Paying Off A Decade of Debt: A Reader Success Story & Quick Interview

I’ve still got my head buried in the production of “Unautomate Your Finances“, however over the weekend I was alerted to the fact that my friend (and MvD reader) Jared Matthew Kessler just became 100% debt-free!

After a ten year, up and down battle with debt, Jared has emerged the victor!  You can feel his joy in his writing and I wanted to share his story as inspirational for others stuck in a long-term battle.

Without further ado… here’s Jared’s story in his own words:


I was introduced to Dave Ramsey in 1999 when I was living off of credit cards barely surviving as a “Starving Artist.”  My mentor in, “The Poet and the Billionaire” recommended that I check out his book called, “Financial Peace.”

And I devoured it.

The only thing was I was “Fighting To Be Me” (the title of my latest album) by refusing to get a “job” to do what I loved. Unfortunately, it wasn’t working.

So it got to the point where I just hit rock bottom. The car died.  The auditions I was going on to try and “make it” wasn’t happening fast enough.  So I did the unthinkable:

I sold off everything and moved back home with my parents.

At about that time, my credit card debt probably totaled about $22,000 (but since 1994, I’ve probably accumulated about $70,000 worth of credit card debt).  Now to someone making decent money, that may not seem like much.  But to someone without a job, living on the other side of the country from their family, and looking the way I did… things were a huge challenge to pay something like this off (to say the least).

“There are times that people can be so blinded by what they want IT to be, that whatever reality they perceive it should be… they lose.” –The Poet and the Billionaire

In short, I was always living in the future saying, “Things are going to turn around, things will get better, this year it’s going to happen…”  But the thing is, I HAD TO face the reality of the situation NOW and do whatever I could to get out of it NOW – not another year down the line.

And I did.

First thing I did was sell my car, move out of California and moved back in with good ole mom. That didn’t last too long, so I moved to Orlando, FL (and got 3 jobs).

After that, I THEN started to make headway and came back to California finally becoming debt free for the first time in about 10 years.  Then 2006 came and a flurry of setbacks along with it… and so I did the UNTHINKABLE (again).

I got a bank loan for $12,000 to fund my business…

Dumb move. Why?  I wasn’t making any money at it.

Three and a half years later I lived WAY below my means to pay that last balance off and DEEP within my spirit I could honestly say that I will NEVER use another credit card/bank loan again.

Why is this important? To me, it is legalized slavery. You think you work at your job… you don’t!

You work for your debtor (and that is a slave no matter which way you cut it).  Not only that, it’s probably one of the most freeing things anyone can do for themselves OR their family.

To know that you don’t owe anyone ANYTHING is beyond life changing (especially when you’ve been in debt as long as I have).

What did it do for me? Well the freshness of it is still very young, but the only way to describe it is “giving myself back to me.”

I’m TRULY whole again and back to being me.  I wish the same for everyone out there.

A few questions for Jared…

Baker: Over the course of the last decade in debt, it seems like you’ve had some ups and down (almost getting out of debt, but then diving back in).  How did you ride out the waves?  Any specific motivations (besides Dave Ramsey) that helped bring you ‘back around’?

I met my girlfriend Kelly about 3 years ago and noticed her exact patterns.

You see something and say, “Oh that looks nice” – then put it in your cart without ANY understanding of what it takes to earn the right to own it.  I wasn’t anything like that, because I was using credit cards to just stay alive.  But the thing was, I couldn’t help her on that plan, if I wasn’t REALLY living what I was teaching her (because I saw how much of a stress it was in her life).  Since then, she paid off OVER $30,000 so far and has been on Dave’s plan for about 2 1/2 years now.  And that inspired me to continue on with it because of how happy she’s been living without credit cards.

Specific motivations?  Pain.  🙂

But seriously I think my girlfriend being on the plan helped make things a LOT easier on me.  You don’t feel so alone and fighting that uphill battle all by yourself.

Baker:  What are your top 3 tips for people based on your own story?  Especially consider those who may have several years left on their own debt plans.

Top three tips?

1 – Find someone else in the similar circumstance and help them out.

This does a few things.  First, it holds you accountable because it’s hard to teach someone to do something you’re not doing.  Second, it’s makes you feel a lot less crazy – knowing someone else out there is dealing with something similar.

