How to Start Paying Off Debt: My Rock Bottom to Debt-Free Journey

Published on June 10, 2025

Back in 2015, I hit my financial rock bottom. I had no idea how to start paying off debt. I felt like I owed money to everyone: family members, credit cards, and student debt that I incurred when I decided to go back to college and finish my bachelor’s degree. I even owed money to one of those old CD subscription services (remember those?). I kept thinking, if I just made more money, I’d finally be able to keep my head above water.

My breaking point came one night at my kitchen table. I was crying, scared, and overwhelmed after finding out that the small business I worked for was unexpectedly shutting down. I had no savings, and I couldn’t afford rent for the upcoming month. In desperation, I called a family member and asked for help. That moment became my personal turning point. I remember thinking, I will never be in this position again. I was so embarrassed about my financial situation.

So, I did what most of us do… I Googled, “How do I pay off debt?”

That’s when I stumbled across Dave Ramsey. He felt like a straight-shooting, slightly grumpy uncle. I didn’t follow his Baby Steps perfectly, but I adapted his advice to fit my life. Over time, I created my own system for how to start paying off debt. It began with three simple questions I started asking myself before writing my monthly budget or making purchases.

1. Do I even use this?

One of my money drains? Subscriptions. I had tons of entertainment services. I think I even still had cable. I realized I only watched one show per platform, then forgot to cancel. Even Amazon Prime had to go. As much as I loved that lightning-fast delivery (there was a time you could get things in an hour!), the convenience made it way too easy to overspend. Canceling Prime helped cut impulse purchases significantly.

2. Can I do this myself?

The answer is almost always yes, but only if I take ownership of my choices. I started asking myself:

• Can I cook instead of ordering out? My biggest variable spending money drain!
• Can I hang out with friends without spending money?
• Can I maintain friendships without always going out?
• And the awkward one for single folks: Can I date without spending money?

The answer? Yes, if you’re willing to date Jesus. (Kidding… mostly.)

3. Am I willing to choose wisdom?

This is the one that changed everything. I had to grow up. I had to act my wage. I leaned into logic, reflection, and my own past mistakes to make better decisions. It wasn’t easy or fun. I had to sacrifice convenience, comfort, and sometimes even social connection. I stopped eating out and told my friends that I was on a strict budget. I took the bus in subzero Chicago winters (miserable, to say the least). I gave up little luxuries like buying mineral water not because they were extravagant, but because I had a bigger goal: peace of mind, control over my money, and the freedom of living debt-free. I also had to accept being alone more than usual, simply because I couldn’t afford to join in on most activities. But I made peace with it, because every sacrifice brought me closer to the life I wanted.

Budgeting isn’t just about math.

We act like it’s all spreadsheets and numbers, but for many of us, money is deeply emotional. Childhood habits, self-worth, and anxiety all play a role in how we spend money.

So, if you’re ready to get serious about how to start paying off debt, start with this:

Take out a piece of paper and write down your variable spending.
Then, start canceling anything that isn’t essential to your survival. Yes, even things you enjoy but can’t truly afford right now. Daily coffee runs. Biweekly salon visits. Food service apps. Streaming services. They all add up. If you’re new to budgeting, you might also like Budgeting Basics: What I Wish I Learned in High School.

If you made it this far, thank you! I hope this post was helpful.
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You can also check out the YouTube video I made on this topic while trying to bake a box cake. Because if you can pay off debt while learning to bake… you can do anything.

Have a lovely day or night.
Bakebit

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