Hey everyone!  Today, we have a dear debt letter by Eric Rosenberg, a full-time freelancer and blogger at Personal Profitability. Eric writes about personal finance and entrepreneurship at InvestmentZen, his own blog, and other sites around the web.

Dear Debt,

We have had an interesting journey together. I was happy to rid myself of you multiple times in the past, but it looks like we will inevitably be back together sometime soon. I’m not upset about it, but I do need to be careful with you this time around. I’m a dad now, after all, and it isn’t just about me anymore.

We first met when I went to graduate school. I was fortunate to earn a full-ride scholarship for undergrad, but wasn’t so lucky with my $90,000 MBA. I worked full-time while earning my MBA full-time to keep you from taking control of my life, but you were certainly a big cloud hanging over my head.

When I graduated from my MBA program in March, 2010, I had taken on $40,000 in student loans and had a net worth around zero, but I wasn’t going down without a fight. I used a combination of automation and aggressive payments to pay down my debt as quickly as possible.

In fact, I started paying off my student loans before I even finished grad school to keep interest from getting the best of me. I put 100% of my bonus from work and 100% of my tax return into getting rid of you. I split my payment into two, paying every payday instead of monthly, and slowly added more and more to each payment until I was paying around $700 per month, well over twice what was required.

And it worked! Two years and six days after graduation, I was debt free. Well, kind of. While my student loans were paid off and I never had credit card debt, a you reared your head in a new form in my life: as a mortgage.

I bought my first condo less than two months before paying off my student loans, so I was never really free of you completely, you just changed forms. But at the same time, I had a roommate and was paying less every month for my living costs while building equity in a home. Now, rather than simply costing me money every month, you were serving a valuable purpose.

It turns out we can get along well, as long as everything goes according to plan. Thanks to my MBA, which I could not have earned without you, my income doubled at my day job. It even led me to be able to leave my job for self-employment! When I owned my first condo, I needed your help, and it turned out well. I sold the condo and made a bundle. This time, I was able to get rid of you completely. When I sold my condo, moved to Portland and became a renter instead of a homeowner, I lived without you for about a year, but we were destined to meet again.

At the end of 2014, we met again. I was now married, so you were not my burden alone. I bought a home and you appeared again in the form of a mortgage. Because things worked out well the first time, I wasn’t too worried about bringing you back into my life. And again, it turned out okay.

Thanks to the booming real estate market in Portland, we made 20% on that house even though we only lived in it for 14 months. And because we moved for work, that entire 20% is tax free! Thanks debt for helping me earn a profit on real estate yet again!

So now I am living without you again, as I have been since selling the house in April, 2016. And I admit, I don’t miss you. I don’t miss looking at my finances and seeing a six figure debt. I don’t miss monthly debt payments, but they have been replaced by something else: rent.

Moving to Southern California gave me plenty of sticker shock on real estate prices, even moving from a hot market like Portland. But my rent here is $400 per month more than my old mortgage payment! It turns out that getting out of debt cost me more than being in debt! Debt, you are so sly!

So, debt, I want you back. I’m ready to take you on for a fourth time, this time for yet another mortgage. But because we’ve worked together to buy a home a couple of times in the past and it worked out well, I’m not too worried about bringing you back into my life. In fact, buying our next home with a big down payment should save us around $900 per month compared to our rent we are paying today!

As with any relationship, I won’t take any crap from you. No teaser interest rates. No balloon payments. Just a boring old 30 year fixed. If we can get back together on those terms, I’m down to give it another shot.

Your pal,



Melanie is a freelance writer currently living in Portland, Oregon. She is passionate about education, financial literacy, and empowering people to take control of their finances. She writes about breaking up with debt, freelancing, and side hustle adventures at DearDebt.com.

Currently she puts more than 50% of her income towards debt, while living a frugal, fun life. In addition to her love of personal finance, art and music, she is also a karaoke master. Follow the adventure @DearDebtBlog.

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