The 6 Money Moves to Make Before You Retire

Because if you do the work in advance, the day itself is anticlimactic. You wake up on that Monday, the portfolio is structured. The cash is sitting there. The beneficiaries are right. Your spouse knows where everything is. Your healthcare is covered. And then, you make a coffee, you walk to the window, and you realize that the calendar in front of you is genuinely, completely fully yours. 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. Quick note before we dive in, July's pre-order incentive for my book Real Wealth is live, and this one is for the investors who are ready to go beyond the basics. Pre-order this month, tell me you did at TylerGardner.com/book, and I'll send you investing 2.0 beyond the foundation. A full hour video presentation on the five things every investor needs to know after they've mastered the fundamentals, yours to keep delivered to your inbox digitally in early August. If you pre-order now, you're locked in for every monthly incentive through December 1st. TylerGardner.com/book, now let's get into it. Back in May, I asked all of you what you wanted me to write about in the weekly newsletter, and over 1200 of you took the survey, with 600 of you writing long, thoughtful, generous notes that I truly enjoyed sifting through for about two weeks. I'm embarrassed at how much better your suggestions were than anything I had planned. But one thing came through louder than anything else. You don't need more accumulation content. You don't need another video about how to invest in your 20s, or how compound interest works, or why the index fund beats the active manager. You've heard that part. You've internalized that part. Most of you, frankly, are done with that part. You've already accumulated, and what you actually want help with is the next chapter. The one so few people seem to be talking about. You want to know how to spend the money you just spent 40 years saving. So, starting today, I'm dedicating the next five episodes of this podcast to exactly that. Five episodes, one topic each week, and we're calling it the Art of Decumulation Series because the technical word for drawing down your savings in retirement is decumulation. And frankly, I think it deserves more airtime than it gets. And yes, it is an art. Now, the word "decumulation" is kind of ugly. The English language has a thousand words for accumulating and almost none for the careful, deliberate spending of what you accumulated. Which is, I suspect, part of the problem we're going to spend the next month trying to solve together. We don't even have a vocabulary for the thing, so we mostly don't think about it. Here's the roadmap for the next few weeks. This week, in part one, we're going to talk about what happens the day you stop working. The logistical setup, the accounts, the rollovers, the cash buffer, the social security decision, the spousal piece nobody talks about, this is your orientation episode. Next week, in part two, we'll go over the withdrawal order. Which accounts to draw from first, second, third, and why the order matters more than almost anything else you'll do in retirement. Week three for part three, we'll cover Roth conversions, RMDs, and Irma Cliffs, the single most technically dense episode in the series, so I would bring a pen to that one. Week four, part four, we'll cover market downturns in the drawdown years. The guardrails will need in place, when to draw from cash, when to draw from equities, and what counts as an actual downturn versus normal market noise. And finally, week five, part five, we'll go a little more philosophical and talk about what happens when we transition from saver to spender. The behavioral and psychological episode, how to actually give yourself permission to enjoy what you spent your life building. That's the series. Five episodes, roughly one month, save this one, and share it with someone who's facing the same set of decisions. And before we get into it, one familiar ask, if you've enjoyed anything about this podcast, if it's proved helpful to you in any way through the art of accumulating or decumulating, please consider leaving a review on Apple or Spotify, as it helps more people find the show, it helps the show grow, and it helps me know that I'm speaking and connecting with more than just by sleeping bloodhounds on the couch, which is, again, just fine with me, because that is and always will be my enough. Episode one, the Wednesday that changes everything. There's a passage in any delirds the writing life that I have thought about constantly over the past few years, and I want to start with it before we touch a single technical thing. Dillard writes, "How we spend our days is, of course, how we spend our lives." That's the sentence, 11 words. People quoted on Instagram all the time without realizing the implication, which is somewhat brutal when you actually sit with it. "How we spend our Wednesday is eventually how we spend our life." The Wednesday is life. The Sunday is life. There is no other life happening somewhere else that the days are interrupting. The