60 Thoughts as I Turn 60

In this special episode of Motley Fool Rule Breaker Investing, Motley Fool co-founder David Gardner offers a collection of 60 convictions, stories, quotes, and observations in celebration of his 60th birthday — all in 60 minutes.

To catch full episodes of all The Motley Fool's free podcasts, check out our podcast center. When you're ready to invest, check out this top 10 list of stocks to buy.

A full transcript is below.

This podcast was recorded on May 20, 2026.

David Gardner: Sixty thoughts as I turn 60: 20 on investing, 20 on business, 20 on life. Not the 60 best thoughts ever thought. Certainly not the last 60 that I'll ever think, and maybe not even the same 60 I'd choose a year from now. But these are things I've come to believe, earned through investing, entrepreneurship, friendship, reading, losing, winning, and trying to stay Foolish — capital F — all along the way. It's a milestone birthday. It's a landmark episode, 60 Thoughts as I turn 60, only on this week's Rule Breaker Investing.

Welcome back to Rule Breaker Investing. This week is a little different. I just turned 60, and to mark that milestone, I've gathered 60 thoughts, 20 about investing, 20 about business and 20 about life. Some are mine. Some are borrowed from writers, founders, investors, philosophers, and fools who've helped shape me. Some are one-liners. Some need a little room. All of them in one way or another, have helped me see more clearly. My hope is not that you agree with every one. My hope is that a few stick, maybe at least one or two, enough that you carry them forward yourself. Let's get started. Pretty much my goal is to give you these 60 now that I'm 60, in 60ish, I never know how long the ad breaks go. These are things I have come to believe. They've helped me win the game of investing. I hope they do the same for you.

No. 1, everyone is an investor. When addressing a room, I've said, raise your hand. If you're an investor, it's a trick question. It catches only those who think investing is what other people do a specialized class, not me or you. Wrong. Put your hand up. Everyone is an investor of both money and time. Your choice to do this, not that, to spend here, not there, are all investments. Everyone is an investor. The stock market always goes down faster than it goes up, but it always goes up more than it goes down. No. 3, and I quote, "forming macro opinions or listening to the macro or market predictions of others is a waste of time." Warren Buffett. You know who waits for dips? Dips, dips, wait for dips.

No. 5, this one comes from behavioral economics, where it's pretty much lab tested at this point, and this is also true of humans outside of the laboratory of behavioral economics. The pain of loss is three times the joy of gain. Think about that. It's hardware into your biology and mine. The pain of loss is three times the joy of gain. Yet, think about it. The joy of investment gains is potentially infinite times the pain of loss. It's simple math. The worst you can ever do is lose a 100% of your investment, and that's pretty bad, and most of us have never quite done that. But what's the best you can do? Well, you know, it's way better than plus 100%. The joy of investment gains is potentially infinite times the pain of loss. If you can get past your own biology and more into the psychology of being a successful investor, this simple math is your best friend. I picked Tesla on Nov. 23, 2011. It was just a few weeks after Elon Musk came to Fool HQ and gave a speech to our employees. The stock split adjusted when I picked it in November 2011 right around Thanksgiving Day was $2.10 a share. It was the third-most highly shorted stock on the NASDAQ. Tesla has since gone from 2-445. It's up more than 200 times in value. The gains of that one stock pick alone exceed all of the losses of every significant loser stock in Rule Breaker history. I know because I picked most of those losers, too. This thought isn't about Tesla. Hey, the Rule Breakers Scorecard actually has several dozen 10+ baggers on it besides Tesla, and by the way, more than 100-bagger. Yet, most people fear bound, don't know how to invest, don't see how they should do this over time.

They never discover this profound Rule Breaker Investing true thought No. 6, that the value of winning completely wipes out the cost of losing. There are no numbers for the things that matter most. As Rule Breakers, we intentionally seek stocks with six traits, the sixth of which is, even despite the presence of the other five, No. 6, people call the stock overvalued. Well, to them, it probably is. They're using their calculators and spreadsheets. It's all about ratios of simple measurables like revenues or earnings or cash flow. Yet, they are not even measuring the value of the CEO. They are not even measuring the brand name. They are not even measuring the company culture. They are not even measuring the innovative capability or lack thereof of the company. By traditional metrics, all the best companies with the best CEOs, brands, cultures, and innovation look overvalued. All the companies with the worst CEOs, brands, cultures, and innovation look undervalued. These kinds of investors, they are, all of them, misled, which is how you pick Tesla at $2.10 a share when it's the third most-shorted stock on the NASDAQ. Why? How? Because there are no numbers for the things that matter most. Spiffy-pop a holy grail moment of investing success when a stock rises more in a single day than you originally paid for it, that is a spiffy-pop. You never forget your first.

