Why the Second Year of Paying Off Debt Is the Hardest


getting out of debtThis post originally appeared on The Billfold.

Last week I made the mistake of looking at Valentine’s Day cards at Whole Foods. One of the cards had a picture of a beach with a couple dancing on it. It is beautiful and idyllic and says in a horrible script font: “Wherever we’re together is paradise.”

This made me angry. No it’s not, card. You are lying, card. Because this is Year Two, and Year Two is three hundred and sixty-five days of hell.

One year ago this week, my husband and I decided trepidaciously to get our financial act together. We had just gotten engaged, and I was having a severe, persistent anxiety attack about the cost of having a wedding. So, like others before us and others since, we enrolled in Dave Ramsey’s Financial Peace University, had a bunch of bibles and shame thrown at us with great force, and figured out that we could probably be making better choices than we were. So we started to do just that.

In Year One, we cut our living expenses down to the barest bones. We took on second jobs. We sold prized possessions. We focused every cent on getting out of debt. And we paid off $28,000. We were really, really proud of ourselves.

And we deserved it. We worked incredibly hard, were incredibly diligent, and were trying to do something nobody does when they are young and idealistic: get out of debt. We are trying to set ourselves up to win with money at an early age, and we made an important step forward.

But that $28,000? That’s just barely the first step. We’re not even halfway done yet. And that’s the realization that kept hitting me during week one of Year Two: We are going to do all of that miserable stuff for another year, and more. It’s no longer the exciting beginning, where we got to watch those tiny, easily paid debts drop like flies. We aren’t in the homestretch. We are not down to that one last pesky bill, throwing gobs of money toward it and only it. We are in Year Two, and we’re in the ugly thick of it.

We have another year of creating one million spreadsheets to try and formulate our way out of this. We will continue to solicit roommates to share the burden of rent in our miniscule house, where we have started to keep the heat at 58 degrees in the middle of Midwestern winter. I will once again consider selling the rest of my clothes, my final possessions, which will leave me with one old hoodie, so many tee shirts from high school, and a pair of shoes that do not fit me or any human person. I will apply for overnight jobs, because I had been getting a solid six hours of sleep most nights, and that’s time I could be working. I will find no solutions, and I will cry while looking at cards in Whole Foods.

Because that’s the truth of Year Two: We will have to do what we did in Year One, except it will be harder. I will have to go from my real job to my horrible part-time second job at the mall for as many hours as they will take my indentured servitude per week, every week. I will have to continue to tell myself that a can of black beans and some baby carrots is a meal because it has two colors in it. I will have to continue my streak of friendlessness, because everything done with friends costs money, and no one wants to be friends with the girl who only talks about paying off debt anyway. I will have to cancel Netflix because my brain does this thing now where it doesn’t just count the $7.99 a month, it factors in the cost of the electricity and Internet service I’m using while watching season one of Law and Order: SVU and the amount of money I could have made in that time and the depreciation of my laptop and then SUDDENLY NETFLIX COSTS $500 A MONTH AND I NEED TO QUIT.

There is promise at the end of this madness, I suppose. Like the idea of getting to keep all that money we’re paying other people right now. A year and seven months from now, what we’re paying other people each month in debt repayments could be funding a trip to a script-font-y island. And that is a nice thought. An even nicer thought is the idea of bringing children into this world without the burden of debt. Or getting to go back to school and pay for it with money, not debt, so that maybe, theoretically, we can work in the fields we actually are passionate about, not the first place to offer us jobs.

But right now, this is Year Two. And nothing’s going to fix it except (endlessly, tediously, agonizingly) more of the same.

More from The Billfold:

My Mom Stole My Identity and Ruined My Credit
One Billionaire’s Attempt to Save a Neighborhood
Unemployed, Discouraged, But Not Hopeless


  • Chelsey

    So. Flipping. True.

    I’ve noticed that friends of mine are much less crazy about paying off debt than I am – and sometimes I think they have something right. Debt sucks. I hate it as much as anyone. 
    We paid as much off in our first year as possible (about $20k), and then our situation changed. What I wound up wishing is that we had paid off slightly less debt, and saved more of that money instead. The budget would have been equally tight, but I would have allocated it differently, as we weren’t saving much at all. We also weren’t contributing to my husband’s retirement, and as they say, ‘those are years you can’t get back.’ 

