October 2026 Mailbag: The Lighthouse

In this episode of Motley Fool Rule Breaker Investing, Motley Fool co-founder David Gardner answers eight mailbag questions spanning investing, sports, money, and life.

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A full transcript is below.

This podcast was recorded on Oct. 28, 2026.

David Gardner: It's mailbag time. What does it really mean when I say I'm trying to get 60% of my stock picks right? Can a lifetime of successful investing leave you with a financial problem you never expected? What if the best way to find your path in life is to stop trying to figure out where it leads? Well, this month, eight correspondents take us from the stock market to some of life's bigger questions. Before we're done, we'll find ourselves at the edge of a dark forest with a lighthouse in the distance and a lesson about how to find our way. It must be mailbag time. It's your October mailbag. Only on this week's Rule Breaker Investing.

Welcome back to Rule Breaker Investing. I'm really looking forward to our eight mailbag items. We have a nice Motley mix here at the end of October. I'm recording Tuesday afternoon, October 27th. I just saw Danny Meyer, the wonderful restaurateur, Union Square Hospitality Group, Shake Shack, and all the rest. I just saw him give a talk at a local club for lunch, and I was reminded of what a wise man he is. And the good news is we've had him on this podcast before. So if you just Google “Rule Breaker Investing,” Danny Meyer, you'll hear my conversation with him some years ago. He is a wonderfully conscious capitalist, and what a warm and positive person. Yet, one of the takeaway points I had sounds a little cranky, but I want to share it back because I think it'll help open some eyes and maybe cause some of my listeners' heads to nod. He was saying this is a point against mobile phones. He was saying, 5% of the time these days, your phone is actually a phone, i.e., you're taking or receiving calls. This is an approximate percentage. He then went on to say, the other 95% of the time, with your phone in front of you, you're faking yourself out that you're feeling connected. You're feeling connected to others, to the world at large, etc., when if you spin back the movie camera and look at the person looking at their phone, 95% of the time, they're just interacting with a little object in front of them.

So again, this comes from somebody who is not a cynic at all. He is an optimist and a builder of things, but that one jumped out to me a little bit and made me think a little bit about my own interactions with my phone. Now, before we get started, I always like to look back at the month that was and where Rule Breaker Investing took us. In October 2026, I let off with October 7th's Pet Perks, Volume 3, seven little things that make everything better. I really love doing that podcast this month. I didn't get any mail about it, but I guess that means everybody enjoyed it. You agreed with my pet perks. Week No. 2 brought breaking the rules of sports, Volume 2, American football. Then last week, of course, financial horror stories, Volume 5, the All Monster Edition. This particular month was as much about life as it was about investing after a very investing, heavy September, and, of course, we'll be doing more of that in November to come. Anyway, that is the month that was. Eight Rule Breaker investing mailbag items this week, but let's go to social media. It's time for our Twitter hot takes as I open up each of my mailbags. I want to thank Andy Gibson for this note. He tweeted out @Andrewgibbs53446. Andrew is reacting here to last week's podcast financial horror stories, Seven Monsters to Look Out For with my friend Robert Brokamp.

He says, My favorite section begins at the 26-minute mark. My father has been managing required minimum distributions RMDs) a lot. So I shared this episode with him. He typically pays the taxes and then returns the remainder to his rule Breaker stocks in his brokerage account. Robert Brokamp was an excellent guest, and I really also enjoy the podcast Hidden Gems. The other Motley Fool podcasts, they have refined the approach over there. And he concludes, Cheers, guys, fool on. Well, thank you for that message. Andy, we'll have a little bit more on RMDs, this Mailbag, by the way. Before we move on to Mailbag item number one, I want to give a special shout-out this month to Jeff Ross at former doctor Jeff on Twitter X, who listened to our Halloween Financial Horror Stories episode last week while out for a walk.

Then he posted this, "It was a great listen with many helpful financial planning tips, especially for those in or near retirement. Kudos @Davidgfool and @Robertbrokamp for another solid rip." I just replied, Halloween always delivers so does Robert Brokamp. Thanks, Jeff. And I want to thank Jeff again here because his post helped spread the word about that episode and brought some new listeners our way. That's one of the wonderful things about this foolish community we have together: when you find something valuable, and you share it with others, through mailbags, for example, with what you're writing and sharing, you help make this whole community smarter, happier, and richer. Jeff Ross, thank you for being such a great ambassador for last week's podcast Fool on. With that said, it's time for Rule Breaker Mailbag item number one. This one from Jason Schoulte — now that's S-C-H-O-U-L-T-E, which means, Jason, I may have just pronounced your last name incorrectly. It might be Schultz. It might be Shulta.