2 – Don’t keep any money or debit cards on you unless you know you’re going to buy something.

Most of the time, people buy on emotion.  This alleviates that.

3 – Put things on hold.

This is a great little personal trick I adopted.  Just the other day I went into H&M and saw a few shirts I wanted.  Knowing I have about $25 in my clothing envelope, this would cover it.

But the thing is, I didn’t necessarily know if I NEEDED it.  So basically, a day later the initial emotion of buying something is lost, and if I NEED it… I go back and get it.

At first I used to feel a bit weird doing this, but I don’t care.  When “normal” is being in debt, I would rather be “weird.”  🙂

Baker:  Lastly, you’ve mentioned that your business is now run 100% debt-free, as well.  Have you noticed any advantages in your approach to business with this new outlook?

Totally.  Yesterday I went out to celebrate with Jonathan Mead (Baker: Jonathan introduced Jared and I!) and we talked a lot about this – since he and his wife became debt free a few months ago too.  I had said that I think a lot of people start a company and say, “Oh I think this would be a great idea to do” (then get a loan, open up a storefront and THINK they are in business).

Honestly that was the last reason for my $12,000 loan in 2006 – the last debt I was paying off.  I was excited that Mtv was interested in the music I was making to use for their shows.  So I got a $12,000 bank loan to afford me the time to make the music to give to them.  Little did I know it was a YEAR later until I got a contract and ANOTHER year on top of that until I got any royalties from it.

Now… UNLESS there is a need, I don’t come out with a product.  As Jonathan and I discussed, there is a TON of research, questions, and determining whether or not people are willing to pay money for something is instrumental…  before most of anything is launched now.  That was the last reason I launched my first eBook, “Your Uncommon Guide to Finding the Ultimate Mentor.

It cost me $0.  If it fails (which it isn’t), I’m not enslaved to anyone.  Talk about a HUGE mind shift?

Also my first book, “The Poet and the Billionaire”, I ONLY get more copies printed based on “the need.”  New music?  I have 2 new albums already done and licensed but I haven’t release them yet until I have the funds!

Thanks to Jared for sharing his story and interview questions!

I know this is the second time I’ve broken my ‘no posting’ rule, however I made an except for Haiti and sharing a 10-year success story.  So, sue me!

…back to work…

63 thoughts on “Paying Off A Decade of Debt: A Reader Success Story & Quick Interview”

  1. Great story. Getting out of long term debt as a exciting and releasing as an orgasm. 🙂

    I remember when I paid off my college loan. Good times.

    It’s a good idea to try and talk yourself out of purchases. If you can’t then buy it.

  2. Hey Gordie,

    Thanks for taking the time to read it.

    I like that. “Getting out of long term debt is as exciting as releasing an orgasm.” That is one to save for the books. 🙂

  3. Congratulations Jared for being 100% debt free! Yours is a great story which rings true for most people who have struggled with debts. I for one also had problems with credit card debt until I finally realized how hard it was to pay up your debt when you only pay the minimum. It was like walking up at a running down escalator. I believe your taking control of your own money habits and shift in mindset, like putting things on hold to make sure you only buy what you truly need, was a great help to your taking control of your finances.

    Great tips! More power to you!

    1. Thanks so much Allan.

      You’re right because it was a HUGE “shift in mindset.” 🙂

      It’s funny how it hit’s certain people different ways. You know? That is great you realized how hard it was to pay off your debt paying the minimum balance – I’m sure what you said hit someone who needed to hear that.

      It’s virtually impossible to pay off your debt in this lifetime paying the minimum credit card balance.

  4. Thanks so much Jolyn! I think it’s important to share. Someone had told me that they don’t know why more people aren’t excited about this (and why I’m grateful Adam let me share this with his readers).

    To add to that… I was recently talking with my girlfriend Kelly and she explained that a lot of people get just as excited about a credit line increase than being debt free – which we both thought was REALLY ridiculous.

    Hopefully I can shift that excitement around for someone and shed some light on how great it feels to live this way.

    1. For some strange reason, people look at a credit increase as money being given to them. I think that says a lot about where our society has gone wrong, don’t you think?

