Exchange-traded index funds offer minimal costs and superb tax efficiency—advantages that investors merrily toss away with wild trading.
In addition, say that the $300,000 portfolio had 75% of it in capital gains and 25% in basis. We can sell an additional $10,500 of VTI per year and will have $7,875 of long-term capital gains, taxed again at a 0% rate. So far, we’ve pulled $36,969 + $10,500 + $3,720 = $54,189 of cash. This would put us right at around a 3.5% safe withdrawal rate.
(Assuming single, no kids) This is ~7% effective tax rate. Because the tax rate is very low, it may make sense to withdraw less from the brokerage account, and increase the 72(t) withdrawal. This can help prevent future RMDs, and can help with step-up in basis for his heirs. Depending on the state, you might also pay no state taxes, either on full income, or partially on capital gains and/or retirement income. What about health insurance? One of the benefits of controlling your portfolio withdrawals is that you can predictably estimate your income. While the enhanced premium tax credit expired as of 2025, because of the lower income you may be able to qualify for subsidies on the state level. Social Security Benefits Before Social Security benefits (SSB) kick in, you can also do Roth conversions to further reduce the size of the 401(k) (and lower your future RMDs) and move more money into a Roth IRA. Withdrawals from a Roth IRA don’t count toward provisional income for the SSB tax calculation, allowing you to minimize your tax liability. In addition, controlling your income will allow you to be below the IRMAA (Income-Related Monthly Adjustment Amount) threshold. This surcharge increases Medicare Part B and Part D premiums for higher incomes but doesn’t apply to income below ~$100,000.
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. 76: WE SHOULD take comfort in knowing we made the best financial decisions possible with the information available at the time, while also realizing that’s no guarantee of success.
SET PRIORITIES for the year ahead. What are your most important financial goals? Your priorities might include saving for retirement, funding college accounts, buying a house, paying down debt and building up your emergency fund. Also think more broadly—pondering whether, say, you need to tweak your estate plan or your insurance coverage.
NO. 36: WE SELL our winners too quickly and hang on to our losers too long. Yet, with a regular taxable account, the smart tax strategy is to do just the opposite. We should avoid realizing capital gains, while harvesting our losses. Why don’t folks do this? Blame it on loss aversion. We’re loath to sell underwater investments and admit we made a mistake.
SELF-ATTRIBUTION. We tend to ascribe our investment successes to our own talents, while blaming our failures on bad luck, bad markets or the advice of others. This makes it harder to learn from our mistakes, while also causing overconfidence. That, in turn, can lead us to trade too much and make big investment bets that hurt our portfolio's results.
NO. 76: WE SHOULD take comfort in knowing we made the best financial decisions possible with the information available at the time, while also realizing that’s no guarantee of success.
WHAT’S THE PURPOSE of life? Is it to die with as much money as possible or, as magazine publisher Malcolm Forbes was quoted as saying, “He who dies with the most toys, wins”? An intriguing and provocative book, Die With Zero, says no.
The book’s author is Bill Perkins, a successful energy trader. In it, he argues that the purpose of life is to accumulate as many fulfilling experiences as possible,
As someone who is independent, I try to do as much around the house as I can. I don’t mean housework or laundry; I mean things like unclogging the toilet and putting up shelves. I try to stay as independent as possible to save money and so that I don’t have to be subjected to someone else’s time schedule.
But most of these require certain skills I’ve never learned. I haven’t used an electric snake, or a toilet auger.
BEFORE HE DIED LAST year at age 99, a friend asked Charlie Munger if he planned to leave his considerable wealth to his children. Wouldn’t it impact their work ethic, his friend asked?
“Of course, it will,” Munger replied. “But you still have to do it.”
“Why?” his friend asked.
“Because if you don’t give them the money, they’ll hate you.”
Few of us are billionaires. Still, I find Munger’s comment instructive. It illustrates a reality about personal finance: that the notion of a perfectly optimal answer to any financial question is just that—a notion.
MY WIFE AND I ARE expecting our first baby in March. In preparation, we’re converting what used to be an office into a nursery. We’ve bought a crib, glider chair, curtains and dresser for the new room. But we also needed to find a place to put the desk and furniture that was in the office. We decided to move the office into what is currently a quasi-sunroom.
When we bought the home, our inspector disclosed that the sunroom was likely built by the homeowner and wasn’t up to code.
MOST OF US HAVE TOO much stuff, and we’re apt to joke about it. But clutter, if allowed to spiral out of control, can turn into hoarding.
Hoarders are people who acquire an excessive number of items, some with little or no value, and yet they continue to add to their chaotic overflow. Unable to manage the clutter but unwilling to let any of it go, they become upset and anxious when others offer to help clear it up.
EVERY DECEMBER, I watch two Christmas movies—movies I’ve been watching for as long as I can remember.
My favorite is A Christmas Carol, based on the novel by Charles Dickens. It’s about the mean and miserable Ebenezer Scrooge, a money lender who constantly bullies his poor clerk, Bob Cratchit, and rejects his nephew Fred’s wishes for a merry Christmas.
Scrooge lives only for money. He has no real friends or family, and cares only about his own well-being.
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- SEPP
First, I would probably roll over the 401(k) balance into 2 separate rollover IRAs (split 60%-40%). This move would allow you to set up the “Substantially Equal Periodic Payments” (also called the 72(t) strategy) and avoid the 10% penalty on withdrawals. This plan would be established only on the 60% IRA. There are three different methods (RMD method, fixed amortization, or annuitization) for calculating the amounts you can withdraw. Using a 72(t) calculator, we can see that a $600,000 72(t) setup can result in a ~$36,969/year distribution, avoiding the 10% early withdrawal penalty.- Brokerage account
With $300,000 in a brokerage account (say invested in $VTI), we are looking at ~$3,720 in dividends (~95% of them will be qualified). Since our taxable income will be below $49,450, most will be taxed at a 0% rate.- Roth IRA Withdrawals
In addition, while not needed in this case, you can also minimize your 72(t) withdrawal amount (by rolling over less into the account to be subject to the rules) by withdrawing your contributions from the Roth IRA. Contributions can always be withdrawn penalty-free at any time (different rules apply to earnings/conversions, though). Taxes From the tax standpoint, he'll pay ~$2,279 of federal tax in 2026:Real vs. Imaginary Returns – Part I
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