Nate Lewis CFP professional, EA

05/29/2026

Two retirees can average the exact same return.

One runs out of money.
The other doesn’t.

Here’s how this can happen.

Most people think retirement investing is all about the average return.

That's not always the case.

Imagine two retirees who both average 8% annually over retirement.

Sounds about the same, right?

Sometimes it is.

Sometimes it's not even close.

If Retiree A gets hit with bad markets in the first few years while simultaneously taking withdrawals, the damage can compound fast.

Because now they are selling investments while prices are down just to generate income.

Meanwhile, Retiree B (Maybe they retired 10 years earlier) experiences those same bad years later in retirement, after the portfolio already had time to grow.

Same average return.
But different outcomes.

That’s called sequence of returns risk.

And it’s one of the biggest reasons retirement planning is more than “pick good investments and hope.”

Withdrawal strategy matters.
Tax planning matters.
Cash reserves matter.
Flexibility matters.

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

Planning helps a lot with that.

If you’re within 5–10 years of retirement, I put together a guide called “Your First 90 Days to a Confident Retirement.”

Download it here: https://lewiswealthmanagementgroup.com/your-first-90-days-to-a-confident-retirement

04/28/2026

Most business owners know they have to pay income taxes.

What surprises them is the “silent partner” they forgot about…

Self-employment tax.

That extra 15.3% for Social Security and Medicare has a way of showing up at the worst possible time.

And if you’re filing a Schedule C, quarterly estimates matter too.

I’ve seen a lot of business owners have a profitable year on paper… only to get blindsided in April because nobody helped them plan for the cash flow side of taxes.

That’s why good tax planning isn’t just about deductions.

It’s about:
✔️ Knowing what to set aside
✔️ Avoiding underpayment penalties
✔️ Building a system so tax season doesn’t become a financial emergency
✔️ Coordinating retirement, deductions, and entity structure decisions over time

The IRS may be your “silent partner”…

But that doesn’t mean they should control your business cash flow.

Sign up for our "Deduct This!" Newsletter.

Practical tax and cash-flow insights for small business owners who want clean numbers, fewer surprises, and better decisions year-round. From Nate Lewis CFP® EA, a local Certified Financial Planner™ and Enrolled Agent.

04/17/2026

Gas prices went up again…⛽☝️☝️☝️

And it’s not just about the extra $10–$20 at the pump.

It’s what it starts to feel like.

Like everything is getting more expensive.
Like something bigger might be changing.
Like you should maybe… do something differently.

That feeling?

You’re not imagining it.

But here’s the part most people miss…

Not every “warning sign” actually means you need to change your plan.

Some of the loudest signals (like gas prices) are also the fastest to change.

And reacting to them the wrong way can do more harm than good.

I wrote a quick breakdown on this because I’m seeing it come up more and more in conversations.

👉 When prices feel like a warning sign, what should you actually do?

When Prices Feel Like a Warning Sign

04/16/2026

Most people don’t realize this until it’s too late…

They make ONE simple Social Security decision…
And it quietly costs them tens of thousands of dollars.

I recently sat down with a couple who were ready to retire.
They had done everything right.

But one small decision about when to claim Social Security?
It was going to cost them over $180,000.

Not because they were careless.
Because no one had shown them how the system actually works.

Here’s the truth:

There is no “perfect age” that works for everyone

But there are costly mistakes you can avoid.

👉 I just broke down the 10 biggest Social Security mistakes in my latest article.

If you’re within 5–10 years of retirement… this is worth your time.

It’s how you claim Social Security… and most people get it wrong

03/25/2026

Health Alliance is gone for 2026.

And if you had it, you’re now in the same position as a lot of people I’ve talked to lately:

👉 “I guess I need to pick something… but I’m not really sure what I’m picking.”

That’s where problems start.

Because most Medicare mistakes don’t show up right away.

They show up later…

When:
• Your doctor isn’t in-network
• You need approval for something and didn’t expect it
• Or your costs don’t work the way you thought they would

And by then… you’re stuck with it for the year.

I’ve already had a few conversations with people who liked their old plan…
and now feel like they’re starting over from scratch.

If that’s you, here’s the good news:

You don’t need to guess.

You just need to understand how the options actually work before you pick one.

What a recent survey revealed... and why it matters more in Champaign this year.

03/25/2026

Most business owners don’t worry about payroll.

Until something goes wrong.

I’ve seen it happen more than once…

Someone tries to “save money” by doing payroll themselves.
They miss a filing.
Or misclassify something.
Or forget about a deadline they didn’t even know existed.

At first, nothing happens.

Then one day… a letter shows up.

And it’s not a small problem anymore.

Penalties.
Interest.
Stress.
Time wasted trying to fix something that never should’ve been broken in the first place.

The frustrating part?

Most of these issues are completely avoidable.

Payroll isn’t hard because the math is complicated.
It’s hard because the rules are.

And the IRS doesn’t really care if it was an honest mistake.

