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June 03, 2009


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Ha! That's easy!

I wouldn't have "assumed" my then-husband was doing what he said he was doing with his salary. I agree with what my divorce lawyer later told me, "you are a total idiot!"

1) I never would have spent ONE DOLLAR to go to college.

2) I would have taken the $4K (more than $20K in today's dollars) to start a business and/or buy a rental property.

3) I would have bought a personal residence after accumulating more money as a result of #2.

I've had car issues I would not have done again. First car was brand new which I paid over invoice, at 9% interest right out of college. Second car was brand new and held it's value like a 2 ton boulder thrown into the ocean. It also had several thousand added to the price since I wasn't done paying off the first one and I was underwater. I did pay it off though. Third car was actually a truck bought brand new and is what I will now drive until it dies. Then when it does I'll buy a USED car with CASH. To be fair, I did get a great deal on the truck and it's held it's value pretty well. I've also paid it off and I'm saving that monthly payment for another vehicle in about 5 years.

Other than the car stuff, I would have started saving in my first job's 401K as much as I could as soon as I could have. Plus I would have started saving for an emergency fund a lot earlier.

p.s. that's the $4K I had saved up (paper routes, mowing lawns, shoveling snow, part-time deli job) by the time I graduated high school.

(1) I would have tried harder to maximize my earnings before we had a child.
(2) I would have lived in our apartment one more year before buying a house (but if we had waited much longer, we wouldn't have been able to afford the house we live in... prices really skyrocketed until very recently).
(3) I would have spent less and saved more in my earlier, dumber years (though my husband always says our main problem was low income, not overspending, I think we could have done better).

1) I would've held onto and rented out our condo instead of selling it when we moved into the house in 1999. If I waited the 5 years till 2004 to sell it, we would've made over $200K. (had no clue the so. cal. RE market would boom the way it did...)

2) I would've moved my brokerage IRA account to all cash in 2007!!

3) I would've stayed home with my children for their first few years; the salary after childcare was not worth missing that time with them. Of course, my husband did not have health insurance, so I felt I had to work to provide it. But looking back - we had no health crisis during those years!!

1. Not go to expensive school
2. Not buying a new expensive ccar when mine was 3 years old and paid off.
3. Not switching to a consumer and spending lifestyle onece my paychecks came in from my first job.

3. Is the hardest to work yourself out of. I'm still working on it. You get accustomed to fake needs that drain $.

I'm 22, payed my way through college and now have a bachelors. I have no debt in any form.

No (major) regrets.

The only one I can think of is I would have saved more money when I was right out of college and single. I was making good money and didn't get into debt but I could have saved a lot more than I did.

1) I would have picked the right college major from the start. Switching to do a 2nd degree set me back 3-4 years.
2) I would have kept contributing to my 401k instead of buying and holding stock in my employer through their stock participation plan.
3) I would have never gotten credit cards in college.

You didn't say how far we could take this fantasy... Since we're talking about 20/20 hindsight here, might as well go all the way.

1. Invest every penny in the perfect stocks (or business or whatever) when they are at their lowest (MSFT, AAPL, whatever).
2. Withdraw every penny when the stocks hit their highest.
3. At this point, you're a bazillionaire, so nothing else really matters. Probably give most of it away to feel good about yourself.

Or if that's cheating then I guess I could go with the boring, "don't roll those credit cards into that HELOC because you're just going to rack them back up anyway".

Also, I would think very hard about whether that private college was worth 80K when the public college down the street cost less than a quarter of that.

I made mistake number 3 verbatim to your description above, except for the fact that I haven't figured out how to sell the condo for a loss yet and my new wife and I are crammed into a 700 sq ft condo that is at least 25k underwater. Can you describe how you were able to let the property go? Did you have to bring cash to closing?

1. Wouldn't have bought a whole life insurance policy while still in college. Boy, did I get suckered on that one!
2. Would have been more aware of closing costs when I refinanced my house several years ago.
3. Wouldn't have thrown a rock into the parking lot that broke some guy's car window when I was 10. That one really took a bite out of my savings!

Troy --

I basically lost a bit less than the 20% I put down in the first place to buy it, so I didn't need any extra cash.

