Nate Lewis CFP professional, EA

11/03/2026

Would you let the person you trusted in 1998 handle your money today? Before you answer… you might want to check your estate documents. Because that person could still be listed. Back then, your brother lived down the street. Your kids needed babysitters. And the person you named to handle everything seemed like an obvious choice. Now your brother lives three states away. Your kids have kids. And you haven’t spoken to that “obvious choice” in years. But the paperwork is still sitting in the same folder. I get it. Finishing estate documents feels like finally getting a root canal behind you. Nobody’s eager to revisit the experience. So “we took care of that” becomes the answer for the next twenty years. Meanwhile, life keeps changing. Before you assume your plan still fits, take a look at six common estate planning myths I’m sharing in my latest newsletter. 👇 Click the link below to read it and sign up. Especially if your first thought was, “Who DID we put down?”

Your estate planning assumptions may deserve a review.

11/03/2026

“I’ll deal with that when I’m 65.”

Some of the numbers may already be on a tax return by then.

That’s the problem with retirement planning.

The bill arrives later.
The decision happened earlier.

Medicare generally looks back two years when determining income-related premium surcharges.

And eventually, required minimum distributions can mean taking taxable money out of certain retirement accounts whether you need it for spending or not.

You still have choices.

But waiting can leave you with fewer years to spread income out and compare strategies.

This doesn’t mean everyone should rush into a Roth conversion.

Or delay Social Security.

Or drain one account first.

It means those decisions deserve to be considered together.

If you’re 55 and retirement still feels far away, that time gives you room to plan.

If you’re already retired, start with the choices you have now.

My “90 Days to a Confident Retirement” guide can help you get organized. Head to my profile and grab it from the featured post.

11/02/2026

“I’ll just work a few more years.”

That may be the plan.

But your employer, your health, or someone you love might change it.

A layoff.
A health problem.
A spouse who needs care.

Suddenly, the retirement date you penciled in doesn’t mean much.

That’s a tough time to discover you don’t know what your household costs each month.

Or when your health coverage ends.

Or how you’d replace your paycheck.

You don’t need to assume the worst.

But it helps to ask:

“If work ended this year, what would we do first?”

Have that conversation while you still have a paycheck and some room to make changes.

And if it’s already happened, start with the decisions in front of you. You don’t have to figure everything out at once.

My “90 Days to a Confident Retirement” guide can help you get organized. Head to my profile and grab it from the featured post.

11/01/2026

Your coworker retired Friday.

By Monday, you were checking your 401(k).

You’ve worked together for 20 years. You’ve complained about the same meetings, survived the same changes, and joked about how much longer you could keep doing this.

Then there’s a cake in the break room.

A few pictures. A cardboard box.

And suddenly, the person who always said “one of these days” is actually leaving.

On the drive home, you start wondering.

Could I do that?
Does my spouse even want to retire when I do?
What would we need to make it work?

That’s a conversation worth having before you pick a date.

Try these three questions over dinner:

• When would we each like to stop working?
• What would we want an ordinary Tuesday in retirement to look like?
• What do we need to figure out before we feel comfortable leaving?

You might find out you’ve been picturing completely different retirements.

One wants to travel. The other wants to stay close to the grandkids.

One is ready next year. The other assumed you’d both work another five.

Better to find that out over dinner than at your retirement party.

If someone else’s last day has you thinking about your own, my “Your First 90 Days to a Confident Retirement” guide gives you a practical place to start.

Get organized, identify the questions you still need answered, and start talking about what comes next.

You’ll find the guide in the pinned post on my profile.

11/01/2026

If one of these was your first phone, you’re old enough to have a financial plan. 😂

And if you waited until after 9 p.m. to call someone because the minutes were cheaper, we should probably talk about retirement.

Somehow, we went from picking a ringtone to picking a retirement date.

But having a 401(k) and having a plan are two different things.

Can you afford to stop working when you want?
Where will your monthly income come from?
What will you do for health insurance?
How much of your savings will go to taxes?

You don’t need every answer today. But it helps to start asking before your last day at work.

My “Your First 90 Days to a Confident Retirement” guide gives you a place to start, with practical steps to get organized and see what needs attention.

You’ll find it in the pinned post on my profile.

Now tell me your number. Which one was your first phone? 👇

10/31/2026

The clocks fall back tonight.

My kids will use the extra hour to wake me up earlier. I’m putting that in writing now. 😂

People tell me retirement is when you finally get to sleep in.

Then they mention the grandkids, the dog, and a lifetime of waking up at 5 a.m.

Maybe sleeping in isn’t the goal.

Maybe it’s waking up early and knowing you don’t have to go to work.

Coffee without checking your email. Breakfast without watching the clock. Saying yes when the grandkids need you.

We spend a lot of time asking how much money retirement takes. It’s worth asking what you want your time to look like, too.

