The Reason That Most People Don't Pay Off Debt

The Reason That Most People Don’t Pay Off Debt

The Reason That Most People Don't Pay Off Debt

As this site has continued to grow (reaching almost 100,000 people a month now), I’ve started to see so many different stories from people that are working hard on their debt. It’s really awesome – I get random emails and messages on Facebook from people that just want to share a cool part of their life with me.

I honestly believe that paying off a big chunk of debt is powerful enough to change the fiber of who you are. Through my own journey of paying off my student loans, everything about my perspective on life has changed.

Every day (and I’m very serious about this) I wake up and take a second to reflect on how bad@$$ life is. From the moment I opened the letter from Sallie Mae, to today where I literally make a living writing about money, I’m just grateful as hell to be alive AND do what I do.

Related: The Real Reason I Live Debt-Free

But the journey here wasn’t easy.

For every second that I reflect on how awesome things are, there’s another second where I remember what it took to get here.

If you’re in the process of getting rid of debt or already finished, what I’m about to say will resonate really strongly with you.

The biggest reason that people don’t pay off debt is that it freaking sucks. It’s not fun. You have to sit there and watch society leave you in the dust while you meal plan and wear the same crap clothes you had in college.

Related: Let Your Friends Pass You Up

I’ve talked to people that are living at their parent’s house. In their sister’s basement. Busting their butts at two jobs while trying to make ends meet, AND throwing some extra cash at their student loans. Obsessing over every. single. dollar. that comes in and goes out.

It’s physically and mentally exhausting.

The majority of people are inherently soft when it comes to money.

Sounds pretty harsh, right? It’s not to be mean though – it’s just what I’ve observed. I think I’ve had access to a big enough cross-section of people now to understand that most of them don’t have whatever “it” is that helps people endure an uncomfortable situation.

When Coral and I were renting a 10×10 room from her parent’s house, I hated it. It wasn’t that they were hard to live with (the opposite actually), but it was cramped and embarrassing as hell. EVERYONE kept asking when we were moving out or “starting our lives”.

Now it’s always how incredible my story is, or if they can sit down and talk about money with me some time. It’s funny how that stuff works isn’t it? 🙂

Related: How I Paid Off $40,000 of Student Loans in 18 Months

I see people online all the time that react to cool debt success stories with comments like: “Well it must have been nice to live with mommy and daddy“, or “Ugh, if I made that much money I’d be debt free too“.

But it’s not, and they wouldn’t.

That kind of talk is just an excuse for not having the ability to do something hard. If they made a lot of money, they would spend it all. Instead of going out and hustling for more money, they would just wish for it via lottery tickets.

People literally won’t do things that make them uncomfortable, and then turn around and complain because their financial situation sucks. It’s one of the most frustrating things about what I do now.

That’s why I’m so impressed with the readers on this site.

And I swear I’m not just writing that to boost anyone’s ego. When I was paying off my loans, I was literally the only person I knew that was doing something “crazy” like that. It was like being on an island.

After starting this site, I’m meeting so many debt bloggers and M$M readers that are paying off crazy amounts of student loans/mortgages/credit card debt. It’s jaw dropping.

So if you’re fighting the good fight by trying to tackle your debt or get ahead with money, just know that I have your back and understand what you’re going through. You’re not weird – you’re so smart that it pisses other people off.

The process probably sucks for a lot of you, but I guarantee that the other side (debt freedom in general) is one of the coolest accomplishments you’ll have in life.

Question for you:

How much debt have you paid off so far?


Live differently. Your bank accounts will thank me later. ~M$M

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61 comments… add one
  • Kyle Feb 10, 2017, 7:47 am

    Well said man! I appreciate the blunt reality that you laid out here, I tend to have the same tone about this stuff. “It freaking sucks” is about the best way to describe paying off debt. Nice work as always 👍👊

  • James Feb 10, 2017, 7:59 am

    I’ve paid off $4,000 in 2.5 months with $18,000 to go. And yes it is just about the suckiest thing I’ve ever done. But I realize that I dug myself down in this hole and with time and perseverance I can dig myself out of it. Thanks for all you do. Your articles are always good motivation.