days are the thing. I bring this up because retirement, the day you stop working in particular, is the single moment in most adult lives when the truth of delirds sentence becomes inescapable. For 40 years, your days have been structured by someone else. The job arrives at 9, the job leaves at 5, the weekend exists because the week exists, the vacation exists because the work exists, the shape of your time has been imposed from the outside. With the comforting, if kind of tragic side effect, that you have not had to design it yourself. And then one afternoon, you stand up from your desk, you collect the small handful of personal items you've kept there for years, and all of a sudden that structure is gone. The following Monday morning arrives, and there's no job. There's also no weekend because there's no week, the architecture of 40 years dissolves overnight. And what is left is a person who has for the first time since perhaps adolescence, full sovereignty over their hours, and for many of us, no idea what to do with those hours. That's where most retirees start to struggle. Not with the money. The money is by and large fine. The struggle tends to be with time. And the time is the harder problem because the time problem is ultimately a self problem. Who are you when nobody is paying you to be somewhere? Today though, we're not going to solve the self problem. We will, however, spend five episodes circling it. Today, we're going to solve the technical problem. The part that if you do it well makes the self problem easier to face when it arrives. Let's say you're roughly 12 to 24 months from the day you stop working. You can see it from here. You can probably name it. You can probably name the quarter. Maybe the month, you've spent the better part of three decades, maybe four, accumulating a portfolio that, by most objective measures, is the result of an enormous amount of discipline, sacrifice, and patience. You did the saving. You ignored the bad advice. You didn't panic an '08 or 2020 or any of the smaller dips in between. You stayed in your seat. The number on the screen is bigger than you ever thought it would be. And now you have the problem that you never had before. You have no idea what to do on the day. You stop working. You know how to save. You have a system for that. You know how to invest. You have funds picked out. Accounts contributing automatically. But the act of stopping, of standing up from the desk for that last time on that Friday and waking up on that Monday morning with no employer, no paycheck, and a portfolio that is suddenly the only source of income you have, that part nobody trained you for. Your 401k administrator didn't send you a manual. The HR person who processed your paperwork was very pleasant and gave you zero practical advice for this section. Your spouse may or may not know what's in the accounts. The cat, quite frankly, has more of a plan than you do because the cat plans to nap and the cat has been training for this moment its entire life. That's what we're solving today. The orientation episode. What needs to actually happen in the 12 months leading up to the day you stop working and in the months immediately after. Six decisions roughly in this order might want to grab a pen because yes, this one is technical. This episode is brought to you by DeleteMate. Here's a strange fact about my life. There are currently hundreds of people on the internet pretending to be mate. Right now, fake accounts with my face, my name, messaging my followers with investment opportunities. I've made my living by being publicly findable on every platform, and the trade-off is that scammers study people like me for a living. But here's what most people don't realize. They study you too. Data brokers legally collect and sell your name, address, phone number, even your relatives' names, to anyone with a credit card, and that's just the raw material they need for fishing, scamming, and impersonation. The less of your real data floating around, the less convincing a scammer can be. That's why I use and trust to delete me. It's a hands-free subscription service that removes your personal information from hundreds of data broker sites, then keeps monitoring and re-removing it because this stuff repopulates like a whack-a-mole with a business model. My privacy report showed me exactly what was found, where, and what got removed. Real humans handle cost-a-mer quests, and Wirecutter named it the #1 Data Removal Service. My face has to stay online. My telephone number and address do not. Get 20% off, delete me consumer plans when you go to joindelete me.com/tiler20 and use promo code "tiler20 at checkout." That's the #2, the #0. This is joinedeleteme.com/tiler20 using code "tiler20." This episode is brought to you by "Caldera Lab." Time for a quick confession. In high school, my AOL screen name might have been pretty boy-durden. That was my actual nickname, because while other guys were collecting baseball cards and playing real sports, I might have been collecting skincare products and taking my appearance embarrassingly seriously. The problem