There is still a little bit of time to cross a few things off your list. No, I’m not talking about your Christmas list.

To start, if you’re going to be spending time with aging family members, think about doing a cybersecurity audit. It’s not very festive, I know. But the holidays are sometimes the only moment we get to handle things face-to-face.

My number one recommendation is to help them set up and learn to use Apple’s new Passwords app. It works across all their Apple devices and it uses Face ID or Touch ID to help them easily access their new strong passwords. Besides retiring the use of a bunch of repeated and possibly compromised passwords, the very best feature of this new app is that it makes password sharing super easy.

Of course, try to tackle the login credentials that matter most – their banks, credit cards, investment accounts and also their email account. Beyond setting up some unique and strong passwords, be sure to check that each of these key accounts have two-factor authentication enabled. While this whole process isn’t a simple one – for those of you who know – trying to fix a problem remotely is way harder.

Switching gears to the upcoming tax season. For those wise enough to donate to charities directly from their IRA – and not their regular checkbook – remember that your Form 1099-R won’t actually report those donations any differently than normal distributions. In other words, it doesn’t split out your charitable activities. So, if you forget to tell your tax preparer about your IRA donations, you’ll end up paying taxes you don’t owe.

Thankfully, starting with the 2026 tax season, brokerage firms will be required to actually split out your IRA donations on your Form 1099-R. I’ve been asking for that for years and I couldn’t be happier. But, for 2025, we’re not yet there. So, remind yourself to tally them up and report them to your tax person.

Finally, the new tax law offered up a change for those over age 65. Unless you make too much money, you are getting a new “senior deduction” that adds $6,000 on top of your large standard deduction. You can double that to $12,000, if you’re married. This change opens up more room in the lower tax brackets and it means you should review a few tax moves before New Year’s Eve.

At the very least, you should take a look at taking some extra IRA distributions at low tax rates. Better yet, you might even upsize your Roth conversion strategy. Best of all, it’s possible you can realize some long-term capital gains – effectively resetting your cost basis – and owe zero federal tax. Be careful, though, each of these moves might take some number crunching to get things just right. The tax code is not as easy as it should be and, unfortunately, it’s gotten more complicated.

This time of year, I meet with my clients to review everything that’s going on in their lives related to their money. In those conversations, I notice common topics and concerns. Today, a central theme has been artificial intelligence. How could it not be? It’s been the primary driver of this year’s surprisingly strong market. And, unsurprisingly, it’s also driving a lot of talk of a bubble-in-the-making.

In my view, the focus on – and the optimism about – AI is deserved. We can all see how it’s being adopted by businesses and changing the way people do their work. Good or bad, nobody is going to put this genie back in the bottle. But, when I think about AI, I envision a number of “circles” and, frankly, none of them are easy to square.

After years of watching the tech giants stockpile enormous amounts of cash, we’re now seeing them pour their profits into AI investments. They are building out huge data centers and buying every Nvidia chip they can get their hands on. And, in turn, Nvidia is now turning around and investing in the very AI companies that rely on their chips. The story is getting quite complex, and it’s highly circular.

It’s becoming clearer that the next phase of the AI investment cycle – the big money that’ll be needed to build these sprawling data centers we all see in the news – will require more than just the tech companies’ current cash flow. The use of debt, especially off balance sheet debt, might weaken things to the breaking point if the AI-revolution pauses for one moment too long.

This brings me to my next circle. I think AI is already replacing workers. We might not see it explicitly, but it’s no doubt happening in both large and small businesses. If this picks up pace – and the tech companies are doing their very best on that front – it begs a fundamental question. Who exactly is going to buy the products and services these efficient businesses produce? Even Henry Ford understood this basic economic formula a century ago.

At some point, policymakers will need to confront this economic math. If profits increasingly flow to a shrinking set of massive tech companies and even small business owners who need fewer human workers, society will need to get creative. The concept of basic universal income won’t be just about fairness. It’ll be about economic sustainability. Unless I’ve missed it, I just don’t see any prominent politicians talking about how to square this particular circle at all.

Now, back to my recent client meetings – where these big picture concerns actually matter – I’m increasingly focused on just how much AI is impacting their money. For example, are you aware that just 10 gigantic companies now make up nearly 40% of the entire value of the S&P 500? Owning that one index fund simply doesn’t diversify things like it once did. Bottom-line, while there is no way around AI, we certainly can and must deal with it.

Q: We recently read an article that said we might actually want to sell some stocks or mutual funds to trigger capital gains. It seems awfully strange to us. Can you explain why it makes sense?

