The dice have no memory. The coin can’t recall the last toss. And the stock market doesn’t care about your investment history.
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.
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.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.
JEFF WAS A NEW engineer who began his nuclear power career a couple of decades ago as part of my group. He’d graduated from a middling engineering school with a stellar grade point average. Quiet, though not shy, he had a serious demeanor.
Jeff had a goal of purchasing a house as soon as possible. Needless to say, this was a tall order for someone just starting his career. He lived a spartan lifestyle,
When I was working full-time, I always saved the maximum to my 401(k). Before my employers had a 401(k) plan, in the early 1980s, I saved the maximum to an IRA—a princely $2,000. Pretty soon I felt rich. I had $40,000 saved.
For this reason, I always pay attention to changes in plan savings limits. And there are higher savings limits for 401(k) plans in 2025, plus a new “super catch-up” category. For those who are interested,
Just weeks into my retirement, while sitting on a beach beside the Giant’s Causeway on Ireland’s north coast, a profound sense of gratitude washed over me. It was for a person whose name I couldn’t recall and a face I’d forgotten.
Forty years prior, in my very first job, I served a customer who turned out to be a pension salesman. To make a long story short, he persuaded an 18-year-old me to open a personal pension,
WHAT DOES IT MEAN to “live within your means”? To answer the question, we first need to define “means.”
If your gross income is $60,000, that income isn’t your means. For starters, you need to subtract income and payroll taxes. To live within your means, you need to spend no more than your net income—income after taxes and other withholdings.
I’ll go further and suggest that your true means are your income net of monthly savings for retirement and financial emergencies.
Everyone wants more security for their retirement savings, and outside of Social Security, the most reliable way to achieve this is often the much-maligned annuity. The main issue for many people is losing control of a large chunk of their retirement pot—they simply don’t like the idea. But what if you could get some of the security an annuity provides without giving up control of your cash?
No solution is perfect, but this idea might be of interest.
HEALTH SAVINGS ACCOUNT (HSA) is the most efficient tax-advantaged investment account because it offers a triple tax advantage:
Contributions are tax-deductible
Earnings grow tax-free
Withdrawals are tax-free if used for medical expenses
One of the best uses of an HSA is to actually invest the balance.
For example, I keep $500 (the minimum required balance) in cash. The rest, I invest in low-cost index funds. This allows me to maximize compounding inside the HSA account.
Moving is Expensive!
DrLefty | May 29, 2026
Time to share our financial info with children?
R Quinn | Jun 6, 2026
The Quiet Failure of Good Advice
Javier Escobar | May 29, 2026
The Ping
Mark Crothers | Jun 4, 2026
Mourning the World
Jonathan Clements | Jun 5, 2026
SpaceX IPO: Is Margin Optional?
Mark Gardner | Jun 4, 2026
The thief of joy
greg_j_tomamichel | Jun 6, 2026
Money & Me (Kindle version) has dropped
William Perry | May 26, 2026
ChatGPT’s Portfolio Advice
Gary Klotz | Jun 6, 2026
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!
Bucket Strategy
ArticleAdam M. Grossman | Jun 6, 2026
Rethinking the “Right” Time for Social Security
Andrew Clements | Apr 23, 2026