Jason J. Hamilton, CFP - Keep It Simple Financial

08/05/2026

One of the biggest retirement surprises isn’t taxes.

It’s Medicare premiums.

More specifically, it’s something called IRMAA (Income-Related Monthly Adjustment Amount)—an income-based surcharge that can significantly increase what you pay for Medicare Part B and Part D.

What surprises many retirees is that IRMAA isn’t based on this year’s income. It’s based on a tax return from two years earlier, which means the best time to plan for it is often before most people even realize it’s an issue.

In my newest blog, I explain:

* What IRMAA is (and why it isn’t a penalty)
* Why one extra dollar of income can increase your Medicare premiums for an entire year
* How Roth conversions, capital gains, and required minimum distributions can affect your premiums
* What surviving spouses should know
* When Form SSA-44 may help reduce an IRMAA surcharge

My goal was to make one of Medicare’s most confusing rules easy to understand—and help you avoid a surprise that catches many retirees off guard.

[LINK IN COMMENTS]

As always, if you have questions about how IRMAA may affect your retirement income plan, don’t hesitate to reach out.

Warmly,

Jason J. Hamilton, CFP®
Keep It Simple Financial Planning

08/04/2026

The most common mistake I see in retirement is not overspending. It is underspending, and it costs people in a way no account statement will ever show them.

The Employee Benefit Research Institute tracked households across three decades of survey data. A meaningful share of retirees, close to one in three, still had all of their original assets or more by their mid-eighties.

Some of that is prudence. A lot of it is something else.

It is a permission problem.

You spent forty years building the discipline not to spend. Every raise you did not blow. Every car you drove three years longer than you had to. Every account you fed instead of using.

Then you retire, somebody tells you the job has changed, and now you are supposed to spend it.

The habit does not switch off because you had a birthday.

So you reach for the safest number you have ever heard, usually 4%, and you treat it like a ceiling. Here is what almost nobody tells you. That number was designed as a floor. A worst-case guardrail built to survive the worst starting year in modern market history. It was never meant to be your target.

What is missing is not more savings. It is a spending capacity range.

One number that has already accounted for your pension timing, your Social Security strategy, which accounts you draw from in what order, your tax brackets across the next two decades, and your healthcare costs.

Without that number, a purchase you can obviously afford still sets off an internal alarm.

With it, you stop arguing with yourself.

I have seen this play out more than once. Someone flies coach for twenty years, declines the trip, skips the place near the grandkids, and leaves an estate their children then use to fly business class.

There is nothing wrong with leaving something behind. There is something wrong with leaving your own best years on the table to do it.

You did not save for forty years so that somebody else could enjoy it.

How would you feel if you knew what your safe retirement spending number was today in actual dollars? Your monthly paycheck..

07/31/2026

Retirement is not a math problem. It is a coordination problem.

The math is the easy part. Any free calculator will hand you a 4% withdrawal number in about ten seconds. Any Social Security tool will show you a breakeven age. That information has been free and instant for twenty years.

So why do capable people who did everything right still arrive at retirement feeling unsure?

Because nobody has shown them how the pieces move each other.

When you choose when to claim Social Security, you have also chosen your tax brackets for the next twenty years.

When you choose which account to withdraw from first, you have also priced every Roth conversion available to you later.

When you choose how much to spend, you have also set your Medicare premium two years from now.

None of those decisions live alone. There are somewhere between fifteen and twenty major decisions in this window. Most are expensive or impossible to reverse. Almost every one of them touches the others.

Picture a house built by three excellent contractors who never see each other's plans. The framer does beautiful work. The electrician does beautiful work. The plumber does beautiful work. Then the electrical runs straight through the space the ductwork needed, and somebody is opening a finished wall.

Nobody made a bad decision. Nobody coordinated.

That is what happens to most retirement plans. An investment opinion here. A tax opinion there. A Social Security opinion from a calculator. Each one reasonable on its own.

Most retirement stress does not come from bad decisions. It comes from reasonable decisions that were never made together.

I walk through the whole framework in my Retirement Coordination Masterclass. About thirty minutes, no cost. [LINK IN COMMENTS]

07/28/2026

Four thousand of you.

Thank you. Sincerely.

Some of you have been here since the beginning. Some found this page last week. Plenty of you have sent questions and notes along the way that I still think about.

It's a privilege to do this work, and I don't take a single one of you for granted.

Jason

07/27/2026

Stop assuming paying less tax this year is automatically the win.

Almost everyone comes into retirement planning with the same instinct: minimize this year's tax bill. It feels responsible. It feels like the obviously correct move. Often, it's backwards.

Here's the scenario I see over and over. A married couple retires with a large pretax account, a 401(k) or a traditional IRA that's grown for decades. While both spouses are alive, they're filing jointly, sitting in a wider tax bracket, and required minimum distributions feel manageable. Then one spouse passes away.

The surviving spouse suddenly files as a single person. The tax brackets for a single filer are roughly half as wide as they were for the couple filing jointly. But the required minimum distribution on that account doesn't get cut in half along with the brackets. It stays close to what it was, sometimes even grows, while the room to absorb it at a reasonable tax rate just shrank dramatically.

