How the Road to Debt Freedom is Filled With Boring Decisions

charlie_imageIn 2007, after reading Dave Ramsey’s Total Money Makeover, my wife and I decided to start putting our family on the road to freedom from debt. We want to live an extra-ordinary life. We wanted to live like no one else, so we could later live like no one else. Que the radio show intro!

With motivation in hand, we had about $25,000 in student loan debt and about $145,000 in mortgage debt. Not a lot by most peoples’ standards, but it was all future commitments that our family was obligated to pay. $170,000 in future commitments to be exact.

Fast forward eight years, with only $75,000 left to payoff, and we are on the home stretch of road to debt freedom! It feels like we are coming to the end of a marathon. At this point we are at about miles 20 of 26.2 miles. This is where our body has been depleted of all glycogen stores, and you are operating solely on endorphins! Each mile feels harder and harder from this point on. With that said, here are a few of my feelings on how paying off debt isn’t for those who are faint at heart.

Paying off debt isn’t like day trading stocks

When we started paying extra on our student loans and mortgage, I thought it would feel like I was day trading. Something like I was playing a casino slot machine and when I clicked submit, then my computer would start dinging and flashing. Instead clicking submit feels very sterile and uneventful. It just says, “Payment Confirmed”. So if you are looking for a lot of excitement, then paying off debt isn’t for you.

Paying off debt can be boring at times

Like I mentioned above, debt payoff can be boring at times and monotonous. Often times it feels like it is more about perseverance than it is about finances.  Ultimately, if you can outlast the monotony of paying extra on all your credit every month, then you can win. It definitely isn’t like playing the slots at your local casino. The whole phrase of, “Payment Confirmed”, should come with bells and whistles that get set off from your computer when you hit submit. I think this would make it a lot more exciting! :) Would you agree?

Paying off debt isn’t always socially accepted

In a marketing driven culture of so many wants being projected on us, it has many people in the financial rat race. Since most Americans are in debt up to their eye balls, then people who are pursuing financial freedom aren’t always accepted. They think, “well my neighbor should have $10,000 in credit card debt, a $300,000 mortgage, and two car payments just like me.” (just like Stanley Johnson)


If you live like or tell people your intention is to pay off all your debt quickly, then they look at you like you just land in Nebraska from a space ship that flew in from Pluto!

Paying off debt is more about psychology than numbers

“If all finances were was about math, then why don’t you see more mathematicians as millionaires?” Interesting question isn’t it? I remember hearing this quote on Dave’s show one day, and thought, “You know what? He’s got a point. If becoming a millionaire was all about numbers, then why aren’t more mathematicians millionaires?” After thinking about it a while and through our own debt payoff experience, I’ve quickly realized the debt freedom is more about small individual choices you make from day to day. Those small decisions are all driven by our wants/needs/desires, which drives numbers. A lot of the psychology behind debt freedom is constantly evaluating and modifying behavior to suppress wants and desires to modify long term financial behavior.

So as our family tries to finish up this hard journey, I just wanted to share some of my thoughts. I would like to hear other people’s thoughts on their road to debt freedom. Do you agree or disagree? What is hard and what is easy for you?

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9 comments

  1. Richard says:

    “Paying off debt is more about psychology than numbers” – I love this and couldn’t agree more! Learning to control your spending, your impulses ad the different between “needs” and “wants” is just as important as actually having the cash sitting around ready to actually start paying off some debt.

  2. POPS says:

    About 30 years ago my wife and I got serious about debt reduction, inspired by one of Dave Ramsey’s fore-runners (and no doubt his hero), Larry Burkett. Larry first gave us the truth that God owns it all, and that we are called to take care of and use wisely the resources with which we’ve been entrusted. Once we got that through our heads, it was a race to see how fast we could get out of debt! It actually became fun to see the totals come down every month. Since then we’ve paid off our home, a lake house, and 3 rental properties, and were able to retire 2 years ago at the ripe old age of 63. If we still had debt I would no doubt still be working. Instead, God has sent us to serve in southern Europe for a couple of years, much to our delight and fulfillment. I think what we’re doing here is a little more worthwhile for us than fishing or playing golf in our retirement years. As a bonus, we also learned a lot about giving. Where did it start? Getting out of debt! Thanks, Larry! (And Charlie for the reminder)!

    • Charlie says:

      I had a friend challenge me yesterday, and ask, “why do I want to pay off debt?” I said, because I don’t have to have this ball and chain around my family. Then he said, “what then? What will you do after that?” I sarcastically replid, “well, I’m going to buy a jet ski. Once I’ve got my jet ski, then I’m going to take it out in the middle of the summer, and take my cell phone along while I’m driving it at 30 miles per hour, and take a picture. With that picture it will have a little text that says, who says debt freedom can’t buy you happiness?” Thanks for reading Pops.

  3. Heather says:

    Boring? Maybe to those that don’t find it socially acceptable. To me it’s a fun game! How can I save today? What habits can I develop to improve myself and my finances? How can I change my way of thinking and grow as a person? I love it! But you’re right that it can be socially unacceptable. Some people in my life find it very strange that I get so excited about using my tax return to make a big dent in my debt.

    • Charlie says:

      For some people, getting out of debt is a thrill. However, I would say that the long journey is rather boring for 90% of people. If that wasn’t the case, then why are so many people in debt?

      It is easier to fall into debt then to fall out. :)

  4. Jason H says:

    I would add to this that buying junk is also a lot more fun than paying off debt!! That being said, I am on the road to getting my debt paid off too. I agree that the “payment confirmed” notice isn’t very exciting, and it sure is hard not to buy the next shiny object (at least for me), but in the long run I know its the best thing. I guess the thrill comes when the balance says zero and those debt handcuffs are off once and for all.

  5. Billy dollar says:

    Hello Charlie
    I just found your site searching debt free living. As someone heading into my 30s with educational loans and housing debt it a common source of worry and frustration. You make some interesting arguments for reducing debt. Much of what you highlight seems to point out that Americans are addicted to buying not simply based on needs but reaction to how we feel. If we are happy about a promotion we buy new car. If when we get pay cuts we buy a few drinks.
    We are bombarded with message that bigger is better, whether it’s a soda or house. We are selling our self for materials. It takes a lot of self discipline to challenge your expectations and attempting to develop a good life not a life full of goods. Something to ponder is the psychology behind those in debt but also those who help creating said debt. School loans, mortgages, auto loans, and credit card system are all systems that we are told are normal. Not engaging in them might draws funny looks from neighbors and as you articulate, has as much a zing as hot cup of decaf. Good luck with completing those last miles of marathon. Hopefully more people will realize they are more than a fico score.

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