      I can remember talking to our bank that held our mortgage and hearing the genuine excitement in the rep’s voice when she told me we qualified for a LOC! She acted like she was telling us we won the lottery!

  5. I like your “put things on hold” idea. Psychologically, it seems pretty fool-proof for most people, since impulse buys are such a major part of our culture. I know they were the main reason for my credit card issues.

    I’ve been spending the last few weeks putting several large purchases on hold unintentionally due to lack of funds…but I suppose that’s not quite as noble. And it doesn’t work as well when the money’s not there…just makes me want things more!

    1. Thanks for the comment Justin. Did you adopt Dave Ramsey’s envelope system?

      In short, you don’t spend the money in the envelope if it’s not there (for me I have a “clothing envelope” and used $15/wk for it). It might be difficult at first, but it’s REALLY key.

      The other important thing is asking yourself, “Do I really need this?” Most of the time you know the answer. 🙂

  6. Great story indeed. At some point in time it’s necessary to be practical. Nobody’s saying give up your dreams but you still have to live. Loans and credit card are really best to stay away from especially when you don’t have an established job/career.

    1. Exactly Mr. Personal Finance Student.

      Just wondering… are they teaching this where you go to school? If I haven’t been introduced to Dave Ramsey’s stuff, there is no way I would have done this.

  7. Congrats, Jared!! I can’t wait until I can say the same thing… 🙂 I plan on that being only a few years to go, though, I hope. (But I bet things will change, because plans never stay the same!)

    Baker, I don’t think it’s *so* bad that you posted twice…. I like reading your stuff, so it’s making the withdrawals less painful. 😉

    1. Thanks Meg. I can’t wait for you to do the same thing either. I REALLY wish people can feel how great it feels.

      Honestly… I had a ton of setbacks, but that emergency fund kept coming in perfectly (as I continued to replenish it).

      Keep on going Meg. You go girl!

      1. Well, paying off the third car will feel pretty good, I imagine, and other than that we’re free of consumer debt… Sorta. (Are student loans consumer debt? In a way they can be, I think…)

      2. I think the key for me is an end goal and that darn emergency fund. I tried last fall to plunge into repaying debt, but it didn’t work because I was doing it for the vague purpose of not feeling guilty and knowing that it was wise to live within my means.

        Now that I know I want to live overseas in two years, the vantage point it provides changes everything. All of a sudden, the emergency fund is the key to being able to accomplish my goals. If I ever touch a credit card again for emergencies, I will forever be enslaved…!

  8. Congratulations Jared! That is an awesome story. My wife and I just became debt free on Friday ourselves, although we still have a mortgage. We are very excited to be in the place we are at, but honestly I’ve been stewing over that mortgage this weekend and thinking up an aggressive plan to hit it next.

    I appreciate your candidness of your story and how despite some roadblocks you got back on it. Fantastic job!

  9. Congratulations, Jared!!! Thanks for sharing your story. I’m glad to see that you’ve embraced this pattern of life for your business as well. My wife and I have made it our priority to get out of debt and love reading about other people doing the same!

    1. Thanks Khaleef (and that is part of the reason for sharing a bit of my story).

      You know I couldn’t do this in my personal life and not my business. It both so intertwined and hope that more and more people like you can embrace this.

  10. Thanks Paul! Awesome about YOUR becoming debt free as well. The more people who know that it’s ok to live this way and also that there are others doing this… the better (so thanks for your comment).

    To add to this…. I’m not sure where you are with your mortgage and all, but I LOVE how Dave Ramsey says “A home mortgage should be a 15 year fixed rate no more than 25% of your take home pay.”

    So tell me… how did it feel to pay off that last creditor (besides the house)?

    1. Jared, we’ve got a long road on the mortgage (the Seattle area was brutal for real estate) but because of our large success blasting our consumer debt we’ll conquer. As to the feeling? It was incredibly liberating. The knowledge that my money is actually my money to direct as I choose is enormous. It’s freeing to know that if I choose to direct that money to those in need I can just do it. Knowing that my kids won’t have to grow up saddled with College Debt is fantastic. And finally knowing that I’m not held hostage by my day job is the greatest reward of all.

      1. Paul that is so great. You are changing your family tree (and that must feel great knowing your kids won’t have any debt).

