more advantage of the time I had when I was younger. Yeah. My book has been pretty triggering
00:09:24.400 for some people in their sixties and seventies because they sort of wish somebody would have
00:09:29.140 made them aware that they could have done things differently. And you have a lot of people that
00:09:35.280 have put off and they have, it's essentially like the ultimate form of a rival fallacy. People felt
00:09:40.100 like they were going to have this amazing life, being able to do all of these things. And when
00:09:44.380 they get there, it's not what they thought it was going to be. Like I've had clients come into my
00:09:48.500 office over the years and very few ever came in before the book with their hand raised, knowing
00:09:53.340 that they didn't want to retire. So I would humor them and I would say, what do you want to do when
00:09:57.580 you, you know, when you stop working? And the couple would say, we want to travel the world
00:10:01.500 together. And I would say, great, me too. When was the last time the two of you went out on a date?
00:10:06.540 And more than 50% of the time, they would just look at each other and not have a great answer.
00:10:11.100 I have other clients who have said that when they retire, they want to play golf five days a week.
00:10:15.560 And I ask them how often they're playing golf now. And the majority of them say that they're
00:10:19.460 not playing golf. And it's like, look, if we're not working the muscles, if we're not developing
00:10:24.640 the relationships to have the physical skills and the relationships to play golf 20 years from now,
00:10:29.640 I think it's going to be hard for us to all of a sudden start to make it happen once we get there.
00:10:34.000 All right. So this idea of a hard stop retirement at 65, it could cause a lot of stress and it can
00:10:39.320 cause you to put off things for the future because you're just like, I got to work more and save more
00:10:43.320 and not take the vacation now with my family because I got to save that for retirement.
00:10:47.680 Another interesting point about the hard stop retirement that people don't think about, it's
00:10:51.260 like, oh, it'd be so great to never have to work again, not wake up early, not have to go to
00:10:56.320 meetings. But a lot of people, once they hit that and they're not working anymore, they have this
00:11:01.540 period where they almost have like an existential crisis. They don't know, what do I do with myself
00:11:05.600 now? That's another problem of this hard stop retirement. Yeah, there was some good research
00:11:10.680 done in 2013 by Barbara Fredrickson, where she was looking at people who were prioritizing
00:11:17.300 personal happiness and people that were prioritizing purpose. So personal happiness was
00:11:22.520 more of a selfish, for purposes of this study, it was people that were saying, what can I do to
00:11:28.240 make myself happy? That was their reason for waking up in the morning. And the other group
00:11:32.300 of people were solving for, what can I do to make this world a better place? And when they looked
00:11:37.640 at them, they hooked them up to brain monitors and heart monitors. And the people that were
00:11:41.060 solving for happiness had the same response in their body that our body has when it's dealing
00:11:46.480 with a chronic adversity. So something like losing a job, losing a loved one, their inflammation,
00:11:52.520 was going higher. Their immunity was going down. They were more likely to get sick and pass away.
00:11:58.240 Whereas the group that was prioritizing purpose, they felt like there was a bigger reason
00:12:02.320 for them to wake up every morning. It had just the opposite effect. Their inflammation markers
00:12:07.700 were much lower. Their immunity was better. They were less likely to get sick, to get a disease.
00:12:13.360 So there is actually a real scientific reason and backing here that says, hey, maybe we should never
00:12:19.360 want to arrive at a place where we're fully checked out in terms of the role that we're
00:12:24.020 playing to make this world a better place. Okay. So the big argument in your book is that
00:12:28.080 instead of thinking, all right, when I hit 65, I'm going to quit working completely.
