The 5 Questions You Would Not Stop Asking Me in 2026

Tyler Gardner (0:00)

The more I do this, the more I realize that 99.9% of the questions aren't exactly about the money. They're about what you can control and what you can't. What you can control is whether you've looked at the whole balance sheet instead of the part with the login page, whether you know what you actually own, and whether you've said the hard thing out loud to the person who needs to hear it. That's most of the job.

Hello, friends. This is Tyler Gardner welcoming you to another episode of Your Money Guide on the Side, where it is my job to simplify what seems complex, add nuance to what seems simple, and learn from and alongside some of the brightest minds in money, finance, and investing. So let's get started and get you one step closer to where you need to be.

One quick thing before we start, October's pre-order bonus for my book Real Wealth is now live, and it's the one I've had the most fun putting together to date. It's my 10 favorite books of all time, Finance and Otherwise. Each one comes with a note on what you'll actually get out of it, who it's really for, and my honest verdict on whether you'll actually finish it. Because important and enjoyable are two very different claims, and the finance shelf is full of the first kind. Pre-order at tylergardner.com/book. Let me know you did, and I'll send it directly to your email in early November. I want to start off this week by telling you how this episode got made, because it actually wasn't my idea. Every week, I get somewhere between 2 and 3 thousand questions across social media platforms. Some arrive by email, some arrive in comment sections, a surprising number arrive as voice memos to an email recorded by people who haven't quite realized how long voice memos can actually be, and I want to say gently that I have listened to them all, including the 11 minute one about the annuity. And a few weeks ago, I did something I had never done. I went back through the whole year, all of 2026, and I started sorting through them and placing them in categories. Not by topic exactly, but more by shape and feeling. What was the actual question underneath the question? And what fell out was that the same five things kept showing up, over and over, in slightly different forms and levels of angst. So that's this week's episode. It's my first Q&A episode, and I'll focus this week on five questions, the five you've actually asked the most frequently, not the five I necessarily find the most interesting, which would be a very different and probably much worse episode. Now, a word on what these all have in common, because it kind of surprised me. Not one of the questions is a question about what to buy.

Nobody asked me for a ticker symbol. Nobody asked me which fund to invest in. The questions were all about how to think about something you already own, or something you can't quite control, or something you're afraid of, which tells you that the audience for this show has largely solved the easy problems and has moved on to the ones that don't have the cleanest answers. Fair warning on that last part. Two of these five do not have clean answers. I'm going to tell you where the honest uncertainty is instead of pretending it away, because the alternative is that you go make a large decision based on my confidence, and I have to live with that, and you have to live with the decision. So never advice. These aren't clean answers. And before we get into it, familiar ask, if you have found this show useful in any way, if you've shared it with a friend who needs to hear the message of low-cost investing, a review on Apple or Spotify genuinely helps. It helps new listeners find the show, and it lets me know I'm not just talking into a microphone in the woods of Vermont, with nobody listening but a sleeping bloodhound at my feet, which ultimately I'd still be okay with because it is in fact my definition of real wealth. Let's get into it.

Tyler, you talk all the time about 401Ks and people who have come from a W-2 life and are relying on their portfolios. I have a pension. How does that change the way I think about my portfolio and about my retirement?

This was the single most common question of the year, and it arrived in about 40 variations. Some people had pensions, some had rental income, some had a spouse still working part time, some had a small annuity purchase years ago for reasons they could no longer reconstruct. But the underlying question was always the same. Here it is. I am 62 I have a pension paying 40,000 a year, and Social Security is going to pay another 32 My portfolio is 800,000, and my advisor has me at 60, 40 Is that right? And the answer in most cases, and I kind of hesitate to say this because again, there's not always a clean answer, but in most cases, the answer is no. You shouldn't actually have a 60, 40 portfolio because the portfolio should transcend not just the assets that you have in that portfolio, but your entire income picture.