Retirement’s big financial risk isn’t dying early on but, rather, living longer than we ever imagined.
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. 73: WE SHOULD be alert to things we think we know—which managers or stocks will shine, which way markets are headed—that, in truth, are unknowable and yet may poison our decisions.
HABIT STACKING. If your aim is to exercise more, you might have more success if you couple that with an existing habit. For instance, right after you put the dirty dishes in the dishwasher every evening, you might take a walk. Similarly, if your goal is to save more each month, you might add $100 to your favorite mutual fund every time you pay the credit card bill.
PONDER HOW MUCH house you can afford—by considering two issues. First, there’s how much you could potentially borrow. You can find out at HSH.com. Second, there’s how much it makes sense to borrow. If you took on the maximum mortgage possible, would you have enough left over each month to save for retirement, the kids’ college and your other goals?
NO. 34: IF WE BET BIG, we could win big—or lose badly. The two outcomes aren’t equal, however. In one scenario, we retire richer. In the other, we may not retire at all. Because we get just one shot at making life’s financial journey, it’s best to avoid strategies that risk disaster, such as investing on margin, or wagering heavily on a single stock or market sector.
NO. 73: WE SHOULD be alert to things we think we know—which managers or stocks will shine, which way markets are headed—that, in truth, are unknowable and yet may poison our decisions.
One of the most well known advocates for elder care, who worked for a prominent national health center, was talking with me about a year ago. When I asked him what his plan was for he and his wife, as they aged, he replied “ I have four daughters”.
This was pretty shocking to me, given that he worked in this industry, and specialized in helping adult children and their parents to talk about future health care planning.
THIS IS THE LAST year that my income won’t affect my Medicare premiums.
At issue is IRMAA, or income-related monthly adjustment amount, which is the premium surcharge for Medicare Part B and Part D if you exceed certain income thresholds. The surcharge is based on your modified adjustment gross income from two years earlier. Like almost all retirees, I’ll begin Medicare at age 65. That means IRMAA will be based on my income for the tax year when I reach age 63,
I TURNED AGE 64 over the Labor Day weekend. One of my goals for my 65th orbit of the sun is to really dig into Medicare.
Luckily, I have a few friends and relatives who have blazed the trail before me. I’ve also studied Medicare as part of some financial planning courses I took a few years ago. Still, one topic I’ve never researched in detail is Medicare’s income-related monthly adjustment amount, otherwise known as IRMAA.
IN A NEW YEAR’S article, I offered eight ways to potentially become a super-ager. A super-ager is a person age 80 or older who has the memory of someone 20 to 30 years younger. Vigorous exercise, a good diet and getting enough sleep were considered some of the key ingredients.
Or is it just luck? A new study conducted in Spain and published in The Journal of Neuroscience examined the world of super-agers by following two groups for five years: 64 super-agers and 55 typical older adults.
DURING THE FIRST FEW months of the pandemic, my almost-daily trips to the gym ceased. I was home more of the time and snacking became a habit. I found myself five pounds heavier than I’d been a year earlier. Knowing that, at age 54, my metabolism isn’t quite as vigorous as it once was, I took action. I started a ketogenic diet and quickly dropped the extra weight.
As we contemplate growing older, much of our time and energy is spent planning the financial aspects of our retirement years.
LIVING A HEALTHY lifestyle is one of the most important aspects of a happy retirement. It is, alas, also one of the most difficult goals for many of us to achieve. A 2005 Boston College Center for Retirement Research study concluded that health was the second most important factor in determining the happiness of retirees—and those with poor health “experience dramatically lower levels of well-being.”
I stopped working fulltime on March 31, 2017. My health,
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- 401(k)
- Backdoor Roth
- HSA/FSA
Here are some other ones you might want to think about: Commuter benefits Some companies offer pre-tax commuter benefits that can be used for transportation expenses such as transit passes or parking. In simple terms, say you earn $1,000/mo. You pay ~$150 in taxes, leaving $850. From that $850, you spend $100 on monthly parking. With commuter benefits, you would earn $1,000, subtract $100 pre-tax for parking, pay roughly $135 in taxes, and take home $765, compared to $750 in the prior example. Of course, the exact tax amounts will vary, but you got the idea. In short, you save taxes on commuting expenses you would have paid anyway with after-tax dollars. Mega Backdoor Roth Some employers allow employees to contribute after-tax dollars to a 401(k) and then roll those funds into a Roth IRA or Roth 401(k). While you do not receive an immediate tax deduction, the growth is tax-free and qualified withdrawals are also tax-free. High earners can potentially contribute $35,000+ per year to Roth accounts. For example:- $24,500 to a pre-tax 401(k)
- $10,000 employer match (will vary)
- Up to $37,500 in after-tax contributions (rolled into Roth)
The total of pre-tax, after-tax and employer match limits is $72,000 in 2026. That $24,500 could also go into a Roth 401(k), but for high earners it is often better to prioritize pre-tax contributions. If you are currently investing in a taxable brokerage account, check whether your plan allows a Mega Backdoor Roth. Compared to a brokerage account, it offers:- No tax drag from dividends
- Easier rebalancing once assets are in a Roth
- No capital gains taxes on qualified withdrawals
The primary drawback is reduced liquidity, which is important to analyze, especially if you are young. NQDC High earners may have access to a Nonqualified Deferred Compensation (NQDC) plan. This is a contractual agreement with your employer to defer a portion of your income until a future date (e.g. 5 or 10 years). These plans are typically offered to executives or highly compensated employees. Deferred amounts can be invested, and taxes are paid upon withdrawal, similar to a pre-tax 401(k). The goal is tax rate arbitrage. For example, you defer income at a 37% marginal tax rate and withdraw it later at a 24% rate. NQDC plans can be especially attractive if you expect to retire within the next 5 years, as future income is more predictable. Unlike a 401(k), NQDC assets are subject to employer credit risk. If the company goes bankrupt, you could lose all your NQDC assets.. Company stability should be evaluated. Tax Loss Harvesting While not specific to W-2 employees, tax-loss harvesting is an easy way to generate up to a $3,000 annual deduction against ordinary income. If the market declines and you have unrealized losses in stocks or ETFs, you can sell them to realize the loss and reinvest in a similar (but not identical!) security to avoid wash sale rules. I discussed this one more in depth in my recent post. Real Estate If you earn less than $100,000 (modified adjusted gross income) you can claim a real estate loss deduction of up to $25,000 and apply it to your W-2 income. If you earn between $100,000 and $150,000, the maximum deduction of $25,000 is reduced proportionally. This real estate loss is a paper loss generated by bonus depreciation and a cost segregation strategy. If you want to bypass these income limits, your spouse could qualify for a “real estate professional” status. W-2 workers typically can’t qualify on their own due to the time requirements. Or another approach could be to get into short-term rentals. Because short-term rentals aren’t “passive” by default, as long as you materially participate, you could generate some tax savings there. Any questions? Comment below!Financial Happiness
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- A balance sheet indicating where your accounts are held.
- A detailed description of assets held outside of brokerage accounts— rental properties, businesses or private fund investments, for example.
- Location of any safe deposit boxes.
- Contact information for your advisors, especially your attorney.
- Life insurance policies.
- Passwords for your computer, phone and email.
- Password for your password manager, if you use one.
I suggest stowing this with your formal estate planning documents. Then communicate the location of that information to family members or trusted friends.Retiree emergency expenses-how to cope
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