Nate Lewis CFP professional, EA

10/10/2026

Do you want the IRS creating your Retirement Plan for you?

When you start taking RMDs they are locking things in for you.

The longer you wait, the more things get locked in.

Yes, I made the conspiracy board meme.
Red string and all 🔍

Because these deadlines really are connected.

And people at 55 don't care about IRMAA or RMDs. Because who knows what those acronyms actaully mean?

Like this:

At 55, you build your plan and give yourself time to make changes.
At 63, your income matters more than most people think.
At 65, Medicare shows up with coverage choices and costs.
Somewhere in there, you pick a Social Security age.
At 73 or 75, RMDs start, depending on your birth year.

🏥 Medicare generally uses your income from two years earlier
📈 So a big Roth conversion at 63 can raise your premiums at 65
💼 A large 401k withdrawal can do the same thing
🫥 And IRMAA does not care that it was a “one-time” move

That is why the deadlines come later, but the planning starts now (should start before 55).

A better order usually looks more like this:

🗓️ Map your income from 62 to 75 before you touch anything
🔁 Time Roth conversions around the IRMAA thresholds
💵 Decide which accounts pay the bills when your paycheck stops
🪣 Use all 3 tax buckets: Roth, deferred, taxable

Social Security timing fits into that same picture.
Claim early, and you may have less room for conversions.
Claim later, and those bridge years may be your lowest-tax window.

None of this works well if you start at 72.

(Under current rules, anyway. Congress loves to move the goalposts.)

You need a timeline for these deadlines and decisions.

If this has you wondering, “What should I be doing now?” start here.

My free guide, Your First 90 Days to a Confident Retirement, walks through organizing your accounts, planning retirement income, and connecting the tax and Medicare decisions that are easy to overlook.

You don’t have to figure it all out today. Start with the checklist.

Get your copy in my profile, there is a pinned post for it. Or just send me a DM.

10/09/2026

Last night I turned off the lights at the little league field for the last time this year.

Fall ball is over.
Baseball is done for the year.

I stood there for a minute after the scoreboard went dark, keys in my hand, listening to the parking lot empty out in Tuscola.

Another year in the books.

Where did it go?

In March we were raking the infield and arguing about who forgot the chalk.
Now it is October and I am packing up helmets (and one lonely waterbottle nobody claims).

By March we are at the field.
Now it is October already.

I keep telling people in their 50s and 60s the same thing:

Live your life like you have a future.
But understand the future gets here FAST.

A lot of people plan like retirement is always “someday.”

Then one Tuesday, HR calls.
Or the body says enough.
Or retirement showed up before you were ready.

At some point, most of your life will be behind you instead of still out in front of you.

For some of you, that point already happened.

That is not a sad thing.

It just means questions change:
👉 When do you claim Social Security
👉 Where does the money come from when your paycheck stops
👉 How do Medicare and taxes fit into the picture
👉 What do you actually want those years to look like

You don't usually get extra innings on time.

So enjoy the season you are in.
Coach the game.
Buy the kids a snow cone.
And make the decisions that let you enjoy the next season too.

⚾ What does your windshield look like right now?

10/09/2026

Can two retirees earn the same average return and still end up differently?

Yes.

Picture two people who both average 8% a year over a 25-year retirement. Same portfolio. Same withdrawals. On a spreadsheet, they look identical.

In real life, they are not.

Retiree A gets hit with bad markets in the first few years 📉

They still need income when the paycheck stops, so they sell investments while prices are down.

That hurts.

Those shares are gone. When the market recovers, Retiree A has fewer shares left to benefit from it.

Retiree B gets those same ugly years later, after the portfolio already had time to grow.

Same average return.
Very different ending.

👉That is sequence of returns risk.👈

A lot of people hear “just pick good investments and stay the course” and think that covers everything.

It does not.

Good investments matter. But the ORDER of returns can matter just as much once you start taking money out.

So what actually helps?

↳ A withdrawal strategy
↳ Tax planning across your tax buckets
↳ Cash reserves (so you are not forced to sell low)
↳ Flexibility on spending

The first 5 years of retirement can shape the next 25.

Your plan needs to account for that.

That is planning.

