The 5 Questions You Would Not Stop Asking Me in 2026

The more I do this, the more I was at 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 a 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 from 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 ten 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 3,000 questions across social media platforms. Some arrive by email, some arrive in comments 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. What 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. We're 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 false 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. 21. Tyler, you talk all the time about 401Ks and people who have come from a W2 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. Most people asking, assume I'm going to tell them they're being too aggressive. I'm going to tell you the opposite. Here's why. When you own a bond, what you actually own is a contractual promise to pay you a fixed amount on a schedule. That's it; that's the whole product, and when you have a pension, what you own is a contractual promise to pay you a fixed amount on a schedule. Social Security is a statutory promise to pay you an inflation-adjusted amount on a schedule. These are all the same kind of thing. The pension doesn't show up on your brokerage statement, so it doesn't feel like you're holding something, but it behaves like an asset in your portfolio. It throws off income regardless of what the market did last week, and that's the entire job description of fixed income. So I want you to run the numbers on our hypothetical person, 72,000 a year in guaranteed income. If you wanted to generate 72,000 a year from a bond portfolio at, let's just say, 4%, you'd need 1.8 million dollars in bonds to do it. That's not a rounding error. That's more than twice the size of the entire portfolio we were just talking about. Which means the honest picture is not 60/40. The honest picture is a portfolio of 2.6 million, of which 1.8 million is already in fixed income. That's 69% bonds and 31% stocks. And then inside the liquid 800,000, this person is holding another 40% in bonds on top of that. So they haven't built a balanced portfolio. They've built a bond portfolio with a small equity garnish, and nobody told them because the pension just happens to live on a different piece of paper. Now before you pick up the phone and call your advisor and demand to be put in 100% total market or equities, I need to give you some qualifiers and they matter enormously. The first is inflation adjustment, and this is a big one. Social security has a cost of living adjustment. Most federal and many state pensions also have one. The large majority of private pensions do not, and a pension without a cost of living adjustment is not a bond, it's a melting bond. At 3% inflation, a fixed $40,000 pension buys about $26,000 worth of groceries in today's money after 15 years. If you plan around the number on the statement, you're planning around a number that is slowly not going to be there in a few years. The second qualifier is credit risk. Your pension is a promise, and promises have a counterparty, a federal pension is backed by the United States government, a pension from a mid-size manufacturer is backed by a mid-size manufacturer, and the pension-benefit guarantee corporation behind it, and the PBGC has coverage caps that can land well below what your statement says you're owed. Most people have never checked that, you should check that. The third is liquidity, and this one gets missed the most. You can sell a bond, you cannot sell a pension. When the market falls 40%, and you need to rebalance, the pension does not help you, it just keeps paying you. So the liquid state of the portfolio has to carry the entire burden of emergencies, of opportunistic rebalancing, and of any large lumpy expense that shows up. That argues for holding real cash reserves, even in a portfolio that's otherwise correctly tilted towards stocks. Put all three together, and here's the takeaway. Your allocation should be measured against your entire balance sheet, not just against the slice of it that happens to have a login page. For a lot of people with meaningful guaranteed income, that means they're carrying far more safety than they think, and far less growth than they They need for a retirement that might run 35 years. So go count everything right now, then decide. This episode is brought to you by Built. You don't need me to tell you that rent and mortgages are only getting more expensive. That's why Built created three credit cards designed to offer the richest rewards on rent, mortgage, and everything else you spend on. So whether you rent or own, you can earn up to 1.25x points on every housing payment without the transaction fee, no matter where you live. Points can be redeemed for flights, hotels, lift rides, a future housing payment, and much more. Turn one of the most unavoidable payments in your life into the most rewarding. 