The dice have no memory. The coin can’t recall the last toss. And the stock market doesn’t care about your investment history.
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. 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. 55: UPSIDE GAINS are a sign of downside risk. Investors will say they don’t care how quickly an investment rises, only about how fast it might fall. But if an investment’s price skyrockets, there's a risk it’ll plunge just as rapidly. The lesson: Pay attention to measures of volatility such as beta and standard deviation—and be leery of soaring stocks and funds.
BUY THE BIG THREE. The market portfolio consists of four major sectors, roughly equal in size: U.S. stocks, U.S. bonds, foreign shares and foreign bonds. Arguably, foreign bonds are optional, offering modest yields but wild currency swings. The other three sectors, however, are crucial to a diversified portfolio. Do you own enough of all three?
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.
IF YOU’RE A HISTORY buff, you know how difficult life was during the 1930s. In our modern American world of plenty, it can be hard to appreciate what life was like during that period. The Great Depression, as it was later dubbed, was a time of incredible strife and struggle.
Today, we have an unemployment rate of less than 4%. During the 1930s, it reached 25% in the U.S. Think about that. A quarter of the country was looking for work to feed their family,
I’VE RECENTLY BEEN reading and listening to health experts who study the brain chemical known as dopamine. I’m no health expert and I don’t claim any specialized knowledge on the subject, but I’ve learned dopamine is widely considered to be the “pleasure chemical.”
Think about the feeling in between bites of chocolate cake, when we know just how good that next bite is going to be. As we anticipate our reward, our dopamine spikes,
FOR THE PAST FEW years, I’ve been on a Radiohead kick. For the uninitiated, Radiohead is an English rock band whose lead singer is Thom Yorke, known for his distinctive whining vocals—I mean that in a good way—and innovative songwriting.
As I read about Yorke, a quote from him leaped off the page: “When I was a kid, I always assumed that [fame] was going to answer something—fill a gap. And it does the absolute opposite.”
I immediately thought of the financial corollary.
MONEY BUYS HAPPINESS—but it may not buy us very much. Indeed, no matter how much we earn and no matter what other steps we take to boost happiness, we may discover the impact is modest and fleeting.
That brings me to a recent academic debate. In 2010, Princeton University’s Angus Deaton and Daniel Kahneman noted that happiness, on average, didn’t appear to increase beyond an annual income of $75,000 or so—a finding that’s since been widely reported in the mainstream media.
I HAVE READ THAT spending on experiences brings more happiness than spending on things. But what about the experience of buying? Can that make us happy?
I’ve lived in my small community for 21 years. Over that time, my regular buying habits have led me to discover people who provide me with excellent service. They also supply me with a generous measure of genuine satisfaction.
Every third Friday, I sit and listen to a great raconteur as he cuts my hair.
ONE OF MY FAVORITE books is The Paradox of Choice by Barry Schwartz. Its subtitle is Why More Is Less: How the Culture of Abundance Robs Us of Satisfaction. The principles that the book discusses have important implications for how we manage our money.
Schwartz distinguishes between “maximizers” and “satisficers.” A maximizer is someone who needs to be assured that he or she is making the best decision possible.
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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!