Investing thought No. 9, the rowboat syndrome. If you know the phrase, then you already know the thought. If you don't, tip open your Rule Breaker investing book and read, reread, or share with a friend Pages 31 to 33. Toss away your rowboat and toss away your canoe. If you want to win the game of investing, which will help you so much with the game of life, join me instead on the sailboat, where we use the market’s prevailing winds, no oars or paddles needed. The sailboat. The Ship of Fools. Dark Clouds, I can see through was one of my earliest essays for members, where I talked about my love affair with finding situations where the whole world sees something doubtful, dubious, that dark cloud positioned just over the head of the company or stock you're looking at. Everybody's saying it will never work. In those situations, when you can see through that dark cloud, you don't believe things are going to play out in the negative way everybody seems to think when you find a dark cloud that you can see through, and you're right, and you hold. These are the investments that lead to early retirement and multigenerational wealth. Dark clouds you can see through.

We're halfway through. No. 11, when I came up with the six traits for Rule Breakers stocks and wrote about them in a book almost 30 years ago, I was starting to think, are there other things a simple tool or two I can help additionally, people find Rule Breakers stocks. One of them I wrote about back in the day, and that's the Snap Test. The Snap Test is, if you snapped your fingers, and the company that you were researching or thinking about buying stock in disappeared overnight, the next day, the question is, would anyone notice? Would anyone care? Companies pass my Snap Test when everyone would notice, and a lot of people would care. That's because the best stocks of every generation are the companies that are doing such impactful and purposeful work that it would really ruin a lot of people's day the next day in the newspaper. Online these days, digitally to read that that thing had disappeared. It would really matter. That's the Snap Test.

Then to that, I've added the Cola Test in my Rule Breaker Investing book. If you've read it, you already know where we're headed. But I always ask myself if the stock I'm looking at the company I'm researching is, let's say, Coca-Cola. They're that dominant in their industry. They're big. They have lots of shelf life and a brand name everyone knows. If their Coca Cola, whatever the industry we're talking about, that stock that you're looking at, is there a Pepsi Cola? Can you find a Pepsi Cola equivalent competitor in that industry? A stock passes my Cola Test, if you cannot find a Pepsi Cola to your potential Rule Breaker stocks, Coca Cola, you can't find a Pepsi, which tells us that there is no direct competitor and that their product or service is clearly deeply needed, often with Blue Ocean Strategy out front. If you take the Snap Test, Snap company disappeared, and you combine it with the Cola Test, wait, there's no Pepsi. The companies that pass what I call my Snap Cola Test. Those are my favorite stocks of all. Those are the most likely to be the great Rule Breakers within their given industries. By the way, so many different industries are out there with lots of different innovators and possibilities. Snap Cola exists in more places than we often look. Snap Cola.

On to Number 12, establish your sleep number. It's the highest percentage you'd allow any holding in your portfolio to reach while still sleeping soundly at night. It's the simplest, most helpful number to manage your portfolio, the simplest, most helpful number that most people aren't using because they haven't thought of it yet. But as you manage your portfolio and your personal and your family's wealth, establish your sleep number and know it, and sure enough, if a big winner for you starts to exceed that sleep number, you'll know it because you'll stop sleeping soundly at night, and you should respect that. That's a time one of the few times I sell is usually when winners overrunneth my sleep number. Everybody's sleep number is different, by the way, and over the course of your life, it'll probably vacillate probably higher when you're younger, a little bit lower as you age, establish your sleep number. A lot of people have a really hard time initially buying into a stock, especially if it's been making new highs.

Now, if you've been following trait Number 3 of the Rule Breaker stock, you know that we like stellar past price appreciation. That's actually a positive indicator, although often we have a hard time convincing ourselves of that. Therefore, I'm a huge fan really, since I started this as a young investor myself, you don't have to buy your full position all at once. That can sometimes just be too much psychologically to handle. Just divide up the amount you'd like to put in that stock and buy in thirds. For example, if you have $3,000 set aside, take $1,000 right now and buy that stock, and then wait a month. A month from now, wherever the stock is very same day, buy your next thousand, and guess what? Do that one month after that. Or you can do it quarter by quarter. But whatever it is, this has been such a helpful tool for so many Motley Fool members and fans over the years. You don't have to buy all at once, and there's even a big psychological payoff here, because as I've often pointed out, here's what happens if the stock runs away and goes up forever. You start saying, I'm so glad I started buying when I did because I was buying in thirds, and those first couple of times I got such a better price. The stock just never looked back. Again, a lot of people would never have bought at all. They would have been staring, goggle-eyed and a little bit intimidated by a stock that kept hitting new highs, but you did, because you bought in thirds, or maybe things go the other direction. The stock starts dropping. That often happens. Feels like for me, whenever I buy a stock, it drops the next day or a week. It's down right away. Don't worry about it because you've only bought your first third. When you buy your next third a month from now, you're getting a better price, and if it keeps going down another third a month after that. In my mind, psychologically, either way, I win when I buy in thirds.

