Why I Will Never Retire. And Why the Premise Itself Might Be Wrong.

0:00Studies show that retirees without a sense of purpose experience higher rates of depression, cognitive decline, and early mortality. The end point that millions of people are grinding toward can, if arrived at without intention, be genuinely harmful. Retirement, for too many people, is not freedom. It is a destination with no map for what happens after you arrive. Hello friends, this is Tyler Gardner welcoming you to another episode of your Money Guide on the Side, where it is my job to simplify what seems complex, add nuance to what seems simple, and learn from and alongside some of the brightest minds in money, finance, and investing.

0:48So let's get started and get you one step closer to where you need to be.

0:55Quick note before we get into it, June's pre-order incentive for my book, Real Wealth, is the most personal thing I've ever agreed to share. pre-order in June and submit your receipt at TylerGardner.com and you'll get an exclusive three-episode audio series that will never appear on this feed. Three pivotal moments in my own financial life. The humbling one, the embarrassing one, and the one that made me rethink everything. Three episodes, three moments, TylerGardner.com. Pre-order, submit your receipt, get the episodes delivered digitally in early July and receive every additional monthly incentive between now and the book's release on December 1st.

1:35And now, on to today's episode. In 1928, a journalist asked John D. Rockefeller, then the richest man in the world, then in his late 80s, then worth what would be billions in today's dollars, when he planned to retire. Rockefeller's response stopped the reporter cold. I've never worked a day in my life, he said. It has all been play. Now, I want to be careful here because if my former colleagues in the financial advisory world are listening, I need them to know I am aware that describing Standard Oil's creation as play is doing some significant moral heavy lifting. Rockefeller's definition of a fun weekday involved things that would today require several congressional hearings and maybe a Netflix documentary.

2:29But the financial psychology underneath his quote is worth taking seriously regardless of the source. Now, maybe his line was hyperbole. Rockefeller was not above a well-placed line or two, but the underlying truth is worth our sitting with. This man did not need to work another hour of his life. He could have, and by any reasonable standard should have, stopped decades earlier. Instead, he kept building refineries, kept managing investments, kept funding charitable foundations. Not out of obligation, not out of fear, obviously he had plenty of money, but because the game itself was the reward, and he wanted to play it for as long as he possibly could.

3:19I want to contrast that with something most of us know pretty intimately. The image of the person counting down. Counting down the days to Friday. Counting down the years until retirement. Clinging to the idea that somewhere out there, at some specific age, or on some specific morning, you'll finally be free. Free from what, exactly? That's the question this episode is about. Because I believe, and I'm going to spend the next 30 minutes making this case with data and with some real honesty about my own life, that retirement, as we have been sold it, is a complete scam. A well-intentioned, thoroughly institutionalized, historically contingent scam.

4:10And the people who have figured this out, the genuinely wealthy ones, the ones who seem to operate by a different set of rules than everyone else, figured it out not by accumulating more money, but by fundamentally rethinking what work is supposed to be. Let's get into it. Chapter 1, A Brief and Uncomfortable History of Retirement. Retirement is not a natural phenomenon. It did not emerge organically from the human experience. It was invented, engineered, and it was engineered for a world that no longer exists for many. For most of human history, the concept simply didn't exist. Farmers farmed, blacksmiths smithed, shopkeepers kept shops.

5:00You worked because if you didn't work, you didn't eat. And the idea of a pensioned escape to a life of leisure was not a distant dream. It was not even a thought. Work wasn't something from which you escaped. It was the texture of life itself. There were no retirement parties, no gold watches, no awkward conference room cake where your manager gives a speech that's clearly been adapted from the one they gave at the last person's retirement party with the name changed. None of that. You worked, and then eventually you didn't, usually because something went wrong that prevented further working. That was the system.

5:40The shift began with industrialization. In the late 19th and early 20th centuries, labor was physically brutal for many. Factory work, coal mining, steel production. By the time workers reached their 60s, many were genuinely broken in body and definitely in mind. The introduction of retirement was, in that context, an act of mercy. in acknowledgement that human beings had physical limits and that the system needed to account for them. In 1881, German Chancellor Otto von Bismarck introduced one of the first government-backed pension systems, originally for workers over 70, later adjusted to 65.

