Nate Lewis CFP professional, EA

10/26/2026

Before you call someone broke....or a financial genius....look past their debt balance.

A big loan doesn’t prove either one.

Here are 6 questions that tell you a lot more:

🏠 What did the debt buy?
An income-producing property and a lifestyle someone can’t afford are very different uses of borrowed money.

💵 Does the cash flow cover it?
Look at what’s left after expenses, repairs, and loan payments. Then ask what happens in a bad year.

📋 What are the loan terms?
The interest rate matters. So do rate changes, refinancing needs, and when the balance comes due.

⚖️ Who owes the money?
A business loan and a personal obligation can carry different risks. Personal guarantees matter.

🛟 What’s the backup plan?
If income drops or a major expense hits, how long can the borrower keep making payments?

🧠 Does the strategy fit the person?
“Keep the loan and invest the difference” requires actually investing the difference.

This is why I don’t automatically side with the “all debt is bad” crowd or the “smart people borrow” crowd.

Show me the numbers.

Then tell me about the person making the payments.

Start with the whole picture before signing for the loan.

For more help organizing your retirement decisions, visit my profile and find the featured post with “90 Days to a Confident Retirement.” You can grab the guide there.

10/26/2026

Would you rather retire with a bigger investment account—or no mortgage payment?

Assume paying off the house would still leave you with a comfortable cushion.

Some people love having the money available.

Others would gladly trade part of that balance for one less bill every month.

I understand both.

Planning for retirement? My “90 Days to a Confident Retirement” guide is in the featured post on my profile.

Which would help you sleep better: more money invested or a paid-off house?

10/25/2026

How much of your Sunday belongs to Monday?

You’re eating dinner, but thinking about the meeting.

Watching the game, but checking email.

Going to bed, already running through everything waiting for you tomorrow.

After enough years, it starts to feel normal.

Then someone asks what you want retirement to look like, and you say, “I don’t know. Maybe travel.”

Maybe.

But maybe you want to drink your coffee without checking the clock.

Pick up the grandkids without asking for time off.

Go somewhere on a Tuesday.

Spend a Sunday evening enjoying Sunday evening.

Those things belong in the retirement conversation, too.

The trouble is, it’s hard to enjoy the thought of getting your time back when you’re worried about giving up your paycheck.

How will you pay yourself?
What happens during a bad market?
How do you avoid creating an unnecessarily big tax bill?

Our free guide, Your First 90 Days to a Confident Retirement, helps you start working through those questions. It covers organizing your income sources, establishing a cash reserve, and considering how withdrawals and taxes fit together.

If retirement has been on your mind, this is a practical first step you can take this weekend.

Get the free guide through the pinned post on my profile.

10/25/2026

“We’re probably fine.”

That’s a pretty expensive sentence to build a retirement around.

You’ve saved in your 401(k). Paid down the house. Raised the kids.

Now retirement is getting close, and the kitchen-table conversation sounds like this:

“Think we have enough?”

“Probably.”

“What about health insurance?”

“We’ll figure it out.”

“And taxes?”

A long sip of coffee.

You don’t need every answer off the top of your head. But you do need more than a good feeling about the account balance.

Which account will you take money from first?
How much will you keep after taxes?
What happens if the market drops right after you retire?

These are things you want to work through while you still have a paycheck.

Our free guide, Your First 90 Days to a Confident Retirement, includes an account inventory, withdrawal planning considerations, and a checklist to help you organize your next steps.

It also covers how retirement income can affect taxes and Medicare premiums, because the amount you withdraw and the amount you get to spend can be very different.

Sit down with it together. See what you can answer and where you’re still guessing.

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

10/24/2026

What if “one more year” turns into the next ten years of your life?

You want to retire. Just not quite yet.

One more bonus.
One more year of saving.
One more year of employer health insurance.

All reasonable.

But what happens next year when you still don’t feel ready?

After decades of putting money into your retirement accounts, the idea of taking it out can be uncomfortable.

So you keep working. You know how to do that part.

Another year might make a meaningful difference. But if you don’t know what your savings could provide each month, how will you know when you’ve worked enough?

You could spend another year adding to an account that was already capable of supporting the life you wanted.

Or leave too soon because the balance looked bigger than the income it could reasonably provide.

You deserve more than a guess.

Our free guide, Your First 90 Days to a Confident Retirement, gives you a place to start. It walks through organizing your accounts, building a cash reserve, and thinking through where your retirement income will come from.

If your retirement date keeps moving, use it to start figuring out what still needs to happen before you can leave with confidence.

Get your free copy through the pinned post on my profile.

10/24/2026

The most expensive words you can say at 55 might be, “I need to make up for lost time.”

Because that’s when a risky investment starts sounding reasonable.

You’ve worked for 30 years. Raised kids. Paid bills. Helped everybody else.

Then you look at your 401(k) and think, “How am I supposed to retire on this?”

Suddenly, the guy promising huge returns has your attention.

A FinanceBuzz article about Mark Cuban’s advice for people feeling behind at 55 makes a point I agree with: chasing a big win can make the problem worse.

Feeling behind doesn’t mean you can afford more risk.