00:12:32.960 You're advocating that people might consider continuing to work past 65. And that could
00:12:38.000 involve a different job or fewer hours. But you highlight that by working past 65,
00:12:44.460 the retirement math becomes less anxiety inducing. So if you have a listeners right now in their
00:12:50.660 thirties, forties, and fifties, and they're thinking, Oh my gosh, I don't have enough
00:12:54.240 safe for retirement. How can working an additional five to 10 years, how can that change your
00:13:00.160 retirement savings plan so that it might not be as stressful for you and you can enjoy the present
00:13:05.760 more? So I tell this story in my book, it's called a tale of two Tonys about a guy named
00:13:09.940 Tony, who's 45 years old, he makes $150,000 a year, and he has $150,000 saved for retirement.
00:13:17.000 And he meets with his advisor, has a conversation like the one we've already talked about, and
00:13:21.340 without giving it much thought, agrees to 65 as his retirement age. The advisor comes back and
00:13:27.600 tells him that he'll have to save $2,400 a month every month adjusted for inflation for the next
00:13:33.780 20 years in order to stop working. That's $30,000 a year. That's 20% of what he's making.
00:13:39.940 And that's a non-starter for most people.
00:13:42.960 So he immediately starts feeling the stress and the anxiety of already being behind, feeling
00:13:47.760 like he can't catch up.
00:13:49.380 He's working longer at the office.
00:13:51.060 He's not going to the gym.
00:13:52.480 He's getting less sleep.
00:13:53.640 He's canceling family vacations.
00:13:56.020 And then I introduce an alternate reality similar to this movie, Sliding Doors, from
00:14:00.700 a long time ago, where it was a movie with Gwyneth Paltrow, where her life could go in
00:14:05.580 one of two directions based on whether she caught a train or not.
00:14:08.600 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.
00:14:15.660 And his wife says, why do you want to retire at 65?
00:14:18.600 You like what you do.
00:14:20.180 You like the people you do it with.
00:14:21.520 And even if you're not doing this, I can't imagine you sitting around not doing anything at all.
00:14:26.540 He's like, you know what?
00:14:27.200 You're right.
00:14:27.980 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?
00:14:35.780 And the amount that he has to save goes down from $2,400 a month to $110 a month.
00:14:42.920 It goes down by 96%.
00:14:45.200 And even if Tony were to say, I'll go tell him 70 instead of 65, it's a 75% reduction
00:14:52.720 in the amount that he has to save.
00:14:54.120 It goes down to $600.
00:14:56.240 So by recognizing and planning that, hey, I'm willing to do this right now, what I'm
00:15:01.540 doing or something else for a little bit longer, it opens up an incredible amount of, of financial
00:15:07.220 flexibility in the short term and lets people lean into spending more of their time and money on the
00:15:12.800 people and things that are most important to them right now. I think that when I saw that math,
00:15:17.860 I was like, that's crazy. Hopefully people see that. It's like, it gives them some hope if they
00:15:21.500 think they're behind on retirement. They're like, I'm never going to have a comfortable
00:15:24.700 retirement. It's like, well, if you just work five or 10 more years past 65, you're probably
00:15:30.060 going to be okay. So I think it can reduce that anxiety and that stress. But then the big point
00:15:35.220 you're trying to make with this book is that by extending your working life a few years, you free
00:15:41.580 up time you would have spent working extra hours and money you would have been siphoning off to
00:15:46.960 your retirement account so you can use it to enjoy life when you're young and vibrant. That's the big
00:15:51.980 case you're making. Exactly. Yeah. I mean, and you talk about you've got kids in their teens
00:15:57.180 and you talk about this in the book, you were very conscious about this and deliberate that,
00:16:03.540 okay, when my kids are teenagers, I want to be able to spend more time with them and do more
00:16:09.340 with them when they're teenagers. What was it about the teen years that made you think,
00:16:13.480 I really want to maximize this stage of life? Yeah, well, I mean, it's been more of an evolved
00:16:19.820 way of thinking for me. So I would say that when I became really mindful about it was A,
00:16:24.640 when my dad got dementia. And B, when my kids were 10 and seven, respectively, my wife and I
00:16:30.620 had this nighttime routine where we would take turns tucking our kids into bed each night. And
00:16:36.860 I found myself with my oldest son one night wishing it would hurry up. And God, I'm not
00:16:42.640 saying this out loud, but I'm thinking to myself, like, hurry up and fall asleep so I can go
00:16:45.980 and hang out with your mom or respond to this email or watch this show on Netflix.
