How I Went From $100,000 in Debt With No Job to Debt-Free in 5 Years


This morning I was thinking about what should be my first article on BiggerPockets and what single story represents me and my financial story the best. My thoughts quickly went to just a few weeks ago when I paid off my final personal loan and became debt-free. I want to share with you the journey that brought me to where I am today and the lessons I learned over the past five years.

The year was 2010, and I had decided to pick up all of my belongings and fit them into my newly purchased Mercedes Benz (~$18,000) to make a big move to the state of Florida. I didn’t have much to pack into my C-Class besides some clothes and a few personal effects. I also didn’t bring along a mortgage payment at this point in my life, but I did bring along my student loans (~$60,000), credit card balance (~$5,000), and personal loan to my parents (~$30,000).

What’s kind of scary about those balances is I thought I was at a good financial point in my life. I had just finished working the last two years straight out of college and was able to put aside a couple thousand dollars to give me a buffer until I found my 9-5 job. This move was made with the future in mind. Was I starting a new business? Searching for a foreclosure property to buy? Of course not. I was moving for a girl — you know, the perfect financial incentive. So it all began in the late summer of 2010. What could possibly go wrong moving to a new state with over $100,000 in debt and no job?


I’m guessing most of you are attempting your best Nostradamus and have already predicted that my financial plan did not work out so well. I went deeper into credit card debt as my savings were used up rather quickly and my new emergency fund was exhausted each month for gas, food, necessities, and quite honestly a lot of things I can’t even remember. At this point you are probably thinking, “Get a job, you bum!” Let me tell you: I did everything I could to make ends meet while I looked for a full-time position. Here are a few:

  • Volunteer Coaching Job: A great experience, and because of my situation, the coach paid me to at least cover my gas. Well, sort of. It was 80 miles one way.
  • Part-Time Mall Kiosk Sales: It would’ve been helpful if I spoke a bunch of languages.
  • Lawn Care Service: This is another way of simply saying that I had a lawn mower, weed eater, and a dream.
  • Online Poker: I remember the first night I was up around $500 when I was on a road trip with the basketball team. I also remember the next day when I gave it all back.
  • eBay Seller: I bought clothes from discount stores like Ross, Marshall’s and Nike Outlet and sold them for more on eBay.

I tell you all of this because it is part of my story. While this is part of my story, it is certainly not how I got out of debt. Four out of five of these jobs haven’t been part of my life since. After not being able to obtain a full-time job or successfully make more money than I was spending, which was a big part of the problem, I tucked my tail between my legs and moved back to Illinois to stay with family. I was able to obtain work almost instantly, first because my summer job during college took me back and secondly because the company I previously worked for hired me back with a little help from an old colleague. I was desperate enough to wash bathrooms if they would have asked. This is when it all began to change in the positive direction. The first lesson I want to share from my story is to get a job, something that supports you and pays the bills.

Related: Can Real Estate Investing Help Me Pay Off $180,000 of Dangerous Debt?

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Lesson #1: Get a Job

It sounds so simple, but I know that’s what flipped the script for me. I had a consistent income. The 15th and 30th of each month, I would look at my bank account and see a direct deposit. It was magical, and all I had to do was show up over and over. If you are drowning in debt, I plead to you: Get something stable that will pay the bills. I don’t care if it’s work as a janitor, garbage man, banker, or manager — it all starts with that base of income.

Every move after that was positive for me financially, at least in the long term. My family member kicked me out of his place — tough love — and I rented a place in the city of Chicago less than a mile away from my work. Even better, I got rid of my car and $18,000 in debt. So my rent went up and my car payment went down, but surprisingly, living a mile from work and renting a room to keep costs down actually put me on the positive side. I was no longer paying for my car payment, insurance, maintenance, and gas. Less than a year later, that wonderful girl that I moved down to Florida for became my wife and pulled a “Beverly Hillbillies” — you know, loaded up the truck and moved to Chicago, the Windy City of snow, cold, and concrete.

