Jason J. Hamilton, CFP - Keep It Simple Financial

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, regi

stered 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.

06/18/2026

Most people I work with are smart, capable, and have done a lot of things right.

They're not one bad decision away from running out of money. That's not the issue.

The issue is what happens when good decisions get made in isolation, without anyone connecting the dots between them.

Social Security timing gets decided based on one set of assumptions. Withdrawal order gets set up based on something else. Tax planning happens once a year in April, after the fact. Medicare enrollment happens when it happens.

Each decision, on its own, looks reasonable.

But retirement doesn't work in silos. Every one of those decisions affects the others, sometimes significantly. And when they don't talk to each other, the gaps add up.

After hundreds of webinars and thousands of conversations, here's the pattern I see most often:

People who could have meaningfully reduced their lifetime tax bill through Roth conversions, withdrawal sequencing, and proactive healthcare planning didn't.

Not because they made a terrible mistake. Because the decisions were made one at a time, without a full picture of how they fit together.

They also stayed more conservative with their spending than their own numbers ever required.

Without a coordinated plan, playing it safe felt like the only responsible choice.

So the years when they were most capable of spending, the early active years of retirement, quietly passed.

None of this is a failure of intelligence. It's a coordination problem.

The default path is simply more expensive than it needs to be.

That's what I try to help people see before it becomes too late to change the outcome.

If you're within five years of retirement and your accounts, income sources, and tax situation have never been looked at together in the same conversation, that's worth addressing.

I created a free 30-minute masterclass to help you learn more about retirement coordination and some of the gotchas to look out for. (Link in comments)

Register, and if it sounds like what you've been missing, there will be a link to schedule a call down below

Jason Hamilton, CFP® | Keep It Simple Financial Planning

06/10/2026

If your financial advisor says “your Monte Carlo needs to be at 90% before you can retire and you can only spend 4% annually” I can confidently say you are missing out on living your best life.

05/30/2026

After the 2008 crisis, my parents learned their 'financial advisor' was just an insurance agent. They lost years of savings to whole life policies instead of growth investments. A hard lesson in why choosing fiduciary financial guidance is so important.

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.

04/28/2026

A lot of people think they’ll feel confident once they hit their retirement number.

But that’s not usually how it works.

I’ve seen people hit their goal… and still hesitate.

Still question the timing.
Still wonder if they should wait.
Still feel unsure about what comes next.

Because confidence doesn’t automatically come from the number.

It comes from understanding what the number actually does.

How it turns into income.
How it holds up if markets change.
How decisions get made once the paychecks stop.

Without that clarity, the number can feel abstract.

Even if it’s more than enough.

That’s why some people keep moving the goalpost.

“Maybe just one more year.”
“Maybe a little more saved.”
“Maybe after the next good market.”

Not because they need it.

Because they don’t feel ready.

There’s a difference between being financially ready…

And feeling ready.

One is math.

The other is clarity.

And most of the time, the people who feel the most confident in retirement aren’t the ones with the highest number.

They’re the ones who understand how their plan works.

What decisions they’ll make.

And how they’ll adjust if things don’t go perfectly.

Because confidence isn’t built by reaching a number.

It’s built by knowing what happens next.

04/24/2026

One of the most common questions I hear when the market hits new highs is:

“Should I wait to invest?”

It feels logical.

If the market is at an all-time high… wouldn’t it make sense to wait for a pullback?

The problem is, that thinking assumes something that isn’t actually true.

It assumes that “high” means “about to go down.”

But historically, markets spend a lot of time at or near all-time highs.

That’s what growing markets do.

They make new highs… over and over again… across time.

What’s really going on here isn’t a market problem.

It’s a time horizon problem.

When people ask, “Should I invest now or wait?” they’re usually thinking in short-term terms.

What happens over the next few months?
What if I invest and it drops right after?

But long-term investing doesn’t work on that timeline.

If your plan is built around years or decades, the exact entry point becomes much less important than people think.