6:28The United States followed suit in 1935 with the Social Security Act passed during the Great Depression specifically to cycle older workers out of the labor force so that younger workers, desperate, unemployed, hungry, could step in. But here's the detail that very few people know. In 1935, when the Social Security Act was signed, the average life expectancy in the United States was approximately 62 years old. The retirement age was set at 65. The system was designed for people who would never collect. This is not a cynical reading. This is arithmetic. It is, if we're being direct about it, the actuarial equivalent of offering someone a very generous dessert menu after you're fairly confident they won't make it to dessert.

7:22The intent was kind. The math was pretty deliberate. And now, nearly 90 years later, in a world where average life expectancy has reached nearly 80 and climbing, where the majority of work has shifted from physically punishing to mentally demanding, where remote work means people can contribute meaningfully from anywhere in the world, like the woods of Vermont, until well into their 70s. We're still operating on the Bismarck model, still treating 65 as some arbitrary finish line, still building our financial lives around the assumption that the goal is to stop. But the wealthy, the truly wealthy, figured out that this assumption is not just outdated, it is actively damaging.

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9:47Right now, you can get up to$200 dollars off Square hardware at square.com slash go slash Tyler. That's S-Q-U-A-R-E dot com slash G-O slash Tyler. Run your business smarter with Square. Get started today. This episode is brought to you by Whisperflow. For the better part of three decades, I have operated under the assumption that I am an exceptionally fast typist. Not just fast, gifted fast. The kind of person who finishes sentences before other people have located their shift key. I once clocked 120 words a minute in eighth grade and have been kind of coasting on that identity ever since. The way some people never stop mentioning they ran a marathon in 2006.

10:37Then I started using Whisperflow, and it turns out I'm not that fast. I'm just slow in a way I had never really compared to anything. You can talk roughly three times faster than you can type, regardless of how emotionally attached you are to your eighth grade Mavis Beacon teaches typing score. My entire self-concept has required a little recalibration. Now I draft podcast scripts, newsletter sections, and social captions by just talking. Whisperflow turns it into clean, ready to send text inside Slack, Notion, ChatGPT, Claude, anywhere I'd otherwise be typing. It handles filler words, mid-sentence corrections, names, context, with no setup, and it works in any app on any device.

11:26It even works on a walk in the woods when I'm with my hounds, which is increasingly where my best ideas show up anyway. Try Whisperflow Pro free for a month by heading to whisperflow.ai slash Tyler. That's W-I-S-P-R-F-L-O-W dot A-I slash Tyler. Chapter two, what the wealthy actually do. Let me give you two examples, and then let me give you a pattern that I see. Warren Buffett ran Berkshire Hathaway at 94. Not because he had to, not because he couldn't afford to stop, because as he has said repeatedly in various forms, he tapped dances to work. He would do it for free if you took away the money.

12:14The work itself is the reward. Jeff Bezos stepped back from Amazon and then immediately turned his attention to Blue Origin, media, and a foundation. He didn't retire. He pivoted. He found the next game, which, depending on your feelings about rocket ships and media empires, is either deeply inspiring or the most expensive midlife crisis in recorded human history, probably a combination of both. Rockefeller, we've already discussed. The pattern is not that these people are workaholics in the clinical sense. It's not that they have no capacity for rest or leisure. The pattern is that at some point early in their careers, or sometimes through a painful recalibration along the way, they made a deliberate decision to align their work with their actual values and, dare I say, interests.

13:10They stopped grinding through something they hated in exchange for a promise of eventual freedom. They built something instead that they wanted to show up for. And the psychological research supports why this matters. Self-determination theory, developed by psychologists Edward Deasy and Richard Ryan, identifies autonomy, competence, and relatedness as the three fundamental psychological needs for optimal human functioning. When people engage in work they have autonomously chosen, intrinsic motivation increases. Satisfaction increases. Productivity increases. The research published in Frontiers in Psychology specifically found that employees with meaningful control over their projects reported dramatically higher engagement and well-being than those in rigid, externally controlled environments.

14:09This is not complicated, it's not surprising, but it is routinely ignored in the financial advice industry, which is far more comfortable telling you how to optimize your 401k than asking you whether you actually want to spend the next 40 years doing what you're currently doing, which, if you think about it, is a remarkable gap. We have entire professions dedicated to optimizing how you invest the money you make from your job, and almost zero infrastructure dedicated to asking whether the job is worth your one life. The financial planning industry has built a very sophisticated machine for polishing your cage.