00:16:51.100 And then it occurred to me that he's probably not going to want to be doing this with me for
00:16:55.120 very much longer. So I tried to like really force myself to be present. And that worked
00:16:59.680 a little bit, but not the way that I wanted it to work. And then I had this crazy thought one day,
00:17:04.560 which was, you know, if I woke up 30 years from now and a company invented a time machine
00:17:09.400 that allowed me to go back in time to have one more nighttime routine with the 10 year old
00:17:15.180 version of my son, how much money would I pay for that? And the number that came into my mind was
00:17:20.000 $50,000 and, and it's all relative, right? It's going to be a different amount for different
00:17:24.520 people. But the point I'm trying to make is that there are these like small moments that are not
00:17:29.540 like, they don't, they don't seem like a big deal. Like we're taking them to an amusement park or on
00:17:33.960 a great vacation, but just laying there with him and knowing this is a fleeting moment in time
00:17:39.680 and that I'm going to really miss it. And I'd be willing to pay a lot of money to revisit it at
00:17:44.160 some point in the future to allow myself to be really present for them when this happens. And
00:17:49.560 And then another thing I'll add is, fast forward to when my oldest was about 13, there was
00:17:55.760 a day, it was around four or five o'clock in the evening and I was getting ready to
00:17:59.540 work out and he asked me if I would play Legos with him.
00:18:03.180 And I was like, gosh, buddy, I'm getting ready to work out.
00:18:05.340 I haven't done this in a couple of days.
00:18:06.780 I really want to make it happen.
00:18:08.600 And while I was working out, I was thinking, you know, I want to organize my day and my
00:18:13.340 life in a way that I never say no to my kid again.
00:18:16.600 I want to make sure that I'm available.
00:18:17.960 I'm done everything that needs to get done by three o'clock. And then I'm around if they want
00:18:23.320 to hang out with me. And a lot of days they don't want to hang out with me. And if that happens and
00:18:26.540 I can get back to the things that didn't have to get done, but are nice for me to do. But the more
00:18:31.620 I'm around, the more that they're asking, the more that I'm saying yes, the more they come back and
00:18:36.460 say, let's do it again. And so now I've got this great rhythm with both of my boys where we're
00:18:41.720 working out together four days a week. We share a lot of music in common. We're playing golf and
00:18:47.140 just really have carved out a lot of similar and shared hobbies and interests that we can
00:18:52.040 take in together. Yeah. So you're prioritizing enjoying your kids while they're still around
00:18:56.760 rather than prioritizing, okay, I've got to do everything I can now to build up my retirement
00:19:01.320 account. Yeah. If my like macro idea is that by recognizing that I'll probably work longer in my
00:19:07.280 seventies, freezing me up to spend a lot more of my time and money differently now, then I'm really,
00:19:12.060 I've got that under the microscope with how I'm parenting right now. So I've got two and four
00:19:16.540 years respectively before my boys go off for college. And it's almost like I'm saying no to
00:19:21.820 a lot of speaking gigs right now. I'm saying no to coaching. It's something I thought about,
00:19:26.660 but I'm not going to do because what I'm solving for on a daily basis is maxing out the time
00:19:31.640 that I'm going to have with them. And it's almost like the version of me five years from now is
00:19:36.840 writing a sponsorship check to free me to lean into this time with them because I know once
00:19:41.780 they're gone. I'm going to be ready to ramp up my activity, ramp up the hours I'm working,