back then almost nothing was actually made for me. Everything was either borrowed from my mom's shelf or smelled like a department store had a mild panic attack, which brings me to "Caldera Lab." They make high-performance skincare specifically engineered for men, and it's science-backed and clinically tested. The regimen is four simple steps that I love. The clean slate cleanser, the eye serum for when I look like I've been up writing YouTube scripts until 2am, because most likely I have been the base layer moisturizer and the good. Their best-selling serum with over 3.4 million antioxidant units per drop, and it's backed by real clinical testing, not just a share rate of marketing claims. One hundred percent of participants said their skin looked smoother and healthier, and ninety-four percent said it looked younger overall. I use it every night, and I'm lucky at the point where the only sentient being judging me in the background is my bloodhound. Pretty Boy Durdon has been playing the long game since 1998, and consistency will always be quick fixes, both in skincare and in investing. So if you've been meaning to take better care of your skin, this is an easy place to start. Head to calderalab.com/tyler, and use code Tyler for 20 percent off your first order. This is called deralab.com/tyler. Decision 1. Build the cash buffer 12 months out. The single, most important move you can make in the year before you retire. The one that prevents almost every avoidable mistake in the first 18 months of retirement is to build a substantial cash buffer while you are still earning a paycheck. Here's why. The first year of retirement is the most psychologically volatile financial year of your entire life. Bigger than buying your first house, bigger than having your first kid, because for the first time in forty years, money is flowing in only one direction. Out. The instinct, when you watch a balance go down for the first time, knowing it might not ever come back up, is to panic. The instinct is to either go back to work or to stop spending entirely, or worst of all, to sell investments during a downturn just to be safe. All three of those instincts are expensive. There's a concept in psychology that we've been over multiple times, called loss of version, conumin and versky's research, eventually one conumin the Nobel Prize. The finding distilled is that human beings feel the pain of losing $100 roughly twice as intensely as they feel the pressure of gaining $100. We're not wired to be neutral about loss. We're wired to over-correct. This is fine when you're accumulating, because the asymmetric pain of losses pushes you towards saving more, which is helpful in that phase. It is catastrophic when you are decumulating, because the same wiring now pushes you to sell exactly at the moment you should hold. Loss of version in retirement is a big enemy, and the enemy in any plan must be neutralized by infrastructure not just willpower. The cash buffer is that infrastructure. It is the thing that makes the loss of version panic stop having anywhere to land. Here's the math you need to know, and I'll keep it quick. You want in cash equivalence, somewhere between 12 and 24 months of your projected retirement spending in a high-yield savings account or a money market fund the day you retire. If you plan to spend $80,000 a year, and again, this is post-tax, that's $80,000 to $160,000 in cash. You could have it sitting in Marcus, Ally, SoFi, or in money market funds inside your brokerage account like SPAXX or VMFXX. You could be earning 3-4% ish, and this is liquid, boring, and perfect. Now, why 12-24 months and not what we usually talk about with things like emergency funds of 3-6 months? Because in any given calendar year, the market drops at some point. As we know, the average intra-year decline in the S&P 500 is about 14%. In 3 out of 4 of those years, the market still finishes positive, but only if you didn't sell your assets. The cash buffer is the thing that lets you not sell. It funds your life for 1-2 years without you having to touch your equities, which means a bad year in the market doesn't force you to lock in losses, it just becomes weather. Now, how do you build the buffer if you don't have it now? Three sources in this order. First, redirect every dollar of new savings for the last 12 months you're working into cash instead of equities. You're done accumulating. The marginal dollar at this stage is not better invested in the market. It's better deployed as the cash cushion that lets you're already invested dollars stay invested. Second, if you're getting a final year bonus, severance, pay out for unused PTO that's added to the buffer. Do not invest it, bank it. And third, you can sell down a small piece of your taxable brokerage in the year you retire when your income drops. If you're in the 0% long-term capital gains bracket, which, married filing jointly in 2026 means taxable income under 98,800 bucks, you can realize gains in a taxable account at zero federal tax. This is the single most underused move in the whole pre-retirement playbook. Most people