Editor’s note: With our offices closed this week for the holidays, we wanted to share the best pieces Jeff’s written throughout his career.

For today, we share a story that will feel familiar to anyone who’s watched a market crash…

[This essay was originally published in April 2009.]

I ran into a taco yesterday during my afternoon jog. Actually, the taco high-fived me as I ran by.

Taco Bell just reopened a restaurant in the little shopping center of my small Northern California town. To draw attention to the Grand Reopening, the franchise owners hired someone to dress up as a taco, stand by the side of the road, and wave to the cars passing by.

Amused by the high-five, and needing a chance to catch my wind anyway, I doubled back and struck up a conversation with what I assumed was a teenager inside the taco costume.

"Dude," I started off, "It looks like you're having a pretty good time out here. I hope they're paying you well."

"It's not bad," the taco responded. "My son-in-law knows the manager here and he offered me $100 cash to stand out here for two days and wave at the cars."

He didn't sound like a teenager. Indeed, the man inside the costume wasn't a high-school student looking to make a few bucks. He was a 72-year-old retiree named "Fran." And the conversation we had will likely keep me up at night for a long, long time.

Fran spent 30 years as an airline mechanic for United Airlines. He retired 10 years ago when the airline offered him an early "buyout" package. Since then, however, the company went bankrupt. Fran lost his benefit package, which was mostly health care and dental. "But," he says, "at least I was smart enough to take control of my own pension funds."

If he hadn't, then he would have lost most of his retirement fund when United declared bankruptcy a few years ago.

"I did okay for a few years trading stocks during the dot com phase," Fran continued. "But I lost a bunch of money in 2000 when the market fell.

"So I moved most of what I had left into real estate. My friends were all making money and it was easier than picking stocks. I bought an apartment building and two rental homes. I had positive cash flow from rents, and I kept refinancing and pulling out the appreciation.

"Fortunately, I sold the apartments a couple years ago for a good profit. The homes, though, are empty. I'm not collecting any rent, and they're worth less than the mortgages I have on them."

So Fran is walking away. He's giving up on the houses and letting them go into foreclosure.

"I don't want to do it," he said. "I believe in paying my debts and I hope I can make good on that promise later. For now, though, I have to take care of my wife.

"And that," he continued, "is why I'm dressed like a taco for $100. My wife turns 70 years old this Saturday and I'm taking her to dinner to celebrate. She doesn't know about our finances and she doesn't know I'm doing this job. No one can see me in this costume and my son-in-law can keep a secret."

"Besides," he said, "the stock market is doing better now. I sold most of what I had in November. That was bad timing as the market moved up afterwards. But I didn't have to suffer through the decline earlier this year. I just put all of my retirement funds back into the market last week because it looks like we're back on track and stocks should move higher the rest of this year. That's a good idea, don't you think?"

Here was this man who had worked and saved his entire life. He bought stocks at the high in 2000 and suffered a big loss. He then bought real estate during the bubble of the past few years and is now facing foreclosure. He sold stocks near the bottom last November and is buying them now, after they've run up 25% in just over one month.

And he just asked for investment advice from an unknown jogger.

I was reluctant to comment because I didn't want to deflate his optimism. At the same time, if my own grandfather were 100% invested in the stock market right now, I would scream at him to get out.

"All I know, Fran," I said to him, "is if I get into a taxicab and the driver tells me it's time to buy stocks then I know it's time to sell. If my mother calls me on a Saturday afternoon and asks if she should start buying into the market, then I'm selling first thing on Monday morning."

Yesterday, a 72-year-old retiree with a dubious investment history put on a taco costume and stood by the side of the road in an effort to earn enough money to take his wife to a birthday dinner. He just put his entire retirement fund into the stock market, and then asked for advice from a stranger passing by.

"Fran," I said, "I think I have to sell into that, too."

Best regards and good trading,

Jeff Clark