        And man… you put it amazingly (as my girlfriend and I were just talking about this): “And finally knowing that I’m not held hostage by my day job is the greatest reward of all.”

        OMG, if more people would TRULY understand that it would be so great.

  11. Debt-free is the true freedom. When you aren’t tied down to your bills you can make your life whatever you want it to be. We’ve been debt-free for a few years now and have saved enough money to take off and travel the world. Seven years ago I would never even have imagined this life was possible…and now I have it. It never would have happened with debt.

    Congratulations, Jared.

  12. Congrats Jared. It’s got to be a great feeling to pay that last debt.

    What I got most out of your story was that you had to come to terms with reality. Most people never do. And most people are in debt.

    1. Thanks RJ. It feels AMAZING!!

      You’re right (most people are in debt because I’m not sure they want to face the reality of the situation). It’s a really painful thing to deal with head on depending on how much it is.

      I had to make this clear when getting my girlfriend on this plan as well. Being conscious of what you are unconscious of is probably the first step to getting on this path.

  13. You see something and say, “Oh that looks nice” – then put it in your cart without ANY understanding of what it takes to earn the right to own it. I wasn’t anything like that, because I was using credit cards to just stay alive.

    For me, this is huge too. I recently donated about 50 books, a few pairs of shoes and a bunch of clothes to the thrift store. Why? Because I was buying stuff I didn’t want or need! Sometimes I would get a package in the mail, open it up and say to myself, wow, why did I buy THAT? And yes, that’s only a few days after the original purchase. So now I have a new rule: I NEVER buy anything the first time I see it, online or in-store. I was spending TONS on Amazon, mostly on books, and picking up things from stores, so now I put anything I “want” it in my “wish list.” I return to it a few days later and, if I still “want” it, I’ll take another few minutes to think it over. 90% of the time I say ugh, I didn’t want that! Saves a ton of money.

    1. Thanks Melissa.

      I really wish you the best on your own journey through this. I know how it feels and at times it can get a bit discouraging – but keep on keeping on. Ok?

      Sometimes there aren’t any shortcuts to it, except the consistent and persistent knawing away at it.

    1. Thanks Richard!

      I figured it would be something positive for a change (instead of all the doom and gloom we’ve been hearing all over the news).

    1. Thanks Thom. I’m glad my story can be a bit of an inspiration for someone. Sometimes it just takes a particular individual stepping out and sharing something like this so that one doesn’t feel so alone.

      If anything, I hope that no matter one’s circumstance… it can STILL be done. 🙂

  14. I love this post- and congrats to you Jared! It’s this kind of post that keeps me coming back to MvD. The road to financial freedom can be long, and stories like this help keep me going! Keep ’em coming, Baker!

    1. Right on Jill! Thanks so much.

      Adam is doing a really great thing here on MvD (and I’m really grateful to him for letting me share my story to help someone here).

      It’s true that the road to financial freedom can be a long one – and I really wished there could’ve been an easier path. But then again, I wouldn’t be able to inspire someone here without going through what I’ve done (as I hope others on this path might see too).

      Rock on Jill!

  15. As a fellow 100% debt free (including our mortgage) Dave Ramsey devotee, I congratulate you on your story and your dedication. The idea of having an accountability partner in the process is excellent, and I was fortunate to not only have my husband in this role, but also a friend who wanted to get out of debt, too.
    Deferred gratification and impulse control are critical life skills, not only for debt payoffs, but in everyday work and family decision-making. Thanks for sharing your story, sir.

    1. AWESOME Sarah! And hey… congratulations on your living 100% debt free (including the mortgage). Soooo amazing!

      “Deferred gratification” and “impulse control” are really a huge part of this process. Aren’t they?

      And isn’t it so important having your loved one involved in it too? When I had $30,000 in credit card debt, I remember having friends that didn’t think it was a big deal because they were $60,000 or $250,000 in debt.

      Having people around you on the same page is really vital. Thank YOU too Sarah! 🙂

  16. Congratulations, Jared! You and Man vs. Debt have been huge inspirations to me, and you’re right about how powerful it is to know that others are in the same boat.