Financial planners have a name for this moment: the widow's penalty.

It's a tax increase that shows up during one of the hardest years of someone's life, and almost nobody sees it coming because it was never the current problem while both spouses were still here.

This is exactly why converting some of that pretax money to Roth earlier, while both spouses are alive and the brackets are wider, so often beats waiting. You're voluntarily paying tax now, on your own terms, at a rate you can see and control. The alternative is an involuntary, larger tax bill showing up later, on someone else's terms, at the exact moment they have the least capacity to deal with it.

Nobody enjoys writing a bigger check to the IRS in a good year. But there's a real difference between paying tax you chose and tax you didn't see coming.

Has anyone in your family actually run the numbers on what your surviving spouse's tax bracket would look like?

Call now to connect with business.

07/27/2026

There's a window in retirement that most people don't know they're in until it's closed.

It opens the year you stop working and it closes when required minimum distributions begin. For a lot of people that's a stretch of five, eight, sometimes ten years.

During that window your taxable income is often the lowest it will be for the rest of your life, and you have more control over it than you ever had while you were working or ever will again afterward.

That window is where retirement coordination does most of its work.

Coordination is a simple idea. Your retirement decisions are connected to each other, so they should be made together instead of one at a time.

The age you claim Social Security changes your taxable income.

Your taxable income determines how much room you have to convert to a Roth.

A large enough conversion could raise your Medicare premiums two years later, so the size and timing matter.

What you leave in a pretax account sets the size of your required distributions in your seventies.

Those distributions set your tax bracket.

That bracket follows your spouse into a single filer's brackets if they outlive you, which is often a higher rate on less income.

And whatever is left in a pretax account at the end goes to your kids, who now have ten years to empty it, usually during their highest earning years.

Seven decisions. One system. Most people make them in seven different conversations with five different people over a decade.

Here's why the timing matters. Once Social Security starts and required distributions begin, most of your income becomes involuntary. It arrives whether you want it that year or not, and it lands in whatever bracket it lands in.

The levers you had are mostly gone by then.

Coordination after that point is damage control. Coordination during the window is planning.

Every year you spend in that window without a plan is a year of bracket space you can't get back. It doesn't roll over and it doesn't come back later. It expires.

I sit on the same side of the table as my clients, as their fiduciary, and this is the work I care most about getting right. These decisions are largely one way. You can't re-run 2026 in 2031 once you see how it played out.

If you're retired or close to it and no one has mapped out what those years should look like, that's the place to start.

Happy to answer questions in the comments if this raised any.

You can also find the link to my Retirement Coordination Masterclass in the links on this page. It's about 30 minutes of your time. If it resonates with you, I would be happy to discuss if our services could be a fit.

-Jason

07/22/2026

Understand why your retirement spending number should never stay exactly the same for thirty years straight.

Most advice about retirement income sounds like this: figure out a safe withdrawal rate, usually somewhere around 4%, and spend that amount every year adjusted for inflation, no matter what the market does. It's simple. It's also not how a coordinated plan should actually work.

Markets don't move in a straight line, and neither should your spending. A static number either forces you to underspend during good years out of unnecessary caution, or it puts you at real risk during a genuinely bad stretch because the number never adjusted downward when it should have.

This is where guardrails come in. Instead of one fixed number, you set an upper and a lower boundary around your spending, based on how your actual portfolio is doing relative to your plan.

If your investments grow well past the upper guardrail, that's not just good news to admire from a distance. It's a signal, a planned, stress-tested one, that you can raise what you're spending.

If a downturn pushes you below the lower guardrail, that's a signal too, but a much smaller correction than most people fear. Think of it like tapping the brakes when you're going downhill a little too fast on cruise control. It's a small, planned adjustment, not slamming on the brakes and pulling into the nearest exit.

What guardrails are not is a license to sell everything and move to cash the moment the market gets rough. That reaction is exactly what a bad plan makes people do out of fear. A good one tells you, in advance, what the actual threshold is, so you're never guessing in the middle of a scary headline.

If you've never had someone show you your own upper and lower number, on paper, that's usually the single biggest gap in a retirement plan I see. Would knowing your own guardrails change how you think about the market right now?

Call now to connect with business.

07/15/2026

Stop assuming Trump Accounts are just something for young parents to figure out.

Quick recap on what actually happened: the 2025 tax law created a new kind of account for kids, called a Trump Account. It's technically a traditional IRA built for children under 18, and contributions started July 4th of this year. As of launch, the default investment is a low-cost S&P 500 index fund, with one of the lowest expense ratios out there.

If a child was born between January 1, 2025 and December 31, 2028, and is a US citizen with a Social Security number, the federal government deposits $1,000 into the account once it's opened. After that, family, friends, and even employers can add up to $5,000 a year combined, until the year before the child turns 18. If your grandchild doesn't fall in that 2025–2028 window, they don't get the automatic $1,000, but the account can still exist for them, and you can still fund it. That makes this less of a "new parent" tool and more of a legacy tool.