Because over longer periods of time, what tends to matter more is:

Time in the market… not timing the market.

That doesn’t mean timing never matters.

It just means it’s very difficult to do consistently.

And waiting for the “perfect” moment often leads to staying on the sidelines longer than intended.

A better question isn’t:

“Is now the perfect time to invest?”

It’s:

“Do I have a plan for how I invest over time, regardless of where the market is today?”

Because investing shouldn’t be a one-time decision.

It should be a process.

One that accounts for different market environments.

One that continues whether markets are up, down, or somewhere in between.

The goal isn’t to guess the next move.

It’s to build a strategy that doesn’t depend on getting that guess right.

Because markets will always give you reasons to wait.

And if you’re always waiting for more certainty…

You may end up missing the very thing you were trying to capture in the first place.

04/23/2026

A lot of retirement decisions come down to one tension:

Enjoy now… or protect later.

And most people feel like they have to pick a side.

But in a well-built plan, that’s not really the goal.

The goal is to create a structure that allows for both.

Because “now” and “later” aren’t equal in every phase of retirement.

The early years often have something unique: more health, more energy, more flexibility.

That’s when people tend to travel more, do more, and experience more.

Later years often require something different: stability, simplicity, and a plan that can sustain itself with less effort.

So instead of asking, “Should I spend now or later?”

A better question becomes:

“How do I align my resources with the seasons of my life?”

That’s where planning shifts.

Maybe that means allowing for slightly higher spending early on, with the understanding that it tapers later.

Maybe it means structuring income so that essential expenses are always covered, while discretionary spending can flex.

Maybe it means building in guardrails so that if markets don’t cooperate, small adjustments can be made without disrupting everything.

The point is, you don’t solve this by guessing.

You solve it by designing a plan that accounts for both.

Because the real risk isn’t just spending too much early.

It’s also being too cautious during the years when life is most active.

The best plans don’t maximize one at the expense of the other.

They coordinate both.

If you’re trying to figure out what that balance looks like for you, put your #1 question below in the comments and I’ll give you my perspective based on my experience.

04/21/2026

It’s interesting to see how people answer that question.

Some of you lean toward enjoying more now. Others prefer building more cushion first.

And honestly, both instincts make sense.

Because this isn’t really a financial decision.

It’s a tradeoff between time and certainty.

The “enjoy now” group understands something important: the early years of retirement are often the most active. Health, energy, and flexibility tend to be highest then. Those years don’t come back.

The “wait” group understands something just as important: having more margin can create peace of mind. A stronger buffer can make the rest of retirement feel more secure.

Neither side is wrong.

But where people can get stuck is thinking they have to choose one extreme or the other.

All now… or all later.

In reality, most good retirement plans blend both.

You don’t have to fully delay enjoyment to be responsible.

And you don’t have to ignore the future to enjoy the present.

This is where planning becomes less about picking a side…

And more about finding the balance.

How much can you enjoy now without putting pressure on later?

How much margin do you really need to feel comfortable?

What tradeoffs are actually worth making?

Because the goal isn’t to win an argument between “now” and “later.”

It’s to build a plan where both are accounted for.

That’s usually where clarity—and confidence—start to come together.

04/20/2026

Imagine two people, both 62, both with similar savings.

Person A retires now. They start Social Security early, keep withdrawals modest, and prioritize enjoying the first 5–10 years while their health and energy are high.

Person B waits. They delay retirement a few more years, delay Social Security, and continue building a larger financial cushion before stepping away.

On paper, both strategies can work.

Both can be “right.”

But they lead to very different experiences.

One prioritizes time now.
The other prioritizes more certainty later.

And most people feel pulled in both directions.

Part of them says, “We’ve worked hard, let’s enjoy it.”
Another part says, “What if we need more later?”

That tension is completely normal.

There’s rarely a perfect answer.

But there is usually a better answer for you based on your values, your priorities, and how you want to spend this next phase of life.

I’m curious…

Which direction do you find yourself leaning toward right now—enjoying more sooner, or building more cushion first?

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