My Debt Payoff Struggle: What I Learned From Paying Off $65,000+

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I originally wrote this article in 2018 after missing a huge financial goal.

When I restarted my debt repayment plan in January 2015, I told myself I would be debt-free by October 17, 2018, my 35th birthday.

That date came and went, and I wasn’t debt-free.

At the time, I was disappointed. I had spent more than three years working on my debt, and the numbers weren’t dropping nearly as fast as I wanted.

Looking back, though, missing that deadline taught me a lot about debt, side hustles, income, and setting realistic financial goals.

My debt payoff journey started with more than $72,000 in debt. Since then, I’ve paid off more than $65,000.

It didn’t happen in three years. The journey wasn’t perfect, either.

Here’s what happened.

My Original Debt Payoff Goal Wasn’t Realistic

When I got serious about paying off debt in 2015, I was hyped.

I had a plan and a deadline. The problem was that the math didn’t match the goal.

To eliminate roughly $72,000 in three years, I would’ve needed to average about $2,000 per month toward my debt.

At the beginning, I was only making an extra $100-$200 per month.

There was nothing wrong with setting an aggressive goal, but I hadn’t really considered whether my income could support it.

Eventually, I had to accept that my timeline wasn’t realistic.

That was lesson number one:

A deadline doesn’t mean much if the numbers behind it don’t work.

I Paid Off $13,000, Then Life Happened

By the time I originally wrote this article, I’d paid off more than $13,000.

My debt had even dropped below $60,000.

Then I needed another car.

I was driving a 1996 Toyota 4Runner that didn’t have airbags and started having major brake problems. I spent money trying to fix them, but the problems continued.

Eventually, I said forget it. I needed something safer and more reliable.

Unfortunately, that meant another car payment, and my debt went back up.

That was frustrating as hell, but it taught me something important:

Personal finance doesn’t happen in a straight line.

You can be making progress and still have something happen that temporarily moves you backward.

Cars break. Unexpected bills happen. Jobs change.

That’s also why saving money while paying off debt matters. Having some cash available can keep every unexpected expense from immediately becoming new debt.

Trying Too Many Side Hustles Slowed Me Down

Focus was another problem.

Early in my journey, I tried too many side hustles at once. I figured more hustles would automatically mean more money. It didn’t.

Things improved when I narrowed my focus. I started freelance writing and put more effort into selling on eBay.

I’d hit thrift stores a couple of times per month looking for items I could flip for a profit.

By 2016, my side hustle income was moving in the right direction.

Then 2017 punched me in the mouth.

Between March and April, I lost all of my freelance clients. My side hustle income dropped from approximately $1,800 per month to around $300.

I was sick.

For a few months, I had to decide whether to chase more freelance clients or spend that time building things that I controlled.

Eventually, I chose the second option. I focused harder on eBay and my own business.

That experience taught me that trying everything isn’t always the answer. Sometimes you need to figure out what’s actually working and double down on it.

If you’re looking for something to try, my 100 Side Hustle Ideas has plenty of options.

Just don’t make my early mistake and try all of them at once.

Making More Money Changed My Debt Strategy

One of the biggest lessons from my debt payoff struggle was simple:

I needed to make more money.

Saving money mattered, but there was only so much I could cut.

Increasing my income had a much higher ceiling.

That applied to my career and my side hustles.

For a couple of years, I had gotten comfortable at my job. In 2017, I finally applied for a promotion and got it. At the same time, I continued experimenting with ways to make money outside of my regular job.

Over the years, I’ve made money with eBay, freelance writing, blogging, affiliate marketing, consulting, delivery gigs, online marketplaces, focus groups, and other opportunities.

Between 2020 and 2024 alone, I made more than $98,000 from side hustles while working a full-time job.

I didn’t know all of that when I started in 2015. I learned by trying different things, figuring out what worked, and getting better at them.

If you’re at the beginning of that process, here’s my guide on how to start a side hustle.

Increasing my income didn’t magically eliminate my debt, but it gave me more money to work with.

