I want to tell you about the worst moment of my entrepreneurial life. No, it wasn’t a business failing. It was sitting in my car, staring at a stack of unopened envelopes in the passenger seat. There were bills from the credit card company, letters from the bank, and a few from friends I owed money to. The stack felt impossibly heavy. I had built a successful business, but I had made some serious mistakes along the way, and the debt had quietly ballooned to over $300,000.

I felt a crippling sense of shame. I had failed. And because of that shame, I did the worst possible thing: I ignored it. I hid the bills. I stopped answering my phone. I was completely paralyzed by the problem, and every day, that mountain of debt grew a little taller.

This is what I’ve come to understand: debt isn’t just a financial problem. It’s an emotional one. And you can’t solve it with logic alone. You have to address the emotions first. My progress, and my eventual freedom, came not from a single heroic act, but from a series of consistent, small, almost laughably simple steps.

The Insight: The paralysis of shame and the power of incremental steps

When you’re deep in debt, the shame can feel like a weight holding you down. You feel like a failure, and that feeling tells you to hide. You avoid phone calls, you delete emails, and you throw bills in a drawer. The logical part of your brain knows this is a bad idea, but the emotional part is running the show. It says, “Don’t look at it, and it can’t hurt you.”

But: what you don’t look at will absolutely hurt you.

The key to escaping this paralysis is to ignore the massive mountain of debt for a moment and focus on a single pebble. Just one. Don’t worry about the $300,000 I owed. My first step wasn’t to tackle the biggest loan. It was to open just one of those envelopes. That’s it. That one tiny act of bravery gave me a flicker of momentum. And that flicker turned into a flame.

Progress, I learned, isn’t about making one giant leap. It’s about building momentum through a series of consistent, incremental steps. Like an athlete training for a marathon, you don’t start with 26.2 miles; you start with a single jog around the block. That jog builds confidence, which builds consistency, which eventually gets you to the finish line.

The Perspective: How to gamify debt repayment

The emotional paralysis I felt was real, but so was the high-interest debt that was keeping me trapped. To break free, I had to combine emotion and logic.

Here’s the powerful perspective that changed my life: every single debt payment, no matter how small, gives you a dopamine boost. That little hit of “I did it!” is a powerful motivator. You’ve got to use that feeling. It’s like a game where you get a point for every debt you eliminate. The problem is that if you only focus on paying off the smallest debt (the “snowball” method), you might be ignoring a high-interest debt that is essentially a financial anchor, pulling you down.

That’s why a logical, well-structured approach is so critical. High-interest debt is not your friend. It’s the kind of debt that can keep you in a financial prison for life. You have to take its cost and consequences seriously. You need a system that not only gets you motivated but also gets you out of debt as quickly and efficiently as possible.

The Action: The two-part strategy that will set you free

My debt-eradication plan was a simple, two-step process that took years, but it worked.

Part 1: The quick wins

Before I did anything else, I paid off a few small debts. This wasn’t a logical move; it was an emotional one. I had a few small, annoying bills – a few hundred dollars here and there. I paid them off immediately. It felt incredible. I took those little “wins,” and they gave me the momentum and confidence I needed to face the bigger challenges. That’s the first step: get a few quick wins to prove to yourself that you can do this.

Part 2: The ranking system.

Once I had some momentum, I made a list of all my remaining debts. I didn’t care about the total number; I was focused on the list itself. Then I ranked them using two criteria:

Cost: What was the interest rate on this debt? This was the most important financial factor. The higher the rate, the more it was costing me every single day.Consequence: What was the potential consequence of not paying this debt? This was the human factor. I had a debt to a very dear friend. While the interest rate was low, the potential consequence of damaging that friendship was devastating. That made it a high-consequence debt.

I put all my debts in order, prioritizing the high-interest ones and the high-consequence ones. The debt to my friend went to the top of the list, right next to a high-interest credit card. I called my friend and had a tough, honest conversation, telling him I was creating a plan to pay him back. This act of communication was more important than the payment itself. I then aggressively tackled the high-interest credit card, making it my primary focus.

Over the next decade, I followed this two-part strategy. It wasn’t fast. It wasn’t easy. But it worked. I paid off that $300,000, and I’ve been debt-free ever since. Like building wealth, getting out of debt is a process, not a moment.

And, it’s a habit.

The first step is to face the truth. 

The second is to get a quick win. 

The third is to create a plan. 

You can do this. 

The feeling of freedom on the other side is worth every single step.

You’ve got this. I mean it. 

-Mike

PS – The Money Habit hits the shelves in January. You can preorder this roadmap to financial freedom here. 

In the meantime, there’s The Money Habit email, where I send shorter versions of blogs like this and strategies to support you. You can sign up here. I promise, NO spam!

 

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