Let's just go with Jason S. Hi, David. I was listening to your Breaking the Rules of Sports, Volume 2, American football podcast on October 14th, and I noted the segment regarding defensive penalties at the goal line wasn't entirely accurate. Jason goes on in the 2025 NFC Championship Game, which was the Philadelphia Eagles against the Washington Commanders; the Eagles were on the goal line threatening to score, and the Commanders repeatedly jumped offsides while attempting to time the snap and stop that Tush, push Eagles goal-line play. After the fourth penalty, by the way, I watched this game. Jason and I completely forgot this.

After the fourth penalty, Shaun Hoke, the referee, warned the Commanders that the officials could award the Eagles a touchdown if they continued to jump offsides. Jason concludes I had to look up the specific rule. It's the palpably Unfair Act. Rule. Jason provides a link to NFL.com. Article about that game, you conclude, Jason. Interesting episode; thanks for the content. Well, thank you, first of all, Jason, for writing in and for reminding us of what was happening in that football game. Let me just share a little bit of that right here. I'm quoting. Anybody can find this article. It was entitled Referee Shaun Hakeli on Commanders Galine Penalties. Colon, if repeated fouls occur to prevent a score, we can award the score. That's one of the longest headlines I've ever seen and a reminder that nfl.com probably is not as media savvy as ESPN or other media companies.

But nevertheless, here's how that article starts. It starts: unless you're an NFL rulebook nerd, you learn something new on Sunday: refs can award an offense a touchdown if the defense repeatedly commits penalties. Washington Commanders linebacker Frankie Luvo desperately tried to keep the Philadelphia Eagles out of the end zone early in the fourth quarter of the NFC championship game; the Wiley veteran flew over the top of the offensive line for encroachment penalties on back-to-back plays, prompting the referee to warn Washington that a personal foul could be called. Then a third commander went offside again on an Eagles hard count. The referee, like a scolding parent, made it known to the world that referees can indeed award a team a touchdown for repeated penalties. Washington has been advised that at some point, the referee can award a score if this type of behavior happens again, the referee said during his in-game announcement, so I'll leave the article off right there and apologize again to people who don't really care about football.

There is an interesting point to make here. Now, I did right away forward this to Kimball Crosley, my friend and guest, presenting his ideas about the ways that the game of American football can be improved. Kimball wrote me back, Wow. I don't remember that, but that's awesome to know. Remarkable that a touchdown would ever be rewarded. Kimball at it. I think, though, that only reinforces the idea that there should be a rule in place that you can't just repeatedly jump offside when the offense is near scoring a touchdown before it ever comes to that idea of the ruling. Now, the ruling is actually called the palpably unfair Act. Rule. I just wanted to underline that again.

Jason, thank you for digging that out. Hilarious. There are so many rules in NFL rule books. One of my favorite moments is when the announcers, who are experts, having played the game themselves, the television announcers get confused or don't understand the rules of their own game, but that was one of the points of our podcast a couple of weeks ago. There are too many rules in the NFL. Anyway, before moving on to item No. 2, Jason, I want to thank you. This is one of the reasons I love our monthly mailbag. I've often said, you get the listeners you deserve. One of the great privileges of doing this podcast is having smart, thoughtful listeners who make this show better. Kimble and I had a good idea, so we thought. Jason, you've just made it better by bringing us something neither of us knew. I would say that's rule-breaking thinking in action. You're questioning, you're learning, and you're helping improve us together. So thank you for making us all a little smarter this week, Jason, fool on.

On to Mailbag item number two. Because sports was a significant part of this month that has been, I'll present one more sports item, again, for sports fans, get ready, get excited. If you don't like sports, feel free to skip to Mailbag, Item number 3, if you like. But this one comes from Dave Hass Hi, David. I'm commenting on your sports episode this month. I agree with all the recommended improvements your guest suggested for football, especially Dave As writes the pass interference rule, it's incredibly arbitrary for both sides. He goes on. However, I really wanted to comment on baseball, my favorite sport. I've been watching for 60 years. I love new rules relating to instant replay, the challenges, the ABS system. I also like forcing relievers to face at least three batters, the time clock on batters and pitchers, Dave's adds, Remember My Cargrove the Human rain delay. And, Dave, I do, indeed. Thank you for that blast from the past. He goes on: “The one thing I'd like to hear your take on is a buy-sell-hold on the pitch count.”

From baseball's inception to about the late 1990s, we never cared about pitch counts. I can't imagine watching Tom Seaver and Steve Carlton in a pitching duel and wondering when they might be pulled based on an arbitrary 85 to 100 pitch count, Mark. What study was produced to show the human body cannot throw more than 100 pitches in a game? Dave asks, rhetorically, perhaps, does it include bullpen warm-up pitches, playing catch between starts, who knows? I miss seeing two great pitchers battle until the ninth inning or extra innings until there is a winner: Drysdale versus Marshal. Gibson versus Perry, Tiant versus Cott, Statelmeyer versus Palmer, Kuzman versus Jenkins. These are old-school references, but I know that truly fervid greyheads like me, listeners, are nodding their head with some appreciation here.

