Spending may make us feel good right now, but we won’t feel so good when the credit card bill arrives.
The table shows that the Traditional IRA would have been the better choice, producing about $3,500 more in available funds, or about 22% more. This demonstrates that the primary driver in choosing between a Roth and a traditional qualified account is a consideration of the tax rates at the time of contribution and at the time of distribution. There have been a number of changes to the tax code in the last decade that have contributed to the result, but I certainly didn’t predict any of them. If you guess wrong, you pay the price in a higher tax bill. In the example above, the extra $1,750 invested in the traditional account produced an additional $6,143.31 in earnings. The lower tax rate at the distribution of the traditional IRA results in the $3,500 in extra funds. Even though the Roth IRA had tax free earnings growth, the initial larger tax rate overcame that advantage, when compared to the traditional IRA. Because of my pension and my wife’s social security benefit, 85% of her social security benefit is taxable income, so that is not a consideration in our tax calculation. I used Dinkytown’s 1040 Calculator to run a series of estimates of our 2026 tax return to assess if we want to execute a Roth Conversion this year. We are still 4 years from taking RMDs, and I will start my Social Security in a year when I turn 70. My current thinking is a conversion of about $40,000 will keep us in the 12% bracket. There would also be a small NJ state tax impact. My simple analysis reinforces what I’ve been taught. Roth contributions make the most sense when you think your current tax bracket is lower than when you expect to withdrawal the funds. There are secondary considerations, like no tax diversification, no RMDs, and uncertainty about future tax rates. If you intend to pass the funds to heirs, it might make sense to perform Roth conversions today at the 22% tax bracket if you intend to pass these accounts to heirs who may be in their peak earnings years. Not sure? I believe I recall several HumbleDollar contributors write something about splitting the difference?
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.
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. 34: FIGURING out what we ought to do with our money is relatively easy. Getting ourselves to do it is hard. Victory goes not to the smartest, but to the most disciplined.
HIRE OTHERS TO do chores you dislike. For each of us, time—not money—is the ultimate limited resource. Research has found that those who use their money to buy time—by, say, hiring others to clean or do yardwork for them—report greater happiness. Why? These folks feel less time stressed, while also freeing up extra hours for activities they love.
NO. 97: IT’S HARD to say “no” to our adult children if they get into financial trouble—which is why we should try to raise money-savvy kids. But how? Set a good example. Talk regularly about your own finances. Tell your kids about your lean early adult years. Involve them in family financial decisions. Encourage them to save up for larger purchases.
HABIT FORMATION. To improve our behavior—financial and otherwise—we need to turn our desired good behavior into habits. That might require doing the right thing daily for perhaps two months. To get through this transition period, helpful strategies include sharing our resolutions with others, visualizing our goals and automating our savings program.
NO. 34: FIGURING out what we ought to do with our money is relatively easy. Getting ourselves to do it is hard. Victory goes not to the smartest, but to the most disciplined.
There’s a world where I can go
And tell my troubles to
In my room, in my room
The Beach Boys, 1963
Alberta and I just returned from what for me was a restorative and emotionally powerful two-week trip to New York. No, not because she got to see seven movies at the International Film Festival in the Hamptons or four shows in the city. But she took pictures of me standing in front of five of the commercial buildings my family owned some fifty years ago.
I’M WRAPPING UP MY final big investment. Going into it, I knew it would lose money, unleash unwanted disruption and chew up time when it’s never been more precious—and yet I still went ahead.
As readers might recall, last year, Elaine and I remodeled the kitchen in our Philadelphia home. This year, we decided we’d revamp the upstairs bathroom, despite my cancer diagnosis and the forecast that I might live just 12 more months.
During his final months, my husband Jonathan worked tirelessly to complete his last book, Money and Me. The book is now available for pre-order and will be released in May 2026.
What’s so special about this book? This book features Jonathan’s best and most personal HumbleDollar articles. The articles are curated in such a way to teach everyone about personal finance through Jonathan’s own money journey. And sadly, his terminal cancer diagnosis is part of this journey about which he candidly writes.
I don’t believe I’ve ever enjoyed life more than I do now. What is there not to like about my life? I have my health, financial stability, plenty of free time to do the things I want, and I have a companion to share my journey with. I wish this stage of my life was never-ending.
But at age 73, I know my life could be turned upside down tomorrow. Lately, I’ve been thinking about what Rachel and I should do if we can’t take care of ourselves.
IF YOU OWN a home or are planning to buy one, there are a few things you need to know from the tax standpoint that could save you money:
1. Mortgage Interest
If you have a mortgage, you can typically deduct the interest you pay on the loan up to $750,000 ($1,000,000 if taken before December 16, 2017) but only if you itemize your deductions (schedule A)
You can also deduct points you paid if you itemize.
TWELVE PERCENT. THIS is a pivotal number in my financial life.
What does it refer to? Is it the average annual return on my investments? I wish. Is it the percentage of my pre-tax income that I dedicate to retirement savings? No. That number, including pension and 403(b) contributions, is closer to 25%.
Instead, that 12% is the slice of my pre-tax income reserved for housing. When picking a place to live, I’m a cheapskate.
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