Traditional retirement is a flawed concept because it assumes work is merely a means to an end, but research shows that retirees without purpose experience higher rates of depression, cognitive decline, and early mortality; the wealthy don't retire but redesign work by building autonomy, leverage, and purpose, which are the true foundations of real wealth.
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Deep Dive
Why I Will Never Retire. And Why the Premise Itself Might Be Wrong.
Added:Studies show that retirees without a sense of purpose experience higher rates of depression, cognitive decline, and early mortality.
>> [music] >> The end point that millions of people are grinding toward can, [music] 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 [music] you arrive.
Hello friends. This is Tyler Gardner welcoming you to another episode of Your Money Guide on the Side, [music] where it is my job to simplify what seems complex, add nuance to what seems simple, and learn from and alongside [music] some of the brightest minds in money, finance, and investing. So, let's get started and get you [music] one step closer to where you need to be.
Quick 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. And 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 [music] 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.
But, the financial psychology underneath his quote is worth taking seriously, regardless of the source. Now, >> [music] >> 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.
>> [music] >> Instead, he kept building refineries, kept managing investments, >> [music] >> kept funding charitable foundations, not out of obligation, not out [music] 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.
I 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.
And 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. You worked because if you didn't work, you didn't eat. And the idea of a pension to 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.
The 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. An 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.
The 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. The 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.
This episode is brought to you by Square.
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This episode is brought to you by WhisperFlow.
For the better part of three decades, [music] I have operated under the assumption that I am an exceptionally fast typist.
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That's [music] w i s p r f l o w.ai/tyler. [music] 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 tap dances to work. He would do it for free if you took away the money. The 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. They 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 Deci 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.
This 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.
Studies 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 three.
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? Why 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 one, the comfort of predictability.
The human brain, surprise, does not like uncertainty. This is not a character flaw, it is a basic neurology.
Daniel Kahneman and Amos Tversky, Nobel Prize-winning psychologists, documented what they call loss aversion. We've been over this in previous episode. The empirical finding that the pain of losing something feels roughly twice as intense as the pleasure of gaining something equivalent. Losing $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.
Which 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.
Because 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, solid oak, artisanal hardware. The cage was custom designed by a firm in Scottsdale and it photographs beautifully. But, regardless of how you communicate it 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.
From 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.
Not 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.
A 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 Momentous.
Here's something I have not talked about much on this show.
I have two titanium hips, >> [music] >> because both hips have been replaced by the age of 43. And while I'm genuinely grateful for modern orthopedic surgery [music] and the engineers who decided titanium was the right material for a human pelvis, the experience [music] did something unexpected and wonderful to my priorities.
I stopped caring so much about being lean, and I stopped caring as much about cardio. I started [music] caring with a focus that borders on obsessive about two things only as I [music] get older: strength and mobility. I want to be able to walk my dogs well into my [music] 80s. Everything else is negotiable.
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This episode is brought to you by Anthropic. How much of your day is spent on work [music] that probably shouldn't require you specifically? The research that takes 3 hours or the first draft that exists only to become the second draft. That is where most people lose their entire day. Claude can give it back. Last week [music] I needed sources for a retirement income podcast episode, credible, varied, and recent. [music] Claude pulled together approximately 60 sources in the time it took me to make coffee, properly cited, organized by argument, and ready to use. A half-day research session became 20 minutes.
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[music] Reason 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. Risk 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.
Hyperbolic 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 2 weeks than build something that might not pay us for 6 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. They delay. They invest in things that do not pay immediately, but instead generate cash flow for life.
They 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 does 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. This 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. Again, 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 cliché, 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.
Finally, number three, and this is the one that 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.
There'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.
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.
I hated it.
Not the industry, not the work itself necessarily, but the arrangement. The structure that said my time belonged to someone else, that my contributions were valued at a number someone else determined, that my ceiling was set by someone else's assessment of what the role was worth.
I want to be careful here not to make this sound more dramatic than it was.
Nobody was mean to me. The office had great coffee. The parking was free.
These are not nothing, but there is a particular low grade of despair that comes from showing up every day to something that is perfectly fine and knowing that perfectly fine is not what you wanted your life to be about.
And I stayed a little longer than I should have because leaving felt risky because the paycheck was certain, because I was following the script and the script said you don't leave a stable job without something guaranteed on the other side.
When I finally left, when I started building social cap and what became Your Money Guide on the Side, people told me I was lucky. I heard that word constantly. Wow, you have good luck.
Let me be clear. It was a deliberate choice.
A terrifying, entirely non-lucky choice to walk away from the certain thing toward the uncertain but possible thing.
A choice that came with real financial consequences in the short term and that has compounded into something I genuinely cannot imagine being without.
And here's the crux of the episode and of my philosophy in life.
I have already reached the point where I don't ever want to stop. That is not performance. That is not content. It is the honest truth that I would do this if the audience were a tenth the size, if the revenue were a fraction of what it is because the work itself, helping people think differently about money, hearing from people who do now think differently about money, making something I'm proud of, creating this podcast, that in and of itself is the reward. That's what Rockefeller meant. I understand it now in a way I didn't when I was counting down the days to Friday.
Here's what I want you to take away from today.
The question is not whether you will retire one day.
The question is whether you will need to.
Because those are two very different questions with very different implications for how you build your life.
The truly wealthy do not structure their lives around a finish line.
They structure them around the game itself. Around work that generates meaning.
Around assets that generate cash flow.
Around a daily existence that doesn't require an escape because it was designed to be something worth showing up for. Plant the tree you will never see. That's the mindset of someone building generational wealth. But plant the tree you will chop down one year at a time in retirement and hope you don't get to the base before you die.
That's the mindset of someone who followed the script without ever questioning it.
Both are choices. Only one of them is honest about what it is. Always remember real wealth is not the number in the account. Real wealth is the freedom to stop running from what you do daily. To stop running toward a vague retirement.
And to start running toward something you actually want to build.
The game, at least to me, will always be better than the finish line.
As always, hope this gives you something to think about throughout the week ahead.
>> [music] >> Thanks for tuning in to your money guide on the side. If you enjoyed today's episode, be sure to visit my website at tylergardner.com for even more helpful resources and insights. And if you're interested [music] in receiving some quick and actionable guidance each week, don't forget to sign up for my weekly newsletter where each Sunday I share three actionable financial ideas to help [music] you take control of your money and investments. You can find the sign up link on my website [music] tylergardner.com or on any of my socials at socialcapofficial.
Until next time, I'm Tyler Gardner, your money guide on the side, >> [music] >> and I truly hope this episode got you one step closer to where you need to be.
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