We get one hour back this weekend.

What would you do with your whole Monday?

10/31/2026

Before Tuesday’s election, read this. Especially if you’ve thought about moving your retirement money “until things settle down.”

I understand the temptation.

You’ve spent decades building your 401(k). Now you’re watching election coverage and wondering whether one night could throw off your retirement.

Moving to cash might feel reassuring.

But then comes the part nobody talks about:

When do you get back in?

After the results? After the market recovers? When Washington finally calms down?

You could be waiting a while on that last one. 😂

This issue of From 401(k) to Financial Freedom looks at what election history actually tells us about stocks, where those averages can mislead you, and the questions worth asking before changing your investments.

Read it before election night gives you the urge to hit the “sell everything” button.

And if retirement is getting closer, subscribe for practical help connecting your investments, taxes, Social Security, and future paycheck. I write it as a CFP® professional and Enrolled Agent with more than 15 years in the financial business.

👉 Go to the featured post on my profile and subscribe before Tuesday’s election.

Send this to the person you’ll be watching election coverage with. You might want to agree on the retirement plan before someone reaches for the laptop.

10/31/2026

Who pays the first tax bill of their life? 🎃

Last night my kids walked about two miles around Tuscola in costumes, knocking on every door that had a porch light on.

They did the work.

They earned the candy.

Then they dumped their bags on the living room floor, and Dad showed up.

Around here, the dad tax is payable in Reese's.

Plus a Kit Kat if nobody is looking.

Not the whole bag. Just a cut.

That is their FIRST tax lesson, and honestly it's a pretty good one.

Nobody voted on it either.

Because adult taxes work the same way.

You earn the paycheck. Then federal, state, social security, and medicare take their share before you see a dollar.

Same with retirement.

You spend 30 years filling a 401k. Pull $40,000 out, and the IRS shows up too (just with less chocolate).

The difference?

My kids can't plan around the dad tax.

You can.

You get to decide:
↳ which accounts you pull income from first
↳ how much you convert to Roth in lower income years
↳ whether a big withdrawal pushes you into IRMAA on medicare

That is what tax planning really is.

A plan won't make the tax disappear.

But it can usually keep it from taking the whole bag.

So, parents, be honest.

Mine is three Reese's and a Snickers.

What are you taking out of the candy bags? 🍫

Retiring in the next 5–10 years?

You’ve spent decades building your retirement savings. Now, how will you turn them into a paycheck—and how much will taxes take?

My guide, Your First 90 Days to a Confident Retirement, gives you a practical checklist to organize your accounts, plan withdrawals, and understand how your income can affect Medicare premiums. It's in the featured posts of my profile. Grab your own copy.

10/30/2026

This post is for your mom. Or your grandma.

Especially if she says, “I’m just keeping the Medicare plan I already have.”

She might be right.

But before she puts that stack of Medicare mail aside, there are a few things worth checking.

Are her doctors still in the plan’s network?
Will her prescriptions be covered next year?
Are her premiums, deductibles or copays changing?
Has her health changed since she picked this plan?

The plan that worked this year might look different next year.

Medicare Open Enrollment runs through December 7. This is the time to review Medicare Advantage and prescription drug coverage for January 1.

That doesn’t mean she needs to switch. It means she should know what she’s keeping.

And she shouldn’t have to sort through a kitchen table full of brochures to figure out where to start.

I have a straightforward, yes-or-no flowchart that walks through what to check and helps you see whether a closer review makes sense.

Message me “MOM” and I’ll send it over. Use it for yourself, sit down with your mom, or pass it along to Grandma.

A few simple questions can make the next step a lot clearer.

10/30/2026

You meant to move your old 401(k). You didn’t mean to send the IRS a chunk of it. But one rollover mistake can turn “I’m finally getting organized” into “Why is this taxable?” It starts innocently enough. You leave a job. Your retirement account stays behind. A few years later, you decide to deal with it. Then a check arrives made out to you. That’s where “I’ll handle it later” can get expensive. When an eligible retirement plan distribution is paid to you, 20% of the taxable amount is generally withheld. You typically have 60 days to complete the rollover. And here’s the part that catches people: To roll over the FULL amount, you generally have to replace that withheld money out of your own pocket. Miss the deadline, and the taxable portion you haven’t rolled over generally becomes taxable income. An early withdrawal penalty may apply, too. A properly handled direct rollover can avoid that withholding and the 60-day scramble. But first, there’s a bigger question: Where SHOULD your old retirement account go? An IRA isn’t automatically the best answer. Neither is moving everything into your new employer’s plan. Fees matter. Investment choices matter. When you’ll need the money matters. Before you move anything, understand your options. My complimentary guide, “5 Options for Your Old 401k, 403(b), or 457 Plan,” walks through the choices and their pros and cons.

Understand the pros and cons before making a move.