A Story About Paying Off Debt and the Obstacles Along the Way

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Breaking: Debt Repayment Journey Gets Delayed By Midlife Crisis!

Before we became financially responsible, we very much lived by the principles of YOLO. We took the vacations we wanted to take, bought the things we wanted to buy, and moved when we wanted to move. We paid little attention to whether we could afford those choices, which explains why we're now digging out of debt.

When we started our debt repayment journey in April of 2017, we wholeheartedly abandoned our YOLO ways so that we could reach our goals as quickly as possible. Every choice we made - from the things we purchased (or didn't purchase) to the jobs we took to the money we started investing - became about setting ourselves up for success down the line.

We've become obsessed with our financial future.

I'm not sure that's entirely a good thing.

I miss YOLO me

I'm proud of how far we've come. I really am. 

But here's the thing: I'm not necessarily happy with who I've become in this process. 

Before we started tackling our debt, I was:

  • Adventurous
  • Spontaneous
  • Relatively optimistic about the future
  • A risk taker
I wasn't always happy - who is? - but I was idealistic. I had faith that things would work out if I just had the courage to take the next step. I was excited about life and its possibilities. Some of the best and most indelible things I've done in my life have been done on credit, supported by crappy health insurance.

Now we're out of credit card debt and well into our student loan repayment. We have real jobs and employer-sponsored health insurance and I am:

  • Unfulfilled in my work
  • Bored out of my mind most days
  • Constantly worried about things that could go wrong, financially or otherwise
  • Cautious
  • Not really excited about the future
This past weekend I sat down to make some personal goals, and outside of some well-defined financial benchmarks, I couldn't bring myself to write down anything. Why? Because I'm completely uninspired right now. Every goal I could think of that fits into our current debt repayment paradigm seems lackluster and pointless.

Something needs to change, and I think the thing that needs to change is that we need step back for a few months and prioritize the present over the future. I don't mean that we should go back into credit card debt or that we should quit our jobs tomorrow. But maybe it's okay to slow this whole thing down a little bit, because I really don't see why I should sacrifice the things I like about myself for the unknowns of tomorrow.

So what's that going to take?

One, I need to find a satisfying career path. That could mean getting a new job, but more likely it means saving up and planning for that career break I've talked about and figuring out a way to work for myself. Which feels scary. What about health insurance? What about a steady paycheck? What about being able to afford our rent? Will we be able to get by on one income for a while?

I don't know, but venturing into the unknown, even if it means occasionally MacGyvering my way along, sounds way more appealing than sitting at a desk for the next 25 years. 

Two, at least for now, we need to change our emphasis from debt repayment to saving. I've had a lot of good conversations on Twitter this week about the best way to use money: pay off debt? Invest? Build up the emergency fund? As several smart people keep pointing out, there's no right answer because personal finance is personal. 

Yes, paying off debt feels fantastic. It's a high, and it's addictive. But. I also want to be able to make this career shift. I want to be able to attend events like CentsPositive and Lola Retreat. I want to be able to take a trip outside the country with my family. I don't want to wait two or three more years to do that.

Is it worth it to me to keep paying $600 a month to student loans a while longer? 

I think so.

So in November, we're going to take a little break from the student loans. We're going on a family hiking trip over Thanksgiving, and then we're going to put the rest of our disposable income into our savings account. We'll build up that savings until the end of next summer while we try to map out a career plan, whether that means me finding a new job, re-training, or building my own business.

It doesn't sound like the wisest move financially, and yet it feels like the right path.

Don't get me wrong: I'm all for planning for the future and making wise financial choices. But not at the expense of the things that make me who I am.


  1. It's SUCH a balance between paying down debt and reaching goals, and not burning yourself to a crisp doing it. The only reason I think I was able to stay intensely focused for ten years was because I refused to live life during that period, I wouldn't get married or start our family, and I thought that it was just one or two more years... until I found myself on the wrong side of a decade with terrible health and just so much wasted time in some respects.

    I wouldn't go back and change anything, I am who I am today and I am happy now, BUT I would never ever tell someone else they should take the path that I took! The cost is too high.

    I think this is a wise move on your part.

  2. Enjoy your hiking trip! We've also struggled with balancing debt repayment with splurging occasionally so that we don't burn out. You've made a lot of progress :)

  3. I love this post - it really resonates for me. In fact, I wrote something along the same vein back in July: https://debtbegoneblog.wordpress.com/2018/07/17/am-i-commuting-or-am-i-road-tripping/

  4. I still have not found where the balance is between paying off student loan debt, saving and living life. The older I get the more I realize how limited our time is. I don't want to work 80 hour work weeks and miss my children's years at home, just to retire when they are gone. It's nice to not have as large of a monthly student loan bill holding us down, but eventually it'll be paid off.

  5. I can definitely relate to this. It looks nice on paper to throw an extra $400 a month at my student loans, but that would leave very little wiggle room in the rest of the budget and I don't want to put so much pressure on myself to keep that up for 3-4 years.

  6. I think the balance is definitely important! My life crystalized a little when my daughter told me my life seemed pretty boring, going to a job I don't enjoy, then coming home - eating, and bed. I never thought about it too much but she's right, there's not a lot going on there that is exciting. Most of us keep thinking there's a great life for us tomorrow, so we keep doing everything today to prepare financially. But we aren't guaranteed anything.

  7. hey, i found your post from TLRE. as someone who has been there already we paid debt and invested at the same time. i just looked back at some family meeting notes and i still owed about 29k in student loans in 2009 at age 41. fast forward 9.5 years and we're debt free including our house but set aside bucks for vacation/leisure all of those years too on middle class pay. seems like you got a little out of balance is all. good luck.