Category: Option Selling

Selling Options Guide

Many investors have never even heard of stock options selling. For most people options trading is synonymous with risk and potential big profits or losses, using leverage by buying options. However, a lot of savvy investors use strategies involving selling options, also known as options writing, to hedge existing positions against the possibility that the stocks that they already own, or are short, will move against them.

Now hedging with options is nowhere near as exciting as leveraging with options and doubling or tripling your money quickly. Perhaps this is the reason you don’t get the details of options selling explained as frequently in books or on websites on stock options basics. It certainly is a lot more Continue reading Selling Options Guide

Options Trading Explained-Writing Options


This is the second article of our options trading explained series, in which I will attempt to help you learn options trading strategies as opposed to restricting myself to a generic explanation of stock options. In the earlier post I explained stock options trading in terms of simply going long, or buying, puts and calls as the simplest but most risky of stock options strategies. In this article I’d like to talk about selling or writing options as it opens up a range of possibilities for an investor to improve the overall performance of his portfolio.

When you move beyond thinking of options only as leveraged, risky investment vehicles you begin to understand them as savvy investors and professional traders do, ripe with opportunities for conservative option strategies. There are many ways to use them besides either making multiples of the premium you pay or losing most or all of that premium. I’ll cover options trading examples like writing puts and calls, which affords you hedging options (as it were) that can help you protect existing gains in open stock positions; you could sell options to create an ongoing income from your portfolio without having to sell stock at all; you can even offset losses in stock positions you are not yet prepared to close out, by writing contracts against those long or short positions. All these trading strategies involve simple options selling, and these are just a small fraction of the ways that you can use these incredibly versatile investment tools, once you get stock options explained to you.

Writing Options As A Simple Hedge

Let’s say that you have a nice profit in a stock that you would prefer not to sell yet. Maybe it’s had a run-up recently, and while you are still bullish on the company, your practical side tells you that the stock might very well be due for a pullback.

In addition to the optimism reflected in the stock price, it seems like the options associated with the stock have relatively pricey premiums, with even the out-of-the-money options costing more to buy than they normally might.


For an investor contemplating buying options, this is a risky situation. If you bought, or went long calls here, not only would the upward stock move have to continue, the volatility in the stock has to stay relatively high, or you will see time value decay eat away at the value of your long calls. Let me be clear: Continue reading Options Trading Explained-Writing Options

Hedging With Options


If you have been getting stock options explained to you via this stock options guide, it should be pretty clear by now there are many ways to use options that do not involve increased risk, that in fact serve to reduce overall risk in our portfolio. In a nutshell writing calls and puts usually gives us this ability. In the largest sense, writing options is about hedging, taking the safer side of a transaction in which the person on the other side of the trade is achieving leverage.

As leverage (such as one can achieve by buying calls and puts) is all about making huge gains on a usually smallish amount of money, hedging (e.g. with options) is about achieving rather small percentage gains on (usually) existing positions that are often quite large. If my aim is to explain stock options basics then I must cover both sides of options transactions- the buy (long) side and the sell (short) side.

Hedging can be a better strategy than simply holding a position and being fully exposed to a possible price downturn. Farmers use the commodity markets to ensure that they get a certain price for at least a portion of their crop, guarding against possible lower prices for a not-yet-harvested crop.

We can do this with stock options by selling someone a right to purchase something we own at a higher price, with the stipulation being that if the market never takes the price that high, by a certain date, that we keep the money that we got for selling that right in the first place.


With stock options you can create an income by selling calls with a strike price higher than the current price of the stock, against shares that are already in your portfolio. If you’re not ready to sell your stock in a given company at its current price, but would be happy to sell it at a higher level, simply write a call for each 100 shares of stock you own, with a strike price at which you would be satisfied to sell. In this way, if your shares continued to rise and the price is higher than the strike at expiration, your call will be exercised and you will deliver the shares at the strike price. If your shares are not priced above the strike price at expiration, the calls that you have written will expire worthless and you will simply keep the premium amount that you received for writing them (as well as your shares, of course). Many, many savvy investors with large portfolios make nice rates of return in this way, against stock that they are still bullish on, but could be persuaded to sell at higher levels. The downside of this strategy is that as you are obligated to sell at the strike price, assuming the call is in the money at expiration, you would miss out on any further rise in the price of the stock beyond the strike price.

