Image: Piggy bank © Fancy, Veer, Corbis

My finances have never been a hot mess.

Some money writers can entertain you with tales of how they piled up massive debt before they saw the light. Their tales of frugality, reform and paid-off plastic warm the heart.

Never been there, never done that. My mom taught me to avoid credit card debt and to save for a rainy day. I listened, so I have no dramatic tales of redemption.

But nobody's perfect when it comes to money. Everybody makes mistakes. Remember that next time some self-righteous nitwit tries to lecture you -- that person has screwed up, too. What matters is that you learn from your mistakes.

Here are a few of my doozies that stand out -- and probably taught me the most.

Buying retirement property in my 20s

I was young and in love, with both a man and the state of Alaska. I thought I was going to live there the rest of my life. When he suggested buying some property near land he already owned, it sounded like a great idea. We'd build a home there someday and retire to the wilderness.

Yes, wilderness. Did I mention that this lovely 14-acre property was at least 80 miles from the nearest road?

There was a trail leading up from a gravel landing strip on a riverbed, and that was it. My boyfriend was a pilot, and I learned to fly as well, but I'm not sure what we were planning to do when our eyesight and reflexes failed.

Liz Weston

Liz Weston

Moot point in any case. The relationship didn't last, and I moved to California. I still have the property, though. It doesn't even make financial sense to give it away, since the cost of getting an appraisal of this remote land is far more than the tax deduction I'd receive from donating it.

What I learned: Oh, so much. Raw land is a risky investment to start, and buying it decades in advance of when you plan to use it is just silly. In a broader sense, the experience taught me that I can't really know now what an older me might want or value. I think of that every time I hear people in their 30s or 40s say that they'll never want to retire or that they can't afford to save. They should save anyway. Otherwise, their older selves may curse them for cutting off their options.

Buying my first house

In 1993, my mother had just died after a five-year battle with cancer. I desperately wanted a home and all the safety and security homeownership seemed to entail. So when a friend suggested investing in a duplex together with a third friend, I jumped at it.

It wasn't a bad purchase (more on that later). But homeownership was so much more expensive than I'd expected. The place had termites, rotted windowsills and dime-size holes in the gas pipes. The roof leaked. We all had different ideas on how much to spend for improvements or even what repairs were necessary. Coming to a decision about anything was like herding cats.

Also, the value of the home kept dropping, at least in the first few years. This was during Southern California's previous real-estate recession, when it took about 10 years for prices to recover to their old peaks.

We sold it in 1998 for $477,000, about 20% more than the price in 1993. After I sat down and totaled up everything I'd put into the house, though, I realized I'd barely broken even. If I had put my down payment in the S&P 500 Index instead during that period, I would have tripled my money.

What I learned: Homeownership is not always a good investment. Maintenance and repairs can really add up. A good inspection (which I stupidly didn't order) can alert you to what you might be getting into, but you still need to stockpile cash to cover the inevitable costs. My experience with the house helped me counter all the real-estate cheerleaders who, over the next few years, would insist that homeownership was a slam-dunk and that prices could only go up. I knew better, and I knew that even when prices do rise, they may not rise enough to cover the costs of ownership.