Want to feel short? Hang out with people who are tall. Want to feel poor? Hang out with folks who are rich.
Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.I WAS RECENTLY asked about strategies that high earners can use to reduce their tax bill.
Most people know the usual options. They contribute to a 401(k), fund a health savings account or make a Roth IRA contribution through the backdoor method. Business owners may have additional opportunities through retirement plans and business structures.
But there's another strategy worth knowing about: the Mega Backdoor Roth (MBDR).
The MBDR allows some workers to put far more money into Roth accounts than the usual contribution limits permit.
Consider somebody who contributes the maximum $24,500 to a 401(k) in 2026 and receives a $5,000 employer match. If the employer's retirement plan allows after-tax contributions, that worker may be able to contribute an additional $42,500 to the retirement plan.
This is because the total 401(k) contribution limit for 2026 is $72,000. That limit includes employee contributions, employer contributions and after-tax contributions. Subtract the $24,500 employee contribution and the $5,000 employer match, and there's room for another $42,500. Workers age 50 and older might be able to contribute even more ($80,000 total 401(k) limit in 2026) because of catch-up provisions.
For savers who have already exhausted other retirement account options, this can be a powerful way to build additional tax-free savings.
Your employer's retirement plan must permit after-tax contributions.
Many plans don't. According to Fidelity, only about 11% of employer-sponsored 401(k) plans offer MBDR conversions.
If you log into your retirement plan and review your contribution options, you may see a category labeled "after-tax." That's the option you need:

Importantly, don't confuse it with a Roth 401(k). They're similar, but different. Small-business owners with a solo 401(k) may also be able to use this strategy if their plan allows.
The MBDR process generally involves two steps:
Depending on your plan, the money may be rolled into either a Roth IRA or a Roth 401(k).
The rules vary from plan to plan. Check your plan documents or summary plan description before enganging in this strategy.
Suppose you've already maxed out your traditional 401(k) contribution and completed a backdoor Roth IRA contribution. You now have additional money to invest.
One option is a taxable brokerage account. Another is the Mega Backdoor Roth.
The Roth strategy offers several potential advantages:
A taxable brokerage account also has advantages:
That flexibility shouldn't be overlooked. Retirement accounts come with restrictions, and those restrictions may matter depending on your goals.
Importantly, some plans allow you to move after-tax contributions to either Roth IRA or Roth 401(k) accounts. A Roth 401(k) may be simpler because some plans offer automatic conversions. A Roth IRA typically offers a wider range of investment choices. It may also provide greater flexibility when it comes to withdrawals.
I generally prefer the Roth IRA option when it's available. Still, either choice can work well.
After-tax contributions are usually invested while they remain in the 401(k).
If the account earns money before the conversion takes place, those earnings are taxable when moved to the Roth account. For that reason, many investors try to complete the conversion quickly. Some plans even allow automatic conversions.
Suppose you contribute $10,000 to the after-tax portion of your 401(k). Before the conversion occurs, the account earns $100.
You then move the balance to a Roth IRA. The entire $10,100 can be transferred, but the $100 of earnings will generally be taxable if you put it all into Roth IRA. There are plans that allow you to split between Roth and Traditional, which could be helpful.
At year-end, you'll receive Form 1099-R reporting the transaction.
Using the example above, your tax return would show a $10,100 distribution, with $100 generally treated as taxable income.
If you work with a tax professional, make sure they understand exactly what happened. The reporting isn't especially complicated, but it should be handled correctly.
The Mega Backdoor Roth isn't available to everybody. But for those whose retirement plans allow it, the strategy offers a chance to put a substantial amount of additional money into a Roth account and enjoy tax-free growth for years to come.
Have you used this strategy to contribute to your retirement accounts? Let us know in the comments!
Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.
NO. 60: WE SHOULDN’T necessarily be investment contrarians, but we should be leery of crowds. When “everybody” is buying, that’s a warning sign—and we should resist joining the stampede.
NO. 72: EXPECTED return and risk change over time. Historically, commodity futures have delivered great returns and been great diversifiers for stocks—but both qualities have waned, as investors rushed to take advantage. The same may be true for the high excess return from owning value stocks, smaller companies and stocks in general.
