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What are your top three debt regrets?

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(Photo Courtesy of Channel R)

When you owe money on a credit card, the size of your debt can become an abstract number. All of the meals, shopping trips and splurges behind the digits fade away as you plot ways to eliminate your debt. Detachment can shield you from anxiety, but it can also prevent you from examining how you got into hock to begin with - a necessary first step to becoming debt-free. So, in an effort to prompt sounder fiscal management (and get some cheap thrills) I’d like to hear your top three debt regrets. To get things started, here are mine:

  1. Absinthe shots in Prague. Dozens upon dozens of them when I lived (beyond my means) there. They didn’t drive me crazy, but they did drive me into debt.
  2. Ironically, a top of the line cordless soup blender won’t be helpful when I’m in line at a soup kitchen.
  3. Books for law school. It turns out that I didn’t need a JD to work in public radio; however it might come in handy if I have to file for bankruptcy.

What are your top three debt regrets? Tell us in the comments section below or tell the newsroom privately.

Discussion: 17 Comments

  • Posted by Sharon McNary on March 25, 2009 2:37 PM

    Okay, I’ll play along. I’m super-frugal, but my top three debt regrets are:

    1. Salon hair styling products that double the cost of my haircuts. (Don’t judge their quality by my photo above!)
    2. Impulse buys of athletic gear off ebay. I have two running skirts I just don’t use.
    3. Many yards of really great wool that I haven’t yet sewn into clothing. Really, I’ll get to it some day, but for now, I’d rather still have the cash.
    Respond to Sharon McNary
  • Posted by Erica on March 26, 2009 6:22 AM
    1. About 75% of the alcohol I drank from the ages of 22 to 25.

    2. The Jeep Grand Cherokee I bought when I got my first real job. Loved driving it but completely unnecessary for a host of reasons.

    3. During unemployment, taking cash advances off my credit cards to… pay the minimum payments on those same cards.

    Respond to Erica
  • Posted by RC Brooks on March 26, 2009 9:09 AM

    While I am not bad off at all with regards to debt, I do regret

    1. Going to get an MRI that came out fine. My end of it was over $1000, for something that took 30 minutes.

    2. A timing belt breaking in my car. Bent all the valves, cost about $2500 to fix, doing almost all the work myself. Still cheaper than buying a new car though.

    3. Renting. Also could be called throwing money in a hole. Sat down the other day and realized that over the past decade I have spent about $100,000 dollars and have absolutely nothing to show for it.

    Respond to RC Brooks
  • Posted by DP Curmudgeon on March 26, 2009 2:11 PM

    My three worst debts have been:

    Leasing a car rather than buying it. I ended up buying the car after the lease was over, essentially paying for the car twice.

    Getting a home improvement loan for a swimming pool. The work cost more than $75K and the house only went up in value $15K. I could have belonged to a country club for less.

    Using any credit card without paying it off completely when the bill comes in the mail. I have avoided this for many years now and am able to keep better track of expenses by using a debit card, cash or check only.

    Respond to DP Curmudgeon
  • Posted by David Bean on March 26, 2009 3:28 PM

    I’ve got one but it is worth three.

    I bought my house Three Times! How? I paid what the bank said to pay. With all the interest over 25 years I paid over three times the value of the house. It still makes me angry and feel like a fool at the same time.

    I recommend: Pay your house off by paying more than they ask for. (Bet I don’t need to say: don’t use your house as a piggy bank) And lobby for usury laws to punish any lender who expects to get more than double their money.

    One final froster: it was a VA loan.

    Respond to David Bean
  • Posted by JM on March 27, 2009 6:30 AM

    Not much as a regret, but more as poor decision making.

    1. The 2k I paid for a nice mountain bike, then moved to the middle of the city because I couldn’t afford an apartment/house in the country.

    2. The business wardrobe I paid for for a position that I stayed at for 2 years, then got a job that I didn’t need to dress up.

    3. The 1k I spent on a top of the line SLR camera for the class I took in college. I thought this would be a great hobby, but I don’t have money for the film/processing, so it sits. I should have worked the hobby a little more to see if I liked it or if it would stick.

    Overall, if i waited or thought things out more, I would have been more thrifty and therefore, live in a location where I would be able to do something.

    Respond to JM
  • Posted by Nicole L. on March 27, 2009 5:15 PM

    I’m sure I could come up with 20 regrets (or more) but here are three that would’ve made a huge difference in my life and might have prevented many of the others.

    1, Not sticking to the ‘Save 10% of everything that you earn’ philosophy. And then, not dipping into anything called “savings”. 2, Cashing out 401(K)s and IRAs when I was unemployed. Should’ve just gotten a second (or third) job, or done without. 3, Taking time (almost 10 years) off before finishing my junior and senior year of college. All those crappy underpaying jobs that I settled for have put me far behind some of my peers in things like buying a house, starting a family, etc.
    Respond to Nicole L.
  • Posted by Alex on March 27, 2009 11:02 PM

    My numbers one through three are all that I’m paying for other people’s mistakes, but never went into debt - mortgage or otherwise - myself. I regret that Geithner and Obama think I have enough money to subsidize other homeowners’ mistakes.