don't know it exists. It is one of the best kept secrets of the US tax code, but it is not a secret. It is part of the code. You need to know about it. 12-24 months of cash. Sitting safely. Earning interest. But 4, you stop working. That's the foundation. Everything else sits on top of no matter what you plan to do with the rest of the money. Decision 2. Decide what's happening with your 401k. Now, so many of you have written to me saying Tyler, most of your drawdown plans don't work, because most of our assets are in a pre-tax 401k. Correct, let's get into that. The day you stop working, you have three options for what happens with your employer 401k. Each has trade-offs, and I'll give you the short version of all three, and then tell you what I'd actually do. Option 1. You can just leave the money where it is. Most employer plans allow former employees to keep their 401k at the plan administrator indefinitely. You don't have to move anything. The investments stay where they are, the fund fees stay where they are, the plan administrator continues administering, and you can quietly forget the account exists for 15 years, which is in fact what many people do. The one issue here to me is usually 401k fund fees are more expensive than individual retirement account fees, and if you are not working for an employer, you usually now take on the administrator fees, which can be 0.5 to 1% on top of the fund fees. So you can probably see what I think about this option, but many people do it. Option 2. Roll it into an IRA. You move the entire balance, tax-free, if it's a direct rollover, that's the key word, direct rollover. To an IRA, you can do this through fidelity, Vanguard Schwab. Now it's no longer governed by your old employer's plan rules. You have complete control over the investments, complete control over the withdrawals, and access to roughly 12,000 more funds than the typical 401k menu. offers. And if you like your current funds, you can usually transfer in kind, that's the key word in kind to your new IRA and keep the funds in less. They were proprietary funds from the 401k. Option three, roll it into your new employers 401k, and that's only relevant if you're going to a new W2 job. Not the scenario for most of you listening to this, but if it is your scenario, congratulations on the next act, please skip this section and meet us at decision three. What I would actually do, roll it into a traditional IRA at the same custodian where I plan to live for the rest of my financial life. Here are the reasons. First, the investment options. Most employer 401ks give you 15 to 30 funds to choose from, and a meaningful number of them have expense ratios fees above 0.5%. Moving to an IRA at Fidelity or Vanguard, you have access to some of their funds with zero expense ratio, literally zero. At Vanguard, you have access to a total market fund like VTSAX with a 0.04% expense ratio. The fee difference compounded over a 30-year retirement is absurd. Next, you get consolidation. If you've accumulated 401ks at three previous employers, you now have three separate accounts, three separate websites, three separate beneficiary forms, three separate statements, rolling them all into one IRA eliminates the cognitive overhead and dramatically reduces the chances that something is lost. This matters way more than people think. The number of orphan 401ks in this country, accounts whose owners have simply forgotten they exist. Ready for this is in the trillions. Trillions with a T do not contribute another account to that pile. Next, required minimum distributions. When RMDs kick in at age 73 or 75 depending on how old you are now, they're calculated separately for each retirement account. One IRA for you equals one calculation, three IRAs, three calculations. Trust me when I'd say you'd rather have one. Finally, beneficiary control, IRA beneficiary forms tend to be cleaner and easier to update than 4ok ones. We'll come back to this. Now, the one major exception to always roll it into an IRA is the rule of 55 and you need to know about this exception. If you're leaving your job in the year you turn 55 or later, your existing 401k, the one that the employer you're leaving from, gives you penalty free access to those funds before age 59 and a half. But if you roll that 401k into an IRA on day one, you lose the rule of 55 access forever. So if you're 55 to 59 and a half, when you retire and you might need to tap that money before 59 and a half, do not roll it. Leave it at the plan administrator, keep the optionality because optionality in finance is almost always worth the small price of an administrative inconvenience. For everyone else, although this is not advice, it's as close as I get to giving you a one size fits all, I would roll it to an IRA at Fidelity Vanguard or Schwab. Same day, ideally, don't let it sit and get forgotten and don't let your assets get eaten alive by fees you no longer need to pay. Now, how do you actually do this? Always call the receiving custodian, Fidelity Vanguard Schwab and you tell them you want to initiate a direct rollover from your previous