REBALANCING. For major market segments—emerging markets, high-quality bonds, small-cap stocks and so on—we should have target portfolio percentages. Every so often, we should bring our portfolio back into line with these targets, preferably making any sales in a tax-deferred account. Rebalancing controls risk—but it can also boost returns.
NO. 25: WE LIKE the idea of choice—but we’re often happier when we have less of it. Welcome to the so-called paradox of choice: If we’re presented with too many options, we can become paralyzed and fail to make a decision, plus all the choice leads to added anxiety. Exhibit A: 401(k) plans, where more options often cause employees to make poorer investment decisions.
NO. 60: WE SHOULDN’T necessarily be investment contrarians, but we should be leery of crowds. When “everybody” is buying, that’s a warning sign—and we should resist joining the stampede.
I belong to a club I never wanted to join: women who have outlived their husbands. Like me, millions of baby boomer women, and now Gen Xers too, will face life without their long-term partner.
Thankfully, today’s widows have more choices than our great-grandmothers did. Some of us embrace living solo. Others are surprised to find companionship again, sometimes even love. That next chapter can be sweet, but it’s also financially complex.
I know this firsthand.
FOUR MONTHS AGO, I was told I might have just a year to live. It’s been a whirlwind ever since.
I’ve been inundated with messages from acquaintances and readers, gone to countless medical appointments, my diagnosis has received a surprising amount of media attention, I’ve been hustling to organize my financial affairs, and Elaine and I have taken two trips.
Where do things stand today? Here’s what’s been going on.
Medical update. After three radiation treatments to zap the 10 cancerous lesions on my brain and an intense opening round of infusion sessions,
It would have been my mum’s 91st birthday this week. She passed two years ago this June after the long goodbye from the thousand small cuts of dementia. Although I experienced grief and sadness, it truly was a relief to bid my mum the final farewell after the long marathon of loss over many years. I gave a final kiss to the echo of the woman before me as the heat of life left mum’s body.
Five months ago, I was loath to take any sort of medication. Today, I have a pillbox.
In fact, the way things are going, I fear I’ll soon be declared a superfund site by the Environmental Protection Agency. A seemingly endless stream of chemicals pours into my body, most notably during my every-three-week chemo and immunotherapy sessions. What about the rest of the time? Depending on the day, I might down three or four pills in the morning and one or two in the afternoon.
There is a Boglehead Conference in October. Has anybody attended previous conferences? I’m considering attending and I’d appreciate your hearing about your experience. Did you find it valuable?
Thanks,
Jackie
In 2020, the Silverado fire broke out near our city. At the time, I couldn’t imagine that fire would threaten our home because it would have to burn a large part of our town to get to us. Surely, the firefighters would have it under control before there was mass destruction. Then, the Palisades and Eaton fires this year destroyed thousands of structures fueled by low humidity and strong winds. I now realize we might not have been as safe as I thought we were.
Would You Be Miserable?
Dan Smith | Jun 8, 2026
Reflections on a Quiet Failure
Javier Escobar | Jun 7, 2026
How to Use AI With Your Portfolio
W.D. Housley | Jun 9, 2026
Peter Cancro from age 14 to 69 covered in oil and vinegar
R Quinn | May 31, 2026
Bucket Strategy
ArticleAdam M. Grossman | Jun 6, 2026
Time to share our financial info with children?
R Quinn | Jun 6, 2026
A $1,000 Conversation With My Daughter
Mark Crothers | Jun 7, 2026
The Quiet Failure of Good Advice
Javier Escobar | May 29, 2026
ChatGPT’s Portfolio Advice
Gary Klotz | Jun 6, 2026
Setting the Hook, Reeling In the Fish
Dan Smith | Jun 2, 2026
Terms of the Trade
ArticleJim Wasserman | Jul 10, 2019
Money and Me
ArticleAdam M. Grossman | May 30, 2026
JONATHAN CLEMENTS’S final book was released this week. Titled Money and Me, it traces the arc of Jonathan’s nearly four-decade career as a personal finance columnist.
