Add training workflow, datasets, and runbook
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828 Part VI: Measuring and Trading Volatility
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make the move to profitability (or not make the move into loss territory, if you're sell
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ing options). This is where historical volatility plays a big part, for it is the input into
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the probability calculator. In fact, no probability calculator will give reasonable pre
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dictions without a good estimate of volatility. Please refer to the previous chapter for
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a more in-depth discussion of probability calculators and stock price distributions.
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The use of probability analysis also mitigates some of the problems inherent in
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the method of selection that compares implied and historical volatilities. If the prob
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abilities are good for success, then we might not care so much whether the options
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are currently in a low percentile of implied volatility or not (although we still would
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not want to buy volatility when the options were in a high percentile of implied
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volatility and we would not want to sell options that are in a low percentile).
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In using the probability calculator, one first selects a strategy (straddle buying,
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for example, if options are cheap) and then calculates the break-even points as
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demonstrated in the previous section. Then the probability calculator is used to
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determine what the chances are of the underlying instrument ever trading at one or
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the other of those break-even prices at any time during the life of the option position.
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It was shown in the previous chapter that a Monte Carlo simulation using the fat tail
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distribution is best used for this process.
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An attractive volatility buying situation should have probabilities in excess of
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80% of the underlying ever exceeding the break-even point, while an attractive
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volatility selling situation should have probabilities of less than 25% of ever trading
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at prices that would cause losses. The volatility seller can, of course, heavily influence
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those probabilities by choosing options that are well out-of-the-money. As noted
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above, the volatility seller should, in fact, calculate the probabilities on several dif
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ferent striking prices, striving to find a balance between high probability of success
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and the ability to take in enough premium to make the risk worthwhile.
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Example: The OEX Index is trading at 650. Suppose that one has determined that
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volatilities are too high and wants to analyze the sale of some naked options.
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Furthermore, suppose that the choices have been narrowed down to selling the
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September options, which expire in about five weeks. The main choices under con
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sideration are those in Table 39-2. The option prices in this example, being index
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options, reflect a volatility skew (to be discussed later) to make the example realistic.
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The two right-hand columns should be rejected because the probabilities of
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the stock hitting one or the other of the striking prices prior to expiration are too
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high well in excess of the 25% guideline mentioned earlier. That leaves the
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September 500-800 strangle or the September 550-750 strangle to consider. The
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probabilities are best for the farthest out-of-the-money options (September 500-
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800 strangle), but the options are selling at such small prices that they will not pro-
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