How to Stay Positive While Paying off Massive Debt

How to Stay Positive While Paying off Massive Debt

Stay Positive

Long time no see! You might have noticed I didn’t have a post on Monday…sorry homies. My wife and I moved over the weekend, so I had to take a brief hiatus from M$M. Don’t worry – it’s game on now!

Jen Hayes over at reached out to me a few weeks ago and told me about her strategy to move in with her parents to pay off her debt. I think it’s an incredible plan, and something more young people and parents should consider as the debt-crisis continues to spiral out of control. (From experience – living with parents is actually really hard to pull off!) Enjoy and give Jen some love in the comment section below! ~M$M

Merry Christmas Eve! 🙂


When I was accepted into a competitive master’s degree program, I was elated.  I was appalled by the price of the school, but I believed that a master’s degree would be a golden ticket to an amazing career.  I thought I would be well off financially.  I was very wrong.

I graduated with $75,000 of student loan debt, and my first “real” job paid so little that 50% of my income was going toward my loans.  I became depressed.  I thought about my debt constantly.  I quickly realized that obsessing about my debt was not productive – it didn’t solve the problem and it only made me miserable.

What I needed to do was take action.  After my husband and I got married, we came up with a plan to pay off our combined $117,000 of student loan debt in just three years.  Repaying a high amount of debt in a short timeframe is not easy.  It’ll be well worth it in the end, but in the meantime, it’s difficult.

Here’s what I do to stay positive during debt repayment:


Focus on the end goal

My husband and I work a lot, we’re extremely frugal, and we live with my parents.  None of these things are easy.  Whenever I find myself feeling sad or frustrated, I remind myself of my future goal.  I remember that in three years, we will be debt-free.  I had originally planned to pay my loans off over ten years, but the thought of being trapped in debt for the next ten years was unbearable to me.  I know that the sacrifices we are making now will be well worth it in three years when we will finally have financial freedom.

Find free things to do

I have a complete spending ban on outings with friends.  I have had people tell me that this is crazy and that I deserve to have a little fun once in a while.  What many people don’t realize is that it’s entirely possible to have fun without spending a penny!  I get together with my friends often, and we always do things that are free (like movie nights, board game nights, 5k walks, outdoor yoga, and festivals).

One challenge is that my friends continue to ask me to go to dinner or to other events that cost money.  I say no and politely remind them that I have a spending ban on outings with friends.  They are aware of my student loan debt situation, so they are understanding.  I know that some people like to do things that are expensive (like going to dinner or bar hopping), but anyone who is a true friend should be willing to check out some free things with you once in a while.

Stop caring what others think

Yes yes yes yes yes! This ^^^ is my favorite freaking part of this post. Caring about what everyone else thinks will keep you in debt. Heck yeah!!! (Sorry, I got fired up and made it weird. I’ll let Jen talk again). 🙂 ~ M$M

There are people who think I’m completely crazy to be living with my parents at the age of 26.  Others think I’m nuts for taking frugality to an extreme.  I love this quote by Dave Ramsey: “If you find yourself in a radical mess, you need to make a radical change.”  With the amount of debt my husband and I have, we are in a radical mess.  Only a radical solution will solve our problem!  When I feel judged by others, I remind myself that they are not the ones who pay my bills and that their opinions do not matter.

Stay Positive

Never compare yourself to others. Success isn’t one size fits all!

Don’t compare yourself to others

Every day when I scroll through my Facebook newsfeed, I see my peers purchasing their first homes, buying new cars, having babies, and traveling the world.  It’s easy to feel envious and to wonder how they can possibly be affording it.  Many of them may be financing their lives with credit card debt.  Others may be extending their student loan payments to 25 years and trapping themselves in debt for many years to come.  I could do the same, but it certainly wouldn’t be worth it to me.  I am “missing out” on these major life events now, but it will absolutely be worth it when I’m debt free in just a few short years.

Be grateful for what you have

It’s natural to feel frustrated, disappointed, and envious of others when we are buried in debt.  Debt repayment isn’t easy and it’s perfectly reasonable to feel all kinds of negative emotions while you’re paying off debt.  Still, it’s important to keep things in perspective.  1 out of 6 people in the world live in poverty.  That’s over one billion people.  I may feel “poor” sometimes, but I have a roof over my head and I always have enough money to feed myself.  Whenever I feel sad about any of the things I don’t have, I remind myself of all the wonderful things I have to be grateful for.