Let's close it out, Dave, you wrote The pitch count has turned every team's best and dominating starting pitchers to the role of number one reliever. The first in a line of four to five pitchers used in every nine-inning game, my vote is to sell signed Dave S. Well, Dave, first of all, love the note, and I want to point out that you and I are probably about the same age, and while people might think we're cranky old guys, you let off your note by listing all the wonderful changes in baseball all in just recent years, and I completely agree with you as you completely agreed with our football improvements; shout out again to my friend Kimball Crosley.

A few weeks ago. I like your baseball thoughts. I agree with these baseball good changes we've seen. You and I agree on that. You're asking a buy-seller hold for me on the pitch count. First of all, I'm going to say, I think we're talking about two different things here, because in your note, you're referencing pitch counts. You're saying, Are they good science. But also, second, even if they are, have they made baseball? A better game. I think there are two different things going on there: the arbitrary round number of, let's say, 100 pitches. Then this idea of great pitcher battles- are they gone in this new era? So I'm going to come down with a solid hold on this one, because I find myself nodding in agreement with you that 100 seems like an arbitrary number, and I think it was being adhered to way too pedantically in recent seasons.

I will say, at least, having watched a lot of baseball in 2026, I did find managers loosening that up. I saw some pitchers pitching into the 100 teens in some cases. It was rare, but that wasn't even happening at all for a lot of baseball I was watching in recent years. So I think that's being relaxed, some. I'm one of those people who believes round numbers are lies. I come from a school of thought that says any round number is a lie. And that's just our way of saying that when people speak in round numbers, they're probably not being specific or thoughtful enough; they're just generalizing. And that's how I felt about the whole 100 pitches pitch count. Clearly, some pitchers can pitch more than that, some fewer than that.

Contextually, as you're asking, what about are we counting pre-game pitching? And what about pitching in between games and all the rest? It did seem a little bit arbitrary. So I would agree with you there that that is more on the sell side. I don't really like that. I'm selling pitch counts if we're saying 100 pitches is good science. Yeah, I'm selling the idea that pitch number 101 is somehow fundamentally different from pitch number 100. But I think overall this is still a hold because this is sort of a complex issue. In some ways, the reason baseball managers are pitching pitchers that way these days is because it's optimizing for winning. I'm pretty sure. For whatever reason, people these days, they throw harder than ever before. They probably strain their bodies more so than they did 50 years ago, and so they can't throw as many pitches, quite literally, I think, and still remain healthy.

Obviously, a lot of these rules are in place to protect pitchers and the health of pitchers. There are certainly a lot of arm injuries these days. Here's the fundamental question as we close sports down for this week and move on to investing. I think the question is: what is optimal for winning under today's rules? Is that not necessarily optimal for fans and the sport itself? That's a really interesting thought, I think. The more you can align those two things- the idea that better strategy, leading to winning, aligns with fan enjoyment and a better game. Well, the more you can align those, the better off any sport, really, not just baseball, is going to be.But when you find yourself with those things at odds, pitch counts may make scientific sense up to a point, and yet not quite as fun or classic. We've lost those great pitcher battles. Jack Morris pitching into the tenth inning of the final game of a World Series as a memorable example for me, that is almost completely gone from the game. The game has changed. I guess to close here, Dave, I'm holding on pitch counts. I'm selling the idea, again, that pitch number 101 is somehow fundamentally different from pitch number 100, and I want to thank you for writing in one fool to another fool on.

On to Mailbag item number three. This one is from Bruce Bailey. Bruce says, recently, I listened to the podcast where you responded to pitches from ChatGPT. Yep, that was back in September. You repeated something I've heard you say a number of times, also written about in your book. I'm paraphrasing, but you said something to the effect that you shoot for a 60% success rate. Bruce goes on. Does that mean you're trying to be correct that 60% of your picks will exceed the S&P 500, and over what period of time? Thinking of that in conjunction with the times when you have picked a five-stock sampler, and now you're reviewing those 10 years after your sampler picks. When you review those 10-year choices, you give the cumulative total and individual totals of the percentage return compared to the . I don't believe you've tried to say how many of those picks have reached the 60% threshold you strive for. Can you try to add that? Thanks, Bruce Bailey.

Well, Bruce, of course, you're referencing my 10 years later series. By the way, the next one's coming up in early December, 10 stocks to put under the tree 10 years later. I want to say that I've tried with each of our 10 years later reviews to mention, of course, how many of the stocks of that five stock sampler have beaten the market, how many haven't. I'm sure you've heard that, but you're right. I haven't really done an aggregate. Overall of all 150 stock picks, I haven't gone back to see how many are beating the market and how many are not. That series is very much focused on each sampler, but occasionally I'll speak to the overall experiment, the 30 different podcasts picking 150 stocks. I want to say maybe just a couple of thoughts since you asked, and then we'll move on to number 4 here.