14:53Studies show, and this is the piece I want you to really hear, that retirees without a sense of purpose experience higher rates of depression, cognitive decline, and early mortality. The research on this is extensive and consistent. The end point that millions of people are grinding toward can, if arrived at without intention, be genuinely harmful. Retirement, for too many people, is not freedom. It is a destination with no map for what happens after you arrive. Chapter 3. Why Most People Don't Break the Pattern So if the model is broken, if you agree with me up to this point, if the truly wealthy, and I don't just mean in a monetary sense, have clearly figured out a better way, why do so many people stay stuck?

15:50Why the 40-year grind? Why the countdown? I'm going to offer you five reasons. I want to go through all of them because I think they are more honest about human psychology than most financial content ever quite gets to. Reason 1. The comfort of predictability. The human brain, surprise, does not like uncertainty. This is not a character flaw. It is basic neurology. Daniel Kahneman and Amos Versky, Nobel Prize-winning psychologists, documented what they call loss aversion. We've been over this in previous episodes. The empirical finding that the pain of losing something feels roughly twice as intense as the pleasure of gaining something equivalent.

16:35Losing$50 ,000 feels worse than gaining$50 ,000 feels good. This is why people stay in jobs they actively dislike. Not because they lack imagination. Not because they don't see other options. But because leaving a known, even a bad known, feels more dangerous than staying because the paycheck is certain. The alternative is not. And the brain, left to its own devices, will choose the certain bad over the uncertain good almost every single time. A 2019 Gallup poll found that 85 % of employees worldwide are disengaged from their work. 85%. And the majority of them stay anyway, because the paycheck is predictable, even if nothing else is.

17:31Which means, statistically speaking, if you are currently at work and you have seven colleagues, six of them would rather be somewhere else. I encourage you to look around the room and consider this information at your next all-hands meeting, and my guess is you might be one of them. Reason two, the golden handcuffs. Here's the cruelest trick that income plays on most people. You get a raise. You feel briefly more free, and then almost without noticing, your expenses expand to meet the new number. bigger house, nicer car, better vacations, incremental upgrades everywhere. This is called lifestyle creep or inflation, and it is the single most reliable destroyer of financial freedom available to the average high earner.

18:25Because here's what lifestyle inflation actually does. It re-chains you. I want you to think about that. It re-chains you. Every upgrade is a new obligation. Every new payment is another month you need the job. And suddenly, the person earning$150 ,000 a year is just as trapped, sometimes more trapped, because of the obligations they've accumulated as the person earning$60 ,000. A 2023 study by the Federal Reserve found that 40 % of households earning over$150 ,000 per year still live paycheck to paycheck. That doesn't surprise me at all. More money, same cage, just slightly nicer bars. The bars are very nice, to be fair.

19:13Solid oak, artisanal hardware. The cage was custom designed by a firm in Scottsdale, and it photographs beautifully. But regardless of how you communicated to your friends, let me be clear, it is still a cage. The wealthy move differently. When income increases, they do not primarily upgrade the lifestyle. They upgrade the asset base. They buy the thing that generates more cash flow. They invest in the thing that will pay them back. Income goes up, assets go up, freedom goes up. Not income goes up, expenses go up, dependence on the paycheck goes up. Reason three, normalizing the crappy script.

20:02From the time we were old enough to understand what work was, we were handed a story. Go to school, get a job, work for your 40 years, retire at 65, enjoy something. Note the specifics were always a little vague when we got to retirement. And the script is so thoroughly embedded in our social operating system that deviating from it doesn't just feel financially risky. It feels socially wrong, like breaking a rule everyone agreed to follow without ever being asked. When I ask parents whether they're planning to send their children to college, knowing that average college expenses are now extraordinary and the ROI is genuinely unclear for most fields, the answer is still, and this should come as no surprise, almost universally, of course.

20:59Not because they've done the deep analysis, but because they cannot be the ones who broke from the script because we are not just fighting financial inertia. We're fighting deeply ingrained social expectations about what a responsible life is supposed to look like. The problem is that the script was written for a different world. It was written when pensions existed, when wages kept pace with inflation, when homeownership was straightforwardly a path to wealth? That world has changed significantly. The script has not. We are, financially speaking, performing a play written in 1955 with a cast that has aged considerably and a set that burned down in 2008 and was never fully rebuilt.

