My Journey to Financial Freedom | Part 1: The Fall

This is a guest post by my “virtual” friend Dena from Evolution You. I have admired her work for some time now, and am happy to be able to share this post with you here on EOD. It is truly inspirational! Be sure to subscribe to Evolution You so you can receive her awesome updates each week.


Three years ago, I was nearly $60,000 in debt. I had a Bachelor’s degree that didn’t appear to be worth its weight in salt and a job that couldn’t cover a fraction of my monthly bills. I was terrified.

Today, I am closer to complete financial freedom than I ever dreamed possible. Last week, I paid off my last remaining credit card balance. This two-part post is a celebration of this incredible milestone in my journey.

In part one, I will explain how I got to that terrible place. In part two, I will explain how I’m getting out of it (and how you can do it, too).


A financial prison is the worst sort of prison to be stuck in. A financial prison does not have steel bars or a prison warden. You will not get sent to financial prison for committing a crime. There is only one person that can sentence you to financial prison. That person is you.

There are two primary types of financial prisoners:

1. There are those in financial prison who got there because they truly did not know any better. This type eventually realizes the error of their ways and breaks free.

2. There are those who knowingly commit themselves to financial prison. This type is well aware of the consequences of living beyond her means; but she does it anyway.

Of course there are also those who fall somewhere in the middle, like me… (Cue dream sequence.) It all started when I was 18. The guidance counseling systems in my high school and college were either completely inadequate or I simply refused to pay attention. I can’t honestly remember which it was, though I think it was the former. Either way, I was screwed.

Before me, no one in my family had ever been to college so I didn’t receive much advice. I was thrilled to be out of high school and ready for the next step. I took my SATs one time and applied to one school. My parents, being average folks, made just enough money to prevent me from receiving financial aid; but not enough money to be able to pay my full tuition. For me, this meant loans: “lovely” student loans from “lovely” Sallie Mae.

My mother co-signed and it was a cinch from there. Each semester I filled out a relatively simple form and like magic, Sallie Mae sent me a check. In fact, Sallie Mae was so generous that they allowed me to take out as much “extra” money as I needed every semester. It was fantastic! Yes, I had money to pay for books, meals, and extra curricula. I also had money to go out and binge drink, buy clothes I didn’t need, designer purses, and more. Sallie Mae was wonderful to me. And the best part of it was that there was no need for discussion. No one guided me, no one advised me, and no one asked me any questions. I showed up at the financial aid office a couple of times each year and it was always smooth sailing.

On top of that, another great thing happened when I was 18! The credit card companies started to send me applications. And that was just as easy. I got one and then another and then another. Whatever I couldn’t cover with those pretty little checks from Sallie Mae, I could simply charge on my credit cards. College was good to me. I joined a sorority, I partied hard, I shopped until I dropped. What more could a girl ask for?

It wasn’t all fun & games though. I worked through college. I worked at a children’s camp each summer; I was a Spanish teacher for two years; and toward the end of my college career I was a bookseller at Borders bookstore. All of the money I made working was spending money for me. I had Sallie Mae and the credit cards to pay all of my “real” bills.

When I finally graduated, I was making a cool $8.25 an hour at Borders. I loved it. I was happy… until one day, out of no where, a letter came in the mail. I had a six month grace period and then I would have to start paying back those loans. My paychecks barely covered my minimum credit card payments. How was I going to make loan payments on top of that?

So I sat down and did something that I’d never done before. I wrote up a budget. It was horrifying when I realized that even if I’d had no other bills, my monthly wages from Borders wouldn’t even cover half of my monthly student loan payments. The jig was up.

All told, I came out of college with about $45,000 in student loan debt and almost $15,000 in credit card debt. I hadn’t even lived on campus; I commuted from home; my parents paid for some of my tuition; and I only went to a mediocre school. How the hell was this possible?

All of a sudden Sallie Mae and the credit card companies didn’t seem so lovely anymore. There was one thought that kept repeating over & over in my head: Why didn’t anyone warn me? I felt cheated, betrayed, angry, afraid, and helpless. I wondered what the people in the financial aid office had been doing all that time. I wondered why my high school guidance counselor didn’t press me harder about applying for scholarships or grants. I wondered a lot of things, but mostly I wondered how the hell I was going to get out of the mess.

