The "Humane" Way to Pay Off Debt That No One Talks About
Why I Stopped Crushing My Debt (and Started Winning Instead)
READ TIME: 4 MINUTES
"I think it's out," I gasped.
Not my shoulder (though that story's for another day) – the motivation to keep attacking debt.
Ever find yourself spending months of throwing every spare dollar at your credit cards, cutting all joy from your life, and feeling like you’re getting nowhere?
Maybe you know that feeling?
Where you're pumped to destroy your debt, throw every spare dollar at it... and then your alternator dies, your kid needs new soccer cleats, or the washing machine floods the basement.
Suddenly, you're right back where you started – except now with added defeat and a side of shame.
The problem isn't your discipline. It's not your budget spreadsheet.
And it's not that you "want it bad enough."
The truth no one talks about: conventional debt advice sets most of us up to fail.
Disclaimer: As always, consult your financial professional for further advice.
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The Soul-Crushing Debt Cycle Most "Experts" Recommend
I rolled my eyes the first time I heard a financial guru suggest the "hair shirt" method of debt repayment:
Cut all joy from your life
Put every extra penny toward debt
Eat nothing but rice and beans
Feel guilty about any purchase that isn't necessary
This might work if you're 22, single, and have no dependents.
But for busy parents juggling careers, kids, and maybe a creative side hustle? This approach isn't just unsustainable—it's soul-crushing.
I was listening to YNAB's Budget Nerds podcast recently when they described their approach to debt payoff as "humane."
That word stopped me in my tracks.
Humane debt payoff? What a concept, and it’s one I want to share with you based on what I learned.
Why Your Environment Always Beats Your Willpower
We love to believe in the myth of financial willpower because we get sold on it every day:
"Just make a budget and stick to it!" "Stop buying lattes and you'll be debt-free!" "No pain, no gain – sacrifice everything until you're free!"
And I get it. Those motivational messages put us in the driver's seat.
They make debt freedom feel accessible through sheer determination. We naturally like that kind of message because it feels empowering.
But it also sets you up for feelings of failure when your financial environment wins. And it will win, most of the time.
In the long run, your environment will almost always win against your willpower.
The Broken Debt Cycle I've Experienced (Maybe You Have Too)
Here's the cycle I've seen play out countless times in my own life:
Feel motivated to tackle debt (usually January 1st or after a particularly painful credit card statement)
Put every available dollar toward debt payments
Car breaks down/kid needs sports equipment/washing machine floods the basement
Have no cash for emergency
Use credit card to cover it
Feel defeated as debt creeps back up
Lose motivation and abandon debt plan until the next crisis
Repeat
It's like bailing water from a sinking boat without fixing the leak first.
No wonder we get exhausted.
The Missing Piece: Breaking Your Reliance on Debt First
What if I told you the order of operations matters more than how aggressively you pay down debt?
This isn't about superhuman discipline – it's about environment design.
The "humane" approach flips conventional wisdom on its head with this counterintuitive sequence:
List all your debts (face the monster directly)
Fund necessities first (you deserve to eat and keep the lights on)
Save for non-monthly expenses BEFORE making extra debt payments
Set aside money for fun (yes, really)
Choose one debt to focus on (smallest balance first for psychological wins)
That third step is where the magic happens—and where most debt advice goes wrong.
Why Saving for Car Repairs Might Be More Important Than Extra Debt Payments
I know this sounds crazy. When I first heard it, my inner Dave Ramsey disciple was shouting, "Baloney! Beans and rice! Rice and beans!"
When we're in debt-slaying mode, it feels counterintuitive to save money rather than throw it at debt. But here's the truth that hit me like a ton of bricks:
Those "irregular expenses" are regular. They're just not monthly.
Car repairs will happen. Medical bills will arrive. Kids will outgrow clothes. Appliances will break.
Conventional debt advice is like demanding you bail water faster from a sinking boat while ignoring the gaping hole in the hull.
The humane approach?
Patch the leak (build savings for inevitable expenses) first, then bail (pay down debt) with confidence.
This Changed Everything for Me
I remember the first time I had enough saved to pay cash for a car repair after starting this approach.
It was nothing major—about $300 for new brakes—but I can't describe the feeling of walking out of that shop knowing I hadn't added to my debt.
Before this approach, a $300 repair would have meant another month of debt payments wiped out and my progress reset. Now it was just a planned expense—no drama, no defeat.
