AFMG - American Financial Management Group

06/08/2026

Many people subscribe to the idea that there are only two certainties in life: death and taxes.

And if both are inevitable, you should put them off as long as possible.
That sounds reasonable.

After all, none of us enjoys writing checks to the IRS. Delaying taxes feels like winning. Maybe you'll be in a lower bracket later. Maybe the rules will change. Maybe you'll never have to pay them at all. Or maybe you simply need the cash flow today.
All of those reasons can make sense.

The problem is that this pretends taxes are a one-year decision rather than a lifetime expense.

Retirement planning changes the conversation.

Most retirees will spend decades paying taxes on some combination of Social Security, pensions, IRAs, investment income, and required minimum distributions. The question isn't whether you'll pay taxes. The question is how much you'll pay over the rest of your life.

That's why some of the best tax-planning strategies seem backward at first.
A Roth conversion means voluntarily paying taxes today.

Claiming Social Security later may mean spending down retirement accounts first.
Taking withdrawals from one account rather than another may increase taxes this year while reducing them over the next 20 years.

None of these strategies are automatically right. If an advisor tells you there is only one correct answer, I'd be skeptical.

But they all stem from the same idea:

The goal isn't to win against the IRS this year. The goal is to pay taxes at the lowest rates possible over your lifetime.

Good retirement planning isn't about avoiding taxes. It's about deciding when you want to pay them.

Taxes aren't a one-year problem. So be careful about making a thirty-year decision based on this year's tax bill.

06/03/2026

One of the biggest adjustments people have to make in retirement is shifting from a "Savings" mindset to a "Spending" mindset.

For 20, 30, or 40 years leading up to retirement, we've been putting money away "for the future." In the beginning, it was tough to do that for many of us, yet by the time we're in our 50s, we'd gotten pretty good at it. We also conditioned ourselves to focus on the value going up when looking at our statements.

However, once the work stops and retirement begins, that pile of money becomes a source of income — along with Social Security and any other income sources — for the rest of our lives. Instead of focusing primarily on the account balance, the more important question becomes: What income and spending can these assets support?

We see this all the time. People with well over a million dollars saved hesitate to book a $10,000 trip because it's difficult to translate a savings balance into a spending decision. That's the mindset shift retirement income planning is really about.

The problem is that most financial messaging still speaks to the "number go up" goal because that's what the industry has traditionally been built around. Which is exactly what makes Vanguard's willingness to publish research focused on this shift noteworthy.

The specific strategies they discuss may not apply to your situation — retirement income planning is highly individual — but the framing is right. And it's a better conversation starter than anything you'll hear in a 30-second commercial.

You can read it here: https://buff.ly/AMD1xqL

06/02/2026

The 2027 Health Savings Account limits have been released.

For us retirement geeks, this is a big day — we can start adjusting our planning for next year. Yes, when the rest of the IRS and Social Security COLAs get announced in October, it's a bigger deal. But we take our wins where we can get them.

The good news: the contribution limit for singles goes up $100 to $4,500, and for family plans it goes up $250 to $9,000. The bad news? Both the minimum deductible and the out-of-pocket maximum increase.

As a reminder, HSAs are among the best savings vehicles out there. You can deduct contributions, the growth is tax-free, and withdrawals are tax-free when used for qualified health care expenses. And health care is one expense none of us are getting out of.

There's more. The law now allows HSA funds to be used for Direct Primary Care (DPC) membership fees — up to $150 per month for individuals and $300 per month for families.

And in case you missed it, starting this year, all Bronze and Catastrophic plans on the ACA marketplace are HSA-eligible. That's a big deal for the millions of people using those plans who previously couldn't access an HSA.

If you're looking for more details and don't want to listen to me ramble about HSA rules for another ten minutes, you can read more here: https://buff.ly/wFEMOek

There's a gap between the contribution limit and the actual medical cost inflation rate.

06/01/2026

✨ Spotlight: AFMG - American Financial Management Group✨

"At AFMG we want you to have the resources, both time and money, to do the things you WANT to do in life, and not just the things you HAVE to. That takes being deliberate about your “ ”. We help you get clear on your goals, decide on the path to get to those goals, and keep you on track along the way."