employers 401k. They handle the paperwork, they contact the old plan administrator, the money moves directly between the institutions, you never touch it, which is critical. Because if you accidentally take a distribution, the IRS will treat it as a taxable event, your old employer will withhold 20% for taxes and you will have 60 days to read deposit that money in a new IRA or 401k or you're going to face additional penalties as well. Long sentence short, do a direct rollover and never touch the dang money. This episode is brought to you by FASIT. If you know who Frank the Tank is and your idea of a nice little Saturday involves Home Depot, some wallpaper, maybe flooring, this one is for you. There are three things your percentage-based financial advisor is hoping you never think about and I know this because I've been a percentage-based financial advisor. Number one, it is not twice as hard to manage $2 million as it is to manage $1 million. Same asset allocation, same phone calls, asking how the kids are doing exactly twice the fee. Someone please make that make sense. Number two, that line they fed you, the "we do better when you do better" sounds great until you realize the fastest way for them to do better is to put you in risk your assets than you wanted or needed. Your risk tolerance and their incentive structure have never been properly introduced. And number three, notice how they never tell you the fee and dollars only the percentage. Same reason casinos take your cash and give you chips. Once it's not in dollars, it doesn't feel like dollars. Ask your advisor what 1% cost you annually and actual dollars, see how they respond. I'll wait. FASIT works differently. One flat annual membership fee, no percentage, no commissions, no casinos chips, just a dedicated team of CFP professionals who help you figure out what you want your money to say about your life. Book your intro call at facet.com/tiler and you'll still have time for a quick visit to bed, bath, and beyond. FASIT is an SEC registered investment advisor, this is not advice. All opinions are my own and not a guarantee of a similar outcome. I'm not a member of FASIT. I have an incentive to endorse FASIT as I have an ongoing fee-based contract for cash compensation as well as a percentage of equity and facet based on this endorsement. This week's episode is brought to you by GELT. Most of you listening probably already work with someone for taxes, but if you're a solo pranor, a real estate investor, or a high net worth individual who CPA has somehow gone completely radio silence in April, this is for you. A great CPA gets in touch with you. They call in July. They ask if you've thought about something. They don't wait until March to react to a bill that was already written. The moves that actually reduce your tax burden don't happen in March. They happen now. PTE elections, S corp timing, K1 cleanup, prior year retirement contributions, real tax strategy takes months to implement and summer is exactly when the smart decisions get made. By January, the year is already over. GELT is built around exceptional tax professionals focused on your strategies and your relationship, powered by cutting edge technology that handles the rest. This is for those who demand talent and welcome innovation and know the difference between ordinary and extraordinary everywhere. GELT is taking on new clients this quarter, including an extension rescue program for anyone who filed an extension and needs a deadline safe handoff. Done right, your tax strategy could pay for a genuinely excellent summer vacation. Done wrong, the IRS is going to get that trip instead. Visit joingelt.com/tyler to get started. That's j-o-i-n-g-e-l-t.com/tyler. Decision 3. The Social Security Question or how to bet on your own longevity without being a little weird about it. I'm going to handle this one quickly because we've already gone over this in a full episode, but here's the framework that will get you 90% of the way to the right decision for you. You can claim Social Security as early as age 62 or as late as age 70. The benefit grows by roughly 8% per year of delay between full retirement age for most of you listening that 67 and 70. So the spread between claiming at 62 and claiming at 70 is enormous. Roughly 250 to 300,000 in lifetime benefits, depending on your earnings history and depending on, you know, your lifetime. Most personal finance advice tells you to delay until 70. And most personal finance advice is, in my opinion, a little wrong about this or at least over confident about it. Because the actual math that I always look at is the break-even age for delaying. The age at which you've collected enough larger checks to make up for the earlier smaller checks that you for went. It's generally around age 79 to 81 depending on the specific delay scenario. So if you live to 90, yeah, delaying is the clear winner. But if you die at 76, claiming at 62 would have been the better move. Additionally, as I've mentioned in a little bit of my short form, a dollar at 62, to me, far outweighs a dollar at 80. I'm sorry. I will want to do