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.

10/30/2026

Medicare open enrollment runs through December 7, and this is the time of year many people consider switching from Original Medicare with a Medigap supplement to a Medicare Advantage plan. The lower premium can be appealing.

Before making that switch, it helps to understand one rule: in most states, moving to Medicare Advantage is much easier than moving back.

Here's why. When you first enroll in Part B at 65 or older, you get a six-month Medigap Open Enrollment Period. During that window, insurers must sell you any Medigap policy they offer, at their standard price, regardless of your health.

Once that window closes, the protection generally ends. If you leave Medigap for Medicare Advantage and later want to return, insurers in most states can review your health history, charge more, or decline to cover you.

There are exceptions worth knowing.

The trial right. If you join Medicare Advantage when you're first eligible, or drop a Medigap policy to try Medicare Advantage for the first time, you generally have 12 months to switch back to Original Medicare with guaranteed access to Medigap.

State rules. A handful of states, including California, New York, and Connecticut, give residents additional rights to change Medigap coverage.

Plan exits and moves. If your Medicare Advantage plan leaves your area, or you move out of its service area, you may gain guaranteed issue rights.

None of this means one option is better than the other. Medicare Advantage works well for some people, and Original Medicare with Medigap works better for others. It depends on your health, your doctors, where you travel, and how much cost certainty you want. What matters is knowing which Medicare decisions can be reversed later and which can't.

10/29/2026

Here's a Medicare mistake that can raise your premiums for the rest of your life, and it usually starts with a reasonable decision.

Picture someone who retires at 66. Their employer offers COBRA, so they keep the same health plan, the same doctors, the same coverage. It feels like the safe choice. Eighteen months later, COBRA ends and they sign up for Medicare Part B.

That's when they find out they waited too long.

When you stop working after 65, you get an eight-month Special Enrollment Period to sign up for Part B without a penalty. But that clock starts when your job or your active employer coverage ends, whichever comes first. It does not start when COBRA ends. COBRA isn't considered coverage from current employment, so it doesn't extend the window by a single day.

Four things to know:

The penalty is permanent. It's 10% of the standard Part B premium for each full 12-month period you could have had Part B but didn't, and it lasts as long as you have Part B.

It stacks. The penalty is added on top of your regular premium, and on top of any IRMAA surcharge if you pay one.

There can be a gap in coverage. Miss the window and you may have to wait for the General Enrollment Period, January through March, with coverage starting the month after you sign up.

Retiree health coverage doesn't stop the clock either. Like COBRA, it isn't coverage from current employment.

The fix is simple when it's timed right: enroll in Part B within eight months of leaving work. If you want to keep COBRA for a while too, check how your plan coordinates with Medicare, since some plans end or pay second once Medicare starts.

Did you know COBRA doesn't count for Medicare enrollment?

10/28/2026

Turning 65 doesn't always mean you have to sign up for Medicare Part B. But whether you can safely wait depends on details most people never check.

If you're still working at 65 and covered by your employer's health plan, you may be able to delay Part B without a penalty. Three conditions decide it.

The coverage has to come from current employment, yours or your spouse's. COBRA and retiree plans don't qualify.

The employer has to have 20 or more employees. At a large employer, the group plan pays first and Medicare pays second. At a smaller employer, Medicare is generally expected to pay first. If you skip Part B there, the employer plan may refuse to pay claims Medicare would have covered, and a late enrollment penalty can start building from your 65th birthday.

You have to enroll on time when the job ends. You get eight months from the end of employment or employer coverage, whichever comes first.

One more detail catches people who are saving in a health savings account. Once you're enrolled in any part of Medicare, including premium-free Part A, you can no longer contribute to an HSA. And if you sign up for Part A after 65, it's usually backdated up to six months, though not earlier than the month you turned 65. Contributions made during those months can be treated as excess contributions, so the common approach is to stop HSA contributions six months before you enroll.

There's also a trap in how Part A starts. If you claim Social Security at 65 or later, you're enrolled in Part A automatically. That alone ends HSA eligibility, even if you're still on your employer's plan.

The right answer depends on your employer's size, what your plan costs compared to Medicare, and whether you or your spouse are still contributing to an HSA. All three are worth checking before your 65th birthday, not after.

Are you planning to keep working past 65?

10/23/2026

There's one part of Social Security that never gets a cost-of-living adjustment: the income thresholds that decide whether your benefits are taxed.

Here's how it works. Social Security looks at your provisional income, which is your adjusted gross income, plus any tax-exempt interest, plus half of your Social Security benefits.

If you file jointly and that number is over $32,000, up to 50% of your benefits can become taxable. Over $44,000, up to 85% can. For single filers, the thresholds are $25,000 and $34,000.

Those numbers were set in 1983 and 1993. They have never been adjusted for inflation.

Benefits, on the other hand, rise with every COLA, including the 3.6% coming in January. So each year, more retirees find a larger share of their Social Security being taxed, even when their real income hasn't changed.

It gets more expensive in the range where benefits are becoming taxable. There, each extra dollar of IRA withdrawals can pull up to 85 cents of Social Security into taxable income along with it. For someone in the 22% bracket, an extra $1,000 withdrawn can be taxed as if it were $1,850. That's an effective rate of about 40.7%, nearly double the bracket they think they're in.

This is often called the tax torpedo, and it's a common surprise in retirement tax planning.

A few ways to plan around it:

Roth conversions in the years before Social Security and RMDs begin can shrink the pretax balances that create this income later.

Qualified Roth withdrawals don't count toward provisional income at all.

After age 70½, qualified charitable distributions from an IRA can cover charitable giving without adding to your income.

The order you draw from accounts each year can keep income below the range where the torpedo hits hardest.