00:19:46.560 ramp up the contribution that I'm making. Yeah. I'm this book. This is really useful
00:19:51.160 for me because I'm a neurotic saver. I just, I love to squirrel away money because it makes me
00:19:55.780 feel safe. And so there's been times in my own working life from like, well, we can't take the
00:20:01.040 time off to do the vacation because I got to get this thing done. So we can make the money and save
00:20:05.220 it for retirement. After reading this book, I'm thinking, oh my gosh, my son, he's 15. I got maybe
00:20:10.940 three summers left with him, maybe four. I want to be able to do stuff with him. I need to take my
00:20:16.480 foot off the gas a little bit and realize it's going to be okay. I can work an additional five
00:20:21.540 to 10 years in my seventies. And I've got a lot more time because I'm going to be by myself with
00:20:25.660 my wife, but I can't get back that time with my son now. So take the vacation. Yeah. And I think
00:20:32.080 all of these things, whether it's the dating example or the golf example, or the time with
00:20:36.100 our kids, right? Like the 18 summers with Jim and Jamie Shields, that's in their book, family board
00:20:42.100 meetings is the first time I heard of this. But like, there's a lot of people that need to hear
00:20:46.060 that that need to be reminded that you only have this limited time with your kids. Like the main
00:20:51.420 thing that I'm solving for my life right now, having a 16 and a 13 year old at my house is I'm
00:20:56.360 trying to do as many things as possible to increase the likelihood that they're going to
00:21:00.340 want to spend time with me when they're adults. So I'm very confident that because I'm making the
00:21:05.200 most of my time with my kids now, then I'm going to have 20, 30, 40 additional summers with them
00:21:10.320 as well. Because the more we're leaning into something now, these relationships are going
00:21:14.200 to compound the same way that your money is going to compound in your portfolio.
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00:26:26.300 All right, so working five to 10 years after age 65,
00:26:29.020 it means you have to save less for retirement now,
00:26:31.360 which means in your 30s, 40s, and 50s,
00:26:34.520 you can spend more of your money and time
00:26:36.600 doing stuff that you enjoy with the people you love now.
00:26:40.420 And as we talked about earlier,
00:26:41.440 some people would just like to keep working.
00:26:43.240 They wouldn't be happy not doing anything.
00:26:45.280 They like working.
00:26:46.320 It gives their life meaning.
00:26:48.080 So stopping work at 65 wouldn't be desirable for them anyway.
00:26:52.580 But let's say someone is not in that camp.
00:26:54.960 Their job doesn't bring them any meaning.
00:26:56.600 They hate their job and they just, they can't wait until they're 65 so they can quit their
00:27:01.440 crappy job and stop working.
00:27:03.580 What do you tell those people?
00:27:05.340 Yeah, I changed the language in my book after the first couple of passes.
00:27:08.840 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.
00:27:21.180 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.
00:27:29.820 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 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.
00:27:57.900 All right. So if you don't like your job, try to find a job in which you wouldn't mind
00:28:01.640 continuing to work after 65. And it's probably a good idea to make that pivot long before you
00:28:06.860 reach 65, since it does get harder to get hired as you get older. But another thing you do is you
00:28:11.900 could pivot to something where you work fewer hours. In your later years, you don't necessarily
00:28:15.360 have to work as many hours, or you just want to have some income continuing to come in.
00:28:19.460 Something people might think about is starting something on the side before they get older.
