Jason J. Hamilton, CFP - Keep It Simple Financial

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Jason J. Hamilton, CFP - Keep It Simple Financial Retirement planning focused on coordinating spending, income & taxes. Hi! What a crazy concept right? Why these two categories?

I’m Jason and I believe financial advice should be delivered with the clients interests put first at all times. But in the financial advice world, this is anything but normal. I also believe advice should be delivered independent of product sales and in clear, simple language clients can understand. This is why I founded Keep It Simple Financial Planning in 2015. We are a fee-only, fiduciary, registered investment advisor (RIA) based out of the city of Orange in Orange County, California but we do serve clients across the United States. To do so, we offer the latest in virtual meeting and financial planning tools that will make it feel like you’re sitting right in the office with us, without having to deal with traffic, parking, finding the kids a babysitter and all the other things that would prevent you from seeing a financial planner. We specialize in helping mainly 2 types of clients although this does not mean we will not help you if you don’t fall into one of the following categories:

Retirees/pre-retirees within 10 years of retirement who want to retire with confidence. Clients in their 20’s, 30’s or 40’s that may not be thinking about retirement, but have other goals that require planning from a long-term perspective and maximizing their income like buying a house, funding the kids college, managing large student loans while working in a high paying career, starting a business or simply taking more vacations now while staying on track for the future. Simply, I’m looking to serve clients that would fit in the same demographic as my parents, or my siblings. I treat all my clients as family and give them advice as if I was sitting with a family member. I’m the oldest of 6 brothers and sisters. When my mother went looking for financial advice many years ago, she was sold expensive and unnecessary insurance products versus receiving advice that would have set her up for an abundant future. And when I was in my late 20’s, and was finally making a good salary with stock options, I couldn’t find anyone to help me that wasn’t trying to sell me a product. I founded Keep It Simple Financial Planning to help people with fiduciary advice and guidance without my clients wondering if I was making a recommendation to earn a commission. Another huge passion of mine is financial literacy. Most, if not ALL of us did not receive any financial education in school and had to learn everything we currently know about finances on our own. To combat the lack of education in our communities, I've partnered with a nonprofit IDEAL CDC to provide financial education in many communities and schools in Southern California. If you would like to schedule a complimentary retirement consultation, please go to keepitsimplefinancial.com/talk


*Disclosures*
KIS Financial Planning, LLC dba Keep It Simple Financial Planning is a registered investment adviser offering advisory services in the States of California, Texas, and Louisiana and in other jurisdictions where exempted. Registration does not imply a certain level of skill or training. The information shared on this page shall not be directly or indirectly interpreted as a solicitation of investment advisory services to persons of another jurisdiction unless otherwise permitted by statute.

10/06/2026

Deciding how much to convert to a Roth is half the decision. The other half is where the tax money comes from.

You have two basic choices.

The first is to have tax withheld from the conversion itself. It's simple, but the withheld money never reaches the Roth. If you're under 59½, that withheld amount can also be hit with a 10% early withdrawal penalty.

The second is to pay the tax from savings outside the IRA. The full conversion lands in the Roth and grows tax-free from there.

Paying from outside money works like an extra Roth contribution stacked on top of the conversion. Every dollar of tax you pay from your checking account is a dollar of the conversion that stays in the Roth.

If you're planning a conversion before December 31 and haven't settled how the tax gets paid, send me a message and we can talk it through.

How much you convert decides your tax bill. How you pay it decides how much of the conversion actually works for you.

10/02/2026

Three reasons Roth conversions come up in almost every plan I build for people in their 60s.

First, required minimum distributions. Whatever stays in pretax accounts eventually has to come out on the IRS's schedule, whether you need the income that year or not.

Second, the surviving spouse. When one spouse passes, the other moves to single filer tax brackets, often paying a higher rate on less income.

Third, your kids. Most non-spouse heirs have to empty an inherited IRA within ten years, usually during their own peak earning years.

None of these depend on where tax rates go next year. They're built into how the rules work.

I put together a Roth Conversion Window Worksheet that walks through these questions for your own situation. If you'd like a copy, send me a message and I'll share it.

09/30/2026

How much should you convert to a Roth this year? The honest answer is that it depends on what else the income touches.

A conversion adds to your taxable income for the year. That extra income can ripple into places people don't expect.

Your tax bracket. Converting up to the top of a bracket is very different from spilling into the next one.

Your Social Security. More income can mean more of your benefit becomes taxable, up to 85% of it.

Your Medicare premiums. IRMAA looks back two years, so a 2026 conversion can raise what you pay for Medicare in 2028.

Your health insurance. If you're under 65 and buying coverage on the marketplace, conversion income can reduce your premium subsidy.

The right number is rarely "as much as possible" or "nothing." It's the amount that fits around everything else happening that year.

Has anyone ever mapped out what a conversion would actually touch in your situation?

09/29/2026

A lot of people wait until they're sitting with their tax preparer in April to ask about Roth conversions.

By then, it's too late for that year.

Unlike IRA contributions, a Roth conversion counts for the calendar year it happens in. Anything you want counted for 2026 needs to be completed by December 31.

The planning happens in the fall. The paperwork happens in the spring.

09/28/2026

Most retirement questions are really coordination questions.

When to claim Social Security. Which accounts to draw from first. How much to convert to Roth, and in which years. Each answer changes the others.

That is why we plan these decisions together instead of one at a time.

09/25/2026

To learn more about our retirement coordination services go to keepitsimplefinancial.com

09/25/2026

Retirement, coordinated

Schedule an initial consultation at keepitsimplefinancial.com

One of the biggest retirement surprises isn’t taxes.It’s Medicare premiums.More specifically, it’s something called IRMA...
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

The most common mistake I see in retirement is not overspending. It is underspending, and it costs people in a way no ac...
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..

Retirement is not a math problem. It is a coordination problem.The math is the easy part. Any free calculator will hand ...
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]

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