Thought No. 14 talked about it many times before. I would be remiss if I didn't include it on my 60 Thoughts as I Turned 60 episode. The etymology of the word “invest “comes from the Latin investire. It means to put on the clothes, to wear the clothes. Many of us, as sports fans always, my mental picture so many of us go to the home stadium with that home jersey on and whether our team wins or loses that night, that week. Whether it has a good or bad month or a winning or losing season, we keep that jersey on. A lot of us have made lifetime commitments to our sports teams. I sure have. Are you a sports fan? I bet you have, too. We don't change our teams very frequently. Why don't we do that more for our stocks and our investing? So many Americans would be so much more successful with their investing if they kept that jersey on treating their money, which, by the way, matters a lot more, ultimately, I think than how your sports team does, your money matters a lot more to you and your family than your sports team. If you just treated your money like your sports team a little bit more and kept that jersey on, I'm pretty sure you're going to do even better.

A lot of people are talking about the Magnificent Seven these days. But my question, anytime the so-called Mag Seven comes up, those seven big performers, the seven big cap companies that we all know so well, I don't have to repeat them for you, but my question has been is and will remain, what's your Magnificent Seven score? Your score is simply each of those seven holdings. How many years have you had any or all of those seven stocks in your portfolio? If you've held one for four years and another for eight, that would be a Magnificent Seven score of 12. My Magnificent Seven score, I only brag a few times each week on this podcast, is now 109. That's my way of saying that, on average, I've held these stocks for about 10 years or more, although I've never had Microsoft, much to my chagrin. But in a financial media environment where people invent catchy phrases and talk in the shorter term, and understandably so to make the market fun and memorable for people, and use phrases like Magnificent Seven, I'd like you and I, too, think one step past that and ask a deeper question. How long have you actually held those stocks?

Investing thought No. 16: Back your thoroughbreds and retire your also-rans. Thought No. 17 came straight from this podcast from a write-in mailbag, my German friend, Henrick, who challenged himself once in a most Foolish, and Rule Breaking way. He said if I'm going to make my portfolio reflect my best vision for our future, I should be able to proudly wear the T-shirt of every company that I'm invested in, and so with about 30 stocks, Henrick took a month out, and he tried to acquire T-shirts for all of his companies. Not sure he succeeded with that, but for each day of that month, he put on the T-shirt, if you will, he wore the jersey of one of his stocks and saw how people reacted to him throughout the day. It's Henrick's T-shirt test. Thought No. 17. Would you proudly wear the T-shirt of every company you're invested in? Make your portfolio reflect your best vision for our future.

One of the more common questions we've gotten on this podcast now in its 11th year, it pops up on mailbags here and there is, David, how many stocks should I have in my portfolio? As I've often said, I understand why people ask that question, but it is the wrong question because there's no right answer to that question. I, of course, think you should start with at least 20 stocks in your portfolio with no more than 5% allocated to any of you have a nice broad base to start from. But as soon as the horse race tips off, right away, some of those are going to race forward, and they're going to become larger parts of your portfolio. The ones that stumble will become smaller parts of your portfolio, and you might have some new money. I sure hope you do coming in. You might think, Well, OK, should I add it to one of my winners, one of my losers or add another stock? So, David Kretzman and I, on this very podcast, somewhere around eight years ago, came up with this. It's the Gardner Kretzman Continuum. You should have roughly the same number of stocks as the number of years you've lived on this Earth. It's time to close out my investing section No. 20. I try to find excellence, buy excellence, and add to excellence over time. I sell mediocrity. That's how I invest.