00:28:24.140 So as they get older, they can maybe pivot into something they're more interested in,
00:28:27.660 that they would like to do more of? Yeah, look, I can share my own experience. My own personal
00:28:32.740 experience was around 2010, 2011, I had about 350 wealth management clients and I was qualifying
00:28:40.300 for these fancy trips that made me about 10 to 15 years younger than most of the other advisors who
00:28:46.060 were there. And I was asking them a lot of questions and, and almost to a person, they all
00:28:50.380 had like 2000 clients and they only enjoyed working with about 20% of them. And in our
00:28:56.880 industry, especially back then, you couldn't use social media. You couldn't use word of mouth
00:29:01.520 marketing very much. You couldn't get testimonials. So you just had to take whatever fell into your
00:29:06.720 lap. And I recognized that there were a lot of people that I was working with that I didn't love
00:29:11.460 working with for one reason or another. And so I shifted my practice. I went from 350 clients down
00:29:17.240 to about 75. And then my wife and I started an organization together called Cadre, which is still
00:29:23.540 around today, we have a community for CEOs and entrepreneurs and find ways to bring people
00:29:27.600 together. But what was fascinating about that is the ancillary benefit that really popped was by
00:29:33.600 me having two things going side by side at the same time. It allowed me to really have the courage
00:29:38.920 and the ability to stick to my guns in terms of who do I want to work with and who do I want to
00:29:43.380 support. And Adam Grant in his book Originals, I think, talked a little bit about looking at
00:29:49.480 entrepreneurs and people that were starting businesses and the success rate that they had
00:29:55.040 with their new business based on whether they had some steady stream of income coming in from
00:30:00.000 another source at the time. So essentially it was two groups of people starting businesses.
00:30:04.680 One group had a job and they were doing this new business kind of on the side to build it up. And
00:30:09.540 the second group just went all in on the new business. And the first group was far more likely
00:30:14.680 to succeed with their business because they had this income coming in that allowed them
00:30:19.640 to be a little bit more mindful and a little bit more deliberate with the way they were
00:30:23.080 building it.
00:30:23.700 And the takeaway is that entrepreneurs are often considered big risk takers, but really
00:30:28.840 the good ones are great risk mitigators.
00:30:31.020 And so I think that there's an opportunity for a lot of people that maybe you start some
00:30:35.700 kind of a side hustle while you add the thing that you have now and allow yourself to get
00:30:40.220 a few clients, to get a little bit of momentum.
00:30:42.120 them. And maybe you keep both going at the same time, but maybe it provides an on-ramp for you
00:30:46.920 to leave the job that you don't love right now and start leaning into something that you enjoy
00:30:50.480 much more. What about someone who's got a job that involves a physical capacity that degrades with
00:30:56.220 age and necessitates an early retirement? I'm thinking maybe you're in a physically
00:31:01.080 demanding job, like you're an HVAC installer, or even surgeons. It requires a lot of fine
00:31:07.320 you know motor skills or whatever and maybe as you get into your 70s and 80s like that sort of
00:31:13.440 degrades how what do you i mean what do they do they've trained their whole life to do this thing
00:31:18.500 and they can no longer do it what about them yeah you know i think that there's other opportunities
00:31:23.900 like in their fields you know i think you see a lot of doctors a lot of surgeons who who take
00:31:29.840 jobs as professors at universities or they sit on boards and contribute their knowledge that way
00:31:36.020 you've got auto mechanics that end up in more of a managerial type role. So hopefully there's going
00:31:42.740 to be some opportunities for them to pivot doing something else. Yeah. Maybe you got to think like
00:31:46.520 an athlete, right? Like a football player, you know, they have to retire in their thirties and
00:31:51.000 then they end up doing something that's related to the field. Like they become a coach or something
00:31:54.620 like that, or an agent, you know, my dad, he was a federal game warden for the fish and wildlife
00:32:00.360 service for his entire career. They had mandatory retirement. I think it was like a 55 sometime in
00:32:05.740 the 50s is a demanding physically demanding job but he kept working even though he didn't have to
00:32:10.460 he had a pretty good pension with his job but he got a contract job with the epa checking oil rig
00:32:17.640 compliance regulation stuff oh cool he's been doing that he just turned 79 he's still doing that
