The First Time I Fell In Love with Debt: Part 2 (Video)

On August 14, 2016, I released Debt Free or Die Trying: How I Buried Myself in Over $30,000 in Debt and Dug My Way Out by Age 30. The book tells the good, the bad, the ups and the downs, the mistakes I and others made, and the lessons I and we learned. Through, my goal is to show others that living a debt free life and living life do not have to be mutually exclusive.

Debt and I have had a very rocky relationship. I don’t hate debt. I don’t love debt. I’d describe our relationship as, “It’s complicated.” If you’re like me, maybe you’re ready to end your relationship with debt. This is the story of how I did it (click here to read Part 1).

Share “The First Time I Fell In Love with Debt” or your own original debt/money story on Twitter with #PayBal to enter to win our $100 gift card giveaway.

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Age 27: Rock Bottom

The year was 2009…

I reached rock bottom at age 27. What they don’t tell you is: when the money runs out the “friends” run out, too…

Plus my dreams of making six figures right out of college didn’t quite pan out either. The real world was a bit harsher than my fantasies.

My post-college reality was falling apart. I would work two, three or four jobs any given time of the year and still struggle just to make the minimum payments.

I didn’t know what to do. I was in a debt spiral.

No one knew how much debt I had. It turns out this included myself. I was too embarrassed to look. I just knew it was a lot. All I did was work. I’d pay what I could each month. I’d go to sleep, and I’d hope when I woke up the next day it would all be gone. But it was always there. Faithfully. Waiting. Hovering over me each morning like a scorned lover eager to remind me of all my years of mistakes.

The offers for credit were far and few now. Creditors recognize a sinking ship when they see it, and I had already hit my financial iceberg.

It wasn’t a matter of if the ship was going down. It was when. My hopefulness drained in an inverse relationship to my nearly maxed credit cards.

One day, among all the soon due bills, I received just one offer for a pre-approved consolidation loan. Given how few I had seen in recent months, I figured this might be one of the last.

What if they don’t say yes…?”

I called with nothing but prayer and hope on my side. When the call center finally routed me to an actual person, they asked me a series of questions:

  1. What’s your credit utilization?
  2. What’s your income-to-debt?
  3. Your credit score?

The questions kept coming but my answers were always the exact same:

I don’t know.”

I couldn’t answer a single personal finance question even though I had several near-maxed credit cards, and I had legally financed several loans since age 18, the day I got that free T-shirt; I no longer owned…

They call it “personal finance,” but I knew nothing of my financial health other than I was sick. I signed a lot of contracts over the last nine years. I read zero. The contents never matter, until now.

Was it too late?

I tried to remain calm, but I had to fake it. My entire financial future hinged on the outcome of this one phone call, so I did everything short of begging them to extend me money.

Ok, I begged!!!

After confirming the obvious — that I knew nothing about my personal finances, maintaining a budget, or credit — out of mercy or exhaustion, they ended the questioning and put me on hold. When they came back with a yes I was grateful to them, but I was disgusted with myself.

That was one of the worst nights of my life. I hung up, and I made the decision to start my journey towards debt freedom. I didn’t know how. I didn’t even know where to start.

I only knew I was going to become Debt Free, or Die Trying.

Age 30: Debt Free

The year was 2012…

For those of you on the wrong side of 30, you might relate to the calmer celebrations that come with three-decades of experience. Honestly? If for no other reason than to improve this retelling, I wish I had a better finale to my own story. In it’s simplest form my debt freedom journey was a 5-step plan:

  1. Set the non-negotiable goal to become debt free
  2. Figure out how much debt I actually had by requesting my free credit report from all three major bureaus at
  3. Use a Debt Calculator to design a plan to be debt free that I would actually follow
  4. Fail miserably and repeatedly at Step #2
  5. Adjust the plan but never the goal by adjusting, re-adjusting, and re- re-adjusting Step #2 until I was completely debt free

Honestly, I don’t remember the exact day or month I paid off over $30,000 in debt and interest because I never imagined I’d write a book about the experience or start a podcast. I was just a regular guy who was tired of being tired, and I knew doing more of the same would lead to the exact same results: more personal debt and misery. To be honest, after a decade of juggling debt since I got that “free” T-shirt 12-years earlier – I no longer owned – I was just happy to live a normal life again.

I now had a plan. I had a sustainable budget. The time was going to pass anyway, so letting it do so was easy.

Life is funny.

There were years of struggling; fighting; a few nights of begging; pleading and possibly, crying, then one day, you perform a series of simple, focused acts and they have one of the greatest impacts on your life. My last day buried in debt was like every other day with one significant difference: I logged online. Scheduled the electronic payment, and one click later?

I was finally completely debt free.

You might ask:

What does it feel like to be debt free?”

Well, if you’re ready to start your plan today, I hope someday soon you and I can share a story about our experience.

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