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I got this question all year from both directions, and I want to be very clear about how I'm going to handle it, which is that I'm not going to say a single word about anyone currently holding office or anyone running for one, not because I'm squeamish, but because it's a relevant to the answer, and I have this pesky thing called data that proves it over and over again. Let's consider what the records show. The stock market has produced strong returns and terrible returns under democratic administrations. It has produced strong returns and terrible returns under Republican administrations. Recessions have started under both parties. The great bull market of the 1990s ran under a Democratic president and a Republican Congress. The 2008 collapse began under a Republican president. The 2020 crash and its violent recovery happened under a Republican president. The 2022 bear market happened under a Democratic one. If there were a reliable, tradable relationship between party control and market returns, it would be the most famous fact in finance, and every pension fund on earth would be running it. But there isn't one so they don't. But I want to make a stronger argument than the data is mixed, because that's boring, and for all intents and purposes kind of useless. I want to talk about timing and specifically about one person who was right. December 5th, 1996, Alan Greenspan, Chairman of the Federal Reserve, gives a speech in Washington and asks more or less how we would know when a rational exuberance has unduly escalated asset values. That's the line. This becomes one of the most famous phrases in modern market history, irrational exuberance. And he was right. He was completely right. The market was in the early stages of a genuine mania that would end in one of the worst crashes in all of history. So here's the part nobody mentions when they quote him. The S&P closed that day somewhere around 744. It didn't crash. It kept going. It kept going for more than three years. And it peaked in March of 2000 at roughly 1,527. It more than doubled after Greenspan's accurate warning. And then it crashed brutally. The dot com bus took the index down roughly half over the next two and a half years. So imagine you were the person who heard Greenspan and got out in 1996. You were vindicated. You were correct. You identified the bubble in real time, which almost nobody does. And you acted incorrect analysis. You still lost. Because when the market bottom, the October of 2002, at the very floor of the wreckage, the index was still above where it stood the day Greenspan gave the speech. The single worst day of the entire crash did not take prices back to the level where the smartest warning in history was issued. You would have sat out a doubling, then watched the crash you predicted, then found yourself still with less than if you had done nothing at all. And that assumes you got back in at the exact bottom, which I promise you wouldn't do. Nobody does, and because the bottom is only visible in retrospect, and it does not feel like a bottom while you're standing on it, continuing to wait for the floor to fall out from underneath you. That's the whole lesson and response to this, and I'd like it tattooed somewhere. We can sometimes know that something's going to break. We never know when, and when is the entire trade being right at the wrong time cost you as much as being wrong, and frequently it costs you more because being wrong at least leaves you invested. There's a second piece of arithmetic that closes this. Market returns are also not distributed evenly across trading days, a very small number of days account for an enormous share of the total return of that year, and those days tend to cluster inside the ugliest stretches. Right next to the worst days, I know you've heard that before, the best day and the worst day are frequently in the same week, which means the emotional signal telling you to get out arrives at precisely the moment when leaving costs the most. So whatever you currently feel about this administration or past administrations, just look at the market. It's continuing to soar. Do we know if it's going to continue to soar or break? No, we don't, but we do know that historical data continues to suggest that you would have to be right twice, which on average nobody is in order to vindicate getting out because you think somehow a certain administration is not going to do well with your retirement account. My point, you cannot dodge the bad days without dodging the good ones. Nobody has a mechanism for separating them. Not you, not me, not the chair of the Federal Reserve in 1996. So stay invested if that was your plan, not because nothing bad will happen, but because you cannot time the bad thing and the cost of trying is measured in decades, not years. Question 3. I want to retire at 58. What do I do about health care? This is the question that changed the most in 2026, and if you retired before this year, the advice you got is now out of date in a way that can cost you five figures. Here's some quick history and I promise I'll make it brief. The American Rescue Plan in 2021 temporarily expanded the Affordable Care Act's premium subsidies, and it did two things. It made the subsidies bigger for people who already were receiving them, and it eliminated the income cliff at 400% of the federal poverty level, so that people above that line still got help if premiums exceeded a set share of their income. The Inflation Reduction Act extended that through the end of 2025. Congress did not extend it again. Those enhancements expired at the end of last year, and the structure reverted to what it was before 2021. Which means guess who's back? The cliff