I put together a Roth Conversion Window Worksheet that walks through the years when conversions tend to make the most sense, before Social Security and RMDs start stacking income on top of each other. If you'd like a copy, send me a message and I'll share it.

10/21/2026

A question that comes up every fall: if I wait to claim Social Security, do I miss out on the COLA?

It's a reasonable worry, especially this year. The 2027 cost-of-living adjustment is 3.6%, the largest in four years. Nobody wants to leave that on the table.

The good news is you don't. Here's why.

Your Social Security benefit starts with a number called your primary insurance amount. It's the monthly benefit you'd receive at full retirement age, calculated from your 35 highest-earning years.

Starting in the year you turn 62, that amount receives every COLA, whether you've claimed or not. So if you're 64 and haven't filed yet, the 3.6% increase still gets built into your future benefit. You don't have to be collecting to receive it.

That means the claiming decision should be made on its own merits, not because of a COLA. A few of the factors that actually matter:

Delayed retirement credits. Waiting past full retirement age adds 8% a year to your benefit, up to age 70. Those credits are on top of every COLA you receive along the way.

The survivor benefit. If you're married, the higher earner's benefit often becomes the surviving spouse's benefit. Delaying that benefit can raise the income the survivor lives on for the rest of their life.

The earnings test. If you claim before full retirement age and keep working, Social Security withholds $1 of benefits for every $2 you earn above $25,560 in 2027.

Your tax picture. Claiming earlier adds taxable income in the years between retirement and required minimum distributions, which are often the best years for Roth conversions.

Each of these deserves more weight than the COLA, which you'll receive either way.

Did you think you had to be collecting Social Security to receive the COLA?

10/19/2026

Social Security announced the 2027 cost-of-living adjustment on Wednesday: 3.6%. It's the largest increase in four years.

Here's what that means for your check, and what can shrink it.

How it's calculated. The COLA is based on inflation. Social Security compares the average Consumer Price Index for Urban Wage Earners (CPI-W) for July through September this year with the same three months last year. The 3.6% applies to your full benefit, so the dollar increase depends on what you receive today.

What it looks like. Social Security estimates the average retired worker's benefit will rise from $2,095 to $2,170 a month, about $75 more. For a couple both receiving benefits, the average rises from $3,238 to $3,355. If your benefit is $2,500 today, 3.6% adds $90 a month.

When it arrives. The increase shows up in the payment you receive in January 2027. Social Security will mail a personalized notice in early December with your exact new amount, and it will also appear in your my Social Security account online.

What can shrink it. If you're on Medicare, your Part B premium is usually deducted from your Social Security payment before it reaches you. In 2026 the standard Part B premium is $202.90 a month. The 2027 premium hasn't been announced yet. It typically comes out in November, and any increase comes out of your raise.

For most people, a rule called hold harmless keeps a Part B increase from shrinking your net payment below what it was the year before. But it doesn't protect everyone. People paying IRMAA surcharges, people new to Medicare, and people who don't have their premium deducted from Social Security aren't covered by it.

So the number that matters isn't 3.6%. It's what lands in your account in January after Medicare takes its share.

Do you have your Medicare premium taken out of your Social Security check, or do you pay it separately?

10/15/2026

Most people find out about IRMAA from a letter from Social Security. By the time it arrives, the income that triggered it is two years old, and nothing can change that year anymore.

IRMAA is the income surcharge added to Medicare Part B and Part D premiums. It's based on your modified adjusted gross income from two years earlier, so the income you report for 2026 sets your premiums for 2028.

That means the time to plan is before the income happens. In retirement, it usually comes from four places.

Roth conversions. Every dollar you convert counts as income in the year you convert it. A conversion that makes sense on its own can still push you over an IRMAA threshold and raise your premiums two years later. That doesn't mean you shouldn't convert. It means the amount should be sized with the threshold in view, and in some years it makes sense to stop just short of one.

Capital gains. Selling a rental, a large stock position, or a home with a gain above the exclusion can create a one-time jump in income. These don't qualify for the SSA-44 appeal, so timing is the main protection. Spreading a sale across two tax years, or pairing gains with losses, can keep a single year from jumping a tier.

Required minimum distributions. Once RMDs begin, they put a floor under your income every year. Large pretax balances can mean RMDs that land above a threshold year after year. Conversions in the years before RMDs start are one way to lower that floor.

Which account you spend from. Withdrawals from a traditional IRA count as income. Qualified Roth withdrawals and cash savings don't, and a sale in a brokerage account only counts the gain. Drawing next year's spending from the right mix of accounts can keep income below a threshold without changing how much you spend.

Each of these shows up on your tax return, and each can change what you pay for Medicare. That's why we model IRMAA in every plan before any of these decisions are made.

I put together a Medicare & IRMAA Planning Guide that walks through the thresholds, the two-year lookback, and the appeal process. If you'd like a copy, comment Medicare below and I'll share it.

10/13/2026

Here's a Medicare surprise that catches a lot of new retirees.

Medicare premiums are based on your income from two years ago. Your 2026 premiums were set by your 2024 tax return.

So picture someone who retires this year at 65. In 2024, they were still working and earning their highest salary. Medicare looks at that year and adds a surcharge to their premiums, even though the paycheck has stopped.

Four things to know:

The surcharge is a cliff, not a slope. One dollar over a threshold triggers the full surcharge for that tier, for the whole year.

It applies per person. A married couple can both pay it.

It isn't permanent. If your income dropped because you stopped working, you can ask Social Security to use your more recent income instead. The form is called SSA-44, and retirement counts as a qualifying event.

A home sale or a large capital gain does not qualify. Those are the ones to plan around ahead of time.

Did you know about the two-year lookback before you enrolled in Medicare?

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.

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