Money and Me starts with the story of a man named George Cope, who was a nineteenth century tobacco baron. At the time of his death in 1888, Cope was one of Britain’s richest men. But within just two generations, his fortune was gone. Why? Cope’s daughter was the sole heir to her father’s fortune, but she lived what Jonathan described as a Downton Abbey lifestyle, on an estate in the Cotswolds with five homes and eight children. Before long, the fortune was gone.
This story was of interest to Jonathan because George Cope was his great-great-grandfather. He called it the “big family story” and explains that this hard financial lesson was imprinted on everyone in his family from a young age.
In part because of this family story, Jonathan got interested in personal finance, and, among his peers, was early in focusing on the psychology of money. “I like to think I’m rational in the way I spend my dollars, and I suspect most readers do, too. We are, of course, deluding ourselves,” he wrote.
Early in his career, Jonathan covered mutual funds for Forbes, then The Wall Street Journal. Each week, he'd review a different fund and interview the fund’s manager. From that vantage point, he was early in recognizing a reality about Wall Street: that they’re great marketers but not such great investment managers. After reviewing scores of actively-managed funds, Jonathan came to the conclusion that index funds were a better way to go for most investors.
Since the investing question was “solved,” as he put it, by index funds, Jonathan turned his attention to other domains in personal finance. The relationship between money and happiness was of particular interest. Though he acknowledged that each of us has a happiness “set point” that is largely fixed, he pointed out that our happiness level isn’t entirely fixed. There’s plenty we can do to move the needle.
A chapter titled “15 Ways to Happy” includes a number of practical suggestions. Among them: Jonathan always recommended making plans—especially vacation plans—far in advance. Why? “Often, the best part of a purchase or experience is the anticipation,” he explained.And since it doesn’t cost more to book early—indeed, it often costs less—that was his recommendation.
Jonathan leaned heavily on academic research and helped translate its findings for everyday investors. In Money and Me, he explains concepts from psychology including the hedonic treadmill, eudaimonic happiness and many others. Jonathan acknowledged that there’s no magic wand for achieving happiness. On the other hand, he explains why a million-dollar salary isn’t a necessary ingredient for financial contentment.
Jonathan also wrote a lot about spending. On the one hand, owing to his family’s experience, he developed frugal habits early in life, and he was grateful that those habits led to financial independence by age 50. On the other hand, he knew that frugality could be taken too far. In a chapter titled “Don’t Overdo It,” Jonathan offers a menu of ideas to help others who might similarly struggleto loosen the purse strings.
Jonathan had two children and thought a lot about how best to convey money values to them. He knew the risk in helping too much. “Money doesn’t necessarily kill all ambition. But it seems to put a big dent in financial ambition,” he wrote. For that reason, Jonathan mostly emphasized education rather than direct financial assistance.
He describes, however, one important way in which his own parents helped him: They always made it clear that they were there for him as a backstop. Though he might have never needed it, simply knowing this support was in the background gave Jonathan the confidence to always invest heavily in the stock market. He describes maintaining an allocation to stocks that was regularly above 80% or even 90%. That kind of aggressive investing ran contrary to the textbook. But recognizing the benefit it had provided during strong markets over the years, Jonathan offered a similar backstop to his own children, thus allowing them to take risks that they might not have otherwise.
In choosing a heavy allocation to stocks, Jonathan explains some of the other factors that went into his thinking. For starters, he points to the role of financial forecasters. They’re often wrong, but that doesn’t stop them from waking up the next day with something new to say. As a result, during both stock market rallies and routs, prognosticators can be found on TV telling stories that often cause investors to overreact. In the chapter “Not Scared of Bears,” Jonathan walks through the math that should give investors the courage to ignore forecasters, to keep their feet on the ground and to stay fully invested regardless of what bad news happens to be in the headlines.
Jonathan was willing to pile on even more risk in his portfolio when markets declined. He acknowledged that this opened him up to the accusation of being a market timer—“pretty much the nastiest insult you can hurl”—but he explains a subtle difference between his approach and true market timing, then offers a helpful strategy for profiting from downturns.