A: The idea that you would voluntarily sell something at a gain certainly sounds odd. But it can be really smart for some people. It’s a tax strategy reserved for people with “modest” income. As you’ll see, modesty is in the eye of the beholder.

Specifically, we’re talking about long-term capital gains and also qualified dividends. They simply aren’t taxed when you live in the 12% federal tax bracket. But, you’ll need to plan carefully.

Let’s start with your deductions. In 2025, a married couple filing jointly gets a standard deduction of $31,500. If you happen to be over 65, you also get to add another $1,600 deduction for each of you. And thanks to the new tax law, there’s now also an additional $6,000 “enhanced” senior deduction for both of you for those over 65. That all adds up to a whopping $46,700 in deductions!

Now, let’s say your adjusted gross income – before applying those deductions and also before any possible capital gains – is $110,000. After your deductions, your taxable income would sit at only about $63,000.

Compare this amount to the upper threshold of the 12% tax bracket. That’s about $97,000. You’d have leftover “room” in the 12% bracket for about $34,000 of long-term gains without paying a penny in federal taxes. You can sell and immediately re-buy your holdings, if you want. It effectively resets your cost basis; an almost-free lunch. Remember, your state tax return will include those gains.

Q: I retired earlier this year after working in a high-income career. I just noticed that my Medicare Part B premium is much higher than the standard amount. I’ve learned it’s based on my income from before I retired. But, I’m now earning way less in retirement. Is there anything I can do to get my premium lowered?

A: Yes, absolutely. As background, Medicare Part B premiums are adjusted based on your income. Technically, it’s called the Income-Related Monthly Adjustment Amount (IRMAA, for short.)

They make you pay more than the standard premium once your adjusted gross income exceeds about $200,000. Here’s the catch. They use your income from two years ago to determine your Medicare premium for the current year. This explains why you’re currently paying so much, even as you’re earning way less. They just don’t know it yet.

You can request an adjustment by filing Form SSA-44. The form is meant for certain “life changing events.” Retirement qualifies as one of eight eligible life changing events. If you file one for 2025, you may even get a refund of overpaid amounts this year. Certainly do it for 2026 after you get your annual notice in a few weeks.

By the way, it looks like the standard Medicare Part B premium is going to jump about $20 per month next year. I suspect many retirees are going to be negatively surprised.

We’re getting close to the end of another year. This one has been wild, for sure. The economy is sending mixed signals viewed through the lens of highly-charged emotions. It’s no wonder investors are having trouble finding their footing. You can put me in that camp. Publicly admitting that as a pro takes a healthy dose of humility. That’s called experience.

I’m obviously watching the economy pretty closely. The job market is always a focus. Hiring has clearly slowed and – despite what President Trump wants to believe – it’s not due to a Biden appointee or a cabal of government employees cooking the books just to make him look bad. That’d be delusional thinking.

At the same time, tariffs are still a big deal, despite the fact that the stock market has more than recovered from the sheer panic in early April. The Supreme Court won’t decide on the legality of the Trump tariffs until some time in November. They look illegal to me. After all, trade deficits are not a national emergency. This whole tariff debacle is yet another sad case of Republicans in Congress willing to abdicate their constitutional duty out of political fear or opportunism.

Speaking of political heat, the Federal Reserve is feeling it. They finally cut rates by a quarter point as they also see our economy slowing. We can expect another cut in a few weeks and again in December. After that meeting, it’s kind of a coin toss. The current government shutdown can now be added to their list of concerns. The shutdown seems like bad politics for both sides. One thing is certain, it reinforces the general view that our political system is broken.

Then there is artificial intelligence. It’s hard to remember another technology that has impacted things as quickly as AI has. Undeniably, it’s a game-changer for so many workers and businesses. But it’s also fueling a wave of investor enthusiasm that feels like either too-good-to-be-true or too-much-too-soon. Once again, in the name of humility, I won’t call it a bubble just yet. What I do know is AI has far-reaching implications that our elected officials are – yet again – failing to address. The tech titans are running circles around them and likely lining their pockets.

In face of these cross-currents, the markets have weathered it incredibly well so far. For the year, stocks are up around 15% and bonds have delivered about 7%. It’d be naive to think things will continue at this pace.

This means some portfolio rebalancing is wise to consider. Yes, it might require the realization of some capital gains before the end of the year. But, with thoughtful planning, the tax bite can at least be minimized. What to do with the cash? Well, that’s a problem best left for another day.