As you pile up the monthly fixed living costs—think mortgage or rent, car payments, utilities, cable TV—you pile on the financial stress.
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. 27: RISK and potential return are inextricably linked. If an investment holds out the prospect of high returns, we should presume it’s highly risky—even if we can’t figure out what the risk is.
SEQUENCE OF RETURNS. Our investment success hinges not only on long-run market returns, but also on when good and bad performance occur. Ideally, we get lousy results when we’re saving, so we buy stocks and bonds at bargain prices. But as we approach retirement age, we should hope for a huge stock market rally, so we can cash out at lofty valuations.
CAP ALTERNATIVE investments. How much do you have in various alternative investments—everything from gold to commodities to hedge funds? As a rule, keep your allocation to 10% or less of your total portfolio’s value, and favor simpler, less expensive options, such as mutual funds that focus on gold-mining stocks and real estate investment trusts.
NO. 40: NOTHING generates spectacular returns forever. Investment trends can last far longer than expected and, after a few years, further gains can seem inevitable. But that sense of inevitability encourages investors to pay prices far above what the fundamentals justify—and those fundamentals eventually drag the highfliers back to earth.
NO. 27: RISK and potential return are inextricably linked. If an investment holds out the prospect of high returns, we should presume it’s highly risky—even if we can’t figure out what the risk is.
Have you ever known someone who has succeeded in something quite remarkable? This could be starting a highly successful business, writing a blockbuster selling book or similar achievement. Did you ever wonder how they pulled it off? They may not appear to have as much talent as you, be as smart as you, or be as attractive as you.
If you have abilities that come at least as close to those of the average person, you are undoubtedly right about the accomplished person not having more talent,
COULD HUMBLEDOLLAR be replaced by a website chock-full of articles created using artificial intelligence? The short answer: It would be remarkably easy—and I fear readers wouldn’t object, especially if they didn’t know how the articles were generated.
To show what’s possible, I requested eight personal-finance articles from three freely available artificial intelligence (AI) tools, ChatGPT, Google’s Gemini and Microsoft’s Copilot. The first of those articles is published today, with the other seven appearing over the next four days.
I RECENTLY LEFT MY fulltime position at an energy trading company. I had a good run and enjoyed the job. It was mainly the people, both my coworkers and our clients.
I also liked the business travel. It broke up the daily routine and put faces to names, plus there were the awesome ribeye steak dinners with clients. Speaking at conferences was fun, too.
But things evolve. To quote Rocky, “If I can change and you can change,
NINE MONTHS AGO, Jonathan Clements shared with readers that he’d been diagnosed with an incurable form of cancer. It was devastating news, especially for longtime readers, many of whom regard Jonathan not only as a journalist but also a friend. I count myself among them, so I was grateful that Jonathan agreed to sit for an interview to share more about his background, his early years and his current thinking.
You’ve joked that,
OUR HIGH SCHOOL principal returned from a teacher recruitment fair and announced to the school board, “Tell your children or grandchildren: Do not get a degree in elementary education.” He went to the recruitment fair looking to hire some very specific specialty teachers for the high school. He mostly met new grads with credentials to teach elementary school—who were looking for jobs that simply don’t exist in our region.
Our superintendent explained that our region had several large,
I HAD SOME GOOD bosses and some bad ones over my 35-year career. The worst was Joe. He tried to intimidate you. I once overheard him tell another manager that he likes to ride his employees and dig his spurs into them.
What was so terrible about Joe? It wasn’t that he was tough on employees. It was that he was unfair. You incurred his wrath whether you deserved it or not.
I remember the first time I attended a meeting held by Joe.
How did you avoid being in the 39%?
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New to building a CD or Bond Ladder?
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HSA Tips
Bogdan Sheremeta | Feb 28, 2026
- 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. I also receive a $1,000 HSA match. Since I’m young and my medical expenses are low, it’s a great way to minimize taxes and grow the balance. I will also not touch my HSA at all, even if I have medical expenses. I will reimburse myself 20-30 years down the road (more on this in a bit). But if you are paying medical expenses with the HSA, you should have at least a portion of the funds in a Treasury fund or money market fund (MMF) for stability. Generally, this amount should be equal to at least one year of deductible costs. Rules To contribute to an HSA, three things must happen:- You need a high deductible health plan (HDHP). You cannot contribute to an HSA without one. A “high deductible health plan” is defined under §223(c)(2)(A) as a health plan with an annual deductible of more than $1,700 for self-only coverage or $3,400 for family coverage. The maximum out-of-pocket limit is $8,500 or $17,000 (family).
Importantly, before enrolling in a high deductible plan, you need to decide whether it’s worth it in the first place. You will generally receive the biggest benefit from an HDHP if you are in good health (more on this in a bit). 2. You aren’t enrolled in Medicare. 3. You cannot be claimed as a dependent. Importantly, the HSA balance never expires. This account is always yours to keep, even if you leave your employer. Some people confuse an HSA with an FSA (which does expire, aside from a small potential rollover option). The account typically works like a “bank account,” where you make deposits and can withdraw money via online transfers or checks, or invest it like a brokerage account. Contributions The 2026 contribution limit is $4,400 for an individual plan and $8,750 for a family plan, with an additional $1,000 catch-up contribution if you are 55 or older. The contribution limit includes both your contributions and your employer’s contributions. If your employer allows it, contributing to an HSA via payroll deduction is generally better than contributing directly, as it avoids the 7.65% FICA (Social Security and Medicare) taxes. Direct, after-tax contributions only save on income tax when filing, missing the payroll tax savings. Withdrawals Withdrawals for medical expenses are tax-free. IRS Publication 502 has information about which expenses qualify as medical expenses. In addition, as long as you keep proper records, you can reimburse yourself in a later year. I keep track of all my medical expenses in a spreadsheet (e.g., with columns for EOB documents, receipts, bills, etc). I plan to reimburse myself in the future, assuming the law doesn’t change. In 2025, House Bill 6183 was proposed to change the reimbursement limit to expenses no older than two years, but it didn’t gain any traction. If there is a change in legislation, I plan to reimburse myself for all prior medical expenses before enactment. Once you turn 65, you can withdraw money from your HSA for any reason without penalty. However, you will owe income taxes on any non-medical withdrawals, effectively making this similar to a Traditional 401(k) or IRA. Inheriting an HSA Per Publication 969, if your spouse is the designated beneficiary of your HSA, it will be treated as your spouse’s HSA after your death. If your spouse isn’t the designated beneficiary (e.g. your child is the beneficiary), the account stops being an HSA and the fair market value of the HSA becomes taxable to the beneficiary in the year in which you pass away. This is why tax free HSA dollars should ideally be spent before passing down an inheritance due to tax inefficiency. On the other hand, naming a beneficiary in a low-income tax bracket to receive the deceased person’s HSA can also be beneficial for tax purposes. HSA can be powerful, but make sure the math makes sense. If you spend thousands of dollars on medical bills, having a standard plan could outweigh all the tax savings you can get.Managing Investment Risk
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The $9.95 scam…
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A Rule of Thumb Is Not a Plan
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Critique my investment strategy or lack thereof
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