Jonathan Clements was one of a kind. Like all of his readers, I miss his kindness, wit and good cheer. For decades, he helped readers navigate the potholed road known as Wall Street. With his final work, Jonathan leaves us with a timeless guide to thinking about money in uniquely sensible ways.
Mega Backdoor Roth
ArticleBogdan Sheremeta | Jun 6, 2026
I WAS RECENTLY asked about strategies that high earners can use to reduce their tax bill.
Most people know the usual options. They contribute to a 401(k), fund a health savings account or make a Roth IRA contribution through the backdoor method. Business owners may have additional opportunities through retirement plans and business structures.
But there's another strategy worth knowing about: the Mega Backdoor Roth (MBDR).
The MBDR allows some workers to put far more money into Roth accounts than the usual contribution limits permit.
Consider somebody who contributes the maximum $24,500 to a 401(k) in 2026 and receives a $5,000 employer match. If the employer's retirement plan allows after-tax contributions, that worker may be able to contribute an additional $42,500 to the retirement plan.
This is because the total 401(k) contribution limit for 2026 is $72,000. That limit includes employee contributions, employer contributions and after-tax contributions. Subtract the $24,500 employee contribution and the $5,000 employer match, and there's room for another $42,500. Workers age 50 and older might be able to contribute even more ($80,000 total 401(k) limit in 2026) because of catch-up provisions.
For savers who have already exhausted other retirement account options, this can be a powerful way to build additional tax-free savings.
The catch
Your employer's retirement plan must permit after-tax contributions.
Many plans don't. According to Fidelity, only about 11% of employer-sponsored 401(k) plans offer MBDR conversions.
If you log into your retirement plan and review your contribution options, you may see a category labeled "after-tax." That's the option you need:
Importantly, don't confuse it with a Roth 401(k). They're similar, but different. Small-business owners with a solo 401(k) may also be able to use this strategy if their plan allows.
The MBDR process generally involves two steps:
Depending on your plan, the money may be rolled into either a Roth IRA or a Roth 401(k).
The rules vary from plan to plan. Check your plan documents or summary plan description before enganging in this strategy.
Why use it?
Suppose you've already maxed out your traditional 401(k) contribution and completed a backdoor Roth IRA contribution. You now have additional money to invest.
One option is a taxable brokerage account. Another is the Mega Backdoor Roth.
The Roth strategy offers several potential advantages:
A taxable brokerage account also has advantages:
That flexibility shouldn't be overlooked. Retirement accounts come with restrictions, and those restrictions may matter depending on your goals.
Importantly, some plans allow you to move after-tax contributions to either Roth IRA or Roth 401(k) accounts. A Roth 401(k) may be simpler because some plans offer automatic conversions. A Roth IRA typically offers a wider range of investment choices. It may also provide greater flexibility when it comes to withdrawals.
I generally prefer the Roth IRA option when it's available. Still, either choice can work well.
Mind the earnings
After-tax contributions are usually invested while they remain in the 401(k).
If the account earns money before the conversion takes place, those earnings are taxable when moved to the Roth account. For that reason, many investors try to complete the conversion quickly. Some plans even allow automatic conversions.
Suppose you contribute $10,000 to the after-tax portion of your 401(k). Before the conversion occurs, the account earns $100.
You then move the balance to a Roth IRA. The entire $10,100 can be transferred, but the $100 of earnings will generally be taxable if you put it all into Roth IRA. There are plans that allow you to split between Roth and Traditional, which could be helpful.
At year-end, you'll receive Form 1099-R reporting the transaction.
Using the example above, your tax return would show a $10,100 distribution, with $100 generally treated as taxable income.
If you work with a tax professional, make sure they understand exactly what happened. The reporting isn't especially complicated, but it should be handled correctly.
The Mega Backdoor Roth isn't available to everybody. But for those whose retirement plans allow it, the strategy offers a chance to put a substantial amount of additional money into a Roth account and enjoy tax-free growth for years to come.
Have you used this strategy to contribute to your retirement accounts? Let us know in the comments!