But I would say, first of all, we have a lot of losers. I think that's already been evident in the 10 years later podcasts I've done. There have been a couple of samplers where one or two stocks carried the whole group, and three or four of them were losers themselves. I'm always going to have a lot of losers as a Rule Breaker investor losing to win in my Rule Breaker investing one of my very favorite sections to write and share in that book, and it talks about how often I've lost. As I look over those 35 stock samplers, I see a lot of losers. By the way, especially for samplers, where I was picking stocks going into and during COVID, there are a lot of losers, 2022 was a devastatingly bad year for Rule Breaker investors. I would also add, since I like talking perversely about losers, 2026 has not been a good year for me as an investor.

My overall portfolio definitely down this year in a year where the S&P 500 is up. As people have pointed out, it's up in part because of some big dogs, well, some of the stocks we pick and talk about on this podcast, like Nvidia, etc, but more broadly, many stocks are well below 52 week highs, not up there with the rest of the market. I'm definitely one of those investors. If misery loves company, you should know, I've pretty badly underperformed as an investor in 2026, my private portfolio. I'm always happy and slightly sad to share that. Looking over those 30 samplers, I think about 15 of them have beaten the market, and 15 have lost. But we have thousands of percentage points of positive Alpha also looking over that group, and that's in part because, of course, as I hasten to point out all the time on this podcast, your winners way out gain how much your losers lose. That's such an important lesson that many people who don't invest, they trade, they don't invest.

They don't know that. I guess I should add before moving on to number 4, Bruce, that habit number 6 of the Rule Breaker investor is to aim for 60% accuracy. That's what you're referencing. That's what I'm referencing when I talk about trying to be right six times out of 10. Now, the reality is, I'm probably right closer to five times out of 10, but I've beaten up on the market averages in every context I can think of over the history of my career. Largely because I know that our Rule Breaker winners crush the losers. That's the secret to beating the market that a lot of Rule Breaker investors understand, but much of the rest of the world, including a lot of the financial media don't. I guess we can keep it our little secret. I'll just remind you, Bruce, that like the pirates code, it's really just guidelines. We're shooting to try to beat the market six times out of 10. That's the mindset that I want you and I to have as stock pickers. I don't want us to think we're gambling. I want us to think that we think we're going to beat the market with each stock that we buy, and we're aiming to do that six times out of 10.

I think it's all about our aspirations, sometimes, not what we actually deliver, because it's that aspiration that leads us, ironically, perhaps, as we don't actually hit it to market crushing returns. Thank you for writing in, and Fool on. Our fourth mailbag item this month follows up on last week's Halloween episode Financial Horror Stories. My good friend, again, longtime fellow fool Robert Brokamp, brought us seven financial frights, including particularly scary one involving required minimum distributions, referenced a little earlier in this podcast RMDs, required minimum distributions. Listener, Bruce, and this is a different Bruce from last items Bruce Bailey. By the way, with two Bruces in a row, I can understand why our Australian listeners may be wondering whether we've wandered into a Monty Python sketch. Anyway, Bruce No. 2 has a question about that one.

He writes, "I have always enjoyed Robert Brokamp's input for The Fool in writing and in podcasts." I think his fourth monster horror story omitted a broad category in which I find myself. However, writes Bruce number 2, those who are already over age 73 and dealing with required minimum distributions, because the RMD percentage is going up, Bruce goes on, does it make sense to take more than the RMD in the early years and pay the taxes? That way, you're reducing the amount you hope that will be subject to the RMD and taxes in the future. One problem I'm finding is that after a lifetime of putting money away into my traditional IRA, I find myself with a large snowball of thanks in large part to the fool, good investments, and they're rolling downhill, making a bigger snowball every year, especially if I just take the RMD. Any thoughts? Thank you for any comments or suggestions and all that you and Robert have done in the past, signed Bruce.

Well, Bruce, first of all, congratulations on that snowball. You've spent a lifetime saving and investing, and now your investments are doing what great investments sometimes do, and that's growing faster than you're required to withdraw them. It's a high class problem. It is a real problem, nonetheless, because as we learned last week, during maybe the scariest moment of last week's podcast, if you're a U.S. citizen, anyway, Uncle Sam actually co-owns your portfolio and would eventually like his share. Now, I know enough about retirement planning to know when I should turn back to somebody who knows a lot more. I forwarded your question to Robert, who generously wrote back with some thoughts from vacation. Here we go. Robert began by reminding us of two strategies he'd mentioned last week. First, holding lower growth investments in traditional retirement accounts while keeping higher growth investments in Roth and taxable accounts. Second, using qualified charitable distributions from traditional IRAs after the age of 70.5. Those charitable distributions can satisfy RMD requirements without adding to taxable income.

