Follow Chad on LinkedIn where he shares short videos and thoughts about creating a strong, clear financial life for retirement.
__
Something I’ve seen over and over for years now in client meetings is the sharp contrast between families who have followed a disciplined approach to debt and those who haven’t.
It almost always comes down to habits (especially around debt) and how those habits either set someone up for a confident retirement or make the whole process much more stressful than it needs to be.
And that’s what I want to talk about here.
Two Very Different Types of Households
It’s a totally different experience meeting with clients who come to me through the Dave Ramsey program compared to those who haven’t. Oftentimes, these are people who have been following his guidance for 15, 20, or even 25 years.
People who haven’t followed that kind of disciplined system tend to carry a lot more debt, and many of them don’t really see the problem.
They go into retirement with:
- Car loans
- Credit card balances
- Mortgages
- And sometimes all of the above
They look around and see everyone else doing the same thing; they think, “Well, this must be normal.” Normal doesn’t necessarily mean healthy.
“Don’t Compare Yourself to Everybody Else”
I told one couple recently, “Don’t compare yourself to everybody else… because you might be surprised how many people are struggling–or quickly approaching it.”
Seven out of ten Americans live paycheck to paycheck. So when people look around and say, “I’m doing what everyone else is doing,” that’s not the reassurance they think it is. It’s actually a warning sign.
A Story from Earlier in My Career
This isn’t new to me. I saw the same patterns years ago when I worked at the prison.
We all made the same amount of money. Same job and same income, but financially, the officers I worked with lived completely different lives.
Some were doing really well, while others were a paycheck or two away from living on the street.
Income wasn’t what made the difference; behavior was. It was whether someone had been disciplined with money or whether they were barely keeping up.
And that’s exactly what I see today.
Why Long-Term Habits Matter So Much
When someone has been following a debt-free program for 15 or 20 years, they come into retirement in a much stronger position.
- They’re not dragging payments behind them.
- They’re able to save more aggressively.
- They have better cash flow.
- And their mindset around money is steadier and more intentional.
Meanwhile, families who haven’t followed any system (or who think everything is “fine” because their neighbors are in the same situation) often face unnecessary financial pressure.
It all comes back to habits and how those choices accumulate over time.
Bringing It All Together
Debt is one of those things that doesn’t feel urgent until suddenly it is. Heading into retirement with unnecessary debt can limit your flexibility and create stress you don’t need.
You don’t have to follow any specific program or be perfect with every decision, but the families who enter retirement in the strongest financial position are the ones who’ve made intentional, disciplined choices for years, long before they stopped working.
If you’re unsure where you stand or want to talk through what a healthier, clearer financial path could look like, that’s exactly what we’re here for. A simple conversation can help you see where you’re strong and where a few changes might make a meaningful difference.
This material is intended for informational/educational purposes only and should not be construed as investment/tax advice, a solicitation, or a recommendation to buy or sell any security or investment product. Please contact your financial professional for more information specific to your situation.
The SmartVestor program is a directory of investment professionals. Neither Dave Ramsey or SmartVestor are affiliates of Safe Harbor Wealth Mgmt, Inc. or Commonwealth Financial Network.