    • Millennial Money Man Feb 10, 2017, 8:00 am

      Thanks for the kind words James – glad the articles are helpful. I just try to write stuff that I would have liked to read when I was paying off my student loans haha! Nice job on the debt so far!

  • David Shepherd Feb 10, 2017, 8:03 am

    Love it. A lot of people have excuse after excuse. It took me a lot of years and struggle to get out of debt, but it has been wonderful having the free cash flow by not having to pay down debt anymore.

  • Amy @ Feb 10, 2017, 8:16 am

    We paid off $85,000 in less than three years! Every uncomfortable and embarrassing second was 100% worth it. We just bought me a new car (well, new to me and 10 years newer than the beater I previously drove) in cash. And now we’ve saved up enough for my husband to quit his job and start his own consulting company. I’m an anxious person, but when people ask if we’re nervous about that new venture I can honestly say no. We have no business debt and we’ve been living on one income for years now, so our lifestyle isn’t going to change, even if he doesn’t start immediately making money. No debt = freedom. Totally worth the temporary pain to get there!

    • Millennial Money Man Feb 10, 2017, 8:34 am

      The business will work out! Being financially prepared makes going out on your own so much easier. You don’t have to take crappy work or do things that go against your morals when you’ve got some cushion.

  • Luke Feb 10, 2017, 8:22 am

    My wife and I have paid off $27,000 in two years. We went from 2 car payments, 3 credit cards, 2 retail cards, financed mattress, TV, appliances, to debt free. Our biggest reason (other than sanity) was that we realized she could come home from work if we paid off our debt and tightened up our budget. She will officially be a stay at home mom in March!!

  • Chelsea Feb 10, 2017, 8:28 am

    Since April 1, 2013 my husband and I have lowered our debt by $68,000 on top of paying $20,000 cash for our wedding during that time. Multiple jobs and keeping our lifestyle down in comparison to our peers will be so worth it! $57,000 to go!!

  • Susan Feb 10, 2017, 8:36 am

    My husband and I paid off $68,000 of student loans in 12 months! It was the worst and best thing we could have done! Now we’re encouraging our friends and family to make the hard decision to be radical against debt too.

    • Millennial Money Man Feb 10, 2017, 8:57 am

      That’s awesome Susan! Hopefully they don’t get mad/offended. That’s pretty common haha

  • Patrick Feb 10, 2017, 8:51 am

    Student debt: I have paid off $70k over the last 3 years… just $38k more to go! This does suck but I can’t wait to be debt free for the rest of my life!

    • Millennial Money Man Feb 10, 2017, 8:58 am

      Yeah!!! Once you’re done with the loans you can focus on cool stuff that you want to do 🙂

  • Ms. Montana Feb 10, 2017, 9:00 am

    People constantly looked down or thought our choices were stupid when we started. Why did we never eat out? Why did we drive older cars? Why did we never spend money? But we were paying off $50,000 in debt and saving our first $100,000. I just had to want more financial freedom more than spending money on stuff I didn’t need to appease people I wasn’t that close to.

    • Millennial Money Man Feb 10, 2017, 9:41 am

      It’s so weird when people do that, right? I’ve kinda learned that it’s just because you’re doing something different than what society is comfortable with.

  • Mrs. Picky Pincher Feb 10, 2017, 9:07 am

    Hahahaha. Welp, it’s true. Paying off debt definitely sucks. But it’s all about being an adult and taking responsibility for the debts you’ve assumed. Few people get “surprised” with debt–especially student debt and mortgages. We usually know what we’re signing up for; we just don’t care about the consequences at the time.

    Mr. Picky Pincher and I were talking last night about how he feels deprived during our debt payoff journey. He’s created mental barriers that make him feel horribly guilty any time he spends money. This is our current struggle, since I obviously want him to be happy and not feel deprived. But yeah, paying off debt requires changes and some people don’t like change.


    We’ve been able to pay off a lot of debt:

    1. $14,000 of credit card debt
    2. Finance a $10,000 home renovation with cash
    3. Start paying down our $65,000 student loans (currently at $55,000 or so).

