Wall Street feeds the fantasy that we can beat the market, because the fantasy is a great moneymaker—for Wall Street.
From HumbleDollar Founder Jonathan Clements
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.
After accounting for the reduction in Medicare related spending, she has similar spending power. But she had to go back to work to achieve that. This, and the previous examples, reinforce the importance of understanding a couple’s financial details before and after the passing of a spouse. Income will likely be reduced, but expenses may also be reduced. Lower income retirees who depend primarily on both partners SS benefits may see the biggest impact. I also ran a comparison of our tax return for 2026, for both MFJ and if my wife filed single. I assumed our income consisted of my pension, my wife’s SS benefit, and my SS benefit had I claimed it on January 1, 2026. When I die my wife will receive 75% of my pension, and my higher SS benefit. The results were not surprising.
Richard Connor is a semi-retired aerospace engineer with a keen interest in finance. He enjoys a wide variety of other interests, including chasing grandkids, space, sports, travel, winemaking and reading. Follow Rick on Twitter @RConnor609 and check out his earlier articles.NO. 3: WE SHOULD focus relentlessly on what we want from our financial life. That’ll motivate us to save, drive our investment strategy—and help ensure we pursue the goals we care about most.
NO. 116: AVOIDING probate is a big cost savings in some states—but not others. A local attorney can tell you how things stand in your state. If probate is costly, you might place assets in a revocable living trust. That can also be a smart move if you own a house in another state—and face the prospect of your estate passing through probate in two states.
ILLUSION OF CONTROL. If we shake the dice vigorously, we feel we’re more likely to get the roll we want. Similarly, if we follow the stock market closely and trade often, we feel more control over our returns. But in truth, this can hurt results, as we act impulsively and rack up costs. A better strategy: Focus on things we can control, like risk, taxes and expenses.
SEARCH FOR UNCLAIMED property. Every state has a program for returning lost and forgotten assets to their rightful owners. Those assets include stocks, uncashed dividends, bank accounts, traveler’s checks, the contents of safe deposit boxes and utility company security deposits. You can find further details and links to state websites at Unclaimed.org.
NO. 3: WE SHOULD focus relentlessly on what we want from our financial life. That’ll motivate us to save, drive our investment strategy—and help ensure we pursue the goals we care about most.
New Year’s Eve is the ultimate reminder that the clock never stops. As we prepare to flip the calendar, it’s natural to look back at the year, and the decades, gone by. We often focus on what we want to change in the future, but rarely do we consider which part of the journey we’d actually like to keep.
Youth has many advantages—health, strength, vigor, and vitality. Everything feels possible, and you’re certain you know what’s right and wrong in the world.
WHEN MY YOUNGER brother Jonathan died, I thought I knew who he was.
After all, we had shared a childhood in England, years together at boarding school, family adventures in Bangladesh, and more than six decades as brothers. I knew the journalist the world admired, the devoted husband and father, and the man whose words quietly helped millions of readers live richer lives, not simply financially, but personally as well.
I was wrong.
Over the past several months,
My hat’s off to the couples that got hitched right out of school and stayed that way, happily. That was not my reality. Young love, often ignited by intense physical attraction, often doesn’t ask the hard questions, or require clear answers even if the right questions are asked. And while achieving the age of 73 doesn’t make me an expert, I think everyone is entitled to my opinion, so here goes😉.
That intense physical energy is going to change over time,
RECENTLY, A FELLOW—let’s call him Tom—contacted me with a distressing story of financial fraud. I’ll describe what happened then review steps you might take to prevent this same sort of thing.
Tom first noticed there might be a problem when he spotted a larger-than-average withdrawal from his checking account. The payee was a 529 college savings plan. But because Tom and his wife—let’s call her Jane—have 529 accounts for their children, the transaction almost went unnoticed.
WHEN A HUSBAND dies, his widow inherits his IRA. Somewhere in the paperwork of the months that follow there is a decision to make, and nobody presents it to her as one. She can take the account as her own, or she can leave it titled as inherited.
Taking it as her own means filling something in. Leaving it means doing nothing, and the IRS tells custodians they may assume that is what she wants.
MY RETIREMENT HAS been wonderful so far. Honestly, sometimes I have to stop and remind myself how lucky I am. Rachel and I have our health and enjoy each other’s company, which is not always true when a couple retires. However, there are four things that concern me as I reach my mid-70s.
Loneliness
I tried calling Mark, my old high school friend, a couple of weeks ago, and I haven’t heard from him.
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- Her total income would be 68% of our combined pre-death income.
- Her annual tax bill would be $1,250 more than our joint tax bill.
- Her effective tax rate would increase by 4.2%.
- 85% of her SS benefits would be taxable
- Her spendable income after taxes would be about 65% of the joint amount.
- She would lose about 20% of the new Senior Deduction
- She would have no NJ State Tax liability
I then ran an additional scenario with the same assumptions, but also assuming we were 4 years older and would both have to take initial RMDs in 2026. This scenario reflects one of the concerns frequently expressed when discussing this topic – what happens when the surviving spouse is responsible for reporting the income from both RMDs on her Single tax return. The results changed to reflect the scenario.- Her total income would be about 79% of our combined pre-death income.
- Her annual tax would be $708 more than the joint tax filing.
- Her effective tax rate would increase by 3.8%.
- Her spendable income after taxes would be about 80% of the joint amount.
- She would lose all of the new Senior Deduction.
- Her NJ State Income tax would be $540 more than the joint tax filing.
- She would be pushed up one IRMAA bracket in 2028.
These results are a simplified look at our finances today. My pension and my wife’s SS benefit cover our non-discretionary, and a decent portion of our discretionary, expenses. The wild card is travel – how much we spend in any year is our choice and may require additional income. I’m about 11 months from claiming my SS benefit, at which point virtually all of our expenses will be covered in a fairly tax-efficient way. RMDs are still 4 years away. This was a good exercise to get a feel of how my demise would impact my wife’s finances. It would have some financial impacts, but I believe our plan can handle them. I’m considering running some more detailed projections varying the age at death to assess the impacts, but a quick look made me reasonably confident our retirement savings will be adequate, even considering long term care. I will also continue to look at Roth conversions each year.In Retirement
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