Meet Leonard. That’s not his real name, and the above picture isn’t of him, but it might as well be.

Leonard has worked at the Wal-Mart that I deliver chips to for the last 5 years. He stands up front, greeting the customers as they come in the store, giving them shopping carts and what-not. He’s the infamous Wal-Mart greeter.

I’ve known Leonard for most of the 5 years he’s worked at the store. He started out as one of the nicest old men I’ve ever had the pleasure of meeting. I always made a point of saying hi to him, asking him about how his day was going and about his garden, which he takes a great deal of pride in. Leonard’s personality made him a terrific greeter.

As the years have gone by though, Leonard has lost some of his pleasantness. He’s clearly irritated when people’s purchases activate the alarm going out the door. He still makes eye contact and says hi to everyone, but he’s lost his smile and rarely says his greeting with any expression anymore. He’s become more and more of a crotchety old man. He celebrated his 75th birthday just a few weeks ago and the staff threw him a party. Leonard scowled throughout the party, even refusing a piece of his own birthday cake.

I always assumed Leonard was bored with retirement and that’s why he was working. As the years went on and his attitude deteriorated, I wondered why he was still working. It’s obvious to everyone he no longer enjoys what he does. Last week, I caught Leonard in a good mood, and we started to chat.

I asked Leonard about his past. Where did he work throughout the years? Leonard told me he had decent jobs, but never any that provided any retirement benefits. He worked as a car salesman for a while. He worked construction for a few years. He would always work somewhere for a few years, then get bored and have to go try something else. He made enough to support his family, but there was never much left over to save for retirement. Like many of his generation, Leonard’s wife was a homemaker.

They bought a modest house to raise their family in, paying off the mortgage on that house in their 50s. At that point Leonard and his wife started to save as aggressively as they could, starting to invest in the late 1990s. Because they were close to retirement, they allocated their portfolio conservatively, splitting the assets approximately 50/50 between stocks and bonds.

At first, their portfolio did quite well. The stock market was booming, and even their conservative portfolio was rising with it. Emboldened by success, Leonard and his wife kept investing, except they were putting all of their new money into the equity part of their portfolio. Their advisor was telling them to, and the results were impressive enough for Leonard to give it nary a second thought.

Just a couple years later, the bubble burst.

Leonard stayed the course though, investing throughout the bear market. This time though, he wanted to preserve capital. So he sold his equities and stayed in mostly bonds. Over the last decade, he’s averaged about a 5% return, not nearly enough to ensure himself a comfortable retirement.

Then, as it always does, life started to rear its head and Leonard was faced with some difficult choices. His two daughters were getting married. Each wanted a fairly average wedding, totaling about $15k for each of them. Leonard gave them the money, even though he had to borrow against his house to do so.

Then his son decided he was going to buy a house. Leonard thought it was only fair to give his son the gift of a down payment, adding another $20k onto the debt. To add insult to injury, his wife’s car crapped out and she insisted on a new one. That added another $20k on the new mortgage.

Finally though, it was time for Leonard to retire. It was going to be tight because he had a mortgage again, but he figured they could make it. And for the first few years of retirement, things were going just fine. Money was okay, so Leonard and his wife dipped into their retirement savings to take a couple of trips. They spoiled their grandkids with all sorts of toys. They were enjoying retirement, just like you’re supposed to.

And then, Leonard’s wife got sick.

She had a fairly rare form of cancer, treatable with a combination of chemotherapy and various drugs. While she was in remission, Leonard started to develop some health problems of his own. Between the two of them, they have to spend a few hundred dollars a month simply on prescriptions. Leonard developed hearing problems, so he had to spend thousands on two hearing aids. By the time it was all said and done, the savings had ran out, and their expenses were too high for their pension income to cover.

If Leonard had been smart throughout his life, he wouldn’t be in the predicament he’s in now. He didn’t do a good enough job planning for retirement. If he had of started to save earlier and more often, he would have had a safety net. Unfortunately for him, he didn’t do it.

I don’t want to be the old man who has to go back to work. I want the freedom to be able to help my children, or to travel, or to do whatever and not have it have a huge impact on my financial well being. Most of all though, I don’t want to be like Leonard.

Tell everyone, yo!