00:32:24.160 and i don't think he like loves it but he doesn't hate it it's just something to do and he really
00:32:30.040 enjoys working and i think it's an example of doing something related to what you're doing but
00:32:35.260 in a different capacity. No, that's a great example. All right. So if we're shifting from
00:32:38.940 a hard stop retirement to a continuous income or phased model where maybe we make less and less as
00:32:45.380 we get closer to 75, how should our investment strategy change? Like what does a portfolio look
00:32:51.200 like when you aren't planning to completely drain it starting at age 65? Well, one of the nice
00:32:56.520 advantages of working longer is that you can allow your money to potentially have more exposure to
00:33:02.760 risk for a longer period of time. So somebody that is planning to retire at 65 is going to
00:33:07.960 want to shift, in my opinion, more of their money to some conservative investments that's not going
00:33:12.760 to be subject to a potential stock market decline of 20%. And if you're still working, and thereby
00:33:18.960 you're using your income primarily to live on and not drawing down from your investments,
00:33:24.060 you can leave your money invested a little bit more aggressively for a little bit longer. That
00:33:28.940 would be one thing. I think another thing is just the idea of getting more and more people
00:33:34.020 comfortable spending their money earlier. You mentioned you're a great saver. And I will tell
00:33:39.140 you that most of my clients now are in their 60s and 70s, and they all have probably eight figures
00:33:45.540 plus of net worth. And the recurring theme in all of these conversations with my clients is just
00:33:51.880 begging them to spend more of their money. Because the problem is, if you've been a great saver your
00:33:57.020 entire life and you've played that game really well, it's incredibly difficult to just flip the
00:34:02.480 switch and all of a sudden lean into spending your money more. And if I have different groups
00:34:08.100 of clients, let's say in one bucket I have clients that have enough money, they're probably never
00:34:13.420 going to run out of it, and they're still earning an income, even if it's like $50,000 a year or
00:34:18.640 $100,000 a year, those clients spend their money in much more of a carefree way than the ones who
00:34:26.360 are completely out. The ones who are no longer doing anything at all have a really difficult
00:34:31.040 time transitioning from this. My portfolio has gone up only for the past 40 years and now I'm
00:34:37.840 taking money out of it. And psychologically, it's been interesting to see how many people
00:34:42.660 have such a difficult time overcoming this. Yeah, I can see that happening. Because you
00:34:47.280 spend your entire adult life saving and now it's like, okay, now you got to spend it. You're like,
00:34:51.420 wait a minute, that's not right. So that can be tough. But like by having that job in your
00:34:57.200 seventies, you know, 70, 70, 75. Yeah. Like you said, it released some of that psychological
00:35:02.780 pressure to not spend. She's like, well, you know, I still have money coming in.
00:35:07.200 My retirement's going to be okay. I can spend and I'll be okay. Yeah. Okay. So the argument
00:35:12.320 you're making is that people could stress out less and enjoy their lives and their younger
00:35:16.200 years more if they plan to work past 65. And this is something that's very doable now because,
00:35:20.360 most jobs aren't physically demanding and people are living a lot longer. I mean, even if you stop
00:35:25.420 working at 75, you could still have 20 years, two decades of not working at all. I think there are
00:35:30.600 some people out there who truly don't want to work any longer than they have to. And there's
00:35:33.700 some careers where it makes a lot of sense to maximize your earnings in your younger years,
00:35:38.640 where maybe it's a physical job and you don't see yourself pivoting to something else later.
00:35:43.280 Or maybe you want to devote yourself to volunteer work after 65. But for a lot of people,
00:35:47.660 this is a path that could allow them to make more of their lives now. And as part of that,
00:35:52.500 you're a huge advocate for continuing to invest in yourself as you age. What does that look like?
00:35:58.660 Yeah. So the last chapter of my book is called just that, investing in you. And I think that
00:36:03.720 sometimes when we're too focused on hitting our number, we do it at the expense of going to the
00:36:09.260 gym. We do it at the expense of the quality of our sleep, hanging out with friends, having a good
00:36:13.940 time. And I think that our society really over-indexes for the long-term benefits of
00:36:20.300 doing these things that are healthy for us and good for us and undersells the short-term benefits.
