Are You Playing With Fire?

Back in the day, a lot of my friends rode motorcycles. I never did get one -- though I did some other stupid, reckless, and disturbing things.

I know, I know. Riding a motorcycle isn't necessarily stupid. Maybe not -- for you. But it was for me, certainly when I was 16. If you'll bear with me, I'll tell you why, but by now you must be wondering ...

What's this got to do with investing?
You may have noticed that we've started talking at The Motley Fool about what, to me, amounts to trading. There's even been some chatter about shorting and buying and selling stock options. Frankly, it's got me thinking about my life and the few good choices I've made, and I'm not sure it's a good thing.

Long story short: I'm 45 years old. I've been investing for 20 years. I've never owned a motorcycle, and I've never bought or sold an option. I don't even have an options account. It's not that I dispute that options are fast, exciting, and can make you money -- or that chicks dig 'em.

I just figured I could get into enough trouble without throwing leverage and expiration dates on the fire. And believe me, I was tempted. Especially in my glory days of the 1990s, when all I had to do was look at a stock, and it would pop 25% or more.

It was the damndest thing
One guy I knew at Thomson/Reuters swore I was getting inside information and holding out on him (you'll hear a funny story about this guy just ahead). In fact, I'd simply got a hot hand. And not by following the herd into Dell (Nasdaq: DELL  ) Microsoft (Nasdaq: MSFT  ) , Intel (Nasdaq: INTC  ) , or any other "stock everybody loved."

I was messing with small biotechs. Names you'd never hear, until one Monday morning they were snapped up by Novartis (NYSE: NVS  ) or Bristol-Meyers Squibb (NYSE: BMY  ) . And tiny exploration and production outfits that summarily popped on rumors that Chevron (NYSE: CVX  ) was out trolling for reserves. There was only one problem: I fell in love with my stocks -- the investor's mortal sin.

Point being, the short-term mentality imposed by options would have served me well in my youth. If instead of buying stocks, I'd entered into 30-, 60-, or 90-day options contracts, I'd have been forced to take my profits. As important, given the added leverage, my quick 25%, 50%, and 100% gains could have been multiplied many, many times over.

Of course, you know where I'm going with this.

The reason I never got a motorcycle is ...
Because I knew I would kill myself, or worse. Even at 16, I had every reason to believe I'd be in an accident of some sort. Everybody I knew who drove a car had survived one, even those who'd only been driving for months. In my social circle, it wasn't a question of whether you got banged up, but when -- and how bad.

In a moment of clarity that I can only describe as otherworldly, I saw that for me there would be no such thing as a minor motorcycle accident. I guess that's how I feel as an investor about options and margin. To my mind, combining leverage and a short-term horizon are like the speed and agility of a bike -- exhilarating but dangerous.

And much as I'd known I had a date with a wrecker at 16, I knew that I'd make my share of bad stock picks -- and that invariably I'd be off on my timing. When you're buying a piece of a real business, misjudgments like these become "long-term investments." When you're trading options, you get wiped, wondering what might have been.

I'm in the zone!
I know what you're thinking: Just because you're perched on a BMW R 1200 doesn't necessarily mean you have to act like an idiot. Again, that may be true -- for you. But I'm an excitable guy. And when I'm "in the zone," I can be pretty convincing, especially to myself.

Again, as an investor buying for the long term, this is a mild annoyance. Yes, I've made some rash investments, some of which I've sold at a loss -- but rarely at a total loss, and never before I was ready. As a speculator, buying or selling options with an expiration date (yes, I do believe "speculator" is the correct term), I wouldn't be able to say that.

Worse, the "hotter" my hand, the more I'd bet. I call this Niederhoffer syndrome, for the squash-playing speculator known for making ridiculous amounts of money then losing it. Again, as an investor, building a diversified portfolio of stocks, the occasional I'm-in-the-zone bout of invincibility won't kill me -- even when the result is a big bet on Citigroup (NYSE: C  ) .