Twenty business thoughts. These are things I've come to believe. They've helped me win the game of business, of my professional life. I hope they do the same for you. No. 1, Stuart Brand, a Stanford grad, is the entrepreneur who co-founded the Whole Earth catalog, and then back in the day, one of the first Internet communities, the Well, as well as today's Long Now Foundation. Here's my first thought for you about business from Brand, who's also a writer, and I quote: “Once a new technology rolls over you, if you're not part of the steam roller, you're part of the road.” Warren Bennis' book On Becoming a Leader is one of my favorite books, and I don't just mean on leadership. In Warren's book, at one point, he quotes Larry Wilson. Now, Larry was the founder of Citadel Broadcasting, which became the third-largest owner of radio stations back in the Golden Age of Broadcasting. Anyway, here's what Wilson said, and I quote. "For most entrepreneurs, certainly for me, the primary pull is the vision. You are simply passionately compelled to make it come about. I think that a compelling vision, combined with a unique ability to manage risk, is the magic behind successful entrepreneurs. It's as if you already handled the risk ahead of time in your mind, so you can go where angels fear to tread because you've already skipped ahead to the gain." Now, for entrepreneurs, well, I bet you can relate. I remember the first time I saw The Motley Fool printed as a phrase in the Wall Street Journal. That moment for me was so small, in a sense, but also so rewarding, it rewarded that vision pull for Tom and for me, passionately compelled to make The Motley Fool come about. That was what I'll call The Jerk moment. You remember the scene in The Jerk where Steve Martin's character runs to the front door to collect the morning mail, grabs the newly delivered phone book, so he can look his own name up, find himself, and sure enough, declare with glee, “Look, I'm somebody.” Well, that's the feeling of the founder entrepreneur. When you first get quoted or called out in a good way in public, you were compelled by your vision. You couldn't not make this happen.

For investors, principle No. 1 of the Rule Breaker portfolio is make your portfolio reflect your best vision for our future. The words vision, I counted, I counted this. The words vision or visionary appear 51 times in my book, Rule Breaker Investing. It's an investment book, but it celebrates locating the visionaries and buying shares in their companies. It also asks you, as the reader, what your vision is as a key portfolio principle to investing your own money. The more you are pulled with Larry Wilson and Warren Bennis, and me, the more you are pulled by a vision. passionately so, the more likely you are to succeed in business. No. 3, John D. Rockefeller once said, "If you want to succeed, you should strike out on new paths, rather than travel the worn paths of accepted success". He's even more famous today, but Malcolm Gladwell was already pretty famous and rightly so when he first penned an essay in The New Yorker, the date was May 4, 2009, entitled “How David Beats Goliath.” In that wonderful essay you can still find online, you're going to see Gladwell tell stories over and over of how people who were huge underdogs, like any start-up, like any entrepreneur, maybe you or me huge underdogs in undertaking what they were undertaking. If they played the game as it was being played in their existing industries, if they did the same thing everybody else did, if they kowtowed or adhered to Goliath's rules, guess what happens. They lose. Goliath wins almost every time.

Gladwell advocates how David beats Goliath is by playing the same game in a completely different way. I would say to you, dear listener, and in this case, dear fellow entrepreneur or business professional, Steve Jobs, think different, except don't just think different, act different. Netflix took on the vastly larger Blockbuster, not by building more stores, but by eliminating late fees, by mailing DVDs directly to homes, and then boldly pivoting into streaming before incumbents believed consumers would abandon physical media. Southwest Airlines challenged the giant legacy airlines by flying only one aircraft type. Emphasizing quick gate turnarounds, of course, low fares, too, and turning operational simplicity into a durable, competitive weapon, and Airbnb entered the travel industry with no hotels, no real estate, no legacy infrastructure at all, and then used the simple idea of letting ordinary people rent out their homes to build a global lodging platform that eventually rivaled the world's biggest hotel chains. That's how David beats Goliath. You can, too.

Business thought No. 5: Win the crowd, and you will win your freedom. This great quote from the movie Gladiator reminds me always that the more you can make your company brand, your personal brand, your investing portfolio to deeply steeped in helping others and doing so with fun and imagination in a way that wins for them and wins for the world at large, too, it's this positive winning pursuit that for your start-up or your professional life will win not just the crowd, but win you your financial freedom, too. Thank you, Proximo, win the crowd, and you will win your freedom. Theodore Levitt, the German-born American economist, professor at Harvard Business School, ran the Harvard Business Review for a while. Here's an absolutely great one-liner that all of us in business do well to remember at all times. I quote People don't want to buy a quarter-inch drill. They want a quarter-inch hole. A brag to begin thought number seven. I co-founded a company that has been an answer on the game show Jeopardy. How did this happen that a print newsletter started for family and friends in 1993 would one day be answered correctly on the nation's most popular TV game show? We haven't been a one-night wonder either. The Motley Fool has actually been a Jeopardy answer four times now over three different decades. What can we learn? Well, more importantly, how can I help you create something that will one day maybe be an answer on Jeopardy?