is back, and a cliff is different from a phase out in one crucial way. A phase out tapers, a cliff does not one dollar over the line, and your premium tax credit goes to zero. Not smaller than it was zero. For $20.26, that line sits around $62,600 of modified adjusted gross income for a single person and around 128 $8,600 for a family of four. Now sit with what that means for an early retiree because it's pretty severe. If you're a couple at 60 and your income lands $1 over that threshold, you don't lose a little help, you lose all of it, and you're buying a benchmark plan at full retail, which in a lot of markets now runs well north of $1,000 a month per person. It is entirely possible to earn $1 additional dollar and be worse off by $20,000. And I want to name that plainly. In your pre-medicare years, your health insurance has become a marginal tax rate. And near that threshold, it is the highest marginal rate almost anyone in this country will ever face. It dwarfs the top federal bracket and it's not even close. So what do you actually do? The first thing is that your income is now a design problem, not an outcome. If you're between retirement and 65 and you're on a marketplace plan, every financial decision you make should run through the modified adjusted gross income calculation, which account you withdraw from matters, realizing capital gains matters, selling that rental matters. The Roth conversion, your advisor, recommended in 2023 matters. And I'd note carefully that the conversion strategy that might have made perfect sense two years ago can now be actively a little more expensive because conversions add to modified adjusted gross income and modified adjusted gross income is what pushes you over. The second thing is that the levers to pull are the ones that reduce that modified adjusted gross income specifically, health savings accounts, contributions, reduce it, deductible traditional IRA contributions, reduce it if you're eligible, spending from taxable savings and from Roth principle generally doesn't add to it, which is exactly why having money in multiple tax treatments before you retire is worth so much more than people realize when they're 45 and just putting everything into a 401k. The third thing and this is the one I'd press hardest is timing. If you're planning a retirement date between now and 65, that health insurance decision is not a detail to sort out in the last month, it may be the single largest variable in whether your plan works. I've talked to people who move their entire retirement date by nine months purely to change which tax year a large capital gain landed it. And it was the highest value nine months of their financial life. One last note, and it's a real one, this is still unsettled policy. There have been extension efforts and there have been bipartisan conversations about it. What's true when I record this on August 10th, 2026, may not be true when you're making the decision, so verify the current rules and the current threshold for your household size before you act and if your situation is anywhere near that line, this is genuinely worth paying a tax professional for. That is not a sentence I say often, so please treat it with respect it deserves. This episode is brought to you by Element. 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It works at any hour, because the reason you tend to feel foggy or head-a-key or flat is usually not that you need more water. It's that you need what's supposed to be in the water. Element is a zero-sugar electrolyte drink mix, no sugar, no artificial colors, none of the dodgy ingredients in the sports drinks you grew up with. And if you don't like it, they'll refund you. No questions. The free eight-count sample pack of elements most popular flavors, with any purchase at drinkelement.com/tyler, that's drinklemnt.com/tyler. This week's episode is brought to you by Fassit. If you pay an advisor 1% of your assets, it's worth appreciating that the fee can move for reasons that might have nothing to do with the advice. Three things to consider. Number one, your mother passes away and you inherit $800,000. Your advisor's bill might go up $8,000 for a year in which the added value was a sympathy card. Number two, the market goes up 20%, their fee can go up 20%. You might have a silent partner who put in no capital, took no risk, and still gets a slice. Huh. Number three, you hand over $500,000 and it sits in cash for a few months. Not invested, but you might be billed as if it were. None of this makes your advisor a bad person, not even close. I know many outstanding advisors who do exceptional work, but I'll always question a model that charges on the size of your assets rather than the work performed. Fassit works differently. No percentage of assets, no commissions, just a team of dedicated CFP professionals who will help you figure out what you want your money to say about your life. Head to facet.com/tyler to book your intro call today and find out what the future of financial planning actually looks like. I'm not a member of Fassit, I have an incentive to endorse Fassit as I have an ongoing fee-based contract for cash compensation, as well as a percentage of equity and facet based on this endorsement. Fassit is an SEC registered investment advisor. All opinions are my own and not a guarantee of a similar outcome. Question four. In 2026 is the S&P 