How One Man Transformed His Spending Problem Into a Debt-Free Life

Spending problem

When someone realizes they have a spending problem, getting to the root of it isn’t often the first step they take. After all, a spending problem is typically uncovered when you start having trouble paying bills.

When Jon Dulin developed a spending problem, he decided the only way out was to dig deep and find out why he was overspending. Now he’s debt-free, in control of his money, and happier than ever. Find out how he did it.

First love, first credit card, and a mound of debt

When Jon was a freshman in college, he got his first credit card. And for a while, he used it well.

Jon would use the card to buy small items, then pay off the card before the end of the month to avoid accruing interest. But then sophomore year happened — along with his first love.

In an effort to show his girlfriend how he felt about her, Jon would regularly take her on dates and buy her things he couldn’t afford. By the time summer rolled around, he was $2,500 in credit card debt.

He paid off the debt with his summer job, but he accrued more debt through the end of college — and the end of his relationship. Even though Jon didn’t graduate with student loans, he still ended up turning his tassel with $4,500 in credit card debt.

Graduating with debt and into a recession

As if graduating with debt isn’t hard enough, Jon also graduated during the 2001 recession. Although Jon thought his degree would lead him to a six-figure salary, he had a hard time finding a job after college.

Unfortunately for Jon, his spending habit turned into an outlet for depression after college. He continued to spend money to feel good, even if it was only a temporary fix. When the positive feeling he got from shopping went away, he would have to spend again to feel better.

Two years of this cycle shot Jon’s credit card debt up to $10,185.

Taking a hard look at spending

Then one day in 2003, Jon went to the mall. As he was getting ready to buy a jacket, a light bulb moment struck. He asked himself point-blank: Why am I doing this?

Suddenly, Jon realized he had a problem with spending money; he was spending to feel better. So he drove home and began the hard process of dealing with the problem and its root cause.

The first thing Jon did when he got home was dump all of the clothes and electronics he’d bought over the years on his bed. He took a picture of the pile and shoved it into his wallet.

From then on, Jon would use the photo to remind himself to think twice before spending.

Then, Jon did what many people are not brave enough to do. He started a process of self-reflection that made him see that his problem with spending money was rooted in his low self-esteem.

He read books on self-improvement, saw a therapist, and confessed everything to his parents. Much to his relief, they were supportive and reminded him that there was no need to be embarrassed.

And with that, Jon got to work on his debt.

A few missteps in debt repayment

Wouldn’t it be great if the moment you decide to solve your problems, every effort you make to that end is met with success? Unfortunately, that’s not usually how things work out.

As Jon worked to pay down his credit card debt, he used balance transfer credit cards to lower his interest rate to zero so he could make faster progress. But balance transfer credit cards are tricky and can lead to more debt when mishandled. That’s exactly what happened to Jon.

Although he was able to pay off his high-interest credit cards with a balance transfer credit card, he didn’t completely stop spending. So he tried again until he got it right.

During this time, Jon’s career was looking up — and he capitalized on that wisely. When he finally found a full-time job, he didn’t quit his part-time job. Instead, he used the extra money from his part-time job to pay down his credit card debt.

By the time 2005 rolled around, Jon was officially credit card debt-free.

Moving on from his spending problem

In the process of paying off his debt and building his career, Jon realized he enjoyed blogging and wanted to help people like him with their finances. He was blogging on the side until 2013, when he was able to switch to doing it full-time.

Now, Jon is busy growing two sites, Money Smart Guides and Penny Thots. He’s also now married to a woman who hates debt as much as he does.

Jon doesn’t spend money to prove his love in his relationship either. Instead, he and his wife are working on a larger financial goal together: an early retirement. They’re also striving to do work they love, not work they feel obligated to do to earn money.

How to conquer your spending problem

Think you might have a spending problem? Here are a few resources that could potentially help you get to the root of the issue so you can take control of your spending:

Remember, the road to financial success is rarely straight and missteps can even happen to experts.

But by addressing his mental well-being first, Jon was able to create a debt payoff strategy that he could sustain. Once he paid off more than $10,000 of his credit card debt, he never let a problem with spending money get in his way again.

And that’s what happens when an issue is worked on at the root, not at the branch.

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