Now, here's the part of Robert's answer that speaks most directly to your question, I think, and I'm quoting him, "Another strategy is along the lines of what Bruce is suggesting. The first dollars that come out of your traditional IRA must be the RMD. But after that, you can do Roth conversions. This will lower future RMDs by lowering the value of your traditional accounts. Plus, Roth accounts aren't subject to RMDs." So there's an interesting distinction, Bruce, you were thinking about withdrawing more money now and paying the taxes, but Robert is suggesting that after satisfying your RMD, you might instead convert additional money into a Roth IRA, where it can continue growing tax free, subject to the applicable rules.

Now, of course, there's a catch. Back to Robert, "However, there are trade offs. The amount that gets converted increases your adjusted gross income, which increases your tax bill and may have other impacts, such as making you ineligible for various tax credits and deductions or increasing the amount you pay for Medicare, due to the income-related monthly adjustment amount; there’s a scary-looking acronym. He includes IRMAA, the income-related monthly adjustment amount. This is how the retirement planning world works, by the way. Lots of acronyms. That surcharge. It's important to understand all of the moving parts." Robert, of course, hastens to add. Finally, he does offer one additional benefit of this strategy, along with a line that I think sounds very much like him. He wrote, "The other benefit of this strategy is that the Roth will be tax-free to your heirs, as well. Nothing says I love you like a tax-free inheritance."

Again, thank you to Robert Brokamp for weighing in during his vacation. I realize this is sort of a technical point, not necessarily of interest to every listener, but to those who benefit and appreciate retirement advice or pre-retirement advice, helping you optimize toward your future chapters. I'm glad you asked. Bruce, I think the larger lesson is sometimes paying more taxes today can mean paying less over the rest of your life or leaving more to the next generation. The trick is actually doing the math because the right answer is going to depend, as we already heard on your circumstances, but also on your tax bracket. I would say what you expect in the years ahead. Robert was speaking last week to retirement calculators and how you can change the numbers, and it changes the situations and outcomes. It's helpful to tinker around with the numbers a little bit if you feel yourself so inclined this is overall one of those situations. This whole mailbag item probably where a good tax professional or financial planner can really earn their keep. One final thought for me, Bruce, I love the year problem arose because your investments have done so well. You spent a lifetime rolling that snowball downhill. Now you're wondering how best to manage its growing size. May we all be so fortunate.

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David Gardner: Onto Rule Breaker Mailbag item number 5. David, I'm 50 and started reading Motley Fool decades ago. I admit that I had lost touch until recently when my old employer, Tim, mentioned that he'd met with you. What a small world. After that, I started listening to your podcast. I noticed in today's episode that a young German listener wrote in to the Mailbag about time freedom. It's so ironic. Brian Herriot writes, because I just published a book on the topic. While listening to your answer, I noticed that you equated time freedom with "free time." I actually see it slightly nuanced. To me, time freedom is the freedom to live with choice, flexibility, and ease while still working before financial independence. I think the way to achieve it is to balance your lifestyle, your money, as you mentioned, and how you work. If you still have that individual's email, please pass along my book. Here is the German Amazon link. I won't read that out. Thanks for your great work and take care, signed Brian Herriot.

Well, Brian, thank you and I appreciate that distinction. I think you're adding something valuable to that conversation, which, by the way, was our September Mailbag a month ago. Our young German friend David Risinger was looking decades ahead, hoping to build a life where work wouldn't crowd out family and everything else he values. Here you are now, Brian, you're reminding us that we don't have to wait decades to start building that life. We can make choices right now about how we work, how we spend, and how we live. Especially appreciate your recognition that work itself can be deeply rewarding. I remember speaking that way to our young German friend. The goal isn't necessarily to work less, it's to have more say over the work we do and the lives we lead and to feel like that work is of great purpose and creating real value in the world at large. I don't think any of us want less of that. Financial freedom is sometimes about what you can afford, but time freedom, I think you would say, Brian Herriot is about what you can choose. Those two can reinforce each other. Throughout our lives. And by the way, since we have the author of a new book writing in for this Mailbag item, I'm happy to mention his book in a sec.

But here's just a little bit more about our correspondent for Mailbag item number 5. This is from his author bio listed on his book. Brian Herriot, that's H-E-R-R-I-O-T is an author, speaker, business coach, and financial advisor who helps entrepreneurs achieve time freedom and financial freedom. Without sacrificing their most important priorities, after founding three businesses, Brian's learned that true success means building a life that works for you. A self described "freetimer", that's all one word, freetimer. I guess that's different from old timer Brian works by choice, not by obligation and designs his days around what matters most to him. Well, Brian, congratulations on your new book. The title is Time Freedom: Rethink Your Work and Money to Create a Life You Love Now. While I haven't read it, that all sounds pretty good to me. I'm happy to give it a shout-out here. Thanks for writing in and adding to our thinking, Fool on.