I started sending out resumes for jobs with starting salaries that would at least cover my monthly student loan payments. I sent out resume after resume but before long, I realized another harsh reality. That Bachelor’s Degree in English with a Creative Writing Focus wasn’t so great either. Nobody was calling me back. I couldn’t even get an interview.

The clock was ticking. I was halfway through my grace period. Then one day, one of my best friends mentioned an opening in her office. I looked over the job description and realized that it had nothing to do with what I’d gone to school for. I didn’t even know what it actually was, but the starting salary was more than what I needed. The rest was history.

I’ve been at my current company for almost three years now. And yesterday I paid off my last remaining credit card balance! Additionally over these few years, I’ve cut my student loan debt almost in half and by next Winter, I will have it down to a quarter of what I started with.

Stay tuned for tomorrow’s post (posting on EOD on Thursday), where I will share how I am doing it and how you can do it, too.

Dena is a life coach, speaker, and self-improvement blogger. She coaches, speaks, and writes about how each of us can live the life of our dreams. You can follow Dena on Twitter @denabotbyl or at her blog Evolution You.

About Brad Chaffee

32 Responses to “My Journey to Financial Freedom | Part 1: The Fall”

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  1. Great story! It’s all too familiar, but hopefully it will prevent someone else from making the same mistakes. Can’t wait to read part two.


    • Dena says:

      Hey Kita! Thank you so much for your feedback. I am really glad that you enjoyed the post. My thoughts mirror your own — I truly hope that my story will prevent at least one other person from making the same mistakes.

  2. Donna says:

    A picture of what happened with our son. We did not realize the hole we were digging so how could we stop him! We are debt free except the house, however we are helping our son until he can make enough to afford those payments. Heed these words from this well written article or you will be where we are and our son is.

    • Dena says:

      Donna, I am so sorry to hear that your family has come through a similar situation. I know full well (obviously) how painful & draining it can be. I am so filled with joy to learn that your family is getting through this together.

      Knowledge is power! Thank you for your comment & for sharing your own story.

  3. Awesome story. Thanks for sharing.

    My college guidance counselor gave me some so so advice too. And I was too lazy to find scholarships. I probably could have knocked a couple grand out if I just spent a few hours online looking for scholarships.

    Can't wait for you to be debt free!

    • Dena says:

      Hey Ted! Thanks so much for your comment, your words of encouragement, and your support! It means the world to me. Lazy counselors = Bad news!

      I can't wait either. 🙂

  4. harvestwages says:

    I'm so eager to read your tomorrow's post. I want to know how you got out of those debts . You were smart enough to get rid of such debts within a short period of time. I never indulge my self in such unnecessary credit card debts. Your college life was really fun

    • Dena says:

      Hey there! Thank you for your comment. Yes, college was fun. I try not to live with regret, but let's just say if I could go back in time, things would be a little different. 😉

      Thanks a million for your kind words!

  5. Penny says:

    Great article on an all too common problem. Once out of college, all I heard about was how I needed to start saving for retirement. How was I suppose to do that when all my extra income was going toward paying off my student loans and credit card debt? And I wasn’t nearly as in the hole as many of my friends. Retirement being so far off for most isn’t just about social security falling apart and medicare going down the drain. Its also about people starting their adult life thousands in debt and never being able to catch up. Can’t wait to read how you are pulling yourself out.

    • Dena says:

      Thanks, Penny! I'm really sorry to hear that you've found yourself in the same position — but I hope you know that there is a way out. Hopefully the tips in Part 2 will help you, too!

      Everything you've said above is so sad… but so true! We've got to turn this cycle around!

  6. Jeff says:

    Dena – I hope a lot of high school and college students and their parents read this. I wrote a post awhile back called Avoid Student Loan Debt: A College Education Is NOT Priceless. In it, I try to warn people of the very issues that you encountered in your story above. Hopefully, between the two of us (and many others like us), people out there will get the message. I'm a big fan of higher education, but I certainly think students need to think twice before burying themselves in huge sums of debt. It is a tough way to start out.

    • Dena says:

      Hey Jeff! Thanks for sharing and I am so glad to hear that we are in this fight together. Knowledge truly is power, so the more people we can affect with our message, the better. Keep up the great work, friend!