    Respond to Alex
  • Posted by Kristina Runciman on March 28, 2009 10:21 AM

    I regret not having a crystal ball. I bought a building for my business that needed considerable renovation, figuring sales were always going to go up, as they had up until that point. Now I owe a whole bunch of money and I have a giant hole in my roof. When it rains heavily I can easily haul out 10 gallons of water in a day.

    Respond to Kristina Runciman
  • Posted by Ray Randall on March 28, 2009 7:07 PM

    Regrets exacerbate stress during recessions. The alluring choices made in good times now haunt in bad times.

    No lesson seems more important than eliminating consumer debt and never accepting a credit card again.

    Respond to Ray Randall
  • Posted by Allen R Gentry on March 30, 2009 5:45 AM
    1. Regret that no matter how much I try to bury the card, some crisis comes up that I don’t have the cash to pay for and I must dig it up again. (Health care, home repair, car trouble, ect)

    2. Regret that the credit card balance keeps going up.

    3. Regret that I was late on a payment and now the APR is 24.99% No matter how hard I try to pay it off, it gets harder and harder.

    Respond to Allen R Gentry
  • Posted by Aubrey K on March 31, 2009 4:23 PM
    1. Chosing to go to an expensive private university and getting private loans to make up the difference that my scholarships and federal aid didn’t cover when I probably could have had almost a free ride at a state institution.
    2. Not fully understanding limits my health insurance coverage and thus having to put surgery bills on credit cards.
    3. Not having an emergency fund for the unexpected to access before using credit cards.
    Respond to Aubrey K
  • Posted by Dana M on April 10, 2009 3:24 PM

    Really big debt regret? Just one, but it’s a doozey. Not finishing a college degree. I could have made thousands more during my work lifetime. Hopefully I would have been smart enough to put some of that in savings for retirement (probably not, but I wish I could have a do-over on this one). If I hadn’t been smart enough, maybe I’d have more debt regrets to report!

    Respond to Dana M
  • Posted by Sue B on April 11, 2009 11:25 AM

    1) Undergrad student loans

    2) Grad school Student loans

    3) Marrying someone with credit problems of his own.

    I don’t know how I could have done college without loans, as my family could not afford it, and low-wage campus jobs did not pay enough to use work alone to save up, but every time I leak $600/mo on those payments, I remember all the people with no formal education who do the jobs I have done and who got to spend that money on a home instead of a past.

    I will never get married again. When you marry someone, you marry their money problems too, and there are very few marriage arrangements that can improve your finances, just erode them or keep you dependent on their financial wisdom…which is usually not what it seems.

    Respond to Sue B
  • Posted by Steve R. on April 13, 2009 11:19 AM
    1. The MASSIVE phone bills I racked up in my early 20’s when I lived overseas and my then-girlfriend lived in the US.

    2. Selling my downtown Chicago condo in 2006, because the near-suburbs would be ‘too expensive’ if I waited.

    3. Buying a house in the hear-suburbs of Chicago (still on the CTA!) in 2006 at the height of the market because it would be ‘too expensive’ if I waited.

    Note: we did not buy more house than we could afford, but we could have gotten a much, much better deal if we had waited. In fact, we could have kept the condo as a rental property and still bought our current home, pricess have dropped that much.

    Respond to Steve R.
  • Posted by Josef M on April 13, 2009 9:18 PM
    1. Buying a Brand New Car when I got my Brand New Job. I’m like a broken record with that one, if you ride in my car you don’t escape the tale.

    2. Time is the debt you can’t pay off - not doing post-secondary classes while in High School. What? College credits for FREE? Nah, I’m too busy sleeping through chemistry….

    3. Not really a “debt regret”, per se, but I should have pushed for more $$$ my first job out of college. Unfortunately, in today’s professional world the only way to significantly raise your income is to leave your current job. You know, the one you enjoy enough to continue doing for less than what you’re worth? That’s the one.

    Respond to Josef M
  • Posted by PJB on April 15, 2009 6:48 AM
    1. Regret as college student: the attempt to come out ahead in a sour deal by taking possession of a 1972 MGB-GT that didn’t run. Attempt to repair car failed (mechanic welched) so lost college savings. City impounded and sold the car; I had to borrow $$ for school; ten years of payments.

    2. Regret as parent: caved in to spouse and child and sent said child to private boarding school. Wiped out funds; said child was asked to “withdraw” for violating honor code. Plus side: said child attends local public school and busses tables evenings for college $$.

    3. Regret as professional: the family trip to Japan; returned to work and was told to clean out my desk. Uh-oh. Some credit cards would only get the minimum payment for the next twelve months.

    Respond to PJB
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