If you run a business, this is one of those areas where “hoping it’s right” can get expensive fast.

I broke this down in this week’s newsletter, including what actually went wrong and how to avoid it:

👉 https://deduct-this-203c40.beehiiv.com/p/he-thought-payroll-was-simple-until-the-irs-showed-up

If you want more stories like this (and how to avoid them), make sure you’re on the list.

One small payroll mistake can turn into a very big problem

03/20/2026

Most people don’t realize their 401(k) has turned into a junk drawer.

You log in once or twice a year…
Maybe glance at the balance…
Then move on.

But underneath that number?

Old funds you picked years ago.
New funds you added without a real plan.
Allocations that don’t match where you are today.

It’s not broken…

But it’s not exactly working together either.

And that’s how it happens.

Not one big mistake.
Just years of small decisions… stacking up.

Until one day, you open it up and think:

“How did this get so messy?”

I see this all the time.

People are saving.
Doing the right things.

But their 401(k) looks more like a collection of random choices than an actual strategy.

And that matters more than most people think.

Because when things aren’t aligned…
You can take more risk than you realize.
Or not enough.
Or just drift for years without a clear direction.

This Sunday in my From 401k to Financial Freedom Newsletter, I’m sending out a quick breakdown on:

How to clean up your finances
And make sure your 401(k) isn’t just a financial junk drawer

If you’re not on the list yet, now’s a good time to fix that. 👇

https://from-401k-to-financial-freedom.beehiiv.com/

03/17/2026

A lot of people in our area got the rug pulled out from under them this year.

Health Alliance Medicare Advantage plans are gone for 2026.

And I keep hearing the same thing:

“I thought I finally had Medicare figured out…”

Now they’re trying to pick a new plan… without really knowing how it works.

That’s the part most people don’t talk about.

It’s not just switching plans.
It’s:
• New networks
• Different drug coverage
• New out-of-pocket risks

And once you pick… you’re kind of stuck with it for the year.

If you had to switch (or just aren’t sure what you ended up with), it’s worth taking another look before something surprises you later.

A lot of people in Central Illinois got an unpleasant surprise this year.

03/13/2026

A few months ago I reviewed someone’s 401(k).

They were doing a lot of things right.

They saved consistently.
They followed the markets.
They even had strong opinions about Roth vs Traditional.

But one small detail jumped out.

They were contributing 3%.

Their employer matched 6%.

They had been doing that… for years.

Which means every single paycheck they were leaving part of the employer match behind.

It’s funny.

People spend hours debating things like:

• Roth vs Traditional
• Real estate vs stocks
• Crypto vs index funds

Meanwhile the most powerful feature in many 401(k) plans quietly gets ignored.

The employer match.

I wrote a short piece about this today after seeing it happen again recently.

It explains why the match is often the first thing people should focus on before they worry about fancy strategies.

Because sometimes the biggest retirement mistake isn’t complicated.

It’s just a checkbox that never got adjusted.

Sign up for my From 401k to Financial Freedom newsletter, it gets sent out Sunday night.

401kFriday

https://from-401k-to-financial-freedom.beehiiv.com/

03/13/2026

If you followed the financial news last week, the headlines moved quickly.

Tariffs were struck down by the courts…
Then reintroduced under a different authority…
Then increased again shortly after.

Markets responded.

Stocks moved lower while some investors shifted toward traditional safe-haven assets like bonds and gold.

But moments like this raise an important question:

What actually changed?

In this post From 401(k) to Financial Freedom newsletter, I break down:

• What happened with the tariff ruling
• Why markets reacted the way they did
• What long-term investors should keep in mind

Because when headlines move quickly, it’s often helpful to step back and focus on the bigger picture.

You can read it here:

A closer look at the policy changes behind last week’s headlines.

03/07/2026

🛍️ It’s Small Business Saturday.

So let me ask you something…

What kind of business owner are you?

Not your industry.
Not your revenue.
Not how many employees you have.

I mean how you operate.

Are you the:
• Spreadsheet-everything, knows-your-margins-to-the-penny type?
• “I’ll deal with taxes in March” type?
• Growth-at-all-costs type?
• DIY-it-all type?

Because here’s what I’ve learned working with small business owners around Central Illinois:

Your personality around money quietly shapes your profits, your stress level, and your tax bill.

Two owners can make the exact same revenue…
One builds wealth.
The other builds anxiety.

That’s why I put this together 👇

👉 “Which Type of Business Owner Are You?”

It’s quick.
It’s practical.
And you’ll probably see yourself in it immediately.

Read it here:
🔗 https://deduct-this-203c40.beehiiv.com/p/which-type-of-business-owner-are-you

If you’re running a small business today, read it.

And if you know another business owner who needs to tighten up their numbers before year-end… tag them or send this their way.

Happy Small Business Saturday.

Let’s make sure you’re not just working hard…

…but keeping more of what you earn.

You personality might be hurting your cashflow 😬