Stop Drowning: A Debt Payoff Strategy That Actually Works
By Derek — Money isn't complicated. People just make it complicated. ·
Look, I’ve sat across from founders who are pulling in high-six figures and individuals just trying to fix their first credit card mistake. You’d be surprised—the stress level is usually identical. Debt has a way of making people feel like they’re losing the race before they even get to the starting line.
I spent five years at Goldman before I struck out on my own, and if there’s one thing I learned, it’s that Wall Street loves to make money seem like a dark art. They want you to think you need a PhD to handle a balance sheet. You don’t. Money isn’t complicated. People just make it complicated because they’re terrified of the math.
Let’s strip away the noise. You’re ready to get out from under the weight of your debt. Here is the blueprint.
Stop Managing, Start Executing
Most people approach debt like they’re trying to solve a puzzle. They move money around, they look at interest rates, they stress-eat over their banking app. Stop it.
You need to treat your debt like a pit stop during a Grand Prix. In F1, when a car comes in, there’s no debate, no philosophy, and no "maybe we’ll change the tires tomorrow." It’s a surgical, high-speed execution. You need to be that efficient. If you spend more time thinking about your debt than actually attacking it, you’ve already lost.
The Truth About the Avalanche vs. The Snowball
You’ve heard the debate: Avalanche (paying off the highest interest rate first) vs. Snowball (paying off the smallest balance first).
Mathematically, the Avalanche method wins every single time because you’re paying less in interest over the life of the loan. It’s the "smart" way. But here’s what the textbooks won’t tell you: human psychology is a fickle thing. If you’re staring down a $20,000 credit card bill with a 24% APR, the Avalanche method is going to take a long time to show a win. If you don’t see progress, you’re going to quit.
My advice? Use the Snowball to build momentum. Knock out the small, annoying debts first. Get the win. Feel the rush of crossing something off the list. Once you’ve got that dopamine hit, pivot to the Avalanche to handle the heavy hitters. You need the psychological fuel to finish the race.
Audit Your 'Hidden' Costs
Before you throw an extra dollar at your debt, you need to know where your money is actually leaking. I don’t mean the $7 latte; I mean the subscription you forgot existed, the gym membership you haven't used since January, and the bank fees you’re paying because your balance dropped below an arbitrary number.
Take one Saturday morning. Pull up your last three months of bank statements. If you aren’t using it, kill it. That money—that wasted, invisible money—is now your debt-killing fund. Don’t spend it on something else. Direct it immediately to the principal of your highest-interest debt. Treat it like a tax you’re paying to your future self.
Automate the Aggression
The biggest mistake I see is people waiting until the end of the month to see what’s left over to pay their debt. Newsflash: There will never be anything left over. Life will always find a way to spend your money if you leave it sitting in your checking account.
Set your debt payments to happen the day after your paycheck hits. Don’t ask for permission. Don’t think about it. If the money isn't in your account, you can’t spend it on nonsense. Automating the aggression ensures you’re making progress even on the days you feel like being lazy.
Understand the Cost of 'Future You'
When you’re paying 20% interest on a credit card, you aren’t just paying for the item you bought. You’re paying a massive premium for the privilege of not having the cash on hand. Every dollar of interest you pay is a dollar that isn't compounding in an investment account.
When I was at Goldman, we talked about 'cost of capital.' Your debt is your personal cost of capital. It’s the most expensive thing you own. Making it disappear isn't just about 'being good with money'—it’s about reclaiming your freedom. Debt is a leash. Every payment you make is a link you’re breaking.
Keep Your Eyes on the Track
I’m a huge F1 fan. You know what happens when a driver looks at the wall? They hit the wall. If you spend all your time obsessing over how much debt you have, you’ll never see the road to where you’re going.
Track your progress, celebrate the small wins, and keep your eyes on the finish line. You’re not going to be in debt forever unless you decide to stay there. Create the system, automate the process, and then get back to building your life.
Debt is just a math problem, and you’ve got the tools to solve it. Now go handle it.
Still feeling stuck or just want a second pair of eyes on your strategy? Hit me up. Let’s grab a virtual coffee and get your plan moving. Talk soon.