In less than a year’s time with this magical thing called a job and by getting rid of one of my largest expenses, I had still not broken the negative six-figure net worth, as my credit card debt went up while in the sunshine state (~$102,000). Within weeks of moving my wife to Chicago, in our new rented apartment, I started a new 9-5 position at a starting salary that was close to 40% higher than I had started with less than a year before. The next year of my life was life in a new place, with a new marriage and a new job. Those are some big changes, and that’s exactly what happened during that new year. During this time I had a few extra dollars, and I made goals to pay off my credit card debt. I read personal finance blogs on a daily basis, and I started to hustle a little harder.


Lesson #2: Learn About Personal Finance

I have always been into reading about investing and real estate. I always pictured myself heading to the golf course on a Wednesday afternoon, taking business calls in between approach shots and discussing business over wine and nice steak at Gibson’s. You see, I’m a dreamer, but the one thing I skipped while dreaming about investing and real estate was the basics of personal finance. I began to realize I didn’t know enough about my personal finances. Here a few examples of my ignorance on the subject:

  • I would use ATM receipts as way of knowing how much is “in my account.”
  • I would use my credit card as a way to “earn” cash back, while the whole time I had a balance accruing 19.99% interest.
  • I would buy single stocks while drowning in $100K+ debt — because that’s how you get rich.

I read about the basics of personal finance, the little things like keeping track of your money and where it goes, setting up a budget to tell your money where to go, and paying off personal debt because it has a high interest rate and a big balance. I know all of this seems really simple and is not complex, but like building a house, you don’t start buying granite countertops and Sub-Zero appliances. Instead, you pour the foundation of the house because without the foundation, your granite countertops will look pretty funny just sticking in the dirt, next to your luxury appliances. For the same reason, you should read BiggerPockets, just as you should read about personal finance. It’s all about learning.

So once you have your foundation, you begin to understand that spending more than you make is not going to lead to any sort of success story. I have not read a success story that says “I made $1 million dollars last month and spent $1.2 million.” In fact that sounds like a 3 a.m. infomercial, so you know it’s not true. In personal finance and paying off debt, you have two choices to get ahead:

  1. Make more money
  2. Spend less money

As long as you are making more money than you spend, you are doing great. If you want to kick debt in the face, go all Van Damme Bloodsport, you have to do either #1 or #2, and what’s really great is you can even do both — you know, like Van Damme Double Team. I had just started to spend a little less than I was earning, but I decided to hustle a little harder, both at work and in my side hustle. This brings me to the reason so many of you are here today on BiggerPockets.


Related: How to Get Out of Debt: 5 Steps Toward Healthier Money Habits

Lesson #3: Hustle Harder

My side hustle was and is selling items on eBay and Amazon. This is not an advertisement to do the same, but it is an advertisement to hustle at something that can bring in money. You know, real estate is a pretty good example *cough* BiggerPockets *cough*. I started using this money to help pay off my credit card debt. A couple hundred over even a thousand dollars makes all the difference when paying off debt. It feels like leprechauns have left you a pot of gold just for waking up in the morning and trying to bring in extra money.

I also tried really hard at work. You know, all the good stuff — show up early, work late, ask for extra assignments, try harder than everyone else. Shockingly, it worked. I received a promotion. Not the promotion where they give you more work and a new title — one that actually pays more. That money went towards debt, all of it. I was earning more money, and it felt fantastic. Not all of my hustle was going directly towards my debt — I created a “man fund” of sorts, which allowed me to go out to eat, enjoy sporting events, attend comedy shows, and even pay for all of the appliances in our new house. I was doing great with “#1 Make More Money.”

While I paid off my credit cards during this time, I could have done better. At the time I knew that I could make more difference in my finances if I just started doing” #2 Spend Less Money.” I took some pretty big leaps to spend less. Here are a few:

  • I cut my cell phone bill by switching providers.
  • I cut my cable company and started using internet only.
  • I kept track of our eating out bills and focused on eating in more and eating out less.
  • I bought a 2-flat where we rented out one unit and lived in the other, which reduced our mortgage payment.

Over the past three plus years, this has been the recipe for success. I have further widened the gap in our “earn more, spend less” action plan. Each time I found a way to reduce costs resulted in another dollar towards reducing my debt. This past June, I paid off all of my student loans — that ~$60,000 is gone forever, and as of today, all of my personal debt is at ~$0 because of all the things I have done in this article.