For more like this, sign up for my "From 401k to Financial Freedom" newsletter. There is a pinned post in my profile, or just send me a DM.

10/08/2026

“I’m just keeping the same Medicare plan.” That’s fine. Have you checked what’s changing? Have you seen any of the new plans? Your plan can keep the same name while changing what you pay, which prescriptions it covers, or which doctors are in its network. You might still have the right plan for 2027. But it’s worth checking before you’re standing at the pharmacy wondering why something costs more. I’m sharing a free Simple 3-Step Medicare Guide to help you understand your options and what to look at before choosing coverage. If your parents or grandparents are on Medicare, forward this to them or tag them below. Especially if they’re the “I already took care of that years ago” type. 🙂

There is a short window where you could save money

10/08/2026

🙄 A lot of retirees are letting the IRS build their retirement income plan for them. Are you going to be one of them???

Nobody does that on purpose.
It just sort of happens 🔍

Like this:

You retire with most of your money sitting in a 401k.
You live off cash for a few years.
You wait.
Then age 73 shows up.

Now required minimum distributions decide how much income lands on your tax return, whether you need it or not.

That often looks like this:

💼 RMDs stacked on top of Social Security
📈 A higher tax bracket than you expected
🏥 Medicare premiums going up because of IRMAA
🫥 “Why did nobody tell me about this?”

The retirees who worry the least about taxes are usually not the ones who made the most.

They are the ones who made their decisions before the IRS made them.

A better approach usually looks more like this:

🗓️ Use the lower-income years before 73
🔁 Do Roth conversions on purpose
💵 Pull from taxable accounts first
🪣 Then tax-deferred, then Roth money

That part matters more than people realize.

Every dollar you convert in a lower bracket now is one less dollar forced out later at a worse time.

(And usually at a worse rate.)

Your retirement tax bracket is not fixed. It moves based on when you take income and where you take it from.

Yes, the right order depends on your income, your health, your spending, and your goals.

BUT TO BE CLEAR 👉 the IRS is not going to plan this for YOU.

Have you looked at your distribution plan yet?

Get more tips like this in my "From 401k to Financial Freedom Newsletter." New issues go out every sunday night. There is a pinned post in my profile where you can sign up, or just send me a DM.

10/07/2026

💰 Someone with $1 and someone with $50,000,000,000 will not invest the same way. Shocking, I know.

Yet online money content keeps acting surprised.

“Here is what wealthy people are buying.”
“Banks do not want you to know this.”

Come on.

If a bank makes money from a product, they are not hiding it from anybody.

They have:

📣 A marketing department
📄 Brochures
🌐 A website

Trust me, they would love for you to know about it.

And yes, wealthy people often invest differently.

They can handle more risk.
They can tie up more money for years.

They can survive mistakes that would seriously hurt somebody else.

Warren Buffett bought an ENTIRE insurance company largely for the cash float.

Then he bought a controlling interest in a Class I railroad.

(There are only six Class I freight railroads operating in the U.S., by the way.)

Is that on your to-do list this year?

Mine either.

I see this happen all the time:

😬 People copy what the “rich” are doing
📉 Take on risk their plan cannot absorb
💵 Ignore the basic decisions that actually matter

Investing like the “rich” can be too risky for you. Sometimes it is just impossible.

Your money should fit the next stage of your life.

If you are trying to build wealth, focus on decisions that fit your income, your taxes, and your retirement.

So now I’m curious:

❓ What “rich people” investing advice have you seen lately?

❓ Did it actually fit your life?

Drop your answer below.

Rant OVER.

🤔Planning to retire in the next 5-10 years?

Start with Your First 90 Days to a Confident Retirement, it's our guide to show you what your first 90 days of retirement might look like. There is a pinned post in my profile, check it out. Or just send me a DM, i'll send you a copy.

10/07/2026

A Roth conversion can lower your lifetime taxes…
Or quietly make Medicare more expensive. (No Medicare isn't Free)

That’s the part the internet usually skips.

Before doing a Roth conversion, I’d rather someone ask, “What problem are we solving?” than blindly convert money because a YouTube thumbnail said so.

