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 there are some positives that I learned 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, 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 hype. I set that 3-year goal not really 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. In the beginning, I was only making $100-$200 extra per month. That was nowhere near enough to pay it off in three years.

Change of Focus

My focus wasn’t the best 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 a little more focused. I started freelancing and upped my eBay game a little bit. Also, I started to go to thrift stores a couple of times per month. I was doing ok, but I was 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 I 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 per month to around $300. I was sick. For three months, I struggled. I didn’t know whether to try to get more freelance clients or work on my own things.

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


I’ve made some mistakes during these last three years. I’ve used my credit card a few times without paying it off the same month. When I started the repayment, I was going to be one of those people that 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 is over.

Another mistake that I did was not fully commit to the debt snowball. There times where 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 with the side hustles either. For 2 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 know that I have to make more to get rid of this debt. It will happen. Not making enough money was one of the biggest 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 that they sold or that 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 just try to stay in my own lane and hopefully I can motivate people that are in similar situations to me.

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 that I wasn’t going to 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 so that I can 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 of 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 y’all, but I don’t like that the amounts are going down so damn slow. At 35, I have renewed focus and I know the mistakes that I made 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 go over some of them in more detail that 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

I truly believe that if you want to do better than average, you have to take calculated risks. People take risks all the time, but they 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, start saving 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. If you’re ready to open your emergency account today, check out the Capital One 360. I have money each month transferred to my Capital One account. They are giving 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. There’s also a good chance that you can find a YouTube video about the topic that 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 others 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. Heck, 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 probably hear successful people say watch less TV all the time. There is a reason that they say that. You can get more things done if you’re not wasting hours watching TV each day. Think about it for a minute. If you want to a side hustle, but you’re glued to the couch watching hours or reality shows after work, how successful do you think that side hustle will be.

Do What Other’s Won’t Do

Sometimes in life, you have to do what other people won’t do. Sometimes you have to sacrifice. By doing that you could get to a level of success where others aren’t at. 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 that is different or scary to you. I’ve noticed that when I step outside the comfort zone, good things happen to me. Two years ago, I would have never thought about speaking in front of a group of people. 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?



  1. You are making positive progress and also constantly learning new ways to make more money and succeed more at life. I’m a super slow runner but I still hoped to qualify for the Boston Marathon. I ran 15 marathons and got within 12 minutes of qualifying but never hit my goal before I ratcheted back my distance to something more in line with the health of my knee and my age. So, I failed but I also became a marathoner who typically finished in the top 25% of the field, not horrible for a super slow guy! Sometimes we just set goals that we can’t meet, that is part of learning I think, but the progress we make is still real. I thought your post was inspirational, thanks!

    1. You’re right. It is about constantly learning and growing. Thanks for the wise words.

  2. I’m rooting for you hard over here, man!! Get it!

  3. Hey Jason, I feel your pain. Sometimes it can be hard when you’re trying to hustle and feel that at times you’re going backwards. That’s why we’re a community who’re here to support each other. Keep going and keep your head up. Everything will work out in the end and if it hasn’t yet worked out then it isn’t the end.

  4. You’re doing awesome! 👏 It’s easy to get down because you missed your goal, but don’t forget that you’ve made progress. Being intentional and working towards paying off your debt, I have no doubt that you will knock the cover off the ball.

  5. I don’t think you failed! And, I think you’re going to surpass your goal because your course sales and side-hustles are on point. Sending good vibes your way.

    1. Thanks, Michelle. Sending good vibes your way as well.

  6. Keep up the great work! My struggle has been gaining and maintaining consistent income. I have a little over 41k to payoff. My goal is to payoff at least 20k by December 2019 as well. I’m making a career change into nursing which I’m super excited about. My plan is to start school next August. Good luck to you as you continue your journey to debt freedom!!!

    1. Thanks, Jessica. Good luck with your career change. Let’s knock this $20K out!

  7. I really love this. I have a saying (because I have ADHD) and that is “Everything takes longer than I think it does.” And I’ve found it to almost always be true. I know you mentioned not wanting to set your sights on a date this time around, but you might find the book The 12 Week Year by Brian P. Moran really helpful with mapping your goals. It’s insanely precise and makes it so that big goals like paying off 24,000 per year of debt, get broken down into a day to day achievement. As someone who also struggles to stay ahead of the debt curve, I’ve found it super helpful. All that aside, Happy Birthday!! and Good luck with everything!

    1. Thanks, Lacy. I’ve never thought about breaking the goals down. I may check out the book.

  8. This is a great post and congratulations on all that you’ve achieved so far! It seems like you’re really on top of a solid plan to pay off your debt and that’s incredible. Happy Birthday!

  9. I truly understand what you’re going through! I started off at the beginning of the year in point and labor focused on paying off my debt! I was doing really well too. Then I fell off around the Summer time. Now, my mind frame is getting back to that point of paying off my debt again. Maybe because it’s the end of the year and I’m going through a moment of reflection. Either way, I will get back on track very soon. I wish you all the luck in your debt free journey!


    1. Thanks, Daniesha. Good luck to you as well.

Comments are closed.