The 6 Money Moves to Make Before You Stop Working

Greetings,

July’s pre-order incentive for my book, Real Wealth, is now live, and this one is for the investors who have already mastered the basics and are ready to go deeper. Pre-order this month, tell me you did at tylergardner.com/book, and I’ll send you Beyond the Basics: Investing and Money Management 2.0, a full one-hour digital video presentation delivered straight to your inbox in early August, yours to keep.

We’ll cover portfolio “tilting,” the details of asset location, sector rotation for those of you who just can’t help yourselves, and how to mitigate sequence of returns risk early in retirement. Pre-order now and you’re also locked in for every monthly incentive through the December 1st release date.

Pre-Order Real Wealth

You Asked for It.

A few weeks ago I asked what you wanted me to write about. Over 3,000 of you took the survey, which I believe makes it the largest group of people ever assembled to politely ask a man to stop talking about index funds. Message received. What you want is the part almost nobody writes about: how to actually spend the money you spent forty years saving.

So for the next five weeks, the newsletter and podcast are devoted to what I’m lovingly calling The Art of Decumulation Series, because the technical term for drawing down your savings is decumulation, a word with all the charm of a parking garage in Cleveland, so I figured adding “The Art” to it was cheaper than rebranding the entire financial industry.

Here’s Part 1.

The 6 Money Moves to Make Before You Stop Working

1. Build the cash buffer twelve to twenty-four months out. Twelve to twenty-four months of projected spending in a high-yield savings account or money market fund (Marcus, Ally, SoFi, SPAXX, VMFXX) the day you retire. Fund it from new savings, your final-year bonus, severance, and zero-bracket capital gains harvesting: for 2026, married couples filing jointly pay 0% on long-term gains up to $98,900 of taxable income, and because that’s measured after the $32,200 standard deduction, a couple can gross over $130,000 and still harvest at zero. The buffer exists because the first downturn is coming. I don’t know when. Neither does anyone on television, though they are, admittedly, better dressed than I am. The buffer is the infrastructure that neutralizes loss aversion when willpower won’t.

2. Roll the 401(k) to an IRA unless you’re taking advantage of the Rule of 55. Move every employer 401(k) you’ve accumulated to a single traditional IRA at Fidelity, Vanguard, or Schwab. You get better funds (FZROX at zero expense ratio, VTSAX at 0.04%), consolidated beneficiaries, one RMD calculation, and dramatically less cognitive overhead, which matters, because you did not save for forty years in order to spend your retirement remembering seven passwords. The one exception: if you’re leaving your job in the year you turn 55 or later and might need that money before 59½, leave it at the plan administrator. Rolling it into an IRA kills your Rule of 55 access forever, and “forever” is a word the IRS uses with unsettling comfort.

3. Make the Social Security decision based on actual longevity, not industry default. The break-even age for delaying from 62 to 70 is roughly 79 to 81, which means the “right” answer requires knowing your own expiration date, a piece of information the actuarial tables have and you, mercifully, don’t. The conventional advice says delay. The conventional advice is overconfident. Claim at 62 if you’re retired and don’t need the income, and let the portfolio compound untouched. Claim at 67 for the middle path. Delay to 70 if you have strong longevity, excellent health, and other income to bridge the gap. Part art, part science, entirely up to you.

4. Plan the healthcare bridge to 65, because the rules just changed on you. Medicare doesn’t start until 65, and as of January 2026, the enhanced ACA subsidies are gone and the old subsidy cliff is back. Here’s what that means: cross roughly 400% of the federal poverty level, mid-$80,000s of MAGI for a couple, by even one dollar, and your entire premium subsidy vanishes. Not shrinks. Vanishes. Under the cliff, an older couple pays around 10% of income for the benchmark plan, roughly $700 a month at an $80,000 income. Over it, the same coverage can run $20,000 or more a year, out of pocket. Because subsidies are based on your modified adjusted gross income, not your assets, this is a game you can actually play (and win): draw from cash, taxable accounts with low gains, and Roth contributions while delaying traditional IRA withdrawals, and keep MAGI safely under the line. One overly-aggressive Roth conversion in the wrong year can now cost you five figures. MAGI management before 65 is no longer an optimization; it’s a cliff walk, and the withdrawal order is the only railing to which you have access. (And conveniently, that’s Part 2.)

5. Audit beneficiaries and have the spousal conversation. Multiple times. Beneficiary designations supersede your will. We’ve been over this before. Every IRA, every 401(k) from every previous employer, every life insurance policy, every annuity: log in, confirm your current spouse is primary, “current” being the key word there, and add your kids as contingent. Then sit down with your spouse and walk through everything: account locations, logins, allocations, advisors, the password manager. Create a single document. Update it annually. The version of your spouse who will eventually need this is not the version sitting next to you tonight. You are leaving a letter, in advance, for that future version of them.

6. Re-allocate the portfolio before you retire, not after. Most people sell equities post-retirement to build the cash and bond positions they should have already had, potentially realizing gains, potentially in a down market. Start twelve to eighteen months before your last day, while you’re still earning, so the buffer and bond position are funded from new savings rather than from selling. For the nautically minded: turn the ship slowly, before the harbor, ideally without a documentary crew. The “100 minus your age” formula is from an era when retirement lasted twelve years. Modern retirements last thirty. You can be smarter than your target-date fund. It’s a fund. The bar is achievable.

Tyler’s Take-Away: If you do this work in the twelve months before you retire, the day itself is anticlimactic (in a good way). You wake up on 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 realize the calendar in front of you is genuinely, completely yours. The way an entire ocean belongs to no one in particular. Just keep swimming, my friends.

Where we’re headed from here:

Part 2: The Withdrawal Order: which accounts to tap first, and why the sequence matters more than almost anything else you’ll do.

