I’ll Admit It— I Failed, The Truth About My Debt Payoff Struggle

This post may contain affiliate links. Feel free to view my disclosure here.

debt payoff struggle

My 35th birthday was two days ago. I can’t believe that I am closer to 40 than I am to 25. When I restarted my debt repayment plan in January 2015, I set a goal to be debt-free by October 17th, 2018. Well, that was two days ago, and I for damn sure ain’t debt-free. Am I disappointed? Yes, I am, but I learned some positives during my debt payoff struggle. I learned a few things about money and myself during the last three years.

My Debt Payoff Struggle

Debt Paid

In three years, I’ve paid off over $13,000 worth of debt which is pretty good. My debt had finally gotten under $60,000 earlier this year, and then I had to get a new car. That sucked, but it was time to get a new ride. I was driving a 96 Toyota 4 Runner that didn’t have airbags. Then I started having major problems with the brakes. I spent money to get them fixed, and that didn’t work. Instead of spending more money, I said forget it. It was time for an upgrade.

Time Frame

When I started my repayment plan, I was hyped. I set that 3-year goal, not paying attention to the fact that I would have needed to apply at least $24,000 per year to my debt. I bit off more than I could chew. Initially, I only made $100-$200 extra per month. That was nowhere near enough to pay it off in three years.

Change of Focus

My focus could have been better in 2015. I was trying to do too many side hustles at once. I wasn’t making much either because of that. In 2016, I started to get more focused. I started freelancing and upped my eBay game. Also, I went to thrift stores a couple of times per month. I was doing okay but making four figures freelance writing, so I didn’t try to grow that stream.

Things were going well for me at the beginning of 2017. I was coming off my highest side hustle income year in 2016 and was poised to keep the momentum going in 2017. Well, that didn’t happen. Between March – April, I lost all my freelance clients. My side hustle income went from $1800 monthly to around $300. I was sick. For three months, I struggled. I didn’t know whether to get more freelance clients or work on my things.

Eventually, I went with option two and started to focus on my things. I focused more on eBay. I also created my course. By concentrating on eBay, I’ve had a record-setting year for sales in 2018.


I’ve made some mistakes during these last three years. I’ve used my credit card several times without paying it off in the same month. When I started the repayment, I would be one of those people who never used their credit card again. Well, things have changed. I’ve become a fan of travel hacking. Once my debt is paid, I’ll probably use my credit card to get travel points. I’ll use it to buy my flights and hotels and pay it off before the month ends.

Another mistake that I made was not fully commit to the debt snowball. Sometimes, I didn’t add as much to the debt snowball as I could have. Not having a lot of money in the beginning was one of the reasons it happened. The extra money that I did have, I used that for myself. That will be changing, though.

Make More Money

This is one of the biggest things I’ve learned in the last three years. I have to make more money. I’m not just talking about the side hustles, either. For two years, I played it safe at my job. I was comfortable. In 2017, that changed. I applied for a promotion and received it. Now I’m looking for more opportunities because I have to make more to eliminate this debt. It will happen. Not earning enough was among the most significant factors in my debt payoff struggle.

Every Situation is Different

During the last few years, I’ve seen hundreds of debt-free stories. Some were legit and motivating, while others were sensationalized stories where someone paid off a six-figure in three years but forgot to tell us that they were gifted a condo they sold or their parents helped them pay half of it. I realize that everyone’s debt repayment story is different. Some people have help, while many of us don’t. I try to stay in my own lane, and hopefully, I can motivate people in similar situations.

Work Smarter/Harder

If you’ve been a reader here for a while, you know that I like to travel. You may remember that I said I wouldn’t stop traveling during this debt repayment journey. I don’t regret still traveling, but I will say that I will have to work smarter and harder to apply more money to this debt. One thing that I have done is take fewer trips, though. That will be the case for 2019 as well. I’m not traveling until after April 1st.

I currently have over $66,000 worth of debt. This time I don’t have a deadline for when I want to pay it off either. I don’t want to say October 17th, 2021, because I will be pissed if it doesn’t happen. I do have a goal, though. It’s one of two goals that I’m setting for 2019. The goal is to pay off at least $20,000 worth of debt by December 31st, 2019. I can do this. That’s $1666 per month starting January. My mindset is a lot different now than it was in 2015. With my side hustles and job income both increasing, this will happen.

I’m ready and a little nervous at the same time. I don’t want to let myself down. I love sharing my monthly debt updates with you all, but I don’t like that the amounts are going down so damn slowly. At 35, I have renewed focus, and I know my mistakes in the last three years won’t happen.

When I turned 31, I wrote a post titled 31 life tips. They were random tips and statements that I posted. Since this is my 35th birthday post, I want to review some of them in more detail than I did in the original post. Hopefully, you can take something from them.

Drink More Water

The average human body is 60% water. It’s very important to drink water. You feel better when you drink it. You’re more alert, and you have more energy.

Take Calculated Risks

You must take calculated risks if you want to do better than average. People take risks but don’t always think them through in advance. Take time to think about possible outcomes before you take the risks.

Read More

Reading allows your mind to stay sharp. Try to read as many books as you can. Below is a post of books that you can start with.

Books I’ve Read This Year

Emergency Fund

If you don’t have an emergency fund, save for one ASAP. Things happen from time to time. It’s better to be prepared for them instead of being blindsided. Over the years, I’ve had to get tires and a cell phone unexpectedly. My emergency fund allowed me to not stress during those times. To open your emergency account today, check out the Capital One 360. I have money each month transferred to my Capital One account. They give new users $25 when they open an account with a certain amount deposited. For more information, check them out here.

Never Stop Learning

There is so much access to information these days. There is no reason for anyone to stop learning. If you don’t know something, you can always Google it. You can find a YouTube video about the topic you are trying to learn. You can also take free courses from some online universities. There is no reason to stop learning.


Travel if you can. You will learn so much about yourself in the process. As stated earlier, I love traveling. Something that I’m seeing more people do is travel shame. People are online hating because of other travel destinations. If you like going to Las Vegas or Miami, do it. Don’t let anyone tell you where to go. It’s your money; travel to the places that make you happy.

Eliminate Debt

This one could have been number one on this list. By eliminating your debt, you have more freedom. You can travel more. You can invest more money. You may be able to have a career doing your passion instead of working at a job that you hate. Don’t have a debt payoff struggle like me. Start paying your debt back as soon as possible.

Watch Less TV

You may hear successful people say they watch less TV all the time. There is a reason that they say that. You can get more things done without wasting hours watching TV each day. Think about it for a minute. If you want a side hustle, but you’re glued to the couch watching hours of reality shows after work, how successful do you think that side hustle will be?

Do What Other’s Won’t Do

Sometimes, you have to do what other people won’t do. Sometimes you have to sacrifice. By doing that, you could achieve a level of success that others aren’t. That could mean getting up early and going to be late. Go the extra mile because many people won’t do it.

Expand Your Comfort Zone

The final tip that I have is to expand your comfort zone. Do something different or scary to you. I’ve noticed that good things happen to me when I step outside my comfort zone. Two years ago, I would have never considered speaking in front of a group. This year I’ve had two speaking engagements. People want to hear my story and learn about side hustles. I’m going to continue to share it. Do something that will expand your comfort zone this week.

What is one thing that you struggled with during your debt payoff?

Website | + posts

Jason Butler is the owner of My Money Chronicles, a website where he discusses personal finance, side hustles, travel, and more. Jason is from Atlanta, Georgia. He graduated from Savannah State University with his BA in Marketing. Jason has been featured in Forbes, Discover, and Investopedia.