That changed everything.

I Made Credit Card Mistakes

I wish I could say I followed a perfect debt payoff strategy.

I didn’t.

There were times when I used credit cards and didn’t immediately pay them off. There were also times when I could have put more money toward debt but spent it on something else instead.

Those decisions slowed me down.

I also didn’t follow the debt snowball perfectly.

Sometimes I’d make a good payment. Other times, I’d have extra money and keep some of it for myself instead of throwing every available dollar at the balance.

That’s one reason I don’t present my debt journey as some perfect blueprint everyone should follow.

I made mistakes.

The important thing was recognizing them and continuing to make progress instead of using a mistake as an excuse to quit.

I Didn’t Stop Traveling

One thing I wasn’t willing to completely eliminate was travel.

If you’ve followed My Money Chronicles for a while, you know I love to travel.

Some people believe you should stop doing everything fun until you’re debt-free. I understand that approach, but it wasn’t the one I chose.

Instead, I tried to find a balance.

I took fewer trips during certain periods. I looked for deals. I used extra income to help pay for travel. Over time, I also got better at finding ways to save money while traveling.

Could I have paid off debt faster if I’d taken zero trips?

Probably.

Do I regret traveling?

Hell no.

I didn’t want several years of my life to disappear while I sat at home waiting for a balance to reach zero.

For me, the better approach was making financial progress while still enjoying some of my life.

I Stopped Comparing My Debt Journey to Everyone Else

During the early years, I read hundreds of debt-free stories.

Some were motivating.

Others would have a headline about somebody paying off six figures in three years, but you’d later find out they received an inheritance, sold a property, lived rent-free with family, or had significant help.

There’s nothing wrong with having help. But comparing their timeline to mine didn’t make sense.

Different income.

Different expenses.

Different circumstances.

Different debt.

Eventually, I realized the only balance I needed to compete against was my previous balance.

That mindset made the process much easier.

From $72,000+ in Debt to More Than $65,000 Paid Off

This is the part my 35-year-old self couldn’t see.

When I wrote the original version of this article, I had more than $66,000 in debt.

I was frustrated about how slowly the number was moving.

Today, I can look at the journey differently.

I’ve paid off more than $65,000 since starting with over $72,000 in debt.

There were good years and bad years.

There were income increases and setbacks.

Some side hustles worked. Others didn’t.

I made smart financial decisions and some dumb ones.

The biggest thing is that I kept going.

What I’d Do Differently

If I could go back to January 2015 and start again, I’d change a few things.

Set realistic goals. I wouldn’t pick an arbitrary debt-free date without figuring out whether my income actually supported it.

Focus on increasing income sooner. Cutting expenses helps, but an extra $500 or $1,000 per month can dramatically change a debt payoff plan.

Do fewer side hustles. I’d spend more time growing the ones that showed potential instead of constantly chasing something new.

Be more careful with credit cards. Paying down debt while creating new debt makes the process unnecessarily difficult.

Stop comparing timelines. Someone else’s three-year debt journey has nothing to do with mine.

And I’d pay more attention to what happens after the debt is gone.

Paying down debt can eventually free up money to save, build a larger emergency fund, put money back into a business, and start investing.

That’s where eliminating debt can really start changing your financial options.

What My Debt Payoff Struggle Taught Me

My original goal was to be debt-free by October 17, 2018.

I failed. At the time, that bothered me.

Looking back, missing that deadline wasn’t nearly as important as I thought. I’m still not debt-free, but the goal has changed, 

The real goal was improving my financial situation. I did that.

I learned how to make extra money. I increased my income. I built side hustles. I made mistakes. I kept traveling. And I kept making payments.

Eventually, those payments added up to more than $65,000 in debt eliminated.

If you’re in the middle of your own debt payoff struggle and the numbers aren’t moving as quickly as you’d like, don’t let somebody else’s timeline convince you that you’re failing.

Look at your situation.

Figure out what’s slowing you down. Make adjustments. And keep going.

A missed deadline doesn’t erase the progress you’ve already made.