One Guy's Investments: Still the World's Worst Market Timer

I've noted before my propensity to make poorly timed buys -- it's not surprising to see one of my companies take a tumble of five or ten percent shortly after I buy shares.

And on selling it's roughly the same -- Overstock (OSTK) is just one recent example of a stock I sold for good reasons (I think) at close to the worst level I could have picked.

I've accepted this, and as a result I work very hard to avoid making short term investment decisions -- in the face of the overwhelming evidence of my abysmal short term predicting ability, I'm afraid that to do otherwise would lead to bankruptcy.

And today brings more evidence.

For the first time in about a year and a half, I thought it was time to cleanse the portfolio and sell some significant number of the companies I could live without. As I wrote about yesterday, I was just settling in to think through which four companies in my portfolio were most expendable and should be offloaded first.

I still think that's the right thing to do, though it'll be hard for me to make these decisions -- I'm probably a little too buy and hold focused, and I'm only one person, so I need a little forced discipline to get me to offload on occasion, whether it's to take profits, get rid of companies I don't like anymore for any reason, or free up cash for more interesting new ideas.

I find new companies that I want to consider investing in constantly, and while I love to work on my portfolio there is certainly a limit to the number of companies I can keep track of. That limit is apparently somewhat short of my current portfolio of 39 holdings -- my portfolio has performed well, but my head hurts.

So I've gotten many emails from folks with selling advice already, and a few comments here in this space.

And a lot of folks have good ideas for me to consider -- from making sure to do diversified selling, to cutting out redundant companies, to simply discarding the obvious losers. But of course, being a slow, plodding dinosaur, I haven't made any decisions yet.

Which means, of course, that the market should be plummeting.

And it is. My portfolio for today is down more than 2%, a biting reminder of the flipside of volatility and the wild ride many of my companies take me on daily.

And many of the companies I was thinking of selling and mentioned yesterday are down much more than that -- 5%, even 7% today.

So again ... I finally decide it's time to think about doing a little selling. The market hears this rumbling, and instantly craters to make sure that I can't sell at a nice, bull market price.

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