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Rolling Stock into Options

Let's say, for the moment, that you aren't hilariously under-invested into this gap higher.

And maybe you picked up some stock a few weeks ago that's doing pretty well.

In my humble opinion, you actually may want to consider converting your stock position to options, as the cost of owning options has dramatically dropped over the past few weeks.

The Rationale

The chart above (courtesy of LiveVol) is a comparison of the 30 day implied volatility (red) and the 20 day historical volatility (blue).

You can see that vol is selling off hard enough to trade at a discount to actual volatility, which often marks attractive levels to pick up premium.

But on top of that, vol is coming back to levels not seen since we really rolled over hard. I'm not a big support/resistance fan on volatility but for the moment it could make sense to own options.

An Example

Let's say that you picked up 100 shares of $CF around the 148 level. The stock is currently trading at 169, so not a bad trade so far.

The stock does run the risk of reversing, so you want to free up some cash, ease up on the direction, and limit your losses.

So what you could do here was

1. Sell the stock at 170

2. Buy the Feb 165 Call for 19.50

The Tradeoffs

What happens here? First, it reduces your delta from 100 to 60. Second, it reduces the cash needed for this position from $7400 (assuming 50% margin) to $1950.

It also gives you a gamma kick, so if it continues to run, you'll be right. It also locks in a good part of your profits.

The downside? Well, because you're a net buyer of options, the time decay (theta) will start to be an issue. But to avoid that simply go further out in time and choose in the money strikes as opposed to out of the money.

by Steven Place

Steven Place is the founder and head trader at