3 Mistakes I Made While Paying Off $81,000 in Debt That Affected My Mental Health

No, working seven days a week is not the answer.

How I Bought That takes a peek inside the process of making a major purchase, whether your budget is big, small, all your own, or supplemented by family and/or financial institutions. In this series, we look at many different spending situations, from how people afforded big purchases like first homes to electric vehicles to splurge-worthy bags.

I’ve been writing about personal finance for eight years and it all started with my own blog DearDebt.com in 2013. I started the blog after graduating from New York University with my M.A. in Performance Studies, when I was on food stamps, only had temp work, and was deeply depressed about my debt. 

I felt so much guilt and shame about my debt and was embarrassed that I couldn’t find a full-time job to pay it back easily. However, the blog led to a writing career and increased my income enough that I paid off $68,000 just short of five years. While before that, it took me nearly five years alone to pay off $13,000. 

Since then I’ve gotten a lot of press about paying off $81,000 in student loan debt, particularly the sexy part where I paid off the bulk of it in less than five years. While I love to inspire others to pay off their debt, now that I am several years removed from my debt-payoff journey (I paid off my debt at the end of 2015), I realize that I wouldn’t necessarily do the same things again, especially now that I know what I know about mental health and wealth. Here are three mistakes I made while paying off debt that affected my mental health. 

Mistake #1: Working seven days a week. 

When people ask me how I paid off my debt, I refer to two main things. The first is that I lived in Portland, Oregon, in a studio apartment with my then-partner and my half of the rent was $400 in 2012. The second part is that I significantly increased my income through self-employment and side hustling

After being on food stamps and cutting back as much as I could (which wasn’t hard to do), it became clear that the only way out of debt was to earn more. So at first, I started taking any side hustle I could. I was a brand ambassador, a pet sitter, an event assistant, and did random gigs I found on TaskRabbit and Craigslist. These ranged from wholesome gigs like assisting someone with planning a 40th birthday party or being a coat check person at a Halloween party to downright weird, like selling water bottles at an overnight rave in some grimy warehouse. 

As my side hustles increased, I also began to write more on the side, which later became my ticket to self-employment. It was through working for myself and side hustling that I earned more than I ever did before.

In fact, I doubled my income from $31,000 to $60,000. That income, coupled with the low expenses, helped me pay off debt. But I worked seven days a week for nearly five years to get there. I was tired all the time, made clumsy mistakes, and it definitely took a toll on my mental health and relationship, which eventually ended after nine years. 

What I would do instead: If I were to do this again, I would allocate at least one day of rest per week. Your mental health and physical health should not be in jeopardy because of paying off debt. I was paying far more than the minimum and it wouldn’t have been so bad to take another few months or even a year or two more to pay it off in order to prioritize my health. 

Mistake #2: Not investing.

When I was paying off debt, you can say I was borderline obsessed. I worked all the time, hungry for money to feed the debt monster. But because of that, I didn’t invest at all. I thought I couldn’t afford to do it. I had read all the articles about how time is your best friend and the difference between investing at age 25 vs. 30 and 30 vs. 35, etc.—but it didn’t phase me. 

So I didn’t invest my first penny until I paid off my debt at age 31. And I regret it. I didn’t realize this was a mistake until after I paid off my debt and I was at ground zero financially. 

Yes, it felt good to be at networth zero rather than in the negative but to have nothing saved for retirement at 31 felt worse than I thought. I’ve been playing catch-up ever since. 

What I would do instead: Though I am grateful to be debt-free, it wouldn’t have hurt to put even $20 per month away in investments while paying off debt. Time is what makes compounding so powerful.

Mistake #3: Not having health insurance. 

In 2012, I decided to go without health insurance while I paid off my debt. I felt I couldn’t afford it. Any time I’d feel a tickle in my throat or cough coming on, I’d be paranoid about getting sick. 

Sure enough, I had a weird incident with food poisoning that landed me in the emergency room. After four hours of being treated, I left happy and grateful to be alive. But then the panic set in. I was in the ER without health insurance

A few weeks later I received a hospital bill of $1,600. At the time, I was making $10 per hour, so it felt like a million dollars to me. Luckily, I was able to get the hospital bill forgiven after applying for their financial assistance program. But it was awful and dehumanizing, as I had to turn over nearly every financial document to prove that I was broke enough to deserve it. Luckily, they agreed and it was forgiven. I was grateful, but the whole experience left me shaken up. The worry and mental anguish made my mental health suffer, on top of always being on edge. 

What I would do instead: I would purchase a low-cost health insurance plan and make sure I prioritize my health. Now I realize that your physical and mental health is everything and trying to cut corners to pay off debt isn’t a good idea. 

Bottom line 

Paying off $81,000 in student loan debt was the single most difficult thing I’ve done. The truth is, you can pay off debt but don’t need to let go of self-care, rest, and your health to do it.