500 still diversified or do I own seven companies? The concern here is real and I want to start by validating it rather than talking you out of it, because the numbers are legitimately unusual. By the end of 2025, the 10 largest companies made up roughly 41% of the S&P 500's total weight. That's the highest concentration on record. And to give you the shape of the change in 1990, those top 10 were about 19% of the index, spread across genuinely unrelated businesses, IBM, Exxon, General Electric, Philip Morris. If one had a bad quarter, the others were doing something else entirely. Even at the peak of the dot com era, the top 10 got to only about 23% at year end 2000, touching roughly 27% during that year, and we are now well past that. And it's not only the size that matters, it's the correlation. Today's top 10 are not scattered across unrelated industries. They are to a substantial degree, various expressions of the same bet on artificial intelligence. In video alone, has been running near 7 to 8% of the index. When you buy an S&P 500 fund today, more than 40 cents of every dollar goes to 10 companies, most of which rise and fall on a shared narrative. So the person asking this question is not being paranoid, they're reading the fact sheet completely correctly. But here's where I land anyway, and it's the same place I landed in question 2. Concentration is not a prediction, it's a description. It tells you what the market currently believes about where value is. It doesn't tell you when the belief will change, and when is the only thing that would make it actionable. We've been here before. Everything I just said about correlation and narrative and unprecedented weight was said correctly in 1998. It was said correctly in 1999. It was said by extremely smart people who were entirely right about the diagnosis and entirely destroyed by the timing. Greenspan again, right in 1996, wiped out by 1999 if he traded on it. And the second reason is mechanical, and I think this one's underappreciated. And index fund fixes itself, not gently, not without pain, but it does fix itself. In 1990, energy and industrials dominated the top 10. They don't now. Nobody had to make a decision, nobody had to be right about the timing, the index rebalanced continuously because that's what market cap waiting does. When leadership changes, the index changes with it, and it does so without you having to correctly identify the turning point, which is the thing you cannot do. Contrast that with the alternative. If you decide that concentration is intolerable, and you move to an equal weight, where you tilt hard to international, or you go to value stocks, you've made an active bet, and now you have to be right twice. You have to be right about the direction, and right about the timing. The people who made exactly that move in 2021 for exactly these reasons have been sitting on that decision for five years. So what do I actually think you should do right now? Your only action step for right now, know what you own. If you have an S&P 500 in the 401k, a NASDAQ fund in the IRA, and company stock from your employer who happens to be a technology company, you may be far more concentrated than the [BLANK_AUDIO] some of those three descriptions suggest. That's a real problem, but it's a pretty easily fixable one. And if you own a total market fund and an international fund in some ratio you set years ago and haven't touched, you are already doing the thing. That international allocation you've been grumbling about is not under-performance. It's an insurance premium. And the entire point of an insurance premium is that in the years you're happiest, it looks like a waste of money. Do not restructure a portfolio around a forecast. Restructure it around a look at what you actually hold and if what you actually hold is not right for you and your risk tolerance at this time. Question 5. What am I supposed to do about long-term care? I saved this for last because it's the hardest and because it's the one where I'm going to be most honest about the limits of what I can tell you. Start with the numbers and yes, you might want to brace yourself slightly for this one. The most recent cost of care survey work puts the national median for assisted living at roughly $6,200 a month. Full time in-home help, meaning around 44 hours a week, runs somewhere near $80,000 a year. A nursing home lands roughly between 150,000 and 130,000 a year depending on whether the room is shared. Memory care typically runs 20 to 30 percent above assisted living and skilled nursing delivered in the home now has a national median around $90 an hour. Those are today's numbers. The trajectory is the harder part. Over the 20 years, through 2024, semi-private nursing home costs rose around 138 percent while general inflation ran about 71 percent. Care costs have been compounding at something like double the rate of everything else because care is labor and labor has been the tightest thing in the economy. And add the piece that most people get wrong, which is Medicare, Medicare does not cover long-term custodial care. It covers limited skilled nursing after a qualifying hospital stay and it covers rehabilitation and then it stops. The daily help with bathing and dressing and eating that most people eventually need is not a Medicare benefit. It never has been. I would guess a third of the people listening