Part 3: Roth Conversions, RMDs, and IRMAA (yep, the dense one). Bring a pen and, ideally, a beverage.

Part 4: Market Downturns in Retirement: what counts as danger versus noise.

Part 5: From Saver to Spender: your permission, finally, to enjoy the thing you built.

And if you want to listen to The Art of Decumulation Series - Part 1, check out this week’s episode of Your Money Guide on the Side. If you find the show useful, a review helps more than you’d think, as it’s how new listeners find the show, and how I know I’m not just another random guy walking through the woods of Vermont talking about money to squirrels.

Listen to This Week's Full Episode

Two Things I’m Currently Thinking About

1. Your Lamb House. I’ve been reading Colm Tóibín’s The Master, which is a novel about Henry James, which I realize is a sentence that just cost me half my readership, but I already gave you the practical money take-aways, so this is where I, in turn, get to ramble about literature & life.

One moment that particularly struck me: Henry finds a house. Lamb House, in Rye, and he wants it the way most of us have wanted maybe three things in our entire lives. This is a man who wants almost nothing, and here he is, wanting. Then his older brother William weighs in. Too expensive. Poorly negotiated. Should have haggled. And Tóibín gives us the impact of the older brother’s gut-punch:

Henry pointed out that he had never lacked faith in his brother’s purchases nor sent him advice not sought for. He added that his joy at the prospect of getting the house had shriveled under his brother’s warnings…[I]t was such a rare joy for him to want anything as he wanted Lamb House.

His joy “shriveled.” One comment from one sibling about what Henry should have done with his money, and the rarest feeling of his life got smaller.

Here’s my confession of the week: I make a lot of content about consumer spending and how to find the best deals. Hidden fees, negotiation tactics, daily discounts, and industry red flags. And the most common comment I get, on nearly everything, is some version of Henry’s response: But Tyler, we LOVE going to Disney and buying the Memory Maker Photo Pass -regardless- of price. We are a nation of younger brothers looking for those things that money can buy that bring us pure joy, and the last thing we want is some ding dong older brother telling us that we should have simply taken the photos ourselves on our $1400 iCameras.

So let me be clear about the actual thesis of everything I write and create: the entire point of getting the money stuff right is so you can spend freely, joyfully, and without apology on your version of Lamb House. The Photo Pass. The daily latte. The seventh bloodhound. Whatever it is that you rarely allow yourself to want.

Negotiate hard on everything else precisely so that when the rare want arrives, you don’t have to negotiate with yourself or your older brother or some random guy in the woods of Vermont.

Oh, and when a friend shows you their Lamb House? You say it’s wonderful. Because it is. Full stop.

2. The Beautiful Game, Plural. The World Cup ended this weekend, and I’m already grieving. Not the soccer, exactly. What I’ll miss most is the Tartan Army singing in places that have never heard that much bagpipe-adjacent joy. The Norwegians doing the row. The Dutch turning entire city blocks into one enormous orange dance floor, bouncing left, then right, in a display of coordinated happiness that should honestly be studied by scientists.

But here’s the lazy take-away that I’ve already seen touted on social media: see, people are fine, it’s just the politicians who ruin everything. I get the appeal. It’s a tidy story. It’s also a single story, and single stories are exactly the problem.

Chimamanda Ngozi Adichie gave a TED talk about this called “The Danger of a Single Story.” It’s nineteen minutes long and worth every second of our attention. She says it far better than I do, but her main point is clear: nobody is one thing. No person, no nation. The danger isn’t that single stories are false. It’s that they’re incomplete, and we cling to them because complete is complicated and we are tired.

What the World Cup did for a month is hand us extra stories, slightly less mediated than usual. Strangers hugging strangers in three languages at once. A defender consoling the man whose heart he just broke. You watch enough of that and the single stories you’ve been carrying about entire countries start to wobble, which is the most useful thing a television can do.

Because that’s the actual beauty of the beautiful game. Not that it proves we’d all get along if we just had a ball. We wouldn’t. It’s that for one month, everybody gets to be more than one story. So maybe next World Cup, the broadcasts show the Japanese fans doing literally anything other than cleaning up Section K, Row 4, because even the flattering single stories are still single.

And Before You Go…

This week’s newsletter is brought to you by LMNT.

This summer has been an absolute scorcher, but good news, LMNT just dropped what is essentially their version of an Arnold Palmer—Lemonade Iced Tea—and I currently have a full pitcher of it in my fridge. A little caffeine alongside the salt and electrolytes is exactly what I want after a long walk with the hounds, or in the late afternoon when I’d otherwise be reaching for a second cup of coffee that I don’t actually need.

Now, here’s what makes it different: Most energy drinks use synthetic, isolated caffeine. LMNT uses full-spectrum organic black tea extract from Kericho, Kenya— 7,000 feet of elevation—so the caffeine comes with its naturally occurring L-theanine and polyphenols. The result is steadier energy, less spike, less crash, and only 50mg of caffeine per serving. Enough to matter. Not enough to regret.

I will also say this: my old cycling crew, people I hadn’t heard from in years, have all suddenly resumed contact with me with remarkable enthusiasm. And my sister—an elite marathoner who is extremely particular about what goes in her body—calls more than she used to. The pattern is consistent: every call starts with “hey, great to hear your voice” and ends with “so when can you send me more LMNT?” I have become, without intending to, a distributor, and I cannot decide if that’s a product endorsement or a personal confession.

So if you want to know what we’re all hyped up about, head to drinklmnt.com/tyler, become an LMNT Insider, and get four boxes for the price of three. And even though I am obsessed with the new flavor, this does nothing to diminish my feelings about mango chili and watermelon salt.

As always, hope this gives you something to think about throughout the week ahead.

—Tyler