more with my dollars at 62 when I believe I will be more physically and mentally able to enjoy that dollar than I will at 80. So I'm not even saying I won't live to 80. I'm just saying I think I will enjoy my dollars even if fewer. at 62, but that's just me. So, what does this mean for you? It means that you're trying to solve a longevity problem and longevity, unfortunately, is unknowable. You're being asked at 62 to place a wager on a number, your own lifespan, that you cannot possibly know, and the wager pays off only in scenarios you would rather not have to evaluate during dinner. So here's the strange philosophical truth of this decision. The conventional advice, delay until 70, is in essence, an instruction to bet on your own long life, to bet that you'll be there to collect. The early claim choice, take it 62, is the opposite. It's a bet on the present, a bet that the years between 62 and 79 are worth more in lived experience than the larger checks that might or might not arrive starting at 79. The key here is that both bets are reasonable. They are also structurally two different theories of what a life is. The delay strategy treats your future self as the protagonist. The early claim strategy treats your present self as the protagonist. Neither is wrong, but pretending the choice is purely mathematical. When in fact, you are choosing which version of yourself you want to favor, is, I think, a small dishonesty that financial industry has gotten away with for too long. My personal framework, which is one framework among many, claim earlier than the advisors tell you to, take it at 62 if you're retired and don't need the income to live on and let your portfolio compound longer untouched. Take it at full retirement age, if you want the middle path, delay to 70, only if you have a strong family history of longevity, you're in excellent health, and you have other sources of income to bridge those years, or if you have a spouse. Two final caveats, obviously look at spousal benefits. That makes a big difference if you have a younger spouse and you're the higher earner. And I'm not gonna go deeply into it right now because you can just Google it, look at the earnings test. Because if you're 62 to 67 and you're still working, you're capped on your earnings before they start docking some of the money, in which case it's kind of a moot point to take early. Run the math for your specific situation at ssa.gov. They have a calculator that uses your actual earnings history. Don't take my framework or anyone else's at face value. But know this, the decision is far less obvious than the conventional advice makes it sound. Decision four, healthcare from the day you retire to age 65. This is the decision people most consistently underestimate and is the one that has wrecked more early retirements than any single market downturn in modern history. Medicare doesn't start until age 65. So if you're retiring at 62, you have three years to cover. If you're retiring at 60, you have five years. If you're retiring at 55, you get the point. That decade badly handled can cost you a quarter of a million dollars. Well handled, it costs you almost nothing. Same decade, different outcomes by a factor of 50. And I'm not exaggerating, this is the actual range. Here are the default options. You could start by looking at Cobra, which continues your employer's health insurance for up to 18 months. The catch, you pay the full cost, which the employer was previously subsidizing. A family plan on Cobra typically runs two to $3,000 a month for a year and a half. Then it ends at which point you discover your 60 and a half and the open marketplace is waiting for you with both hands extended. So you could go with the ACA marketplace. Healthcare.gov sells individual plans to anyone. Unsubsidized premiums for a couple in their 50s or 60s can run 1,500 to $2,500 a month. I know it's eye watering. But here's the move most people miss. ACA subsidies are based on your modified, adjusted gross income, not your assets, not your net worth, your income, and in the first years of retirement, when you're not earning a paycheck and you can choose how much to draw from which accounts you have an enormous amount of control over what your taxable income looks like. Think about that again, because it is one of the most important and least understood facts in early retirement planning. Your taxable income after you stop working is largely a choice. You pick it, you build it, account by account, withdrawal by withdrawal, with whatever combination of cash, taxable gains, traditional withdrawals, and Roth withdrawals adds up to the income you want to show on your tax return. The IRS sees the final number. The IRS does not see your $3 million in assets. The IRS just sees the line on the $10.40. So if you can keep your modified, adjusted gross income under about $80,000 for a couple in 2026, your ACA premiums drop to $300,000 to $500 a month total. Some couples pay essentially nothing. That's a difference of about $20,000 a year in premium costs available to you if and only if you manage your income deliberately