Mailbag item number 6. Now, Fools, we're going to do something just a little different with this particular Mailbag. Most of our Mailbag comes from you writing in, but this one comes from something many of you said to us in person earlier this month at FoolFest. FoolFest, of course, the Motley Fools Annual Member gathering where people come in from across the world and visit us here in the Greater Washington, DC area, our annual member event FoolFest. This Mailbag item concerns a question that I care deeply about related to some of what we've talked about this week. How do we pass financial freedom along to the next generation? Well, to help answer that, I'm welcoming back my friend and colleague George Khalaf, Executive Director of The Fool Community Foundation. George, you spent time at FoolFest just a few weeks ago introducing our community to the Freedometer. That's our new tool we've developed to help people find their own pathways to financial freedom. I understand you came away from those conversations with something of a revelation. What did you hear?

George Khalaf: Well, David, thank you. Always great being here. We came to FoolFest really eager to put the Freedometer in front of Fools to share what we're building, hear their feedback, and learn how to make it better. I'd say the biggest surprise is how quickly people connected it to the next generation. I spoke with dozens of members who immediately thought of their children, grandchildren, nieces, nephews. They're just naturally making that connection in their extended family around, how can I impart this knowledge to the next generation?

David Gardner: George, if I'm a Fool listening right now, and I have a young person in my life. Might even be just a mentee of some kind. I'd love to help that person become smarter about money. What's the first thing you'd encourage me to do?

George Khalaf: David, what struck me about this community that we have of our Fools is this community doesn't want to just build wealth. They want to share what they've learned and help others do the same. They're looking to pay it “Foolward,” as you like to say. We've developed this tool, the Freedometer to equip them to pay it forward. I would encourage any listener here to try the Freedometer, go to foolfoundation.org/freedometer, share it with a young person in your life. Tell us what you think there's an easy feedback tool there. We're preparing. If you want more guidance, if members want to share it with their nieces, nephews, grandchildren, children, we're also developing a teacher's guide that'll help guide how you want to walk through the Freedometer with your family member or friend.

David Gardner: I think, George, part of the reason you're mentioning that is because the Freedometer is launching this fall into classrooms. It's natural that for a lot of teachers, they don't necessarily feel fully equipped themselves to teach finance or particularly some aspects of investing in wealth creation. I can see why you're thinking about the teacher's guide, and also just for any of our members, it's something you yourself could just log into now and check out. That is Freedometer and George, I think you've made a good point because at FoolFest, what we're often encountering are people who are not necessarily looking just for financial freedom for themselves. These are people at a stage of life that have in many cases achieved financial freedom. That's why they've taken the time to fly from somewhere around the world to National Harbor in Washington, DC, and attend FoolFest. But we're increasingly encountering people who have financial freedom or some measure of it and recognize the benefit and the beauty of it and want to spread that and share that, especially probably with family members, but also the communities around them. George, I think it's a special, it's rarified air for you. Obviously, a lot of what we're doing at the Fool Community Foundation is about people living paycheck to paycheck, but having that opportunity to spend time with people at or near retirement who feel that urge to begin making a count, paying it forward. George, I'm wondering, is there a particular conversation that sticks in your ear that you remember from just a few weeks ago?

George Khalaf: My colleague, Martin, and I had breakfast on day 2 with John Beyers. John is a member who we shared a common passion for having lived in Princeton. But he has grandchildren who are being homeschooled and was passionate about, how can we teach them personal finance and specifically help them prepare to invest and learn the power of compounding and teach them how an extra decade of learning can translate to so much compounding growth over time. John was particularly interested in the Freedometer and was eager to share the Freedometer with his grandchildren as part of their homeschooling curriculum.

David Gardner: George, I love that. Perhaps one of the best investments we could ever make is in somebody else's financial future. Fools you can find the Freedometer @foolfoundation.org/freedometer. Give it a try. Share it with someone you care about. Please tell us what you think we're building this for you and also with you. George Hallof, thank you for helping us make the world smarter, happier and richer.

George Khalaf: Thank you, David. Always a pleasure to be here.