Well, my first easy thought is, build something big enough to be noticed, yet many bigger and more impressive enterprises than my little company have likely never been mentioned on Jeopardy. I'd say the key insight is in our name. If you're a stressed-out, professional writer of game show questions and answers, that's your full-time job. coming up with what is The Motley Fool, has to be a lot more fun and colorful than 99% of other potential corporate answers. Not only that, but the word “Fool” for those who enjoy wordplay and puns, like people who write Jeopardy questions, the word “Fool” fits into a lot of different potential topic categories. We arrive now at my takeaway for all my fellow entrepreneurs hoping to have their companies one day be an answer on Jeopardy. Pick a name that stands for something. probably not “trust,” probably not Verizon, or I like the stock, or Accenture. Real words and make it fun, arouse curiosity with your company name, and have it tell or maybe connect to a story. Then do something big enough to be noticed.

This next one is a short essay. I'm going to call it The Hardest Thing in Life. I've had five jobs in my life, cutting grass at Georgetown Convent for two months here in Washington, DC, as a teenager, interning at the Rochester, New York, Police Department for two months, interning at Solomon Brothers on Wall Street for two months. Writing for Louis Rukeiser's newsletter for six months, and The Motley Fool for 33 years. Apart from many humorous reflections on where I've worked and or how long, one thing is clear. I have no past experience in sales. Now, there's a line of thinking that goes, we're all in sales, and I agree with this. It's in the sense that you should always be marketing the things to which you are committed, ABS, always be selling. But apart from this mindset, I have no actual experience whatsoever in sales. I have no database with leads, never any targets or incentives. I don't really have deadlines, which is why I learned a lot from this brief exchange on my podcast with my friend and fellow Fool, Brian Feroldi. I asked him, Brian, how about your own experience selling medical equipment? What was the hardest thing for you to do when you were the sales guy going into a doctor's office or a hospital? Brian responded, by far, the hardest thing was if the device you have requires the doctor to change something about the practice, change something about the way they currently operate, you have an enormous task. In so many cases, they've invested a huge amount of their time. They've trained their staff on the way to do one thing. If you have a solution that slightly alters that, there are enormous barriers. Even if your solution is better for the patient, better for the insurance company, better for humanity, the doctors many times have enormous resistance to anything that's new. That's what Brian said. For a decade, Brian was in doctors' offices and hospitals trying to break other people's habits. It's hard enough to break our own. Imagine needing to break others in order to put your family's supper on the table each night. Turns out the hardest thing in medical sales is the hardest thing in life. If your new solution ushers in a better future, you'll get there.

Business Thought No. 9: Jay Beyer, author of a fine book called Youtility, and that's you, by the way, spelled Y-O-U. Here's a line from Jay's book. “If you sell something, you make a customer today. If you help someone, you make a customer for life.” Jeff Bezos got criticized in the early days of Amazon for allowing customers to put up reviews, especially one-star reviews, even two-star reviews. Who was doing that criticizing? Well, it was the booksellers, under the assumption that this was bad for business. Bezos said booksellers were telling me my job was to sell things when it was actually to help our customers make good purchase decisions. It's easy to forget how doubtful, truly the media and short sellers and the world at large was that Amazon would ever one day, succeed, would ever, really win. For years and years, AMZN stock was doubted, demeaned, downplayed, decried, which, for this next thought puts me in mind of one of my favorite quotes here from Arthur Schopenhauer. I quote ''Truth goes through three stages.'' First, it is ridiculed. Second, it is violently opposed. Third, it is accepted as self-evident.

My next three thoughts are all about winners and winning. No. 12, winners win. What do winners do? They win. Past performance is no guarantee of future results. You know that phrase? You've heard it before. While it's technically true, it's one of the most misleading statements ever devised that it appears constantly as a financial disclaimer, past performance is no guarantee of future results, doesn't help matters at all. Past performance may well be the single best indicator you and I have of future results. What do winners do? Winners win. My next thought: winners lose. Losing to win is one of the most profoundly true dynamics in life. Every Olympian gold medalist has fallen or fallen short hundreds of times in their lives. Every winner you know has lost grandly, and most with some frequency, two. As Winston Churchill was reputed to have said, erroneously, by the way, but the point is still so sound, and I quote, ''The secret to success is stumbling from failure to failure without losing your enthusiasm.'' Winners lose.

Thought number 14, winners win, winners lose. Ah, and one additional thought. Real winners win for everyone. In business, they win for their customers. They win for their employees, and they win for the shareholders, too, almost as a consequence. Maybe for their local community, depending on what type of business we're talking about, maybe for Mother Earth, depending on other types of businesses. I bet they win for their proud partners, too, and for their longtime suppliers. Winners win, and winners lose. Real winners win, Business thought number 15. Let's talk for a minute about fads. After Tobey Maguire starred in the 2002 Spider-Man reboot. Do you remember this? Superhero movies were called a fad. Starbucks. The idea back in the day of a national chain of, of what? Coffeehouses? Seriously? Starbucks was called a fad when it came public in the early ‘90s. Pokemon. Fad. Crocs. Surely, a fad. Maybe still. Can't quite tell yet. Sales did drop a bit this year, but $900 million in sales still ain't too shabby. Video games themselves when they debuted in the 1970s, a fad. Now they're bigger than Hollywood. Many great businesses have been written off too early by the media or by traders as fads. But especially the ones with brand names that you and I recognize, those businesses rarely are.