    • Millennial Money Man Feb 10, 2017, 9:43 am

      Nice! I actually think a lot of college grads legitimately feel surprised. Everyone says that an 18 year old is an adult…but after teaching them in high school I pretty strongly disagree. Their still basically kids when they take on the debt. Some people mature quickly and figure it out, and others never really grasp the reality of debt until the letter comes in the mail. Pretty interesting stuff.

  • Claudia @ Two Cup House Feb 10, 2017, 9:37 am

    We’ve crushed $194k of the $204k we had two years ago. We are just one student loan away from 100% debt freedom. And it does suck–you are so, so right. We have only one loan to go and it still sucks. I love (and loathe) making these payments, but it’s only for a short time. Soon, we’ll be able to make progress on other goals that are a LOT more fun.

  • The Grounded Engineer Feb 10, 2017, 10:02 am

    Before we got serious about our debt, we had close to $135k in debt between student loans and car loans after graduating college. We had paid down the debt pretty well for the first five years we were out of school. When I started listening to Scott Alan Turner’s podcast in late 2015, his message of paying off debt resonanted with me and we accelerated our efforts. Between a nice inheritance from my late great uncle, buckling down on our budget, and dipping into our emergency fund, we eliminated the final $97k in debt in less than a year.

  • Patrick Feb 10, 2017, 10:07 am

    I’ve paid about $21k of principal in the last two years…I basically pay my bills and student loans and I’m not left with much after that. I’m of the mindset that this debt needs to be paid off aggressively in order to truly be able to “start your life”. My savings account has struggled to grow because of this (although I do have my emergency fund). My SO on the other hand is of the mindset that saving is more important than paying her loans. Her savings account would crush mine, but on the other hand her debt is still there.

    I’ve been contemplating cutting back on the loan payments for a bit to increase savings and have a little more flexibility. Once my savings is more established I can find the happy medium of loan payments/saving.

    • Millennial Money Man Feb 10, 2017, 10:11 am

      I actually made minimum payments for a few months (about halfway into my debt-payoff journey) so I could build a really good emergency fund. I try to recommend that people do that – I know $1,000 is a popular number but I actually like a little closer to $3,000.

    • Patrick Feb 10, 2017, 10:13 am

      I’ve also been going against the argument of “We’re in our 20’s! We need to enjoy life NOW! We can’t let these times pass us by!”. That’s a hard one for me…but I am determined to pay off my debts by 2020!

  • Bria Feb 10, 2017, 10:07 am

    Hey Bobby, one question I’ve always wondered about is WHY you decided to pay off the debt that early after college. I ask that because for me, my parents were TERRIBLE with money and got themselves (and then us kids subsequently) into a massive money mess (how’s that for alliteration?) yet their mothers were both penny pinchers from the great depression era and always seemed in control of what little money they had saved up. They were smart and frugal but generous because of that. I saw two extremes growing up and I wanted to be like my grandmothers and not my parents. That’s what pushed me to pay it all off. What about you? What was it that made just ignoring it like most kids our age do unacceptable to you?

    • Millennial Money Man Feb 10, 2017, 10:15 am

      Massive Money Mess. Someone will use that name to start a blog haha!

      Actually it was pretty simple for me – I just took the right advice at the right time. My wife and I were waterskiing with a friend of her family right after I graduated college. He basically just told me to pay off the loans and explained why it would help me in the future. He was a successful businessman, so I figured he was probably right.

      My personality kinda did the rest. Once I start something, I get pretty obsessed about doing it until I feel like I succeeded. That’s probably why I’ve been able to make money blogging, who knows. 🙂

  • Mad Money Monster Feb 10, 2017, 10:08 am

    Over the course of our lifetimes, we have paid off tens of thousands of dollars in debt. It might even reach into the 6-digits if you count everything. It can absolutely be done. We made plenty of financial missteps along the way, but we also made a few good choices that carried us through. One was graduating with our undergrad degrees with hardly any debt AND both getting our Master’s degrees for free. When I graduated undergrad, I had approximately $12k in CC debt that I was able to obliterate within a few months. How? Just by putting my nose to the grindstone and throwing all my extra income at the debt.