Before swinging harder, you need to know what you’re actually trying to solve.

How much will retirement cost YOU? What income will you already have? How much more can you realistically save?

And how much of what you’ve saved will you actually get to keep after taxes?

Those questions deserve more attention than somebody’s next hot stock.

That’s why I write From 401(k) to Financial Freedom.

It’s my free email newsletter for people who’ve spent years working for their money and want to understand how that money can support them in retirement.

I’m a CFP® professional and Enrolled Agent with more than 15 years in the financial and tax industry. I explain retirement income, taxes, Social Security, and Medicare in plain English, so you can spot costly mistakes and ask better questions before making big decisions.

You can’t redo your first 30 years of work. You can make more informed decisions about the years ahead.

Sign up free through the newsletter link in my pinned posts.

10/23/2026

Yes, I can make a retirement plan on a conspiracy board.

Red string.
Question marks.
A bunch of ages connected to each other.

My search history probably looks concerning.

But try explaining why someone’s income at 63 could affect their Medicare premiums at 65 without reaching for the string.

Then add Social Security.

Which accounts will pay the bills.

Whether a Roth conversion makes sense.

And the withdrawals the IRS will eventually require from certain retirement accounts.

Pretty soon, you need a bigger board.

Here’s why this matters:

A decision can look perfectly reasonable by itself and still create a problem somewhere else.

That Roth conversion might help with future taxes.

It could also increase your Medicare premiums.

That withdrawal might cover the new roof.

But what else does it do to your income that year?

You don’t need to memorize every retirement acronym.

You do need to connect the decisions before making them.

Preferably while you still have time to change the plan.

Wondering where to start?

Head to my profile and find the featured post with “90 Days to a Confident Retirement.” Grab the guide there.

10/23/2026

🤔 Is your old 401k still sitting at a job you left? A lot of people have one. Usually more than one. Nobody plans to forget it. It just sort of happens 📦 Like this: You leave a job at 52. You switch again at 58. Now you have a 401k, a 403(b), and a 457 plan from the county. Then HR mails a rollover form, and you sign whatever is on top of the pile. That often looks like this: 📄 Three logins and three fee schedules 💸 A check made out to you, with 20% withheld ⏰ A missed 60-day deadline 🫥 “Wait, why is this taxable now?” That last one is the real problem. Miss the window, and that money can become PERMANENTLY taxable. Nope. There is no easy do-over. You usually have five common options: • Leave it in the old plan • Move it into your new employer plan • Roll it into an IRA • Convert some of it to a Roth • Cash it out Each one can make sense for someone. Cashing out is usually the most expensive. And the details matter more than people realize. (Many 457 plans let you take money out after you leave work without the 10% early withdrawal penalty. An IRA usually does not.) Moving money is a planning decision, not paperwork. So I put together a complimentary guide: “5 Options for Your Old 401k, 403(b), or 457 Plan.” Inside, you’ll find: 📘 All five options and when each one may make sense 💵 Steps that may help you avoid unnecessary taxes ⚖️ The pros and cons of each, side by side Yes, the right choice depends on your income, your taxes, and your retirement date. But the decision should be made BEFORE the money moves. Grab the free guide Below.

Discover your next step with this complimentary guide.

10/23/2026

What if your last day of work was somebody else’s decision?

You planned to retire at 65.

Your employer apparently had 58 in mind.

Now you’re trying to figure out health insurance, income, and whether you can afford to stop working.

All while you’re still processing what happened.

This is why retirement planning deserves a spot on the calendar before the retirement party does.

For help getting organized, find “90 Days to a Confident Retirement” in the featured post on my profile.

If your paycheck stopped tomorrow, what would worry you first: health insurance or monthly bills?

10/22/2026

If you didn’t come home tonight, would your spouse still get to retire?

Or would they be calling their boss to say they need to work a few more years?

I know. Nobody wants to think about that.

But “we have life insurance” doesn’t really answer the question.

How much do you have? Why that amount?

If you’re like a lot of people, you bought it when the kids were little. An agent suggested a number, the payment fit your budget, and you moved on.

That was a few jobs and a couple of decades ago.

Now you’re talking about retirement. Maybe you’ve even picked a date.

Have you talked about whether that date still works if one of you dies?

Would there be enough income to pay the bills? Could your spouse keep the house? Would they have to take more out of the retirement accounts than you’d planned?

And that life insurance through work? Do you know what happens to it when you leave?

You may already have enough. You may have more than you need.

But if your answer is “I think we’re fine,” it’s worth taking another look.

I write about questions like this in my free newsletter, From 401k to Financial Freedom.

After more than 15 years in the financial and tax business, I’ve found that people often have questions they didn’t even know to ask.

As a CFP® professional and Enrolled Agent, I help explain how retirement income, taxes, Medicare, and decisions like this fit together.

My goal is to help you understand your options before you’re sitting across from someone saying, “I wish I’d known that sooner.”

Want to get it?

The sign-up link is in the pinned post on my profile. It’s free, and you’ll get practical explanations you can use as you get closer to retirement.

A new edition goes out every Sunday night.