Like a whiny child that throws the occasional tantrum, the stock market demands our attention—and wastes our time.
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. 32: WE SHOULD start with the global market portfolio—the investments we collectively own—and decide what we don’t want in our portfolio. Often, foreign bonds are the biggest subtraction.
IMAGINE YOU WERE the executor for your own estate. What would make your job easier? You might consolidate financial accounts, shed illiquid assets like collectibles and investments in private businesses, draw up a letter of last instruction that details all assets and debts, organize key documents, and compile a list of usernames and passwords.
CURRENT VS. FUTURE self. Our daily lives are a constant battle between the whiny demands of our current self and the needs of our future self. We know it would be better for our future self if we exercised, ate healthily and saved diligently—and yet, all too often, we give in to our current self, who wants to sit on the couch, eat junk food and shop online.
NO. 59: WE'RE anxious to minimize risk, but at what price? We might hold an overly conservative portfolio, thereby avoiding short-run losses but sacrificing handsome long-run returns. Our loss aversion might also infect our insurance choices, such as opting for very low deductibles or buying extended warranties on products we could easily afford to replace.
NO. 32: WE SHOULD start with the global market portfolio—the investments we collectively own—and decide what we don’t want in our portfolio. Often, foreign bonds are the biggest subtraction.
WHEN I STARTED winding down my psychology practice two years ago, I anticipated freeing up oodles of time for reflection and for hobbies long cast aside, such as collecting oldies albums and the coveted rookie cards of sports legends. But my patient hours were merely replaced by my own spiraling doctor visits.
I was disappointed and concerned about my declining medical status. Still, I was reassured by the reputation of my health insurance company and the comprehensiveness of my policy.
Love and heartbreak are human experiences. Heartbreak is not restricted to the end of a relationship. It can be unrequited love, the death of a loved one, divorce, unmet expectations we have of another. Or other severe emotional conditions.
Harvard Medical School recently published an article about a phenomenon known as Broken Heart Syndrome. It is a real condition known as Stress Cardiomyopathy or Takotsubo syndrome, and can be deadly. But most people recover quickly without any long lasting effects.
WE HAVE A MEDICAL profession apparently wedded to the notion that quantity trumps quality. That’s why, although I have no problem with being dead, I have serious concerns about the process of becoming dead. I have no wish to linger for months attached to tubes, or to disappear for years into the mists of dementia.
I have few childhood memories, and I wouldn’t swear to the accuracy of those I have. Still, one from my teens has remained with me.
MY DAD LIVED TO BE age 92 and my mom is going strong at 95. I was involved with my father’s care as he struggled with dementia, and I continue to assist my mother, who still lives independently.
Helping an elderly family member? Here are 16 important lessons that I’ve learned.
1. Don’t be blind. My dad started developing dementia five years before his cognitive ability totally fell off a cliff. No one in the family wanted to recognize his deterioration,
In my analysis it will be less expensive for him to stay on employer sponsored coverage than going on Medicare. My understanding is that he could sign up for Part A but if he does he cannot contribute to his HSA.
Anyone have any insight on this, in general?
IT’S OPEN SEASON for many of us—time to choose our health insurance for the year ahead. It’s a topic I got seriously interested in when I took over management of 500 mathematically astute engineers. They challenged me daily to understand how the various plans stacked up against each other. I spent a lot of time looking at various ways to assess the value of the different plan choices, and came up with a framework that worked for my family.
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- 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.New to building a CD or Bond Ladder?
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