    • Ashleynt

      I’m working on paying off debt too but have also been diligent about putting some into savings each month. It’s hard to find that balance when you have an end goal in sight for the debt but a more ambivalent goal for the savings. I’m additionally trying to work in funding a bit of retirement each month. $50 may not be much but something is better than nothing!

  • Fellow Saver

    I love the overall premise of this article, and I applaud your efforts. My one question is, if you are trying to cut costs, is Whole Foods really the place to do your grocery shopping? :)

    • Jamasian

      Depending on what she’s buying, I’d say she’s right. Losing your health is the worst possible thing you could do when in debt.

  • Jamasian

    I love this honest article! The 2 weeks before re-signing my contract job, I considered the “what if they don’t re-sign me?” and that brought up the “how much did I even pay off?”

    The only change this year is, I’m making it a point to save some cash for just in case, but that means almost becoming a hermit. -_- Either way, when I finish at such a young age it will be all kinds of worth it. Just wait until you’re the friend always hanging out with absolutely no cares of what you just spent. Theoretically.

    Always keep the faith!

  • Zounds

    There was a time (5yrs ago) when I used to use my credit card to the max, the student loan to the max and pay it all back in small insignificant amounts (that always crawled back by the end of the month).

    Then I met my wife who was good at not spending too much. Together we started Budgeting with a capital B. We drafted an excel spreadsheet for 2 coming years with lines for every income and expense. We started to pay off our loans as quickly as possible, reassessed our future savings and income and at the same time started to put aside some of the money earned. And most of all – we shared every little detail about our money with each other – to the last dime – this allowed us to plan efficiently ahead and see the real pace we were able to save and repay. 

    Fast-forward 5 years, we have repaid our loans and set aside a considerable amount for security. 
    OK, we also took two other loans now, using some of the saved amounts as downpayments in order to make our dreams come true (an apartment in the city + a retreat centre in the countryside), but since our financial planning is forecasted so that it takes into account all sorts of force majeures, it can be relatively easily managed. 

    The key to all this: 
    Long term detailed planning, weekly super-detailed budgeting. Some might say it is too much work, but if you consider that we are on our way to make our dream come true, it is a non-existing effort. 


  • nut

    I found this article to be very un-helpful. The title is “Why the Second Year of Paying Off Debt is Hardest,” but all I gleaned from it was complaints and negativity. Why exactly is the 2nd year hardest?

    • robin

      Because her intial enthusiasm is gone.  When you first start you don’t know how much your life will change.  It was sort of an” ignorance is bliss” situation at the beginning.  NOW she KNOWs how hard it it and has to grit her teeth and keep going.   I hope she remembers that there WILL be light at the end of the tunnel.

  • http://twitter.com/Nancer Nancer

    While I applaud the effort, I worry that this person is making herself unduly miserable. There has to be some balance in life, and cancelling a $7.99 subscription to Netflix (when you don’t allow yourself any other entertainment) seems like unnecessary punishment. I believe in living debt free, but you have to have some enjoyment in life or what is the point? It seems like perspective and balance needs to enter into the picture here.

  • Fighting2BDebtFree!!

    I applaud this article. I also believe that there is solidarity for those of doing this exact same thing. Find each other and stick close!  We’ve got to keep reminding ourselves that we are doing the right thing…. only 313 day, 3 hours, 18 minutes and 7 seconds to go…….

  • Alexis McGhee

    I am not saying that paying off debt isn’t hard; however
    making it sound this horrid is not a positive experience either. She
    traumatized me. I experienced the same and I was alone. I kept Netflix,
    Rhapsody and maybe eating out with friends 1 once a month. They understood my
    circumstances and didn’t make me feel bad about it. It was a learning and
    powerful experience for me. After 3 yrs, I rewarded myself with a trip to
    Ireland all paid for in cash. It’s still a learning experience, but I am all
    the stronger for it. I wasn’t miserable making the debt, I wasn’t miserable
    paying it off (unhappy sometimes, but not miserable).