September 2026 Mailbag: 16 Years Old to 25 Years Foolish

David Gardner (0:00)

It's mailbag time, and this month, our correspondents range from 16 years old to 25 years foolish. A young German reader is already thinking about something many of us don't think about until much later in life, time freedom. Another listener asks whether in a world changing faster and faster indexing might make more sense now than ever. We'll hear from a self-directed investor who's underperformed the account he wasn't managing and he has no regrets.

Later, one of the tougher questions any investor can ask, how do you know whether your losers simply need more time or you just didn't pick enough winners? Seven correspondents, seven stories and questions from across our foolish universe. Your September 2026 Mailbag only on this week's Rule Breaker Investing.

SPEAKER_2 (0:54)

It's the Rule Breaker Investing Podcast with Motley Fool co-founder, David Gardner.

David Gardner (1:03)

Welcome back to Rule Breaker Investing. This is the fourth consecutive week that Bart and I are doing and producing this podcast. After hours, I've mentioned this once or twice. I'm not going to complain about it, but I have grand jury duty here in Washington DC, which is a five week, that's right, five days a week, nine to five, five week commitment. It's something quite remarkable. I'm not asking for praise for anybody. I want to give a shout out to my 22 other grand jurors, because everybody's got their own backstory.

I will say this about jury duty. Obviously, almost everybody roots against it. A lot of people who've seen the Amazon Prime video, jury duty think it's funny. I do too. Those are a couple of thoughts about jury duty.

It's also inspiring to know that this is how our system works. In the case of grand juries, we have a different mission than typical jury duty. Those of you who are jurisprudentially inclined will already know this. I didn't though. Grand juries don't sit on cases. You don't all have to agree and say guilty or innocent over a few days. Grand juries are only passing through possible cases saying, yes, there is enough evidence or no, there's not in order to create trials that other juries will sit on. So over the course of, well, it's been four weeks for me now. I have participated in 46 separate cases with my fellow grand jurors voting in which ones we think, yeah, should one day be a trial. They're all felonies. It's all the hardest, worst things that you'd want to see in your city or any other. It's been a really interesting few weeks. I look forward to doing this podcast again at normal hours come October. I do want to give a shout out to a new listener, Patricia, because Patricia, you are a new friend of mine. We met at jury duty and you said you're going to listen to the podcast this week. So thank you for listening in and thank you as always to every new fool who joins this podcast Rule Breaker Investing in any given week. And especially thank you to those who turn their friends onto it, who make an effort to let other people know about the beauty of investing, of breaking the rules, of being positive, going through life, how to win the games of investing and business and life. That's what I'm trying to help us all do. And you help me too back with every monthly mailbag. So yes, Patricia and every other new listener, you have happened upon what happens at the end of every month for this podcast which is that I take in mail. Most of the time it is email. Our email address is rbi.fool.com. We invite all comers, drop me a line if you have feelings or thoughts about podcasts we did over the course of the month. I'll be going over the September 1 shortly. But you're also welcome to drop questions, thoughts about investing. We sometimes have poems and other delights. We even sometimes, we don't have it this week, but we have audio mailbag. So if you'd like to drop an audio file, you can just paste that in to an email, rbi.fool.com. We have seven mailbag items this month. So it's been a very full month. And let's look briefly back at the month that was. This is the fifth Wednesday. Therefore, we've had four podcasts. The first was on September 2nd, Old, New, Borrowed and Blue, Volume 11 Well, a September hodgepodge, spanning a World Series lesson for investors, an old investing truth in exactly 350 words, Kevin Kelly's invitation to live your most improbable life. Yes, blueberries.

On September 9th, it was 10 years later, five low-risk stocks for the next year. Rick Munarez joined me and we reopened the only five-stock sampler ever designed on this podcast for just one year.