00:36:25.160 So like, yes, you should get a good night's sleep tonight because you might feel better 20 years
00:36:29.920 from now. But in my experience, you should really get a good night's sleep tonight because of how
00:36:33.740 you're going to feel 20 hours from now. And I think that the idea that I'm trying to promote
00:36:38.680 here is that I think that if you're currently working, let's say, nine hours a day and you
00:36:44.440 feel like you don't have time to go to the gym, you don't have time to see your best friend,
00:36:48.580 you don't have time to take your wife out on a date, that by actually making time to do those
00:36:53.140 things, you're going to be filling up your cup. You're going to be giving yourself more energy.
00:36:58.240 You're going to be giving yourself more clarity. And even though you might be now working eight
00:37:02.620 hours a day instead of nine hours a day, in my experience, you can be a lot more productive with
00:37:07.720 those hours because you're better rested, you don't have the brain fog, and you're showing up
00:37:12.800 with more vigor than you were before. For someone listening right now who's exhausted by the grind,
00:37:18.300 but feels trapped by this traditional retirement timeline, what is the very first step they can
00:37:23.280 take today to start applying your framework? So look, I think I'm selling. I'm not really
00:37:28.060 selling anything, but I think I'm selling a lot of the same things that other people are selling.
00:37:31.660 Like lean into these relationships that are important to you, take better care of yourself,
00:37:35.540 have more fun, but I'm hopefully solving the elephant in the room for a lot of these people,
00:37:41.260 which is like, how can I afford to do this? So I have a calculator on my website, which you can
00:37:46.700 link up, hopefully, DerekCoburn.com forward slash never retire, where people can enter in like their
00:37:51.900 income and the assets that they have, and they can experiment with, well, what happens if I work two
00:37:57.240 more years or what happens if I work four more years and be able to really embody the financial
00:38:02.800 impact, the flexibility that will come from agreeing to say, I'm going to do this for
00:38:07.120 a little bit longer. Like I gave the tale to Tony's example before, but even like working
00:38:12.500 just one extra year, somebody were to say, I'll go till 66 instead of 65, typically correlates
00:38:18.720 with about a 15 to 20% reduction in the amount of money that they have to save on an annual basis.
00:38:24.160 So, so really think about, you know, how committed are you to your plan? How much of your plan right
00:38:29.860 now is on autopilot. Did you pick 65 because that's really the age that you know you want
00:38:34.540 to stop working? Or did you pick 65 because that's typically what everyone else says to do?
00:38:40.620 Well, Derek, this has been a great conversation. Where can people go to learn more about the book
00:38:43.460 and your work? Yeah, I've loved our chat here, Brett. My website, DerekCobron.com,
00:38:48.360 I've been writing a lot more, just kind of piggyback on a lot of the ideas in my book
00:38:52.480 around what I'm doing from a parenting and how I'm spending time with my wife, how I'm spending
00:38:56.640 time with my friends and just really trying to tie all this together and keep building on what
00:39:01.400 was in the book. So I encourage people to go there, sign up for my email newsletter. I hang
00:39:05.260 out on Instagram a little bit too. So, but yeah, it'd be great to keep in touch with some of your
00:39:09.040 folks. All right. Well, Derek Coburn, thanks for your time. It's been a pleasure. Thanks so much,
00:39:12.340 Brett. My guest today was Derek Coburn. He's the author of the book, Let's Retire Retirement. It's
00:39:17.360 available on amazon.com. You can learn more information about his work at his website,
00:39:20.820 derrickcoburn.com. Also check out our show notes at awim.is slash retirement, where you find links
00:39:25.200 to resources. We delve deeper into this topic. Well, that wraps up another edition of the A1
00:39:37.120 podcast. If you haven't done so already, I'd appreciate it if you take one minute
00:39:39.980 to give us a review on a podcast or Spotify. It helps out a lot. And if you've done that already,
00:39:44.160 thank you. Please consider sharing the show with a friend or family member who would think
00:39:47.620 was something out of it. As always, thank you for the continued support. Until next time,
00:39:51.020 is Brett McKay. Remind you to not listen to anyone podcast, but put what you've heard into action.