✅ 5 Green Lights
• You’re between retirement and RMD age with temporarily lower income
• You expect future tax rates to rise
• You have significant deductions this year
• You can pay taxes with outside cash (not from the IRA itself)
• You have a long time horizon for the Roth to grow

🚩 3 Red Lights
• The conversion could trigger higher IRMAA brackets (extra Medicare premiums)
• You’re bumping into tax phaseouts or higher brackets
• You’ll need the IRA money soon anyway

Roth conversions aren’t automatically “good” or “bad.” Context matters. Timing matters. Tax buckets matter. (Yes, I’m the guy who says “tax buckets” at dinner.)

I put together a simple decision flowchart:
“Should I Consider Doing a Roth Conversion: A 2-Minute Decision Guide”

Download it here:

This Roth conversion flowchart covers tax brackets, IRMAA, the 5-year rule, and when paying conversion taxes may make sense.

10/06/2026

This may sound strange from a financial advisor who doesn’t hate Dave Ramsey, but: not all debt is the enemy.

I’m also tired of seeing advisors bash Ramsey on debt.

Look,his hardline stance has helped a lot of people get their financial lives back.

However, we can add nuance without dismissing discipline. Every situation is different.

For most people, debt is a treadmill: credit cards, cars, and “buy now, pay later” that quietly taxes their future. That kind of debt steals options and sleep.

But debt can also be a power tool. Like any power tool, it’s dangerous if you don’t know how to use it. When clients ask about using debt to build wealth, we run a quick framework:

☑️Purpose: Will this debt buy an asset that appreciates or produces income?
☑️Proof: Do the numbers work after taxes, interest, and reserves?
☑️Protection: What’s the plan if rates rise, rent drops, or income slows?
☑️Parameters: Caps on leverage, term, and rate.
☑️Payoff: Clear timeline or exit strategy.

If your “debt” buys dinners and gadgets, it’s a drain. If it buys durable cash flow with guardrails and a cushion, it might be a lever.

Whether you’re debt-free or working toward it, the win is peace of mind.

The first 90 days of retirement are where that peace either takes root or gets shaken.

I put together a free guide. Your First 90 Days to a Confident Retirement, that shows you what to do first, what can wait, and how to avoid the big “gotchas.”

Grab your own copy, there is a link in the pinned posts in my profile. Or send me a dm.

10/06/2026

You’ve spent 30+ years growing your 401(k).
But the moment you retire, it stops being a savings plan… and becomes a tax plan.

That’s the surprise most people miss.

Every dollar in your 401(k) comes with a built-in tax bill — one the IRS can change whenever it likes.

It’s like climbing a mountain only to realize the descent is steeper than the climb.

The last five years before retirement are when the real planning begins:
✅ Roth conversions are on the table.
✅ RMD planning starts early.
✅ Social Security timing becomes a tax strategy.
✅ Medicare income thresholds suddenly matter.

If you wait until you retire to think about taxes, you’ve waited too long.

The tax code rewards the proactive, not the reactive.

And the difference between those two can easily be a lot over your retirement.

That’s why I built a simple guide called the Pre-Retirement Checklist — a practical roadmap to coordinate your income, Social Security, healthcare, and taxes before you retire.

If you’re 55–70 and within five to ten years of retirement, DM me to get a copy

10/06/2026

Most people think the magic retirement age is 59½.

Sometimes it’s actually 55.

I’ve seen people accidentally lock themselves out of their own retirement money because they rolled their 401(k) into an IRA right after leaving work.

Here’s the problem with that.

If you leave your job in the year you turn 55 or later, you may be able to access your current employer’s 401(k) without the 10% early withdrawal penalty.

But that usually does NOT apply to:
• Old 401(k)s
• IRAs
• Your spouse’s retirement accounts

I’ve seen one rollover mistake cost early retirees $10,000–$50,000 in unnecessary penalties and taxes.

The biggest retirement mistakes usually happen right after someone leaves work:
• Rolling over the wrong account
• Pulling income from the wrong place
• Starting Social Security too early
• Having no plan for the gap years before 59½

Retirement isn’t just about building wealth.

It’s about knowing how to use it efficiently once the paycheck stops.

I have a "From 401k to Financial Freedom" Newsletter.

I've got the signup link as a pinned post in my profile.

Or send me a DM