Nate Lewis CFP professional, EA

06/11/2026

Most people think the people who win in retirement are the ones who get the best investment returns.

Sometimes.

But that's not usually what I see.

The retirees who seem the most confident and least stressed often aren't the ones chasing the hottest stock or trying to predict the next market move.

They're the ones who:

✅ Know where their income is coming from

✅ Have a plan for taxes

✅ Understand Medicare and Social Security

✅ Keep enough cash for surprises

✅ Make decisions before they become emergencies

Retirement isn't just an investment problem.

It's an income problem.

A tax problem.

A healthcare problem.

And sometimes a "what do I do now?" problem.

The people who usually win aren't necessarily the smartest investors.

They're the people who prepare for more than just the market.

I wrote more about it here:

👇

https://from-401k-to-financial-freedom.beehiiv.com/p/the-people-who-usually-win-retirement

What do you think is the biggest challenge people face in retirement?

They just tend to make fewer expensive mistakes in the decade before retirement.

06/10/2026

Why DIY Financial Planning (and DIY Financial Planning with AI) Can Be Dangerous

We live in a world with an abundance of information.
📺YouTube.
🧑‍💻Blogs.
🎧Podcasts.
🤖ChatGPT.

The “Do-It-Yourself” approach feels empowering. More control. Fewer fees. What could go wrong?

Plenty.

I once tackled a home project thinking YouTube would carry me. It started easy… then got messy. The “cheap DIY” turned expensive and time-consuming. A pro finished it—better and faster than I could have.

That’s the trap with DIY financial planning.

Surface-level info can look right while missing the critical details:
💸Tax interactions
⌛Timing of withdrawals
👵IRMAA thresholds
💰RMD sequencing
🤦‍♂️Capital gain “gotchas”
⚖️Estate and beneficiary quirks

Now add AI to the mix…

I’ve played around with AI. A lot actually

I asked AI about the contents of a restaurant menu, and what i should eat based on the diet I was trying. It confidently listed items that weren’t on the menu. Just made them up.

I uploaded a PDF and asked questions. The answers didn’t match the document… then the AI admitted it never actually opened it.

AI sounds authoritative, even when it’s wrong.

AI is a tool, not a tailored plan. It doesn’t know all your variables, goals, and trade-offs. And it can’t own the consequences of a bad call.

Good financial planning isn’t about finding A strategy, it’s about finding YOUR strategy, and coordinating taxes, investments, Social Security, Medicare, and cash flow so they play nicely together.

Hiring a professional isn’t giving up control. It’s enhancing it, so your decisions are smarter, sequenced, and stress-tested.

I write weekly about retirement planning, taxes, IRMAA, and smart withdrawal strategies in my newsletter, From 401(k) to Financial Freedom. It goes out every Sunday night, written by a local CFP professional and Enrolled Agent with 15 years of experience.

Get on the list here: https://from-401k-to-financial-freedom.beehiiv.com/

06/09/2026

"I missed my chance to do Roth conversions."

I hear that a lot.

Usually from people who are already retired, already on Medicare, or already taking Social Security.

The assumption is:

❌ Roth conversions are only for people in their 50s.

❌ Once retirement starts, the window closes.

❌ If you're already collecting benefits, it's too late.

Not necessarily.

In fact, some retirees may have more opportunities than they realize.

The key isn't your age.

The key is understanding how a conversion could affect things like:

• Taxes

• Medicare premiums (IRMAA)

• Future RMDs

• Your surviving spouse

• Your long-term retirement income plan

Sometimes a Roth conversion makes sense.

Sometimes it doesn't.

The mistake is assuming the answer without running the numbers.

I put together a simple guide and flowchart to help you think through the decision.

👇 Download it here:

https://the-golden-years-playbook.beehiiv.com/p/is-it-too-late-for-roth-conversions

Because "too late" and "not a good fit" are two very different things.

A lot of retirees assume they missed the window. Have you?

06/08/2026

🏆🍕 Congratulations to our Collections Day winners! 🍕🏆

A huge shoutout to Team Iron Bull Taxes for stepping up in a big way at this year's Collection Day! Thanks to their incredible effort and teamwork, they collected the most donations and earned a well-deserved pizza party! 🎉

05/31/2026

Two people can retire with the exact same balance in their savings and investment accounts.

Yet, one can be much better off.

While the other feels trapped every April after they retire.

How can that be?

It's not always about how big your balance is.

It’s about which tax bucket(s) the money is sitting in.

I come across this a lot.

Someone spends 30+ years saving.
• Maxing out the 401(k)
• Getting the company match
• Staying invested
• Building a healthy nest egg

Then retirement shows up…

…and almost all of their money is sitting in the taxable bucket. (Their 401k)

Now every withdrawal stacks on top of:
• Social Security
• Required minimum distributions
• Capital gains
• Medicare IRMAA thresholds

The IRS becomes one of their largest bills in retirement. (It can compete with healthcare)

Meanwhile, someone else with the SAME balance may have spent years intentionally building different tax buckets:
• Pre-tax
• Roth
• Taxable brokerage/cash

Now they have flexibility.

Need extra income one year?
Maybe they pull from the Roth bucket.

Trying to stay below an IRMAA threshold?
Maybe they use the taxable bucket instead.

Want to do some actual tax planning before RMD age?
Now there’s room to maneuver.

Looks similar on paper, but the difference is in the fine print.

Completely different retirement experience.

That’s why the last 5-10 years before retirement matter so much.

At some point, your 401(k) stops being an investment plan.…and starts becoming a tax distribution plan.

For more ways to be more flexible in retirement, sign up for our "From 401k to Financial Freedom Newsletter." It goes out every sunday night, Written by a 15 year experienced financial professional who is both a CFP® professional and Enrolled Agent.

Sign up here https://from-401k-to-financial-freedom.beehiiv.com/?_gl=1*gtbac7*_gcl_au*OTY4NTE1MzU4LjE3NzQyNzg0NTguMjEwMjA5OTg0MC4xNzgwMDcxOTY2LjE3ODAwNzE5NjU.*_ga*MTIzOTkzMjQxLjE3NjY0MzIyODM.*_ga_E6Y4WLQ2EC*czE3ODAwNzE5NTEkbzIyNCRnMSR0MTc4MDA3MTk3MyRqMzgkbDAkaDE1MDkxODYwMDg.

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.