One slip and you're dead
Earlier, I mentioned a friend from my days at Thomson. One day, I was in his office running my yap, and this guy looked up at me and said, "Dude, I just went into the bathroom and puked!"

You guessed it: An options trade blew up. I forget the figure, but 50 grand comes to mind. Ironically, the trade was on a stock I owned myself -- a telecom company called Radyne. I later sold at a big profit, but he was wiped.

Smarter investors than me will tell you that smart people don't get into this kind of trouble with options. You'll hear how options smooth out your returns -- even protect you from your own emotions. Again, that may be true -- for you. But I think I know what emotions I need to be protected from. The urge to dump my stocks at the bottom is not one of them.

Seriously, I don't even get that argument. The fact that I don't use margin and don't have an expiration date hanging over my head is why I never sweat it when the market gets ugly. I'm a long-term stock guy who knows that on average, stocks go up more often than down -- and that they always go up long term. I know I'll survive my stupid calls. Can George Soros say that?

"Tell it to me like I'm a child"
When I was 18, my buddy came home on break from West Point on a Kawasaki Ninja. We rode home from the bars that night on I-270 -- me on the back, no helmet -- topping out at 110 miles an hour. Looking back, I don't know if we felt invincible or didn't care. But it was precisely the kind of thing I didn't want to be doing every Saturday night. I can go plenty fast in a car -- and get plenty rich investing in stocks for the long term. I'll certainly never go broke.

Of course, you might be nothing like me. You may be the type who can use options judiciously. Not speculating, but rather hedging your current positions and generating income while you wait for your stocks to move higher. If so, more power to you. And I think you should meet my pal Jeff Fischer.

Unlike those fast talkers you see on CNBC every night, Jeff is a smart long-term investor who truly believes that options can help any investor earn better returns. So if The Motley Fool is going to talk about options, it's better that Jeff's doing the talking.

So how about a compromise?
If nothing else, I know that Jeff will give you a thoughtful, reasoned counter-argument to the one I've made today. Though I imagine you've got one for me already. Should The Motley Fool even be talking about options and trading? Let me know what you think in the comments section below.

And, by all means, hear Jeff out. Over the next few weeks, Jeff and his team of analysts will help another friend of mine, Ollen Douglass, make some money. You're invited to follow along in real time as they unwind some wickedly profitable options trades and reinvest the winnings.

To hear Ollen's unusual rags-to-riches story, and see why Jeff is so convinced that options can help you make more money with less risk, put your email in the box below. Or simply click here to learn more.

This article was originally published on July 29, 2009. It has been updated.

Paul Elliott owns shares of none of the companies mentioned here. Dell, Microsoft, and Intel are Motley Fool Inside Value choices. Novartis is a Global Gains pick. Motley Fool Options recommends a diagonal call on Microsoft and a call on Intel. The Motley Fool's disclosure policy loves the feeling of wind in its hair.


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Comments from our Foolish Readers

Help us keep this a respectfully Foolish area! This is a place for our readers to discuss, debate, and learn more about the Foolish investing topic you read about above. Help us keep it clean and safe. If you believe a comment is abusive or otherwise violates our Fool's Rules, please report it via the Report this Comment Report this Comment icon found on every comment.

  • Report this Comment On December 08, 2009, at 8:32 AM, au90cu10 wrote:

    When I made my 1st foray into stocks (1983) I came

    right of the chute, armed with options . I kept reading

    about a bull market, and I kept losing money .

    I also approached the market with a sense that

    timing was important . Eventually, I took stock of

    other , non-equity, investments that I had done well

    on .. they were all buy and hold for a looooong time.

    3 years ago, I set up another portfolio with NO options.

    Today, I still feel the lure of options, but will not

    allow myself to do anything with them, strict rule ..

    I use margin some times, but only when I have plans

    to sell a long holding soon ....

    I sure do enjoy sleeping easier at night !!!

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