Nobody ever got giddy over practicing caution.

The other day I was looking through a “new feature” being offered by E*Trade, their “Online Advisor”. It”s not terribly different from the myriad of other such tools in that essentially the same questions are asked, particularly with regard to your tolerance for risk, the number of years until retirement and other seemingly important questions.

Single ply or two ply, I believe is a proxy assessing your spending habits.

When it’s all said and done, there’s nothing more exciting than having “Fixed Income” recommended for your stage in life.

You know the stage. Respirators, catheters and orderlies that don’t know how to use any of them.

Caution is pretty boring and I really don’t want to be reminded that I’m at that stage of life.

I may be ready for Depends, but  I’ll fight until the end to avoid those Fixed Income investments.

CondomsI had a friend in college who always thought that he was the desire of every woman’s dreams. He used to proudly show me the condom that he kept in his wallet, as he always needed to carry “protection.”

After a while, I recognized the crease in the foil of that condom and realized that for years he was showing off the very same one. he was taking the exercise of caution to an extreme that really wasn’t terribly appealing, but he was behaving otherwise.

He had a business card that read something to this effect:

“My name is Harold. I want to sleep with you. If you want to do the same, please call my number. If not, please return the card, as I’m running low”.

In this instance no names were changed to protect anyone.

He also used to talk about how he was going to go to the “free clinic to get “tested.” It seemed that he needed to be tested everyweek. Whenever I would hint that I might want to go with him to get tested, he would always come up with a reason why he wasn’t able to go at that particular time.

Somehow, I don’t think he was quite as accomplished as he had been inferring. I don’t think he really needed much protection, except perhaps from reality.

I made no such pretense and was never a big fan of “protection”.

To be clear, I’m still talking about FIxed Income investments. I like protection in most other aspects of life.

Although I’ve never been a big fan of reckless behavior, especially when it comes to investments, I’m not a big believer in living a life of over-caution, either.

The problem is that when giddiness does set in, caution is thrown to the wind.

Certainly there has to be a graph somewhere that shows the association between alcohol and unwanted pregnancy, just as their has to be a graph someplace showing the association between a rapid rise in the stock market and stupid decisions. Greed will do that, as will the fear of missing out.

Unless you were in FIxed Incomes or in cash, which are essentially the same, you’ve been very happy the past couple of weeks. Surprisingly, that feeling would have alternated with having been very sad the previous few weeks.

So happy, that you probably think that everything is just going to keep going unchecked in the same direction. One of these days, the “this time it’s going to be different” feeling is going to come true, but that’s not likely to happen this time or the next.

And then, along come days like today.

After a couple of weeks when grasping at rumors of good news was all that it took to drive the market higher, today was the day that Germany’s pessimism on an EU solution came back to haunt.

Pissing in the wind, punching a whole in a condom and buying high are all reckless behaviors. Pinning your hopes on a promise to resolve a crisis is probably not a good strategy.

But from my perspective, not having downside protection is every bit as reckless, especially when the market goes up and down in completely unexpected spasms.

Sure, I was saddened to see Halliburton drop $3 after announcing earnings before Monday’s opening, but the $38 call options that I sold on Friday for $1.02, that happen to expire this coming Friday soften the pain.

Of course, the downside is pointed out by those that believe that stocks are all poised to make spectacular climbs at any given moment in time.

There’s no shortage of examples where that’s happened.

This year, I can look back at shares of Green Mountain Coffee Roasters and VIsa among others, that I’d lost to assignment after unexpected run-ups.

Those are easy to remember and hard to forget.

But I’ll also remember that last week I didn’t bank any option income on my downbeaten shares of Mosaic because there were rumors of a buy-out and I didn’t want to get caught flat-footed.

I’ve thought of alternatives to selling covered calls, but that would require picking better stocks and making their purchase and sale at just the right time.

That solution would require effort and skill, so that makes it a “no go”. Although I’d be willing to use insider information to help arrive at the same end point, I don’t appear to yet have those kind of connections.

The reality is that there are very few surprise break-outs of a stock’s price. For every Visa that gaps from $80 to $90, or very Green Mountain that goes form $45 to $60, there are a couple of thousand each day that don’t.

Today, El Paso did, but space doesn’t allow me the opportunity to list those that didn’t.

The fear of missing out on one of those great moves is unfounded. They just don’t happen that often.

What does happen often is that stocks go up, they go down and they go up again, right before going down and then up again.

After that has all happened, you can reliably predict that cycle will repeat itself.

On Monday, I started the day with cash coming from the assignment of British Petroleum, Freeport McMoRan and Alcoa and was looking for a quick bang for my investment buck. For the day, at least, I got it by picking up additional shares of Riverbed Technology, DuPont, Sallie Mae and ProShares UltraShort Silver ETF.

I immediately sold in the money calls on all three of those purchases. After all, when do you put protection on? After the proverbial horse has left the barn?

For my trouble of selling near the money and in the money calls expiring on this Friday, if assigned, I’ll net a 3.4% return on the options income alone

Sometimes the protection is worth more than the asset it’s protecting.

I’m not exactly certain how that same analogy can be applied to condoms, but at least in my world of investing, it seems to be true.

For the shares that I picked up today, I don’t have very many high hopes of an El Paso like surge.

Whatever surge there may be will be restrained by the protection, but enjoyable nonetheless.

As the markets have been evolving I’m looking forward to even more variety in the protection available.

As we begin selling derivatives on derivatives, such as options on the VIX or short options on the VIX, I’m looking forward to the inevitable appearance of some of those UltraSheer options to help make the experience that much more enjoyable.

And what investor wouldn’t want to be long in UltraSheers? 

 

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