    1. Sure thing Melanie… sorry for the big delay in answering back. I’m glad I can be a bit of an inspiration for others in the same boat. 🙂

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  19. Jared, you are absolutely right..debt is slavery! Awesome story. I will scream at the top of my lungs the day I am debt free. Actually I rejoice as I get further down my debt snowball. 🙂

  20. Jared, Thanks so much for sharing. For the last year and a half, I’ve been committed to paying down substantial credit card debt. It can be a discouraging process along the way. It’s good to read of other people on the same journey. I’ll keep going and I know it will be worth it when the balances are zero. The mortgage is next.

    1. Hey Robin…. my girlfriend is in the same boat (and still has about another 6 months left – so I know it can be discouraging).

      Keep on keeping on with it. Ok? The feeling you get from knowing that you don’t owe anyone anything, is one of the most freeing experiences.

  21. Congrats! I love the Dave Ramsey method. It has helped my husband and I pay off 24K to my student loan in one year, as well as save 14K in the same year on a 60K yr combined salary. My student loan is 123K so we are hoping to pay it off in another 4 years. It is hard work, but once you commit to it and see results, it feels soooo good!!!

    1. Wow Amy… congratulations to you on paying off one of the student loans. How great does that feel?

      I know it can be “hard work” at times, but yes… seeing the results and being a part of this community AND using Dave Ramsey’s method is enough artillery to wipe up just about anything. 🙂

  22. Hey Xpat… I REALLY know it can be a tough process and sacrifice at times. Hopefully being a part of Adam’s community, my story and using Dave Ramsey’s tools to the fullest extent, can help make it a lot less painful. 🙂

    Keep on keeping on. Ok?

  23. That’s awesome! An inspiration for us all. It just goes to show how easy it is to get into debt but how hard it is to get out. Against debt slavery!

  24. ‘this is so inspiring.. I am really coping hard right now. It is good to know , I am not alone. I like the term used here “legalized slavery”… this is so right. Many thanks and keep goin’, were are drawing a lot of strength here….

  25. Hey Ira,

    I’m so glad. You know you are NOT alone in this quest. If it makes you feel any better, my girlfriend is still back in California paying off the last of her credit card debt (while I’m in Seattle building the biz). It’s not easy for her. It’s not easy for us – but we BOTH know it’s the right thing to do.

    Now going on over 6 months of being 100% debt free, looking back… it was the best thing I could do for myself and our relationship. Freeing the shackles of yes “legalized slavery”… it let’s me take more chances with my business, and also be able to fail more times than the average individuals (without selling my soul for a dollar).

    Keep on rockin!

  26. Definitely an inspiring story. It’s reassuring to hear stories from people who in a worse position than you’re in, but they still manage to turn things around and even build successful businesses after a series of setbacks. It’s that “if they can do it, so can I” mentality that’s very powerful.

    1. I’m glad you’re inspired Janet. Very true with the “if they can do it, so can I” mentality. I used to watch Dave Ramsey on Fox Tv a lot and some of the nightmares I heard people going through… made me feel a TON better. 🙂

      Keep rockin!

  27. This was just what I need to read/hear at this moment. I, like you, Jared, didn’t accumulate debt by lavishly spending on things I couldn’t afford. I racked up the debt paying for everyday expenses – car repairs, paying rent when I became unemployed, etc, all this while I was a student and working low-paying part-time jobs. Sometimes when I admit to people I have debt, I feel a certain sense of shame because people automatically think you must be an irresponsible spend-thrift and I have never been that. And like you, I have ridden the wave of debt – paying it down only to fall on hard times and get it right back up there again.
    It took being in debt a decade plus to finally realize exactly what you realized– when you keep debt in your life, you can never truly be free. You life does not belong to you, it belongs to your creditors and you are an indentured servant. The thought of it is depressing because I consider myself a very independent person. But I now see how having this debt has truly impinged upon my quality of life, happiness, and self-confidence. I’ve been unemployed for nearly 2 years now and have somehow managed to maintain good credit and make the min. payments on my cards (the equivalent of throwing money down the toilet every single month). I finally had to give up my apartment because I realized I could not keep living beyond my means and racking up more debt. I am trying, ever so slowly, to take my life back. Thank you for reminding me that it is possible! 🙂

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