It has taken me a while to pour that foundation for my financial house to be in place. It took five years to rid myself of my six-figure debt. I didn’t do it by buying Google stock at its IPO or purchasing at the bottom of the real estate bubble to produce big cash flows. I just did some of the basics — some of the things that are often overlooked when talking about personal finance and paying off debt.

I obtained a job to have a stable income every 15th and 30th of each month, I took extra time to read about personal finance basics, I hustled a little harder at my job and my side hustle, and finally I took the “earn more and spend less” strategy and applied this to my debt. I know my lessons are simple, but that’s truly what helped me get out of debt over the past five years. I hope as you read my story, you took the inspiration that getting out of debt is possible and that this leads you to the same place I am today: debt-free.

If you’ve conquered debt or are working your way out of it, what strategies are you taking? What advice would you give to others who are struggling under this burden?

Leave all your comments below!

About Author

Steven Donovan

Steven lives and works in the city of Chicago. He's an "accidental" real estate investor and landlord with plans and a goal to reach financial independence by May 2020. When not at the 9-5 job, he's walking his Siberian Husky, traveling with his beautiful wife, selling on eBay, and writing on his blog at


  1. Douglas Skipworth

    Thanks for your willingness to share so much, Steven. Kudos to you for what you’ve learned and accomplished!

    Your experience reminds me of the book titled The Richest Man in Babylon, which Brandon Turner wrote about a couple of weeks ago. You should definitely pick up a copy of the book (as should ever reader). I am half way through it right now and wish I would have read it years ago.

  2. James R.

    Steven, great first article. I look forward to reading more from you!

    In personal finance and paying off debt, you have two choices to get ahead:

    Make more money
    Spend less money

    Ideally, you have only one choice: make more and spend less. These two done together will get you independent from “da man” faster than you could imagine. Too many people buy “stuff” they don’t need to impress others.

    Happy 2016!

  3. Great article and sounds like a similar but different situation with an identical goal in mind. If you don’t mind me asking what were the to 5 books/articles/podcasts/videos that you would say we’re most informational about personal finance? What are the top 5 things you would say are the key points for personal finance you have learned over the last 5 years (beyond spending less and making more)?

    • Steven Donovan

      Thanks for the positive words. Love the questions. Some of the biggest influences me over the past 5 years include J.D. Roth who used to write and own Get Rich Slowly, Mr. Money Mustache, and Dave Ramsey Book/Podcast were my most influential.

      The key points over the past 5 years for me has been to identify where my money was going, create a budget to tell where the money should go, find ways to eliminate expenses(eg cut cable, change cell phone plans, etc), increase income (side hustle, 9-5, real estate), and probably the most important part for me was to have it be a major factor in my life EVERY SINGLE DAY. Hope that helps, there is so many great resources out there just have to find the one that fits you best.

  4. Jean Bolger

    Love this article. A lot of people come to Biggerpockets looking for a quick fix to their financial woes. For most people it takes time and work – just like you described. But as you showed, the big piece is getting that financial education so you can see where your choices are taking you.

  5. Kim Martin

    GREAT article! I appreciate your vulnerability and willingness to share what you learned along the way. It seems that the harder you work, the luckier you get. Me too by the way! I look forward to reading more from you. Thanks again!

  6. Ionie Scott

    Very informative and educational Steven. There is a ‘nugget’ in in all this for everyone to chew on (food for thought). One never know how glorious it is to be on the mountaintop, unless one has been down in the valley. You have climbed your way out of your valley one step at a time, knowing that there can never be a repetition of this harrowing experience.

    I like that EBay concept, and have been trying to get some information on how to get started, because it does bring in fast cash, and people are cashing in big time. I have been through Dave Ramsey’s Financial Peace university and it was excellent! The key is to try to stay out of debt (especially credit card debt). If you can’t pay in cash, it means you can’t afford it – wait and save for it.