    My husband also racked up quite a bit of CC debt when he was in his early 20s. One day he sat down with all of his cards and balances and made a plan to obliterate it. He even had to borrow money to give as a wedding gift to a friend because he had paid too much towards his debt and forgot about his required attendance and expected gift.

    But as you said, it’ll never happen if you’re not hungry for it. These days, we’re pretty much debt-free except for the two mortgages (our primary home and a rental property). We predict they’ll be annihilated within a few years. Ahhh.

    Mad Money Monster

    • Millennial Money Man Feb 10, 2017, 10:17 am

      Yeah I think it’s pretty common for people to want some type of magic bullet for paying off debt. Once you boil it down – it’s really just choosing to make bigger payments, and then you do whatever you need to in order to make it happen. A lot of people try to complicate it (and then never end up doing it).

  • Rachel Feb 10, 2017, 10:31 am

    Yes! We got married and decided to do the hard thing and pay off $20,000 in school loans within 2 years. We did it in 18 months! It totally sucked at the time. The whole “it’s like being on an island” sentiment is so accurate! But today, we don’t have to worry about school loans following us around, we got a pretty good deal on our mortgage because we were smart with our money. Now, we’re working to pay off our mortgage early. It’s so worth it in the long run!

  • ilubro Feb 10, 2017, 10:41 am

    These are excellent points! Paying off debt is hard and nobody wants to “miss out” on things while doing so.

    While we aren’t aggressively paying down student loan debt, we definitely sacrifice extra and miss out on things that others aren’t putting off. That way, we can pay extra and ensure we are reducing our debt load faster. Sometimes, it feels like everyone else is doing the opposite – adding to their debt pile in order to do “all the things.”

    Some seem to learn the “value” of saving early on, others not so much.

    • Millennial Money Man Feb 10, 2017, 10:44 am

      Yeah you’ll definitely get passed up for a few years by all the people that make minimum payments, but you’ll catch up pretty soon (and then pass them).

  • George Feb 10, 2017, 11:02 am

    Great post on this topic, Bobby. In addition to it sucking, I also think the reason most people don’t get out of debt is the same reason they got into debt in the first place – lack of discipline. Now, not everyone that goes into debt lacks discipline; when they are 20 years old they may think that debt to fund education is “good debt” (speaking from personal experience). But in order to push through and knock out alot of debt in a short period of time, you really have to have a wake up moment where you realize that staying in debt is robbing you of your future and your ability to live your life now and make the best choices along the way. I paid off $20k of student loan debt (only debt I had other than a mortgage) in 12 months (finished in August 2015), and almost a year later my mom went through some tough times and I was able to give her a car and pay cash to buy myself another one.

    Thanks for running this blog.

    • Millennial Money Man Feb 10, 2017, 11:14 am

      No problem – I love running the site so it doesn’t really feel like work to me!

      You’re totally right, lack of discipline is another issue. I didn’t even really think about my student loans when I was 20 – it didn’t hit me until after I graduated. Late bloomer I guess haha

  • Nicole Feb 10, 2017, 11:19 am

    I’ve paid off 17,000 in a year and a half… It’s hard but worth it. Living in a tiny one bedroom now but will appreciate everything later!

  • Ryan Feb 10, 2017, 11:20 am

    “You’re not weird – you’re so smart that it pisses other people off.”

    Isn’t this the truth. While I’m busting my ass and living like none of my friends i see them getting pissed off at their situation, but their the same people rolling over balances on cars & buying houses that they can barely afford.

    Since graduating college in 2010 I’ve paid off that $20k student loan debt, bought a house in 2014 with $20k down, and added another $24k in equity all while paying for a wedding last year in cash. Next is my wife’s car loan of $15k that will be gone by the end of the year!

  • Sara Feb 10, 2017, 11:41 am

    We have paid off about $48k so far and have about $35k left to go. It’s been am intense journey and no one around us understands but we are hanging in there and will be free soon!

  • Gentleman of Leisure Feb 10, 2017, 11:50 am

    Nice article today! I hate paying off debt, but I hate having debt more so its a process that needs to be completed. My stats: Over the last 2 years
    Student loans: Reduced by 37,000
    Mortgage: Reduced by 19,000
    403b: Contributed 21,000
    I paid early on my mortgage to eliminate my PMI which cost 79 per month. Also, our student loan interest is pretty low now, so I thought the 403b was a good option. We will be done eventually!