  7. Thanks for sharing your story, we all need encouragement because the story is all to familiar.

  8. Len Penzo says:

    Great retrospective, Dena. One thing really concerns me though: "No one guided me, no one advised me, and no one asked me any questions. I showed up at the financial aid office a couple of times each year and it was always smooth sailing."

    I think those people who are in position to make decisions need to reassess exactly what the loan counselors in the financial aid office are there for. Is it simply to make sure all the paperwork is filled out, or is it to provide real guidance for young men and women who are very vulnerable to the financial trap you got yourself into?

    All the best,

    Len Penzo dot Com

    • Brad Chaffee says:

      @Len Penzo – Wonderful point!!! What are they there for? They seem to be detached from the fact that the young people coming through those doors are possibly setting themselves up for failure, and put all of their focus on how great it is to receive money for school. When I applied for aid and grants they were more interested in me applying for loans, "to make sure I had enough to reduce the financial stress of going to college." How about the financial stress that it causes? I'd say what it causes is way more financial strife that what it was trying to avoid.

      EXCELLENT comment!

    • Dena says:

      Great point, Len! I am not really sure what the purpose of those counselors was/is. I think that there lack of structure and direction is probably a symptom of a much larger, deep-rooted broken system. One of two things needs to happen:

      1. The system needs to be completely overhauled.
      2. EVERYONE needs to educate themselves so they don't end up in this position.

      Unfortunately, I don't see #1 happening anytime soon — so it's our job to spread the word! Knowledge is power!

      Thanks so much for the great comment.

    • Ashley says:

      Your point is exactly the reason I think financial education classes should start in high school or middle school. In most cases, no one will ever be more concerned or invested in your financial well being as you are. We should equip young people with the information they need to make sound financial decisions on their own starting at a much earlier age than our current system allows. Knowledge is power!

      I think loan counselors and those in the financial aid office should be present to help students understand what the loans they take out will really cost them in end. Also, guidance counselors should help students get an understanding of a realistic amount to expect out of college with their degree depending on the area they plan on living in. They should also be more realistic with students in helping them understand that a job is not delivered at your door the day you have a diploma. Those are two things in which I felt I was greatly mislead in my journey through higher education.

      • Dena says:

        Ashely, I could not agree more. Starting financial education classes for high school students would vastly improve the situation. There is no doubt that if I had been properly educated on these issues, I would have ended up in a much different situation. And I am sure that goes for countless others as well.

  9. Brad Chaffee says:

    I wanted to stay out of the way since the comments were directed at Dena, but I thought I would post my response to her original posting instead of saying it again here. 🙂

    "Wow Dena, that is some story. It sounds similar to so many other students out there, and that’s the scary part. This is the kind of post I absolutely love!

    I for one, am extremely proud of you for coming as far as you have. That is so awesome! I cannot wait to hear the rest of the story on tomorrow’s post.

    I have said it before. You are an inspiration to so many that have experienced the same reality. Unfortunately, it is very easy to find yourself where you ended up, but getting out, is a different story all together. That’s where you have shown strength, determination, and resolve! Those are some amazing characteristics for someone to have!!

    Most people refuse to accept their circumstances, and sit around blaming others for how they ended up where they are. You took responsibility for your actions and came up with a plan. Your plan is working and I know you are so glad to have accomplished what you have. No CREDIT CARDS! (Awesome job Dena!)"

    • Dena says:

      Brad, I can't thank you enough for this opportunity! I am amazed by the incredible response from your readers. My heart is actually soaring right now! I could not ask for anything more. I thank you from the bottom of my heart.

  10. Derek Clark says:

    Great post Dena. Luckily I managed to escape college with much less debt than that, but I'm now working on my wife's college loans. I have no idea what the financial counselors are doing. I'm suspect filling out the paperwork so the college gets money is their only goal.

    The thing that is crazy to me that nobody really considers how much their new degree is worth. I know I didn't really consider it. My wife spent about 90K to become a teacher. I'm glad she did because I wouldn't have met her otherwise, but somewhere along the someone should have questioned whether that is a good investment. I'm sure you felt the same way when you were struggling to find a job in the field you got your degree in.

    • Dena says:

      Derek, that is exactly how I felt! It was a mixture of really deep sadness & anger. What a terrible place to end up in just because we want an education! Well, I am really glad that your wife has you to help her sort all of this out.