in those bridge years. So how do you keep that gross income low while still funding your life? You draw heavily from cash, taxable brokerage with low realized gains, and Roth contributions, which don't count towards the modified adjusted gross income. You delay tapping traditional 401K and IRA money, which would count as ordinary income until Medicare kicks in. You realize long-term capital gains strategically in the 0% bracket where possible. This is one of the highest value, lowest effort moves in early retirement planning. And almost nobody does it because nobody connects ACA subsidy to withdrawal sequence. They are, in fact, the same decision viewed from two different angles. Once you see it that way, hopefully you can't unsee it. Welcome to one of the great hacks of the American Tax Code. Decision 5. The spousal and beneficiary audit. Or the conversation nobody wants to have that will save someone from 18 months of part of my language, financial hell. This is the decision that based on your survey responses gets mentioned the least and matters the most. Multiple newsletter readers wrote to me almost identically, how do I structure things so that if I die, my less engaged spouse can actually manage the money? That question is the entire reason this part of the episode exists. I want to be plain, the version of this scenario that hunts me, and that I've watched play out in real life more times than I can count goes like this. A perfectly healthy retiree dies unexpectedly at 68, heart attack on a Monday morning. A wonderful person, beloved by family. Also, the only person in the household who knew where any of the accounts were. The spouse in the middle of the worst week of their life is now also trying to figure out the password to a fidelity account at the same time that a funeral home is asking about caskets, and the church is asking about hymns, and the kids are flying in from three time zones. It is genuinely one of the worst experiences a human being can have, and it is almost entirely preventable. The Stoics had a concept called Memento Mori. Remember always that you will die. I know it sounds morbid in a podcast, but it is, in fact, the most loving thing a financial planner can ask you to consider. You will die. Your spouse will die. One of you will die first. The probability that you live the same lifespan for the same year is essentially zero. So plan for the asymmetry now, while both of you are alive and clear-headed and have the luxury of treating the conversation as theoretical. I want you to have the conversation in two parts. Part one, you're going to do a beneficiary audit. Every retirement account, every life insurance policy, every annuity has a beneficiary designation. That designation supersedes your will. The Supreme Court has affirmed this multiple times. If your 401k beneficiary is still listed as your ex-spouse from 20 years ago, and statistically, many people's are, because no one ever updates these things. Your current spouse gets nothing. Regardless of what your will says, there's a published estate case for almost every variation of this disaster. People have lost houses, college funds, and the better part of their financial lives to a single, unupdated form from 1998. And the audit is simple. Every IRA, every 401k, from every employer you've ever worked at, every life insurance policy, every annuity, log in, find the beneficiary page, confirm your current spouse is primary, add your children, adults or otherwise as contingent, do this before you retire. while you can still focus on it. Part 2 - The Spousal Financial Literacy Session This one's harder because it could get slightly emotional. If one spouse has handled the money for the entire marriage, and in roughly 80% of households one spouse has, the other spouse may have almost no idea where the accounts are, what they're invested in, or how to access them. To fix before you retire, you and your spouse sit down multiple times, not once, and walk through everything where every account is. The institution, the website, the username, the general investment allocation, why it's allocated that way, who your CPA is, who your estate attorney is, what the password manager looks like. Then create a single document, a Google Doc, an encrypted note, whatever works for you, that contains every account, every login, every institution. Put it somewhere your spouse can find without your help, and update it annually. Joan Didian in the Year of Magical Thinking describes the period after her husband's sudden death as a kind of cognitive emergency, a state in which simple decisions become impossible, and the brain refuses to process information that contradicts the reality the person is desperately trying to preserve. She was a working writer with extraordinary intellectual resources, and she could not handle the smallest logistical tasks for months. Now imagine a spouse who has never handled the financial logistics trying to do that work in the same state of mind. It is not survivable and doable without extreme preparation. So have the conversation, have it multiple times, have it