  • Jorge Quezada Feb 10, 2017, 12:05 pm

    I appreciate your blog because it’s one of the things that keeps me motivated in this journey. My wife and I started the Dave Ramsey baby steps in Jan 2016, and have paid about $44,000 since then. Student loans, car loans, credit cards, you name it, we had it. In that time I was also laid-off and we relocated from Georgia back home to Arizona. The truest thing you said is very simple, yet it describes the journey perfectly: it FREAKING SUCKS! but you do come out a different person…

    • Millennial Money Man Feb 10, 2017, 2:00 pm

      Glad to hear that it helps Jorge! Definitely makes it worth putting all the time in (it’s more than most people think haha). $44k in a year is incredible progress!!!!

  • Michael Feb 10, 2017, 12:59 pm

    I agree with you , most people are simply not ready to make and endure the plainness of life that occurs while de$troying debt. This past year I paid down 44K in debt, put away 20K for a wedding, and bought a 10K ring with cash. I was talking with someone about growing my reader base and they told me, “show em what success looks like!” Unfortunately it looks like, old clothes, a 15 year old car (that runs like a dream), and a 680sq.ft. studio in downtown Raleigh… not too impressive! But I trust that the years to come will make it all worth while! I think you’d agree.

    • Millennial Money Man Feb 10, 2017, 2:02 pm

      Oh heck yeah it will be worthwhile. And I agree on the audience building advice. I’ve found that people respond much better if you show them how you are doing it vs. telling them how they need to do it.

  • Karl Feb 10, 2017, 2:07 pm

    Thanks for the encouragement. We only have the mortgage left, and only 1/3 of the original balance left, but it still sucks trying to get the rest of it gone to give us some more choices and freedom in our finances.

    In contrast, my sister-in-law and her three kids are living with my wife and I because she’s got debt preventing them from getting their own place. We’re trying to show her how doable this is, but your message is right on, it’s just hard.

    • Millennial Money Man Feb 10, 2017, 2:52 pm

      No problem! Yeah I mean that’s really the game – how much crap can you put up with and how willing are you to watch people do fun stuff while you don’t temporarily. Definitely not easy.

  • Julie @ Millennial Boss Feb 10, 2017, 2:58 pm

    We’re now up to $96,000 paid off! You’re totally right. People were not that supportive when I was skipping their bachelorette party or not going home for Christmas in order to save money. It’s strange how people are instinctively not supportive when someone is making changes to improve their life. It’s probably how they rationalize their own decisions. I think your story is helping people so keep telling it!

    • Millennial Money Man Feb 10, 2017, 3:05 pm

      Haha yes I’ll keep telling it! I’m kinda stuck with the site now since I quit my job 🙂

      Jeez $96k…freaking awesome.

  • Alan G Feb 10, 2017, 5:02 pm

    After a not-so-fun last few years, I have no personal debt. That part feels great. But I still have a little bit of business debt. I’m struggling with this issue… It seems that paying down business debt, on the face of it, is a great idea. But it’s also kind of anti-growth? I mean, if you’re always using every last dollar to pay down business debt, aren’t you maybe staying stuck in a personal life that’s more mediocre than it has to be, so to speak? Since you can’t grow your business (and thereby increase your income) while you’re simultaneously paying down business debt? Not sure… Posting this question to get some thoughts. Thanks All… 🙂

    • Mike Feb 10, 2017, 9:21 pm

      As a CPA, I would say business debt is a little different. Like you said, paying it down quicker can be anti-growth. Obviously you don’t want to be over-leveraged, but having some business debt allowing you to expand or improve can pay off in the long-term. One good measure is if you are netting a higher percent return on assets than what you are paying on the debt. Basically means that you are effectively managing the assets of the company.

  • Gary @ DebtFreeClimb Feb 10, 2017, 9:43 pm

    I have paid off over $50k in Student Loan debt in 3 years and have $4.5k left. I’m targeting payoff in about 40 days.