      Knowledge and a good support system are two of the key ingredients to turning things around. I wish you and your family continued success in reaching your goals. Thanks a million for the comment & for sharing your story.

  11. Dena–don't be so hard on yourself. You didn't know any better because you weren't meant to. Student loans are the grease on the college wheels, so why would anyone anywhere on campus advise you against going deep in debt to buy what they're selling?

    Like Jeff said above, a college education is not priceless. There's a vast difference between valuable and priceless. Right now, our culture thinks that it's priceless, and that's the cue it's delivering to young people.

    One of the things I really find disturbing about our day and time is that despite all the education and all the information freely floating around, there's a troubling lack of critical, independent thinking. There's a very pronounced one size fits all mindset that isn't serving us well, particularly in the area of becoming individuals.

  12. Dena says:

    Thanks for your thoughtful comment, Kevin. You are right. There is a disconnect there. The knowledge is out there, but clearly it is not getting into the right hands because (unfortunately) my situation is extremely common.

    The key is going to be finding a way to educate the masses so that this tragedy does not affect the next generation.

  13. Mark says:

    How can you state there are two types of financial prisoners then say you fall somewhere in the middle. That's hypocritical. In any case, you should be proud of your progress but seeing how young you are, it will be interesting to see how you react down the road when an unforeseen event arises where you may need to resort to some kind of debt leverage to balance your goals. Even J. Money over at Budget Are Sexy ended up using his credit card again after paying it off.

    I look forward to reading your part two.

  14. Brad Chaffee says:

    Mark – In all honesty dude, I am having a hard time figuring our where you get "hypocritical" from. They also say there are two types of financial behaviors. Savers and spenders. That doesn't mean that you are either ALL one or ALL the other. One can have a little of both, even if their behavior tends to favor one over the other. Could you clarify your use of the word hypocritical?

    You may be new here, but the way we do things here is we have an emergency fund for unforseen events without the need for debt "to balance things". It seems as though you are saying congratulations on one hand and "good luck living without credit cards" on the other. I have lived without credit cards for more than two years and I am still alive and kicking.

    I'm also trying to figure out why you said "even J Money". So because J Money decided to use credit cards after paying them off then everyone should? J Money is one of my best buds in the blogosphere but he is not God and just because "he" did it doesn't mean others should follow. Furthermore, I am 200% sure he would agree with that.

    Thanks for your comment although I am confused about your intent.

  15. Kimberly says:

    Dena, your story really hit home with me. I, too, was the first in my family to attend college, much less graduate. I then went on to graduate school. My parents had the money to assist me; however, they were of the belief that once you turned 18 you took care of yourself. I came out of school owing a little over $90,000 in student loans! Yes, $90,000 big ones!! I received zero financial advice throughout my years in school. Reality set in once those payments came due and it was a harsh awakening. I've been paying back this debt for about 12 years. I now owe $18,000 in student loan debt and my goal is to have it paid off within a year to 1 1/2 years. My only other debt (now) is a mortgage. I've paid off all other debt in the past year and Brad's blog has been a huge inspiration for me. Thanks, Dena, for your sharing your story. I wish you much success.

    • Dena says:

      Kimberly, your story is absolutely incredible! I am amazed by how far you have come. You are an inspiration to me and to many. Thanks so much for sharing and best of luck reaching your goal within the next year or so. I'll be rooting for you! 🙂

  16. Forest says:

    Ha ha, you fitted a lot in the post and it made me chuckle…. It's easy to say that you should have known but seriously none of us are schooled very well in these things. I have around $40k debt that I am starting on now and I don't earn very much at all…. However I am on track now and the debts will go.

    Thanks for a laugh this morning I really like your writing style.

    • Dena says:

      Glad you got a laugh out of it, Forest. 🙂 Best of luck in your continued journey and so glad to hear that you are on track now.

  17. I'm really happy you turned everything around and I am about to read Part 2.

    I understand your overwhelmed feeling when you figured out that you needed to pay back your loans, but I don't understand the surprise? I didn't have a high school guidance councelor and I know financial aid offices aren't meant for advice (they are expressly told not to give lending advice…I worked in that building). But your parents didn't explain debt? Or a friend? My parents were the ones who taught me, that's why I ask.

    I truly believe in personal financial responsibility, but how could you know about that without some financial education?

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