David Gardner: On to Mailbag item Number 7, this one from a 13-year-old. Thank you for writing in. Usher. Hi, David. My name is Usher, and I'm 13. I'm really interested in investing, and I'm starting to learn how the stock market works. You've been investing for a long time, so I wanted to ask, what's one lesson you learned early that you'd want a 13-year-old to know? Thank you for reading. Usher. Well, Usher, that one's easy for me because the first lesson I learned, I think I was about 6 or 7-years-old, and it's a story I've told many times. I'm about to tell it right here right now, but most probably haven't heard it. When we were kids, we would go Saturday mornings to our local grocery store where our dad with his kids, would go in and buy groceries for the following week. As we would walk into the Safeway in Washington, DC, near where I grew up, dad would say, Hey, kids, look. Chocolate pudding. He'd be pointing at the chocolate pudding on the shelf in the grocery store that Saturday morning. We own some of the company that makes that chocolate pudding, a few shares through the stock market. Let's go get more chocolate pudding. That made him a very popular dad with his kids because we love chocolate. I still love chocolate pudding today and so the key lesson that I learned at an early age is that you should love the companies of the stocks you're buying.

I hear a lot of times people say things like, don't fall in love with your stocks. I think they're referring to being too emotional. Up and maybe down when the stock market goes up and down. They'll say, Don't fall in love with your stocks. I think you should truly love the products and services, the culture. I think you should love as much as you can. Every human enterprise is flawed in some way. You have to look past flaws, too, but you should love the stocks that you buy. You should know the products and services. A lot of people love their Apple iPhones. Apple has been one of the best-performing stocks in the market over the last 20 years, or even 30 or 40 years. Most of the great winners, a lot of people love Starbucks. Some people, I guess, pick it outside or don't like Starbucks. A lot of people love Amazon. Some people don't like Amazon, but you should love the companies whose stocks are in your portfolio. When you love them, you're going to pay more attention to them. That's why it's such a good idea to build a portfolio as early as you can. At the age of 13, that's a fantastic time to be starting saving and investing for the rest of your life. Usher, you might have even started before 13. But the earlier we can get started, the better, and the more that we are in touch with the companies we're invested in, the better off we're going to be both financially because I think you're going to prosper more and, of course, learning, the education you get is much more meaningful when you're studying things that you love, that you care about.

That is my lesson for a 13-year-old, and I want to thank you for writing in Usher and give you my Foolish best. From a 13-year-old for Mailbag item Number 7, asking, basically, Usher, you're asking, What should I know? We're going to close it out this month with a 19-year-old asking a slightly different question, I would say more akin to what should I do? Dear David Gardner, I'm Lecan 19, a student athlete studying management. I'm writing to you specifically because of your work with Rule Breaker Investing at The Motley Fool, Lecan writes, I'm trying to find my path right now. Honestly, I feel lost. I'm also currently in debt, and I'm trying to figure out how to build something real in school, in work, and financially, without making the wrong moves early. I'm not asking for money or a job. I'm asking if you'd be open to 20 minutes of mentorship advice or even just pointing me to the first 2-3 things you'd do in my position. Thank you for reading this and for the work you put out. Best, Lecan Satanwa.

First of all, Lecan, let me thank you for writing. I would say it takes some courage to say, I'm feeling lost. I suspect many listening right now feel something similar, and not just at the age of 19, but at 39 or 59. These are good questions to ask at every age, and I admire that you're asking them, and thank you for writing in to me. The first thing that comes to mind is the three degrees of influence. Let me share that with you in case you haven't heard that phrase before. You can Google it and read a lot more, but I think you're going to get the concept right away. A lot of people know the six degrees of separation, which is this idea that if you know someone who knows someone who knows someone, if you do that six times, you actually know everyone on planet Earth. That's the six degrees of separation. Every fellow human on Earth is six degrees away from every other. It might even be down to five these days, thanks to the Internet, social media, etc. That's the well known six degrees of separation, but less well known is the three degrees of influence. Here's my way of explaining that.

Your friend is obviously influencing you. That is degree No. 1. Your friend's friend is also influencing you, and your friend might say, Hey, my buddy this or that said this or that thing or is doing this new thing. You hear that your friend's friend. That's degree No. 2. But scientific studies suggest we're actually being influenced out to a third degree. That, of course, would be your friend’s friend’s friend. The reason I'm talking about the three degrees of influence is that what that implies is that we're all being influenced very obviously by our friends and maybe by their friends, too, but we're not actually aware and can't be, in most cases, of your friends' friends’ friend. You mentioned you're a student athlete. This would be the friend on your team's mom's co-worker. You'll probably never meet that person, but in fact, your friend on the team's mom's co-worker just did or said something that influenced your friend's mom, and that comes through to your friend, and then it filters back through to you.

This is all an elaborate way of saying that I think spending time with the best people that you can, the best people on your team, the best people in class, the best people in your friend group, the best people in any room, the best adults that you're around, the best teachers that you have at your university spending time with the best people is what gives you and me the best opportunity to be the so called best version of ourselves. Beyond just people, which I'm emphasizing here, I would say books. I would say podcasts. I would say all of the things that you invite in to influence you. Each of us is truly going to be best served by looking for the best.