1. I would have bought a used car with the settlement from wrecking the car my grandmother gave me instead of leasing a new truck. I loved that little truck but I turned it in because I didn't want to take out a loan to pay the overpriced buyout amount at the end.
2. I would discover Dave Ramsey earlier. I don't know how I would make this happen but I needed it earlier in my 20s. I had a bad habit of spending up a credit card, paying it off over the course of a year or so, only to do it again.
3. I would not have bought Mary Kay inventory when I thought I wanted to sell it. I ended up selling it back to the company to try to recoup some of my mistake, but when you do that you have to give up being a "consultant". If I had just ordered the minimum, I'd still be a "consultant" and buying my personal product at 1/2 price.

Honorable Mention: I would not have spent so much on Magic: The Gathering cards when I was 22.

My motto is to live with no regrets... just move forwrad, there is nothing you can do about this stuff now :-)


Well then I guess I should change mistake number 3 to include not saving 20% to put down - boy is hindsight 20/20

Or, is it a positive thing that I dont' have any equity into this place at this point? I guess it depends on what you're viewpoint is on whether or not the market will ever come back to 2005 levels (when I bought the place 0 down)

I just have one. When I got my first job at 16, I should have opened a Roth IRA at the same time as getting my first credit card. Even if I'd only saved $20 or $50 a month at 16, it would have started my retirement savings and got me in the retirement saving habit that much younger.

I would have stopped reading personal finance that made me a cheap miser.
I would have spent rather than saving/investing in my IRA which took a nose dive.
I would have could have should have...

so is it hard to sell condos? if you want to buy property and cant afford the house, should you buy a condo? This is considering you make at least 60K.

I would not dismiss the slow and steady savings/investing over many years, for the get rich quick.

I would watch my bottom line closer, and make sure each month increased my net worth rather than finding a new toy to buy.

1-I would buy my 4 kids a lot less toys and clothes at sales and at Christmas. Too much stuff - especially in multiples.
2-I would sell my company stock close to the high (I wanted to, but was talked out of it) or at least when they stop paying dividends.
3-I would return to the workforce sooner part-time and develop a long-term strategy for a career and financial plans.


I only have one regret and that is buying a condo so quickly. I put 13K down on it and have a balance of 89K now. The association is horrible and a lot are rented out to less than desirable people. I couldn't sell it now without bring money to the table and I can hear my upstairs neighbors walking around and something is eating holes in my deck. I will never own a condo again. I was living with a couple and it was horrible so I was just trying to get out.

1. I wouldn't have bought and sold that new car within a year.
2. I would have waited another year to buy my condo after prices dropped another 20%, and would have gotten the $8000 tax credit.
3. I would have never bought my second dog, who tore my already depreciated condo to shreds.

Hindsight is 50/50.

1. Wouldn't have financed a car directly out of undergrad. I bought a nice car (it was used/pre owned) but immediately felt consumed by having that monthly payment and debt. Quickly put all excess money each month toward that car payment and paid it off quickly. I still drive that car today...
2. Would have started in my company's automatic increase plan for my 401k right away. I did this after a few years, but didn't realize initially how critical it is to do this at the beginning of your career as this is when you salary tends to increase on a more frequent basis.
3. I would have sold my boat earlier (sold it in November right before selling our 2nd house on a lake), could've got an extra $1000 if I had sold it during the summer!


Too many to list!
1. Would have taken the full scholarship rather than the out-of-state school which i 'thought' Dad was paying for. Wouldn't have changed majors, either--stayed an extra two years. TOTAL: at least $40,000 in the hole.

2. Wouldn't have sold my first home through a slimy cut-rate realtor. Ended up selling way under market value. In fact, wouldn't have moved at all--loved the rancher and close to daughter's private H.S. TOTAL: $35,000.

3. Wouldn't have sent my 3 kids to private school when there's a great charter school around the corner (just need to get a job at the school or have your # 'picked from a hat'. TOTAL: $60,000 at least. still counting.

Please let me win the lottery!

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1) Would not have invested in a friend's dying game shop - total loss of about $10,000.
2) Would have started saving in a Roth IRA in my teens instead of when I was 24, but that was when I heard about it.
3) Would have tried harder to think of something I would love to do that paid better...still working on that.

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