When we make financial choices, we usually have a pretty good idea what we’re getting. But what are we giving up?
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. 44: WE SHOULD view our debts as negative bonds. Instead of earning interest, we’re paying it. Tempted to buy bonds? First, we should see if we can earn more by paying down debt.
NO. 99: A REAL ESTATE agent’s greatest financial incentive isn’t to get us the best price, but to get us to act quickly. If we spend an extra month hunting for the right house to buy—or holding out for a higher price if we're looking to sell—the real estate agent might make little or no additional commission, but he or she will have to put in substantially more work.
TAKE REQUIRED minimum distributions. If you’re age 73 or older, the government insists you pull a minimum sum each year from your retirement accounts, except Roths. The deadline is Dec. 31, unless it’s your first year taking RMDs. Failure to comply can result in a tax penalty equal to 25% of the sum that should have been withdrawn but wasn't.
LAPSE PRICING. Some buyers of long-term-care (LTC) and cash-value life insurance drop their coverage, which means they paid premiums but got little or nothing in return. Aware of this, insurers often charge lower premiums to all policyholders. But this backfired with LTC insurance: The lapse rate proved lower than expected—hurting insurers’ profitability.
NO. 44: WE SHOULD view our debts as negative bonds. Instead of earning interest, we’re paying it. Tempted to buy bonds? First, we should see if we can earn more by paying down debt.
The new U.S. tax legislation extends today’s relatively low tax-rates that were implemented in 2017. While this tax legislation includes some new nuances that may impact retirees, the main tax-rate impact for Roth conversions has been extended for 2026 and beyond. Here are four reminders of the benefits and challenges with Roth conversions. “Roth on.”
Who should Roth:
https://humbledollar.com/2020/05/to-roth-or-not/
How Roth conversions can impact Medicare premiums:
https://humbledollar.com/2023/04/that-28000000-tax/
Rothing can lower future taxes especially when considering the widow’s tax after the first spouse passes and estate tax impacts:
https://humbledollar.com/2023/01/securing-lower-taxes/
Rothing may not gain ground on future RMD tax obligations due to growth in tax deferred accounts:
https://www.theretirementmanifesto.com/my-biggest-surprise-in-retirement/
WHEN JANET YELLEN was nominated to be secretary of the treasury, the Senate Finance Committee staff went over her tax returns with a magnifying glass. Yellen, an economics PhD who taught at Harvard, always prepared the returns for herself and her husband, economics Nobel laureate George A. Akerlof.
“She discovered to her surprise that she had been doing the family taxes wrong for years,” reports Owen Ullmann in his excellent new biography of Yellen,
IT’S PROPERTY TAX time. Amid the holiday mail from friends, many of us get notices of payments due from our friendly local tax assessor.
No one likes getting taxed. But in many places, property taxes make up a huge part of the funding for public education. What always surprises and irks me are those who say the tax is unfair because they don’t “use” the public schools.
One neighbor says he has no children.
The Joint Committee on Taxation today posted their analysis of proposed changes to the current tax code. The 400+ page document is long but certainly easier to read than the tax bill that posted yesterday 5/12/2025.
Nothing final here but I think it will give a flavor to what may be coming in 2026.
https://www.jct.gov/publications/2025/jcx-21-25/
I JUST COMPLETED my fourth year preparing tax returns as part of the federal government’s Volunteer Income Tax Assistance (VITA) program. I’ve seen first-hand how confusing our tax code can be for many taxpayers. Here are the 10 areas of confusion I’ve encountered most often:
1. Income. Anyone looking through a tax return will see multiple definitions of income. There’s total income, adjusted gross income (AGI), modified adjusted gross income, provisional income and taxable income.
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