Here's an idea we're planning to use ourselves: bring a QR code to the birthday party. One US senator has already pointed out that contributing is as simple as scanning a code, and family and friends can put in whatever they want, even $5. New IRS guidance from just a few weeks ago confirmed that gifts like this, well under the $19,000-a-year gift tax exclusion, don't trigger any tax paperwork for the giver.

Here’s how it works in practice for 2026:

* The annual federal gift tax exclusion is $19,000 per recipient.
* Contributions to a child’s Trump Account count toward that $19,000 annual exclusion—they are not in addition to it.
* If your total gifts to that child during the year (including the Trump Account contribution) are $19,000 or less, you generally do not have to file Form 709 (Gift Tax Return), assuming you don’t otherwise have a gift tax filing requirement.

Example 1 (No paperwork)

* $5,000 contributed to the child’s Trump Account
* $10,000 cash gift for a birthday

Total gifts: $15,000

No Form 709 required (assuming no other gifts to that child).

Example 2 (Paperwork required)

* $5,000 contributed to the Trump Account
* $16,000 cash gift

Total gifts: $21,000

Now you’ve exceeded the $19,000 annual exclusion.

* You’ll generally need to file Form 709.
* Filing the return does not necessarily mean you owe gift tax. The excess typically reduces your lifetime gift and estate tax exemption (currently around $15 million+, adjusted for inflation) before any gift tax is actually due.

Instead of another toy that gets forgotten in three weeks, grandparents, aunts, uncles, and friends can all add a little to something that's actually going to matter in fifty years.

So how much does that actually add up to? If a family maxed this out every year, the $1,000 seed plus $5,000 a year from birth through age 17, that's $91,000 total contributed. Using a commonly cited long-term historical average return for the S&P 500 of around 10% a year, that account would be worth around $256,000 by the time the child turns 18. Left untouched and simply compounding for another 50 years with no more contributions, it could be worth somewhere between $5.5 million and $30 million by age 68, depending on which long-term average actually holds over the next several decades. That's not a promise or a projection. Markets don't move in a straight line for 68 years, or even 18. It's a math exercise about what time does to money, not a prediction of what any specific account will actually be worth.

Even a smaller commitment adds up. If a family started at age 5 and put in $2,000 a year through age 17 instead, that's $26,000 total contributed, worth around $54,000 by 18, and somewhere between $1.3 million and $6.3 million by 68 under that same range of assumptions.

Now here's the part I want you to actually pay attention to, because it's the part that can bite you. While the money sits inside the account growing, it isn't subject to the "kiddie tax" the way a regular custodial brokerage account would be. That's a real advantage. The risk shows up on the way out. Once your child turns 18, this becomes a regular IRA, and withdrawals, or an early Roth conversion, count as taxable income. If your child is still your dependent, or a full-time student under 24, unearned income above roughly $2,700 a year gets taxed at your rate, not theirs. Pull money out or convert it at the wrong moment, and you can hand your kid a tax bill sized to your bracket instead of theirs.

This is exactly why the "when" matters as much as the "how much." A Trump Account isn't a set-it-and-forget-it gift. It belongs in the same coordinated conversation as your 529s, UTMA's, your beneficiary designations, and your estate plan, with an actual plan for when that money eventually comes out.

Anyone here already opened one, or thought through when you'd actually want your child to access it?

06/26/2026

Link to Masterclass in Profile

04/29/2026

It’s interesting how often people keep working… even after they’ve reached the point where they could retire.

Not because they have to.

Because they don’t feel ready to stop.

On paper, everything works.

The savings are there.
The plan is solid.
The numbers check out.

But something still holds them back.

So they say things like:

“Maybe one more year.”
“Let’s just build a little more cushion.”
“I just want to be sure.”

And one year turns into two… then three… then more.

Sometimes that’s a choice—and there’s nothing wrong with that.

But sometimes it’s not really about wanting to keep working.

It’s about not feeling confident enough to stop.

Because stepping away from a steady paycheck is a big shift.

You go from earning and saving…

To drawing from what you’ve built.

And without clarity around how that works, it can feel like you’re taking a risk.

Even when you’re not.

What I’ve noticed is this:

The people who keep working longer than they need to often aren’t missing money.

They’re missing clarity.

Clarity around how income will be created.
Clarity around how decisions will be made.
Clarity around what happens if things don’t go perfectly.

But here’s where the shift gets interesting.

For many people, the goal isn’t actually to stop working completely.

It’s to reach the point where work becomes optional.

Where you can keep working if you want to…

But not because you have to.

That’s a very different feeling.

It changes how you think about your time.
It changes how you approach your work.
It changes the pressure behind every decision.

Once that level of confidence is in place, something shifts.

People don’t feel stuck between “work” and “retire.”

They feel free to choose.

Maybe they keep working, but on their terms.

Maybe they scale back.

Maybe they explore something new.

The goal isn’t always to retire as soon as possible.

It’s to get to a place where your decisions are driven by preference… not necessity.

Because there’s a big difference between working because you have to…

And working because you want to.

And for a lot of people, that’s the real definition of financial independence.