When you're the leader, constantly aiming for better and truly never being satisfied with status quo, is one of the better traits you can develop. It's great for your employees to know that's how the boss thinks. If you're the founder and you're really quite satisfied with your offerings, realize that you might be creating a culture where people are going to yes you too. If you're maybe even a bit too satisfied with your business offerings, no one's going to challenge the boss unless you start acting a bit more like Netflix co-founder, Reed Hastings. I feature this quote on a Past Great quotes, Rule Breaker Investing podcast, and here it is, again, I quote ''I see all the imperfections in Netflix. I see all the things that aren't working. At the office, I'm the one that says, we suck.” Don't get me wrong. We're better than everyone else, but we suck, compared to what we are going to be.'' Of course, in general, I'm constraining myself from saying these things because they're too easy to take out of context. But as an entrepreneur, that's how you have to look at your product. Compare yourself to what you want. To be what you will be in five years. That should be so much better than what you have today.

My next Business Thought No. 18 for those keeping score at home is a great thought that I first read about 20 years ago in the Harvard Business Review, back to my favorite living entrepreneur. Jeff Bezos. I quote. ''It helps to base your strategy on things that won't change.” Bezos said, there's a question that comes up very commonly, what's going to change in the next five to 10 years? But Bezos continues, I very rarely get asked, What's not going to change in the next five to 10 years? At Amazon, we're always trying to figure that out because you can really spin up flywheels around those things. Epictetus, the Greek Stoic philosopher who was born in the year 50 AD and lived the year 135, no great thing is created suddenly. My final business thought, dear leader, dear founder, dear entrepreneur, and listening, dear Fool, if you listen carefully to this final thought, which is one of my favorite quotes, this one coming from Antoine de Saint-Exupery, the pilot, the author of The Little Prince, you'll see that these words help you speak as a leader alike both to your employees and to your customers, and here they are. "If you want to build a ship, don't drum up the men to gather wood, divide the work, and give orders. Instead, teach them to yearn for the vast and endless sea. Now and on to life. These are things I have come to believe. They've helped me win the game of life. I hope they do the same for you.

No. 1, first thought. It's my one key line about personal finance in the entire Rule Breaker Investing book, which is otherwise pretty much not at all about personal finance, but here it is. Thought No. 1, I urge you to live below your means every day of your life. Paraphrasing American 20th-century radio commentator Ralph Sackman. Here we go. The greater the island of knowledge, the longer the coastline of mystery. This next No. 3 from Mae Jemison. Born in 1956, still with us today, an American engineer, physician, former NASA astronaut, Mae Jemison became the first African American woman to travel into space when she served as a mission specialist in 1992 aboard the Space Shuttle Endeavor. Here's her line. Never be limited by other people's limited imaginations.

No. 4. Our greatest fear should not be a failure, D.L. Moody once said, but if succeeding at something that doesn't really matter, I don't know if he said it on this podcast when I had him. It was definitely in his book, though, Atomic Habits, author James Clear, and I quote, "habits are the compound interest of self improvement, the same way that money multiplies through compound interests, the effects of your habits multiply as you repeat them.” They seem to make little difference on any given day. Yet, the impact they deliver over the months and years can be enormous.

No. 6, each of us with no map or guide is standing at the edge of a dark forest. There's a Lighthouse in the distance, self-actualization. Getting to the Lighthouse is a goal. Taken one step at a time, at any given step, my friend Shirzad Chamine, genius author of Positive Intelligence, urged us on this podcast, at any given step, take the step that has more light in it. Only after you take that step, will the next be revealed. Light symbolizes positive emotions we're drawn to like empathy, curiosity, creativity, fulfillment. Their opposites are fear, anxiety, self-doubt. With several choices in front of you, ask, which step has more light? Take that step. As a consequence, there'll be more light on your path, and the next step will be revealed. As you keep taking each new step toward the light, things will get brighter, and you’ll discover tools you didn’t know about, new friends you now recognize as crucial. Every step is full of discovery and growth, Shirzad says, and you keep getting closer and closer to the Lighthouse. Yet, here's the surprise ending. You will never make it to the Lighthouse. Nobody is ever fully self-actualized. Every step you take, you are becoming more and more your true self. The value lies in the journey to becoming your authentic, unique best self.