    In the last three years, my whole mindset has changed regarding money. I’ve always strived for more money, but now it’s for different reasons. Before, it was to buy a nice house, car, etc. Now I try to avoid material things and I am striving for Freedom.

  • terry Feb 12, 2017, 6:01 pm

    I am 60 years young – one year ago I paid off a huge credit card debit ( due to being unemployed for two years) – I have been at my current job for 5 years now. I have always been rather thrifty, but when I got serious about clawing my way out of debt – thriftyness became an obsession ! I am debt free now. It is a huge freedom and I sleep easy. My vehicle is 13 years old and I am renting a house, I would love to buy a home, but the thought of a mortgage fills me with fear. Debt free is amazing !

  • Isaac Williams Feb 12, 2017, 7:16 pm

    My wife and I moved to Houston 4 years ago for her to go to Pharmacy school. We bought a condo (even though we shouldn’t have) and already had plenty of “normal” debt. Mortgage on a house in San Antonio, where we moved from, $11,000 in credit card, $6,000 left on my student loans, $60,000 on her student loans, which we were about to add a great deal to, $5,000 borrowed from my 401k, and $5,000 left on a car. Well, we scratched through her not working much during the last 4 years, and about half way through it, read total money makeover, and got started. We paid everything off but her student loans, and the mortgages on our condo and small rental house back in SA almost a year ago. Since she graduated 7 months ago, we’ve already paid off over $35,000 on her student loans, and plan to have all of her loans and the rental mortgage paid off in about 3 years. We get made fun of for driving crappy cars, wearing older clothes, not going out, etc. but we will both be under 35 with no debt and a paid for house, and making great money.

  • Katie Feb 13, 2017, 9:05 am

    First off, thank you so much for pointing out that it’s not nice to live with mom and dad, and no you wouldn’t have paid off that much debt just by making more money. When my now-husband and I were living in my parents basement for 2 1/2 years it would piss me off when someone would tell us “how nice it must be” to be able to do that. And how I didn’t deserve more hours at work bc I “didn’t need the money” like they did since we lived in my parents basement. EXCUSE ME?! Yes, it was incredibly generous of my parents to allow us to live there (we did pay a small amount of rent- so it wasn’t free) and it saved us big time when my husband was off work for several months after having surgery (which is why we moved in), but by no means was it where we wanted to be. It was a difficult and humbling decision to do that so we would not be financially burdened. People always look at successful people with envy rather than trying to figure out what they have done to be successful.

    I don’t have an exact debt pay-off number (it would be small in comparison anyway because we live in the midwest and have a very low cost of living here) but we are successfully budgeting and just recently paid off the last of my husband’s student loans. I still have about $3k in student loans but with an interest rate of 3.15% (which is lower than my mortgage interest rate) I’m not in the biggest hurry to pay it off. It will happen probably within the next year. Our biggest financial success so far is budgeting. We use YNAB (You Need A Budget) software (which I highly recommend) and for the past year have been budgeting this month’s income during next month’s budget. We are spending money that is 52 days “old” and have savings categories for several future goals. Being able to successfully budget is a bigger, longer-lasting accomplishment to me than the actual $$ amount of debt paid off.

    Glad I stumbled across your blog, the 3 posts I’ve read so far are gear!

  • Connor Feb 16, 2017, 2:48 pm

    I love this article as I am in the process of throwing everything above our monthly expenses towards paying extra on student loans. It’s sometimes frustrating since there are some articles out there that say there are other arguments to be made for paying the minimum on student loans to free up more money for investing or for starting up a business and you’ll end up ahead in the long run. What they never seem to address is the fact that student loan interest is continuously compounded unlike most other loans or investments. That’s why they grow so exponentially fast when you are on IBR and they never seem to get significantly lower after paying the same level payments year after year. Other people make the argument that you could foreseeably get a 12% return on investments that should outpace a 6.8% interest rate on loans, but has anyone actually done the calculations that compare a continuously compounded interest on a student loan (with a principal commonly in the hundreds of thousands of dollars) to a quarterly compounded dividend on an investment (usually in the tens of thousands of dollars)? My suspicion is you actually end up losing in the long run, since people like to think of compound interest when it comes to investments but not when it comes to loans you have to pay back. What do you think?

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