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July 8, 2008

When Should You Sell Options?

I had an interesting conversation with an executive yesterday. We got talking about his stock options, and when he should sell them.

I started in the usual place, talking about time value and strike value of the things, with the usual volatility/cliff issues. He kept coming up with reasons why he should sell, despite the stock trending up, despite good numbers, etc. I said, fine, then sell. But, he said, then I miss the time-related upside in the options.

Sigh. You can't have it both ways, I pointed out. And if you really like the stock, then hold the stock after exercising rather than immediately selling it.

But that would be risky, he said, neatly ignoring that he should be indifferent about the risk if he is willing to hold the unexercised options.

Anyone else run into people like his? I'm always amazed at how emotionally messed up some people -- including executives -- get about stock options.

Go ... Elsewhere, Young Man

A question for people to ponder: Say you were 22-years-old, unattached, and recently graduated and looking for your first job. You want to be part of something big and dynamic, a truly dynamic economy where you're going to be able to rise up with it.

The U.S. has long been that place, and maybe you think it no longer is -- or maybe you do. Whatever. Where in the world -- visas aside -- would you go?

I got that question the other day from a recent graduate, and I surprised myself with how quickly I could answer it. I knew immediately where I would go, hands down, with hardly a moment thinking about it. But how about you? Any city, any country, anywhere in the world. You're 22. Where would you go?

RIO_Rio_de_Janeiro_Corcovado_panorama_2_2_bIn the spirit of full disclosure, where would I go? Brazil. While I'm painfully aware of the many problems -- infrastructure, crime, capital, corruption, etc. -- that the country still has, I love the dynamism, growth, optimism (mostly -- see my trip notes for more), etc. And it doesn't hurt that the economic numbers are generally good too, with some exceptions.

How about you? Where would you go, from San Francisco to Sao Paulo, from Singapore to Shanghai, from Sydney to Slovenia to Saskatoon. The world is changing rapidly, and the "right" answer from 1998 isn't likely the right answer in 2008.

Make your call in comments below.