I felt like I was walking on air. Like I had discovered a superpower.
It was the first time I could see the end of the debt cycle. Not because the numbers on my spreadsheet looked good, but because I could feel a fundamental shift in my relationship with money.
I was breaking my reliance on debt, one small non-monthly expense at a time.
What This Actually Looks Like in Real Life
Let's imagine you have $300 extra each month after covering necessities and minimum debt payments.
The Conventional (Soul-Crushing) Approach:
Put all $300 toward the highest interest debt
Feel amazing about your progress
Scramble when the car needs $800 in repairs
Put it on a credit card
Feel defeated and wonder why you even tried
The Humane Approach:
Put $50 into a car repair fund
Put $50 into a medical expense fund
Put $50 into a home maintenance fund
Put $50 into a "fun money" fund
Put the remaining $100 toward your focus debt
Yes, mathematically, you'll pay more interest in the short term with this approach. But when you factor in the cost of new debt from emergencies and the increased likelihood you'll stick with your plan long-term, the humane approach often wins—even on paper.
Let's look at a real example:
Conventional Approach (Over 6 Months):
Pay off $2,000 in debt
Add $1,500 in new emergency debt
Net progress: $500
Mental state: Exhausted and discouraged
Humane Approach (Over 6 Months):
Pay off $1,200 in debt
Add $0 in new debt
Build $900 in emergency funds
Net progress: $1,200
Mental state: Confident and sustainable
That $15 coffee date with a friend or $30 for a new book might seem frivolous when you're in debt-slaying mode.
But that small investment in your mental health prevents the $300 "I can't take it anymore" spending spree three months later.
The Permission Slip You Didn't Know You Needed
Consider this your permission slip to:
Enjoy small pleasures while paying off debt
Save for future expenses, even when you have current debt
Focus on long-term sustainability over short-term intensity
Treat yourself with compassion through this process
As busy parents and creators, we need approaches that work with our complex lives, not against them. That means building self-care and sustainability into our debt payoff plan.
Debt isn't a moral failing.
It's often the result of life happening—medical bills, job loss, or yes, sometimes poor decisions we've since learned from.
The person you are today deserves better than to be punished for decisions made by the person you were yesterday.
One Small Action for This Week
Pick one non-monthly expense that always seems to catch you by surprise.
Create a dedicated savings category for it, and commit to putting a small amount—even $10 or $20—toward it with each paycheck before making extra debt payments.
When that expense inevitably arrives and you can pay cash instead of reaching for credit, you'll experience a kind of financial freedom that has nothing to do with your debt balance.
That feeling of "I've got this covered" is addictive in the best possible way.
I'm curious, though...
I'll share the results next week and specific strategies for the winning category. There's one particular approach to the most common answer that's completely changed how I handle it—and I can't wait to share that with you.
Until next week,
-Matt
🔗 This Week's Links and Resources
Read: The Psychology of Money
Tool: YNAB's free 34-day trial
Quote: "Part of this process is not just about cleaning up the old mess and paying off past debt—it's about breaking your reliance on debt."
Into Mindfulness?: Be sure to check out my other publication, Daily Refill and get a free 7-Day Morning Mindful Challenge!
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Be Your Own Algorithm: If you’re struggling with how to be more authentic in your online content, I have a quick, free PDF that can help with that.
P.S. If you found this helpful, would you forward it to one friend who might need this perspective on debt? For parents, especially, the conventional approach to debt can feel impossible, and I'd love to help more people find a sustainable path.
P.P.S. I've been tinkering on a simple framework called "The Non-Monthly Expenses Calculator" that's helped me figure out exactly how much to save for those irregular expenses. Is this something you'd find helpful? Hit reply with "YES" if you'd like me to share it in the next newsletter.
I love this perspective! So simple but profound.
Having compassion for yourself is just as important as having it for others. Our society oddly juxtaposes a strong emphasis on individualism without prioritizing our self-worth. We focus on external deadlines and goals at the expense of our own well-being and personal growth.
My go-to strategy for developing training that optimizes company services is a person-centered approach, keeping all stakeholder and employee needs in mind. I never thought to apply this lens to myself!
Thank you for sharing. You've given me a lot to think about!
I finally figured this out—too late. But the one item that was never budgeted in my house was food. Two teenage boys plus two more who practically lived there (and ate all the food) wrecked that kind of thinking quickly.