    • Steven Donovan

      Thanks Ionie. I was just thinking something similar last night. Would I have made it out of debt if I was on the mountain top golfing on a Wednesday or would I be just piling on more debt. eBay has been good to me, it’s something that is a nice small income stream that at this point for me requires only a little work here and there.

      As you can imagine I’m pretty debt averse so staying out of debt including credit cards certainly is on my radar, I’m OK going against the masses, I kind of like it actually.

  7. Today, a good starting point for your own business can be a project on the Internet. You can open your own website with your favorite hobbies or open its first online shop. To go to this step is not easy, but something you need to start. My friends are so open your online project with reviews about the companies, say they are doing well, so that all recommended

  8. Andrew Hofing

    @StevenDonovan Great article! I am currently in a similar situation with high debt, getting close to $100K with only a low paying PT job. It was so timely to read this article for me and give me some HOPE. I have 2 money partners that I formed an investing LLC with over 1 1/2yrs ago and we are not working very well together and thus have nothing to show for our efforts. So, with personal economic situation becoming very bleak I have come to the conclusion that a steady JOB is necessary @ this point. I am in search of a full time JOB currently. I have read Dave Ramsey’s books and have some of his tools from Financial Peace University. I also read Chad Carson’s blog post “5 Highly Actionable Steps to Make REAL Progress Towards Your Investing Goals”. I just need to try to stay focused and implement these concepts and strategies. I will definitely make what you have posted part of the equation. Thank you for the HOPE you have provided!

    • Steven Donovan

      Thanks for kind words Andrew. I know everyone has different routes to get out of debt, but for me and maybe for you, it’s getting that direct deposit every 2 weeks and then taking that momentum to the “side hustle”. Either way, I wish you the best, let me know how things go along the way.

    • Steven Donovan

      That’s a great question Adam. To use a Bigger Pockets term we “house hacked” the 2 flat, so for us we(married) only needed 3.5% down for the property, we also bought a foreclosure in 2011 at a great price which helped out as well. My debt certainly didn’t help the situation but it didn’t kill the deal either.

  9. Jeremy Jackson

    Wonderful article Steven! I’ve been on the same mission for the past few years. One more debt of 20k remains. My “side hustle” is reselling vehicles, motorcycles, trailers on craigslist. Time to step things up so I can pay that remaining 20k off this year. Oh, its tax time folks. Apply that return to your debt!

    • Steven Donovan

      Thanks Jeremy very nice of you to say! That’s a great side hustle and sounds like it could make a few extra dollars. Yeah based on the month or so I have been out of debt and even when I paid off my student loans in June it has just been a huge weight off of me, I have a bounce in my step and a smile on my face. Best of luck, let me know when you reach your goal.

    • Steven Donovan

      Thanks Joe! Yeah having that base or monthly payment and then having your side hustle really helped to put me over the top, sometimes it was small maybe $100 and other times it was $1000, but 100% was aimed right at my debt. Side Hustle away sir.

  10. Phyllis Sims

    Mr. Donovan, God Bless you and yours..I haven’t heard of that kind of determination and proof of hard work together for many years, today it seems that everyone is out to get it quick, without the organization of thought, method and knowledge growth. Also these kids are being taught that you can get anything done one this computer, and make fast cash and high life doing it, because that is what they are told and of course a picture still shows a thousand words. Thanks for letting me know that it still takes the same dedication that it did in the olden (Golden) days, to be able to be as proud as you are and deserve to be. Also you know how to keep it !

  11. Hi Steven
    I would like to agree with Phyllis Sims’s comment. It is very rare to come across stories of such willpower and proof of hard work in one go. In a world where everything is about fast cash and instant results, this kind of result oriented strategy is like a fresh breeze.

  12. Diedrick Nagle

    Man… You have no idea how much this article means to me.

    Actually, you probably do. My current situation is almost identical to what you described.

    I’m 100,000+ in bad debt and it all started with a dream for me and a girl (whom i now call my wife as well)…

    We went through the initial dark place and overwhelming feelings of a seemingly insurmountable number…

    Fast forward about 2 years and we are now getting on track and have a solid plan to take on this debt.

    Your story is inspiring and reassuring. Thank you for sharing. Seriously.

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