21:47A 2022 Transamerica study found that 65 % of Americans have less than$100 ,000 saved for retirement. The plan isn't working, and most people continue to follow it anyway. This episode is brought to you by Momentus. Here's something I have not talked about much on this show. I have two titanium hips, because both hips have been replaced by the age of 43. And while I'm genuinely grateful for modern orthopedic surgery and the engineers who decided titanium was the right material for a human pelvis. The experience did something unexpected and wonderful to my priorities. I stopped caring so much about being lean, and I stopped caring as much about cardio.

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25:38Reason four. Fear of the unknown. We're wired for the familiar. Status quo bias, the documented tendency to prefer existing conditions over change, even when change would be beneficial, keeps people in bad jobs, bad financial situations, and bad systems simply because the alternative requires stepping, once again, into uncertainty. People watch wealthy entrepreneurs and investors living on their own terms and they think, that's not for me. I don't know how to start. And most importantly, and most commonly, what if I fail? And here's the irony that I want to sit with for a moment. The longer you avoid taking the risk, the fewer options you accumulate.

26:23Risk avoided in your 30s narrows your 40s. Risk avoided in your 40s narrows your 50s. The thing you are afraid of doing to protect your security is, over time, the thing that is most threatening it. A 2021 Fidelity study found that people who took calculated career risks, switching fields, starting businesses, making deliberate pivots, had higher lifetime earnings, and reported significantly greater job satisfaction than those who played it safe. The real risk isn't in trying. It's in staying stuck long enough that trying becomes impossible. Reason five, hyperbolic discounting. This is the psychological phenomenon that I think explains more about why people stay trapped than almost anything else.

27:17Hyperbolic discounting is our tendency to overvalue immediate rewards and dramatically undervalue future ones. We would rather have$100 today than$200 in a year, even when, by any rational calculation, that$200 is obviously the far better outcome. Applied to careers and financial lives, we would rather have the certain paycheck every two weeks than build something that might not pay us for six months, but could fund our freedom for 60 years. We choose the immediate comfort over the compounding asset. And the wealthy, the ones who have figured this out, do the opposite. it. They delay. They invest in things that do not pay immediately, but instead generate cash flow for life.

28:06They understand that wealth is not built in a quarter. It is built over decades of compounding small decisions, each one individually small, collectively massively transformative. Chapter four, the three things the truly wealthy are building instead. So what is the alternative to this W-2 work actually look like? What are the wealthy doing that most people aren't? Here are the three things that the people I know who I believe are truly wealthy in mind and in spirit are doing consistently. Number one, building autonomy. They build careers, businesses, and investment structures that give them control over their time.

28:56This is not incidental. It is the primary design principle. The question is never just what will this pay. It is who controls my time if I do this. Because time autonomy is, as the psychological research consistently shows, the single most reliable driver of human well-being and satisfaction. And on a personal note, I cannot tell you enough how much I value autonomy at this point in my life. and you could offer me$10 million a year, I'm not kidding, to go work for someone again, and I would tell you no. Number two, leverage. The truly wealthy create income streams that do not require their constant personal effort.

29:43Again, if you remove yourself from the endeavor and there is no endeavor, it is not a business. So they buy dividend stocks, rental properties, business equity. They create royalties, intellectual property, digital assets. The goal, and this is the one I want you to actually internalize, is to stop trading time for money and start trading money back for time. I know it's cliche, but there's a reason it has been preached for so long. Every dollar that generates income passively is a dollar buying back an hour of your life, at least. That's the entire game, and it's a game you can start playing on any income, at any age, with any amount of capital.

30:28Finally, number three, and this is the one most financial education misses entirely, purpose. Personally, this is why I too will never, ever retire. The wealthy don't just accumulate, they build things that matter. Companies, foundations, ideas, solutions to real problems, not because it makes them richer, though it often does, but because purpose, meaning, and contribution are not optional extras for a well-lived life. They are the fundamental requirements. Without them, even the wealthiest people, especially sometimes the wealthiest people, and the research on this is very clear, report feeling incredibly empty.

31:17There's a specific kind of misery that belongs exclusively to people who have achieved everything they set out to achieve and then stood there wondering if that was really it. It is, in my opinion, one of the saddest possible outcomes. So do not optimize your way to that point in life. The goal is not the number. The number was just the mechanism. them. Chapter five, the honest personal part. I want to tell you something about my own life here because I think it matters. For years, I worked in a W-2 job. Stable, solid paycheck, the kind of thing that from the outside looked like exactly what you were supposed to do.