Mistakes? Where do I start:
(a) I bought a home thinking it was an investment. Still trying to right the financial damage this has done to the size of my investment kitty.
(b) I bought 1000 shares of data software company Legato at $60. On margin. The stock was down another couple of bucks a few days later, on the eve of earnings. So Gordon Gekko here doubled down. Now, you may ask, "who's this Legato?" Exactly. That earnings report was the beginning of the end for the company. The next day it opened down 50%, at which point I sold. (I think it eventually went bankrupt. But I really don't know, or care).
(c) in late 2006 I attempted to persuade anyone who would listen that financial crisis was immanent. I cashed out all my accounts (the IRA's too, kept a few things) and went into hunker down mode. By March 2009, at the nadir of the crisis, I had begun to accumulate at S&P 680 some stocks -- GE and Citibank -- which represented about 5% of my investment stache. My plan was to scale down and up the size of the purchases every 20 S&P points, so at SPX 660 commit 10%, at SPX 640 commit 15%, etc, so that by SPX 580 I would be fully invested (I actually though the S&P would reach 500 by the end of the month, but I didn't want to be greedy). But alas, those initial purchases were all I got in, I watched the market rally 50% into the summer of 2009, and then I proceeded to sell my scant longs and short the market week after week through the fall and winter of 2009. I gave back some great gains in Citigroup (less so in GE) and lost another 10% off my account to boot. I was literally depressed for a year because of this.
I've clawed back to flat in the meantime, and moved most of my money over to Vanguard (in 2011) with the intention of "putting it to work" after the current cyclical bull runs its course and the market pulls back 25% (it's my honest plan for the next 5 years). And if the market runs from here to Dow 30,000 and I'm all cash the entire way this will obviously be the next installment (d) on the list.
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