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A deeper look at one way AI is changing everyday life.

Good morning.
I still bring a short list of AI-built questions to every meeting with my own adviser. It's become a habit I don't skip anymore, and these are the five questions I hear other retirees ask most, one prompt for each.

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Several months ago, my brother, a good friend of mine, and I got hung up on one thing: the size of the national debt, and what it might mean for people like us down the road.

So the three of us sat down with ChatGPT, Claude, and Gemini and worked through the scenarios, then landed on the actual questions I wanted to bring to my financial adviser. I walked into that meeting more prepared than I ever had been. It worked well enough that it became one of the two real reasons I started this newsletter. Health was the first. This was the second.

I still meet with my adviser regularly, and that same approach works for the bigger, more common questions retirees bring to those meetings too. Here are five of them, and a prompt for each to help you think it through before you go.

This is usually the first thing sitting there unresolved. You left a job, or retired outright, and the 401(k) is still parked with your old employer's plan, quietly collecting fees you have probably never looked at closely.

Moving it into a self-directed IRA at a place like Vanguard, Fidelity, or T. Rowe Price often opens up a wider range of investment choices than an old employer plan offers. A direct rollover, where the money moves straight from the old plan to the new one, avoids taxes and penalties entirely.

There is no single right answer here. Some advisers will move everything into an IRA, some will leave it exactly where it is, and some will split it between the two. What actually decides it is a specific look at your old plan's fund lineup and its costs, not a one-size-fits-all rule.

That is the part worth sorting out before the meeting: what is actually in that account, and what it's costing you to leave it there.

Try this:

Try it now: ChatGPT · Claude

For a closer look at getting your money organized before you make a move like this: Before You Move That Money, Ask AI This First.

This is the question underneath most of the others. Not "how much do I have," but "am I going to be okay."

A good adviser starts by looking at the whole picture: retirement accounts, savings, other investments, and yes, the value of your home. Then they look at your monthly budget, what is coming in and going out, and your plans for the years ahead. Do you expect to travel? How is your health? Those answers shape the plan as much as the account balances do.

The problem is most people walk into that conversation with the numbers scattered across three different logins and a shoebox of statements. Getting it into one place before you sit down changes the whole meeting.

Empower is a free financial dashboard that pulls your accounts into one view, which makes this exact exercise faster.

Try this:

Try it now: ChatGPT · Claude

If you want to check whether your number is actually on track before that meeting: Is Your Retirement on Track? Use AI to Discover Your "Magic Number".

Once the paycheck stops, this becomes the question that keeps people up at night. How do you replace it, without draining the account too fast or living smaller than you need to?

The starting point most advisers reach for is the 4% guideline: pull out about 4% of your total savings in the first year, then keep drawing that same dollar figure, bumped up for inflation, in every year after. Depending on your specific mix of income sources, some will nudge that closer to 5%.

Alongside that, most advisers want to see roughly twelve months of expenses sitting somewhere liquid, like a money market or high-yield savings account, so a rough stretch in the market doesn't force a sale at the wrong moment just to cover this month's bills.

There's a pattern worth naming here too: plenty of retirees end up spending far less than they safely could, simply because they never ran an actual number, and the uncertainty itself becomes the reason to hold back. A rough estimate going in beats no estimate at all.

Boldin is retirement planning software built for modeling exactly this kind of decision, including how those inflation adjustments actually play out over 20 or 30 years.

Try this:

Try it now: ChatGPT · Claude

Almost every adviser hears a version of this question first, before anything else gets discussed. It makes sense. It is the one number that feels the most permanent.

Waiting matters more than most people realize. Full retirement age falls somewhere between 66 and 67 depending on your birth year, but every additional year you hold off past that, up through age 70, adds close to 8% to your eventual monthly check. That growth stops the moment you hit 70, so there's nothing to gain by waiting any further than that.

The mistake to watch for is claiming early out of habit or impatience, without ever weighing what waiting would have actually bought you. It is also not automatically the right move for everyone. Health, other income, and how long you expect to need the money all factor in, which is exactly the kind of thing worth walking through before you decide.

For a deeper look at timing that decision: The Social Security Dilemma: Should You Take It Early or Delay for a Bigger Benefit?.

Try this:

Try it now: ChatGPT · Claude

This is the one that sounds simple and is not. Here's the mechanic: you take money sitting in a traditional IRA or 401(k), where it hasn't been taxed yet, and move it into a Roth IRA. That move counts as taxable income for the year, so you pay the tax now. From that point forward, the money grows without being taxed again, and you owe nothing when you eventually pull it out.

Nobody converts the whole account in one shot if they can help it. The usual approach is converting a slice large enough to matter but small enough to keep you inside your current tax bracket, sometimes spreading a bigger conversion across several years instead of doing it all at once.

One rule worth knowing before you commit: money you convert generally needs to sit for five years before you can withdraw it penalty-free, unless you're already past 59 and a half, in which case that restriction doesn't apply.

Here is the part that trips people up. Because a conversion counts as income, it can push up your Medicare premiums for the following year and change how much of your Social Security ends up taxable. None of these pieces move on their own. A decision that helps your taxes this year can quietly cost you somewhere else.

H&R Block is worth knowing about here too, since a conversion year is exactly when a second set of eyes on the tax return earns its keep.

Try this:

Try it now: ChatGPT · Claude

None of these five questions require you to become a financial expert overnight. They require you to walk in with a real question instead of a vague worry.

The distance between "I don't know where to start" and "I have three specific things to ask" is smaller than it feels, and AI is genuinely good at closing that gap. It cannot replace your adviser. It can make the hour you spend with them worth a lot more.

This week: pick whichever question above is actually keeping you up at night. Run the prompt. Bring what it gives you to your next adviser conversation, or use it to decide if you need one. Fifteen minutes.

(If your adviser looks a little surprised that you showed up with questions instead of just nodding along, that is a good sign, not a bad one.)

Try This With AI

What it does: Helps you figure out which of these five questions actually matters most for your situation right now, so you know where to start.

Here is a starter prompt that works across all five questions in this piece:

Customize it: Swap in whichever two or three of the five questions actually apply to your situation right now.

Try it now: ChatGPT · Claude

Then ask this: "Now write out what I should actually say to open the conversation with my adviser about that first question."

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