The concept is exactly the same with puts incidentally, except reversed: for stock that you are short and still bearish on, but interested in hedging, you could write a put contract for every 100 shares that you are short and would like to include in the position, puts with a strike price at which you’d be satisfied in covering your short shares. If at expiration the stock is above the strike price the puts will expire worthless and you will keep the premium, and if this stock price is below the strike price, you’ll simply be forced to cover the applicable shares at the strike price.

Option Trading Strategies-Selling Options

The Easiest Money And The Dumbest Trade I Ever Made

Here at stock options explained we have covered options trading strategies such as simply buying stock options and also selling options, with the idea that stock options basics could best be conveyed from the standpoint of actual examples behind trading strategies, rather than simply limiting our discussion to theoretical ideas. At any rate, in this vein I thought it might be of interest and helpful to illustrate option trading strategies from a real-life example that’s of particular interest to me. I’ll show how selling options involves more than the risk of having your options exercised so that your stock is called away from you (if you’ve written calls) as it rises well beyond the strike price and you miss out on further gains beyond the strike price. There is an additional danger, one not related to opportunity cost.

In this type of trade, while you will receive some protection from selling options because of the reduced cost basis for your stock (as you receive a premium amount from the option buyer), this lower cost basis might be no match for the amount by which the underlying stock could fall. In other words, using this trading strategy one may sell covered calls against stock he owns and get to keep the premium if those calls expire worthless, but still take a much larger hit because of a drop in the stock price. You might think you’re buying some protection after a run-up, but the market might have much bigger plans!

I would like to illustrate selling options in this context not with call options, but with a trade involving put options. I had a front row seat on this particular trade, as it was I who was doing the trading! The mechanics with selling puts are the same as with selling calls, though your directional preference is reversed with puts. One can write covered, out of the money puts as a way to insure a short position, hoping that the worst that will happen is a drop below the strike price, below which he no longer benefits at expiry as he must cover his short position at the strike. If a trader employs fairly complex option trading strategies of this kind is also fully aware that the stock price could rise, which could easily outweigh that put premium amount that he receives for writing his covered puts. I said “he” but I might just as well have said “I”. Well, here we go.

Flash Crash!

If you were anywhere near planet Earth during the week ending May 7, 2010, you might remember how quickly the market dropped from above 1200 on the S&P 500 down to a low on the day of the “flash crash” (May 6) of 1056. The market bounced off the flash crash lows, closing the day out at 1128, but the next day, Friday, May 7 was also ugly, with the S&P 500 closing that day at 1110. The reason I remember the events so clearly is that I sold put options a few minutes before the close of trading on that Friday, a move that I have thought of ever since as both the easiest money and possibly the dumbest trade I ever made.

I’ll elaborate a little. For once in my life I had made a correct move and was short SPY from above 120. SPY is a heavily-traded ETF based on the S&P 500, and is a convenient proxy for the overall market. The VIX (a popular volatility indicator) was low and the markets, though they had been grinding higher for months, seemed to me to be ripe for a fall. I decided not to use options for leverage, so I could wait. Well, like everyone else I was stunned by the events of Thursday, May 6, when the Dow Jones Industrial Average fell almost 1000 points. I remember watching CNBC, which had a live feed from Athens, Greece, where there were real tensions over austerity measures imposed by the Greek government. As things appear to start to get out of control there on the streets of Athens, action in the markets worldwide seem to mirror the possibility of real calamity. Even though I was short, the speed of the events unfolding left me utterly flat-footed vis-à-vis my position, and while someone with a clearer head might have chosen to cover his short position when the market was down over 10% in just one day, I did not do so.

The next day I watched again as the bounce that the whole world seemed to be hoping for after the chaos of the “flash crash” did not occur. That Friday was nowhere near as ugly as the previous day but the market was again down nearly 4% intraday.

As the market neared the close on Friday I remember my thought process very clearly: while the market was clearly very oversold it seemed that the upward trend had broken so violently that we were headed dramatically downward again over the next few weeks. Still, with the volatility so high at that moment options premiums were extremely inflated, especially for put options. What this means is that if one were to write put options against an existing short position one would receive, relatively speaking, a very large premium amount simply for promising to buy back shares-or cover his short position-at lower levels, even much lower. One way to look at is is that you could be paid for profiting even further from your short position. Now, there are legitimate option trading strategies for every market situation, and at a time like this capturing volatility is often smart, because even if the market continues down at a slower rate (or stays even) one could see a reduction in the component of the premium that had been inflated due to the volatility (if we are talking out of the money options, that would be 100% of the premium, of course).