Check out all that they offer: https://afmgplanning.com/

06/01/2026

Probably the biggest problem with the Roth IRA 5-Year Rule is that there are actually TWO different 5-year rules. (Thank you Congress for your continued lack of originality.)

The first is the Lifetime 5-Year Rule.

This rule determines when Roth IRA earnings can come out income-tax free. Once you've had any Roth IRA long enough to satisfy this rule, that clock applies to all of your Roth IRAs — even accounts you opened later or have already closed. This one is about income tax.

The second is the Conversion 5-Year Rule.

This one is completely different — and it's about the 10% early withdrawal penalty, not taxes. It applies to each Roth conversion separately. When Roth IRAs first became law, some clever people figured out you could convert a traditional IRA (taxable, but no 10% penalty), then immediately withdraw from the Roth (tax-free, no penalty). Free money! Congress was not amused, and the conversion 5-year rule was born. (Have to defend Congress on this one.)

Fortunately, the Roth IRA ordering rules help with both. Contributions come out first, then conversions oldest-first, and earnings come out last. That means many people never actually run into either rule — and if you're already well past 59½, the lifetime rule is almost certainly a non-issue anyway.

The real danger is when someone does run into one of these rules and doesn't realize there are two of them — covering two completely different issues.

For more details, today's Slott Report does a great job explaining this confusing corner of the Roth IRA rules.

https://buff.ly/r9FkNdz

If you are under age 59½ and you converted your traditional IRA to a Roth IRA, you will need to watch out for the five-year rule for penalty-free distributions of converted funds. Not understanding how the rule works can result in unexpected penalties when you withdraw your Roth IRA funds. Here are...

06/01/2026

05/21/2026

Reminder: Hope is NOT a plan

05/21/2026

When I'm asked what we do, I tend to surprise people by not answering "Make great investments" or "Help build huge wealth." Instead, I say, "I help people spend money."

And this is the unspoken problem with retirement income planning. Clients spend decades sacrificing, saving, delaying, and preparing for someday — but when someday finally arrives, few find it easy to switch to "spend mode."

I try to plant the seed of this switch by calling savings not "savings" but "future spending." The idea is to keep in everyone's thoughts that this money is designed to be used. It isn't a number to protect — it's a pile of experiences, dinners, trips, and memories that haven't happened yet. Reframing it that way matters because how you think about the money determines whether you ever actually touch it.

And apparently I'm not alone in this thinking.

"The true test of another man's intelligence is how much he agrees with you." By that measure, Dan Haylett is a genius because he just published a Substack discussing this very issue.

Dan covers a lot of ground that we work through in client meetings, but he has one line I am going to steal — correction, borrow — and I'll be giving him full credit every time I use it: "For the first time in your entire adult life, you are about to need permission from yourself, and you have absolutely no idea how to grant it."

Think about it. Up until now, your spending was constrained by someone else. As kids, it was our allowance, and when we got jobs, it was our paycheck (I'm ignoring credit cards and borrowing since why let details get in the way of a good analogy). Every significant purchase came pre-loaded with a structural alibi — you earned it, the bonus covered it, the salary justified it.

In retirement, however, we are the paymaster. It is up to ourselves to decide how much to spend, and that can be scary as hell.

This is exactly why the "future spending" reframe matters so much. If you've spent 30 years thinking of that account as savings — something to preserve, protect, and grow — the psychological leap to spending it is enormous. But if you've been thinking of it all along as future spending, just waiting to be deployed? That's a different relationship with the money entirely. At some point, the goal has to shift from protecting the money to actually using it to enjoy the life you spent 30 years building.

I'm not expecting this post to suddenly rewire your brain, but hopefully, it starts conditioning you to enjoy the retirement you imagined when you started this journey.

Dan's full piece is worth your time. Please read it here: https://buff.ly/1qDcKgP

Why the freest people still can't bring themselves to enjoy it