believed otherwise until roughly 27 seconds ago and that's not a failure on their part, it's a genuinely confusing system. So here are four honest paths that you can take and I'm going to tell you the drawback of each one rather than trying to sell you on any of them. First traditional long-term care insurance. It exists, it works when it works and it has a genuinely troubled history. Insurance dramatically underpriced these policies in the 80s and 90s because they assumed more people would let their policies lapse than actually did and they assumed lower care inflation than materialized. The result was decades of premium increases on people who already held policies, sometimes very large ones arriving at exactly the age when the policy holder had the least ability to absorb them. So if you're considering it, the underwriting question is whether the carrier can raise your rate and by how much and you need to model whether you could still afford the policy at double today's premium. Hybrid policies are number two. These are life insurance or annuity contracts with a long-term care writer and they're selling point is that if you never need care the money goes to your airs rather than evaporating. That solves the emotional objection to traditional coverage, which is real, what it costs you is capital efficiency. You're tying up a very large amount of money and a product with modest internal returns to buy a benefit you might not use. It's a legitimate choice. It is not a free lunch and it is sold as one with some regularity. Self funding is the third and it's what I plan on doing. Now I want to be careful here. Self funding is not a strategy that consists of not buying insurance. It's a strategy that consists of designating a specific pool of assets, keeping it invested for growth given a likely 20 plus year horizon and knowing exactly what it's for. If your net worth is such that a three year nursing home stay for one spouse would materially impair the survivor's life, you are not self-funded, you are uninsured. Those are different things and the distinction matters enormously. Finally Medicaid is the fourth and it's the one nobody wants to discuss and it's how a very large share of American long-term care actually gets paid for. It requires spending down assets to qualify the look back period on transfers is substantial and it constrains where you can receive care. It is a real backstop and it is also not what most people picture when they imagine they're 80s. Now what should you actually do this year at 55 or 60 or 63? Start by having the conversation, not with an insurance agent with your spouse and separately with your adult children if you have them because here's what the financial framing obscures in most American families long term care is not currently purchased. It's absorbed by a daughter or daughter in law who reduces her hours or leaves her job. That transfer is invisible in every projection I've ever seen and it is enormous and it has its own second order costs in her retirement in her earnings and in the relationship. So deciding in advance whether that's the plan and saying it out loud to the person who would be doing it is worth more than any product comparison. It might not be comfortable but it is necessary. It is also potentially the single most uncomfortable conversation you will ever have regarding personal finance which is why almost nobody has it and which is why it happens by default in a hospital corridor at two in the morning. So do it on a walk, do it awkwardly but do it before you need to. So there you have it. Five questions and I'll tell you one closing thought that struck me while putting them together. Four of the five were not really about money. The more I do this, the more I talk about it, the more I write about it, the more I think about it, the more I converse with all of you about it. The more I realize that 99.9% of the questions aren't exactly about the money. You can't control who wins an election or when a bubble pops or whether Congress extends a subsidy or whether you'll need care at 84. What you can control is whether you've looked at the whole balance sheet instead of the part with a 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. It's much less glamorous than picking the right fund and it matters about 40 times more. I hope this was useful. If it was, please consider leaving a review on Apple or Spotify as it helps more people find the show and as Dixie is now looking up at me with those bloodhound eyes, it is now time for me to go experience my real wealth and take a walk in the woods and make some more content for you. As always, hope this gives you something to think about throughout the week ahead. Thanks for tuning in to your money guide on the side. If you enjoyed today's episode, be sure to visit my website at tylergardener.com for even more helpful resources and insights. And if you're interested in receiving some quick and actionable guidance each week, don't forget to sign up for my weekly newsletter where each Sunday I share three actionable financial ideas to help you take control of your money and investments. You can find a sign up link on my website, tylergardener.com or on any of my socials at social cap official. Until next time, I'm tylergardener, your money guide on the side and I truly hope this episode got you one step closer to where you need to be.