when you don't need to. The version of your spouse who will eventually need it will not be the version sitting next to you tonight. The version you're preparing for has not yet arrived. You're leaving a letter for that version of them in advance while you still can. Decision 6. Write size the portfolio before, not after. The final move in the 12 months before you retire. And again, this is one almost nobody talks about, is to actually reallocate your portfolio to its retirement composition while you are still earning a paycheck. Here's what I mean. For most of your accumulation years, you've probably been heavy in equities, 80, maybe 90, maybe even 100%, and that's correct for many of us in accumulation. Time in the market and the magic of compounding favors high equity exposure when you have a long runway. In retirement, as many of you know, that composition and theory shifts, not dramatically, but it does shift. The bucket framework I've described in past episodes still applies. You want cash for years 1 and 2, balanced for years 2 through 10, full equities for a 10 plus year runway. Now for a typical retiree at 65, with a 30 year horizon that math works out to roughly 70% equities, 30% cash and bonds. Not the conventional 100 minus your age formula, which gets you to 35% equities and is wildly too conservative for most modern life spans. The 100 minus your age rule was invented in an era when retirement was assumed to last 12 years. It now routinely lasts 30. The math just hasn't caught up to the medicine, and most target date funds still default to the older formula, be smarter than your target date fund. But here's a trap. People often do this reallocation after their retire, which means they're forced to sell equities, potentially realizing gains, potentially in a down market, to build the cash and bond positions they should have already had. The right move is to start the reallocation in the 12 to 18 months before your retire, while you're still earning, so that the cash buffer, Dec. 1, and the bond or conservative position, are funded out of new savings rather than out of selling existing equity positions. You don't disturb the principal. You just gradually steer the contribution flow. Think of it as turning a large ship slowly several months before the harbor. From destination, none of the dramatic last minute maneuvering that breaks things in retirement portfolios. By the day you stop working, your portfolio is already structured for the decumulation phase, no selling required, no tax events, no market timing risk, just sitting there, properly aligned, ready to start producing the income that will fund the rest of your life. That's the orientation. Next decisions in roughly this order. One, build the cash buffer 12 to 24 months out, using new savings, bonuses, and zero bracket capital gains. Two, decide what's happening with that 401k. Default to rolling it into an IRA, unless the rule of 55 changes your math. Three, make the social security decision based on your actual longevity expectations, not whatever your advisor told you or on what I plan on doing with my social security decision. Four, plan your healthcare bridge to 65 with deliberate, modified adjust to gross income management to access ACA subsidies. Five, audit your beneficiaries and have that spousal conversation multiple times, not just once. And six, reallocate the portfolio to its retirement composition before you stop working, not after. Your spouse knows where everything is, your healthcare is covered. And then, and this is the part nobody warns you about, you make a coffee, you walk to the window, and you realize that the calendar in front of you is genuinely, completely, fully yours, not in the way of Saturday as yours, not in the way of vacation as yours. Yours, the way an entire ocean belongs to no one in particular. Dillards days are now your days, all of them, all the way down. The question of how you spend them is no longer rhetorical. It's the actual question. It's the only question. And we're going to spend the next four episodes answering the harder version of this. The withdrawal order, the tax strategy, the downturns, and eventually, the permission you will need to spend it. And more importantly, the permission to spend the time, which is the thing the money was always supposed to buy back for you in the first place. This is the Art of Decumulation Series Part 1. If it was useful and given how many of you asked for this, I really hope it was. Please consider sharing it with one person who is 12 to 24 months from making these decisions. That's the highest leverage thing you can do for someone who's about to do something they have never done before. I'll see you next week for Part 2, the withdrawal order. And 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 TylerGardiner.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 the sign up link on my website, TylerGardiner.com, or on any of my socials at SocialCap official. Until next time, I'm TylerGardiner, your money guide on the side. And I truly hope this episode got you one step closer to where you need to be.