One of my investment lines that I've used many times, it's there in my book Rule Breaker Investing is I try to find excellence, buy excellence, and add to excellence over time. I sell mediocrity. That's how I invest. I would also change that word invest and say live. I'm saying that back to you, Lecan. Try to find the best people and things, spend time with those best people and things, and add to that time with those best people and things over the course of your life, stay away from the mediocre or worse things. That's a great way to live a life. Now, I'm speaking generally. I don't know you, so that's the best I can, and I'm trying to speak in a way that would not just for you but for anybody of any age, just based on my own experience.

Now, I will plug a past author on this podcast, and I highly recommend this person's work, if you haven't come across it before, and that would be the book Positive Intelligence. The author is Shirzad Chamine. I won't spell that name. Just Google Positive Intelligence, and you'll see that on Amazon or wherever you enjoy buying books. You can also Google Rule Breaker Investing Positive Intelligence and hear one or more of my multiple conversations with this fantastic author and thinker on this podcast in recent years. Shirzad Chamine and his work.

I’m going to close with it in a sec, but I just want you to know- being able to look for the positives. Danny Meyer, the successful restaurateur. I mentioned him earlier in this podcast. His new book is entitled What Could Possibly Go Right. That's right. He didn't write wrong. He said, What could possibly go right? In fact, he said, almost every great business — he said this in the lunch lecture I heard today. Almost every great business is started by somebody who says something like, What if this actually worked? What if things went right? It's a great question to be asking, and Positive Intelligence will teach you and have you asking that question more often than most of us before coming to that book and that thinker. I highly recommend that.

Again, I'm going to close with something about that in a sec. But one other piece of advice this came to me recently. I think I mentioned this a few weeks ago, but this was advice provided a new job seeker. Somebody just a couple of years older than you going for their first job, this person had multiple offers, and they were asking me, Hey, which one should I take? What's the best choice for your first job? Advice that I'd gotten from a friend, I provided to this person, and they seem to like it a lot. Maybe you'll like it, too. This isn't just finding a job. This is about life, Lecan. Think ahead of time about what is going to give you the widest range of experiences in life. That, again, was for a job seeker. Which job would give you the most different types of experiences that you could learn from and grow from, especially your first job, especially at a young age?

I feel like you're already doing that. You are not just a student, which is all I was. You're a student athlete. You are having a wider range of experiences probably than I had already. I would encourage you to continue to seek those things out, the widest range of experiences you can with the best people and things around you that you can spy out as you go. I hope those things are helpful. Let me close with a little bit more for you, Lecan. Rulebreakerinvesting.com, which is a support website for my book and my book launched last year, but I've been using it as a way to improve my podcast and to collect my podcast to make it more accessible and more understandable. Twelve years later with a new one every week, I've started organizing by categories, but I also on that site, have a blog page. I once wrote 11 short blogs, and I just put them all out right on that page. If you go to rulebreakerinvesting.com/blog, you're going to see 11 short essays. Each one is 350 words. They're very short.

I'm going to present one now to close that I hope is helpful for you. If you like this, there are 10 others that you might enjoy @rulebreakerinvesting.com/blog. This one is entitled The Lighthouse. While many humanistic concepts go back to the Greeks, the phrase Self-Actualization only showed up in the 20th century, most famously popularized by American psychologist Abraham Maslow. He put it at the top of the pyramid of his so-called Hierarchy of Needs. If we can get there, we have gone beyond merely fulfilling our biological and egotistical needs to our psychological ones; we have, in effect, maximized our potential. Now, you may already be familiar with Maslow's hierarchy, but do you know the wisdom of Positive Intelligence genius, Shirzad Chamine? Shirzad says we approach this in the wrong order. Oh my God, we think, I have to figure out what my big achievement will be on this earth. Then we must focus and achieve it. Having achieved it, well, I'll be self actualized. Wrong.

Each of us, with no map or guide, is standing at the edge of a dark forest. There is a lighthouse in the distance, self actualization. Getting to the lighthouse is a goal taken one step at a time. At any given step, Chamine urges, Take the step that has more light in it. Chamine urges, 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, and 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 will 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, surprise ending, you will never make it to the lighthouse. Because 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. That's The Lighthouse. As we close out this Mailbag, let me just say this one had a really nice generational dimension. We've got a 13-year-old, a 19-year-old, a 50-year-old thinking about time, freedom, and a retiree navigating required minimum distributions because of a too-large snowball that kept making money rolling down the hill. I would say that's practically a lifetime of financial questions in just one podcast episode. I was delighted to be able to bring back The Lighthouse. Happy Halloween.Looking forward to November. Fool on

David Gardner has positions in Alphabet, Amazon, Apple, and Starbucks. The Motley Fool has positions in and recommends Alphabet, Amazon, Apple, and Starbucks. The Motley Fool has a disclosure policy.