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.
I’VE RECENTLY MADE the most significant change to my own portfolio in thirty five years. For the first time I’ve moved away from pure market-cap investing, tilting meaningfully toward Europe and Southeast Asia and bringing my US technology concentration down to around fifteen percent.
I’m retired. I don’t need to chase the outperformance that concentration might deliver, and I don’t need the potential volatility that comes with it. This is a personal position rather than any kind of recommendation;
A POPULAR JOKE about retirement is that it can be hard work. That’s because financial planning is like a jigsaw puzzle, and retirement often means rearranging the pieces.
In the past, I’ve discussed two key pieces of that puzzle: how to determine a sustainable portfolio withdrawal rate and how to decide on an effective asset allocation. But there’s one more piece of the puzzle to contend with: taxes. Especially if you’re planning to retire on the earlier side,
For all my mentions of my prior life as a beer truck driver, and the monthly meetings of the ElderBeerMen (retired beer truck drivers), you might think I have a drinking problem. In reality I average about eight drinks per month. And usually, that involves having two at one sitting, so most days, I’m a teetotaler, but I do enjoy my transgressions. Many who imbibe can’t control the habit; the alcohol owns them. Many pastimes are the same way.
Return with me now to the year 1990. George H. W. Bush was President. The Buffalo Bills had a heartbreaking loss to the NY Giants in the Super Bowl. The Cold War ended with the dissolution of the Soviet Union. The Gulf War started when Iraq invaded Kuwait.
In the investment world, Peter Lynch, the long-time mutual fund manager of Fidelity’s Magellan Fund, retired to be replaced by Morris Smith. In my chapter of Jonanthan Clement’s book My Money Journey,
New research presented by Kiplinger shows significant variations in typical withdrawal rates. As you may suspect, some of that is based on age, marital status, the existence of a steady income stream and when the RMD kicks in.
Among the interesting observations: “The “Lifetime income” effect: Retirees are willing to spend roughly 80% of their “lifetime income,” which includes Social Security, pensions, and annuities. But they are only willing to spend about half of what they could safely afford to from their investment assets,
Spring arrived bang on cue at the start of March, and the weather gods actually delivered some proper early sunshine. I seized the moment, dug out the power washer, and set about bringing the yard back to life. Forty-five minutes in, my trusty 20-year-old yellow Kärcher started making alarming noises and belching smoke. That was that.
I’ve said it before and I’ll say it again: Things don’t stop breaking just because you’ve retired. The last week has been a particular case in point.
According to a May 2025 Gallup survey, only 61% of Americans age 65 and older own stocks in any way, including IRAs, 401ks, etc. I found that a bit shocking and a little sad. I’m pretty certain HD readers and writers are not among the 39%.
If that is an accurate percentage, no wonder many retirees are in poor financial shape, no wonder social media is full of videos with seniors claiming they need and deserve higher social security benefits and higher COLA adjustments.
Donating to charity used to be simple. Not anymore. I am reaching out for opinions on the most efficient way to donate in 2026. I have identified several ways to donate but can’t decide on the best approach.
The most direct way is to write a check which would be deductible; $2,000 for a married couple or $1,000 for a single taxpayer who takes the standard deduction. Itemizers can deduct up to 35% of AGI (I think).
One of the stranger paradoxes in finance is volatility — the degree to which an asset’s price swings up or down over time. Most investors hear the word and flinch. But once you understand what volatility actually is, and what it makes possible, you might start to see it very differently.
Think about it this way. A savings account is about as predictable as it gets, your money sits there, safe and stable, and grows at a modest rate.
It appears that Vanguard on 9/20/2025 changed their lack of an option to transfer a joint taxable brokerage upon the death of the last owner to survive via a Transfer On Death designation. My understanding is you now may do so via completing a online form, printing, executing the form and mailing the completed form to Vanguard. Making that change does not yet appear to be an action you can currently do online.
I think you can find their form here.
I am retired and am making withdrawals from my taxable retirement accounts. At my last meeting with my advisor they claimed I should still be putting money into investments. Aside from rebalancing accounts, it doesn’t make sense to me to be putting money in at the same time I am taking money out.
Thoughts?
Here’s something that might surprise you. Until I retired, I don’t think I’d used an automated teller machine for at least twenty years. If I needed to use a credit or debit card, I usually had to spend a significant amount of time locating the AWOL cards. On more than one occasion, I discovered the card was out of date and had to get my wife, Suzie, to complete the transaction. In short, I had a very close relationship with physical cash.
I want to thank all forum members who commented on my last post about helping my adult son and his new wife. Last night, my wife and I applied all of the lessons to have “the talk” with my son, his wife and my daughter over an impromptu family dinner at our house. Just a quick background for context and then back to the conversation. My daughter lives in Maryland, some 3.5-4.0 hours away. My son also lives south of us about 2.5 hours away.
HEALTH SAVINGS ACCOUNT (HSA) is the most efficient tax-advantaged investment account because it offers a triple tax advantage:
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.