For Thought No. 7, how about 19th-century German philosopher Arthur Schopenhauer one more time, and I quote ''Talent hits a target no one else can hit. Genius hits a target. No one else can see.'' For these next several, how about some shouts out to the optimists out there with these thoughts, including some of my favorite oft repeated quotes, whether you think you can or whether you think you cannot. You're right. Henry Ford. Lord Macaulay, British politician and historian, I see his dates 1800 to 1859. That's sad. He only lived in 59, died of a heart attack, had no children, yet had much to recommend him.

This quote, which may be on my Mount Rushmore of optimist quotations, and I quote, “On what principle is it that with nothing but improvement behind us, we are to expect nothing but deterioration before us?” Harry Truman, "A pessimist is one who makes difficulties of his opportunities, and an optimist is one who makes opportunities of his difficulties." Kevin Kelly, founder of Wired magazine, if you read today's headlines, you'll conclude things have never been worse. But if you read history, you'll conclude things have never been better. On to life quote No. 12, "I've increasingly come to think that both creativity and life itself tend to follow two broad phases, divergence and convergence. Divergence is expansion, exploration, saying yes, wandering, trying things on, opening doors, accumulating experiences and skills, friendships, stories, and possibilities, divergence. Convergence is different. It's narrowing. Editing, chipping away, deciding what truly matters, what remains, and what you most want to build, keep or become.

A few favorite writers and thinkers have helped me see this pattern more clearly." In his wonderful book, Building a Second Brain, Author Tiago Forte writes, and I quote, "A creative endeavor begins with an act of divergence. You open the space of possibilities and consider as many options as possible. The purpose of divergence is to generate new ideas. The process is necessarily spontaneous, chaotic, and messy. You can't fully plan or organize what you're doing in divergence mode. You shouldn't try. This is the time to wander." Warren Burger, multiple-time guest on this show, author of wonderful books like A More Beautiful Question, writes "The experiences you say yes to now will be the stories that are remembered and shared by future you. Whenever you face a decision between two diverging paths, ask yourself, when I look back in five years, which of these options will make the better story?" My friend and friend of this podcast Arthur Brooks, Harvard professor, author of the Atlantic Column How to Build a Life, wrote, and I quote "Midlife is the point at which your medium of choice should change from a canvas to a sculpture in which the work of art appears as a result of chipping away, not adding." Then Tiago Forte again in Building a Second Brain, "Convergence forces us to eliminate options, make trade-offs, and decide what is truly essential. It's about narrowing the range of possibilities so that you can make forward progress and end up with a final result you're proud of. Close the door, put on noise-canceling headphones, ignore every new input, and ferociously chase the sweet reward of completion. Trust that you have enough ideas and enough sources, and it's time to turn inward and sprint toward your goal."

These concepts divergence and hear convergence, sure enough, appear in another of my favorite guests from this podcast's work, and that would be acclaimed novelist Amor Tools. His most recent full novel is The Lincoln Highway. Therein, he wrote this, and I quote, “The manner in which the convergence takes you by surprise. That is the cruelest part. Yet, it's almost unavoidable." In those first years, as the rays begin to angle inward, the world still seems so open, you have no reason to suspect its diminishment. But one day, one day years after the convergence has begun, you cannot only sense the inward trajectory of the walls, you could begin to see the terminal point in the offing, even as the terrain that remains before you begins to shrink at an accelerating pace, the narrowing of life at the far tip, of the diamond. I think one of the great mistakes we can make is trying to converge too early to prematurely narrow our lives before we've explored enough of them. Yet, eventually, convergence comes for all of us, not just creatively, but existentially. Time itself begins doing the editing. Perhaps wisdom is recognizing which phase you're in. When you're young or young at heart, sure, wander more and say yes more and gather stories, diverge. Then later, with increasing intentionality and gratitude, converge toward the people, the work, the values, the loves that matter most. Because eventually, for all of us, the diamond narrows, the great opportunity is to arrive at that narrowing not accidentally, but beautifully.

Life thought No. 13, declutter. From Irish playwright George Bernard Shaw, who lived to the age of 94, by the way, from the dedication included in his play Man and Superman, here's one of my favorites, and I quote, "This is the true joy in life being used for a purpose recognized by yourself as a mighty one, being a force of nature, instead of a feverish, selfish little clot of ailments and grievances, complaining that the world will not devote itself to making you happy. I am of the opinion that my life belongs to the whole community. As long as I live, it is my privilege to do for it what I can. I want to be thoroughly used up when I die. For the harder I work, the more I live, I rejoice in life for its own sake. Life is no brief candle to me. It is a sort of splendid torch, which I've got hold of for the moment. I want to make it burn as brightly as possible before handing it on to future generations."