On this particular day I was able to sell five SPY May 100 puts against the 500 shares of SPY that I was short, for 1.05. SPY was just a hair over 110 when I wrote these puts, so that means that with only ten trading days left before expiration that SPY would have to go down a full ten points for them to be in the money. After that terrible week it seemed very unlikely that it could happen so quickly, but I told myself that if the overall market experienced another 10% decline during those two weeks I’d be happy to get 20 points on the SPY out of the trade that fast (I was already ten SPY points lower than my entry, remember). The approximately $500 I received from selling options to a trader or traders who were willing to bet $100 per contract that SPY would be over ten points lower in ten days (just to reach the strike price), seemed like the easiest money I’d ever made. Hopefully the puts would expire out of the money, worthless, I would keep the premium and then in the next several weeks I’d eventually see SPY below 100, maybe much lower, with me looking great on my still-intact short position.

Well of course anything might have happened, but what did happen was that the market bounced on the open Monday and into the earlier part of the week. When I covered my short position several points higher I got to keep almost all of the $500 I’d received in premium for selling the puts (yay!). However, my gains from my short position were a few thousand dollars less than what they might have been had I simply covered my short on the preceding Friday, rather than fixating on how likely it was that I’d keep most of the premium!

I don’t fault myself for not being clairvoyant, and I think that the only mistake I really made selling options here was overemphasizing the likelihood that I would keep most or all of the put premiums, relative to the possibility that a violent snapback could occur and quickly negate that $500 position. Still, both trades were profitable, and my actions were in line with the old adage “cut your losses and let your profits run”. Well, they also say that no one ever went broke taking a profit, and might have been was a large one! Maybe I have overemphasized how silly I feel not simply taking a huge, quick profit (heck, I’m sure I’ve made dumber trades) but in any case, for purposes of getting option trading strategies explained to readers of this site, I think this anecdote has value.

Why Options Selling Increases Safety


If you are a new investor looking to diversify your portfolio for the sake of safety, chances are you haven’t really taken a look at stock options for a couple of reasons. First, you might be a little intimidated by the complexity of options. Secondly, you probably associate options with a high level of risk, and this gives you little incentive to scale a learning curve as you’re interested in protecting your money in these uncertain times.

The thing is that buying stock options is only one option trading strategy you can use. Instead of buying an option, which is the right to purchase 100 shares of the stock at a given price point by a certain date in the future, you can take the other side of the trade and sell an option contract that covers shares that you already own. Options selling is usually overlooked by new investors, and this is a mistake.

Here’s what you need to know: options selling means is that the option buyer pays you a small amount of money-known as the premium-for the right to purchase your shares at a given ‘strike’ price, usually a higher price than where the stock is currently trading. If the stock reaches that price before the expiration date the option buyer has the right to purchase your shares at the agreed-to price. Now if the stock continues up beyond the strike price before expiration, you have still benefited by the move in the stock between where it was when you sold the option contract and the price at which the option buyer bought the right to purchase the shares from you. You also, as the option seller, get to keep the option premium that the buyer paid you.


This doesn’t sound very risky does it? The answer is that it is not risky. There are, however, two potential downsides to this scenario if you are selling options. One is that you do not participate in any upward move in the stock above the strike price, at which you sold the right to purchase your shares. For example if you sold the option buyer the right to buy your shares at $100 per share when the stock was trading at $90 per share, if the stock is trading at $120 per share by expiration you must sell your shares at $100 (but you have still profited from the move between $90 and $100).

The other potential downside for you as the seller of the option is that the stock price may fall. Between now and the expiration date the stock may very well be trading lower than where it was priced when you sold the option. But in this case you’re still better off than if you had simply held onto your shares rather than selling the option, as again, remember that with options selling you get to keep the premium amount that the buyer paid you, and you get to keep your shares as the right to buy them at the now far-off strike price is worthless. You have a paper loss on the shares that you own, but your cost basis for the shares is slightly lower due to the premium amount paid by the buyer, that you get to keep.

I hope I’ve shown that there is more to options trading than just taking a gamble. The fact is that many savvy investors use options selling to create an income from their existing portfolio by selling, aka writing options against shares that they already own. As you get stock options explained to you further be sure and paper trade them for a while before actually committing any real money. The options market moves very quickly and the relationship between option premium prices than that of the underlying stock is not always clear cut.