Maintaining a positive attitude during debt repayment can be tough at times.  I have found several strategies that help me to stay positive.  Focusing on the end goal (financial freedom), finding free things to do for fun, ignoring the judgments of others, avoiding comparisons to others, and choosing gratitude are all useful strategies that keep me feeling optimistic and motivated.

Should more Millennials consider living with their parents to pay off debt? Is it something to be ashamed of or proud of?



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19 comments… add one
  • The Saving Nerd Dec 26, 2015, 9:40 pm

    Jen, you hit the nail on the head with your advice. I especially like the point about forgetting what others think.

    Some people want to impress others so much they will go into debt. I used to be that way.

  • Jahne Dec 27, 2015, 7:52 pm

    I have been in a massive debt situation and paid it all off in five years. I have to admit that they were the hardest five years of my life but now I am free! Freedom from debt is a great place to be and was worth the blood, sweat and tears. This article has tips for staying positive while still tied to the debt which is very helpful–I had many very sad days before my debt was paid off and sometimes it was hard to continue to look long term. Great tips, Jen!

    • Millennial Money Man Dec 28, 2015, 12:41 pm

      I feel the same way about the time that I was paying off debt – wasn’t glamorous, friends passed me up, etc. The freedom to do what I want now is incredible and totally worth the hard times!

    • Jen @ Frugal Millennial Dec 29, 2015, 6:36 pm

      I agree that getting out of debt is extremely difficult, and it requires making many sacrifices. Financial freedom is definitely worth it though!

  • Neva wencl Dec 27, 2015, 9:01 pm

    I think for Jen this will be extremely difficult 3 years of her life but its all worth it in the long run. Nobody wants to live with there parents when they are 26 but her and her husband are setting themselves up for success for the future and its the smartest thing they can do in their situation. I believe they should be proud of themselves.

    • Millennial Money Man Dec 28, 2015, 12:42 pm

      Same here, I think they should be proud! They have NO idea how far ahead of their peers they will be when it’s over.

    • Jen @ Frugal Millennial Dec 29, 2015, 6:38 pm

      Thanks Neva! Living with parents at 26 definitely has its challenges, but it will be worth it in the long run!

  • Mrs. Groovy Dec 29, 2015, 12:02 pm

    Yes! Stop caring what others think! Be “weird” like Dave Ramsey says.

    Mr. G used to bring his lunch to work, and according to him, most days he “ate like a rat in his cubicle’. He went out to lunch with his co-workers on Fridays. But they still made fun of him. We’ll see who’s laughing when he bids them all farewell in 2016.

  • Anonymous Jan 2, 2016, 7:41 pm

    I’m glad you are working your way to getting rid of debt in a shorter amount of time than a greater amount of time. While it’s good to have some fun which I see you doing by doing free stuff. I also think you’re doing other great things such as not thinking what others think and being grateful in life. My advice is take a breather and make sure you live in the moment and not always worry about the end goal, which im not saying youre doing but if you are then heed my advice. Enjoy the journey, not just the destination.

    • Millennial Money Man Jan 2, 2016, 9:09 pm

      Great advice – love the “live in the moment” comment. Actually something I need to do as well. I spend most of my time thinking about how I’ll build wealth in the future but need to focus on the now!

    • Jen @ Frugal Millennial Jan 3, 2016, 3:42 pm

      I definitely hear what you are saying. I do think an extreme approach is necessary with the amount of debt we have, but it’s good to live in the moment once in a while (without going overboard). One good thing about being married to a spender is that he encourages me to loosen up a little (and I get him to focus on the end goal and save more). The part about the complete spending ban on outings with friends is a little misleading because I do make occasional exceptions (for birthdays, etc), just not very often. Recently, I received a holiday bonus which was completely unexpected. Almost all of it went to car repairs and student loans, but $15 of it went toward my husband and I getting lunch at our favorite restaurant. I think living in the moment is great as long as it doesn’t happen too often and you don’t go crazy with it 🙂

  • Angela Madera Jan 11, 2016, 11:06 pm

    The thought of your loan encompassing so much of your paycheck is exactly how I felt, and feel to this day. It’s so very difficult to reconcile being happy and in the moment, but also feeling this unbearable weight from our loans. It’s like a mental illness. By the way, don’t give a crap about living with your parents, its part of the process. Thanks for sharing your thoughts.

    • Jen @ Frugal Millennial Jan 12, 2016, 5:19 pm

      Thanks, Angela! It’s terrible how much student loans can affect your life and your mental health. Having a plan to pay them off quickly definitely helps me!

  • Tom Feb 1, 2016, 9:26 pm

    Great article – LOVE the image, captures “what others think” perfectly!

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