No. 15 from American film critic and corporate governance scholar and expert Nel Mino, who once said these words at a Motley Fool event to our members, and I quote, "Never use the word busy as an excuse. It's an insult to whomever you're talking to. It pushes them away, makes it impossible to think honestly about your own priorities. Never use that as an excuse, as a brag. You'll become much more in tune with what you're doing." In 2020, I did a Great Quotes Listener edition in which I asked you, you all, to send in your favorite Foolish quotes. We'd make an episode out of that, which we did. It was great. Writing it at the time, calling himself a young investor was Zack Tempe. Zach, you showed with your recommended quote that you are a young man thinking well beyond his years. I loved it. Zach shared this classic from Tecumseh, the Shawnee Native American chief and warrior who lived from 1768 until he was killed by American troops in 1813, causing his Confederacy to collapse. Thought Number 16. Live your life that the fear of death can never enter your heart. Trouble no one about their religion. Respect others in their view and demand that they respect yours. Love your life. Perfect your life, beautify all things in your life. Seek to make your life long and its purpose in the service of your people. Prepare a noble death song for the day when you go over the great divide. Always give a word or a sign of salute when meeting or passing a friend, even a stranger, when in a lonely place, show respect to all people, and grovel to none. When you rise in the morning, give thanks for the food and for the joy of living. If you see no reason for giving thanks, the fault lies only in yourself. Abuse no one and no thing for abuse turns the wise ones to fools. That would be, of course, with a small F and robs the spirit of its vision. When it comes your time to die, be not like those whose hearts are filled with a fear of death, so that when their time comes, they weep and pray for a little more time to live their lives over again in a different way. Sing your death song and die like a hero going home.

Frank Lloyd Wright once said, and I love it, "The longer I live, the more beautiful life becomes." No. 18, call this one sure, my fundamental truth. It's my life and lived experience when it comes to being a Rule Breaker, it's kind of the inspiration, if you will, for this week's podcast. What wins in investing wins in business wins in life. No. 19, I had to throw this one in. It's from where I pulled our name. It’s why, for 30-plus years, we at The Motley Fool, along with so many of our members and listeners. You, too, perchance, call ourselves fools. It's the greatest scene in all of drama, celebrating court jesters and challengers of conventional wisdom fools. Heck, since this is my podcast, no one can stop it, I'm going to call it the greatest scene in all of Shakespeare, Act 2, Scene 7 of his play As You Like It. Somewhere in the middle of it is this rather nondescript quote. I'm so glad it spoke to me in June of 1993, and I quote a fool, "A fool. I met a fool in the forest, a Motley Fool."

Last thought. The year was 2005. Out of nowhere, I started getting some emails from friends. Fools on our forums were pointing to it, too. I didn't see it live, but thanks to YouTube, I could watch it back then, and you can still watch it today. Is it fair to call this my favorite commencement speech moment ever? Steve Jobs was addressing fresh new Stanford graduates, and there he was talking about the Whole Earth catalog, which I referenced earlier, and I quote. "When I was young, there was an amazing publication called The Whole Earth Catalog, which was one of the Bibles of my generation." Jobs said, "It was created by a fellow named Stuart Brand, not far from here in Menlo Park, and he brought it to life with his poetic touch. This was in the late 1960s, before personal computers and desktop publishing. It was all made with typewriters, scissors, and Polaroid cameras. It was like Google, in paperback form, 35 years before Google came along. It was idealistic, and overflowing with neat tools and great notions." Jobs went on, "Stuart and his team put out several issues of the Whole Earth catalog, and then when it had run its course, they put out a final issue. It was the mid 1970s, and I was your age. On the back cover of their final issue was a photograph of an early morning country road, the kind you might find yourself hitchhiking on if you were so adventurous. Beneath it were the words, ‘Stay Hungry. Stay Foolish.’ It was their farewell message as they signed off, Stay hungry. Stay Foolish. I have always wished that for myself." Jobs concluded, "And now, as you graduate, to begin anew, I wish that for you. Stay hungry. Stay Foolish." Here's to the Next 60. Yours? Mine and ours together. Stay hungry. Stay Foolish. Fool on.

David Gardner has positions in Alphabet, Amazon, Crocs, Netflix, Starbucks, and Tesla. The Motley Fool has positions in and recommends Accenture Plc, Airbnb, Alphabet, Amazon, Microsoft, Netflix, Starbucks, and Tesla. The Motley Fool recommends Crocs, Southwest Airlines, and Verizon Communications and recommends the following options: long January 2028 $260 calls on Accenture Plc and short January 2028 $280 calls on Accenture Plc. The Motley Fool has a disclosure policy.