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.
SOARING STUDENT DEBT is putting the kibosh on another major financial goal: buying a home. According to a study by researchers at the Federal Reserve Bank of Cleveland, 40% of those age 18 to 30 have student debt, up from 27% in 2005. For these borrowers, the debt burden is staggering, with student loan payments estimated to devour more than 20% of their income in 2015.
With so much of their income devoted to servicing student loans,
SETTING OUT INTO the business world, I was age 27 with a negative net worth. Among life lessons, there are many strong contenders, but nothing introduced me to “adulting” like debt. For that, I had undergraduate and graduate school expenses to thank.
Having secured a good job out of business school, I started to rebuild my finances. My grad loans had a relatively high principal amount and an interest rate of 6.8%, so I prioritized that debt over my undergrad loans,
YOU’VE PROBABLY already asked yourself this question: Is it better for my credit score to have just one credit card—or many?
There’s no magic number, because it isn’t really about how many credit cards you have. Rather, what matters is your financial situation and how you handle your cards. For example, if you are just beginning to build a credit history, it’s best to have a single card. Try to follow three rules:
Pay your bills on time—and avoid late payments at all costs.
I HATE DEBT. A very happy day was when we paid off the mortgage. I’d rather walk on broken glass than pay a penny of interest on my credit cards. But there have been a few exceptions to my usual rule, all involving car purchases.
The first was many years ago when I reached what I thought was an all-cash deal on a new car. The salesman surprised me when he offered the same price with 0% financing.
IF YOU’RE LIKE MANY people, you’ll cringe when I mention reverse mortgages. The perception is that they’re loans of last resort for desperate retirees who don’t have any other options. But I suggest keeping an open mind. I believe reverse mortgages can be a shrewd way to unlock liquidity during retirement.
Reverse mortgages have evolved significantly, and retirees are often pleasantly surprised when they learn how today’s loans work. They find that many of the negatives they’ve heard are no longer true.
New to building a CD or Bond Ladder?
Dan Smith | Feb 27, 2026
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
Adam M. Grossman | Feb 28, 2026
Vanguard’s Transfer on Death Plan Kit
William Perry | Mar 3, 2026
How did you avoid being in the 39%?
R Quinn | Mar 4, 2026
Volatility is your Best Friend
Mark Crothers | Mar 4, 2026
What is the best way to donate to charity in 2026?
Howard Schwartz | Mar 4, 2026
Why I use a Donor-Advised Fund
David S | Feb 21, 2026
Helping Adult Children, pt. 2
gnussen623 | Mar 1, 2026
The $9.95 scam…
R Quinn | Feb 26, 2026
A Rule of Thumb Is Not a Plan
Mark Crothers | Feb 26, 2026
Critique my investment strategy or lack thereof
R Quinn | Feb 25, 2026