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Most listings report days to expiration on a calendar basis. A one-week expiration is expressed as 7 days, even though only 5 trading days remain. The defense of using calendar days is because time decay continues to occur even on days when markets are closed. For example, between the Friday prior to expiration (with 7 days remaining) and Monday (one session later but 3 calendar days later), about one-third of remaining time value typically disappears. For those writing short-term short positions, this is a significant fact. By selling a position on Friday and opening to close on Monday or Tuesday, a profitable result is more likely than not. This assumes no significant movement in the underlying. Although the opportunity is a great one, so is the risk. With three days transpiring between Friday and Monday, many changes are possible. The evolution of option pricing is not dependent solely on time decay. Volatility is also a factor. However, volatility is not as severe a risk factor on weekends as many traders believe. It is true that changes can occur, and that a logical position could end up losing due to unexpected changes, often for reasons not fully understood. The “weekend effect” occurs due to lack of market activity. With markets closed, when large volume of selling takes place on Friday, lower implied volatility follows on Saturday and Sunday. The danger in this is relying on the weekend effect, because on Monday, volatility will be likely to return to normal. This could create a sort of “catching up” effect between the two trading days. Three factors should be kept in mind when going short on Friday before expiration: timing of opening the short position on Friday, moneyness of the option, and liquidity of a position. Timing: If the underlying is relatively dormant, as you would expect on the weekend, a short position will become profitable due to losing one-third of its remaining time value. However, this all depends on when positions are opened on Friday. Selling late in the day is not desirable, because by then most short traders have already opened short positions. Selling late may create an immediate gain but selling earlier in the session places the short trader at an advantage. This explains why it occurs that selling near Friday’s close results in little or no change by Monday’s open. The best outcome is more likely by selling to open early on Friday and buying to close late on Monday. In effect, this sets up close to two trading days over a four-day span. Moneyness: Another consideration is moneyness of the option. A short-term short position at the money is likely to gain the most, compared to other strikes. The ultra-conservative idea of selling OTM options the week before expiration is based on the rationale that time value declines but gaining intrinsic value is also difficult. However, the decline in time value is the core issue in selecting the moneyness of the option. Liquidity: Finally, when bid and ask are exceptionally wide apart, the option is illiquid. Even the reported levels of bid and ask do not always exist in the market and are not possible to get in a trade. Most traders have experienced the frustration of delayed or unexecuted trades due to this problem. It typically happens for deep ITM options, later-expiring positions, and options on much smaller than average stocks. The “zone” for trading should be limited to those on underlying issues with healthy option activity and open interest, to maximize how expiration and time decay work out. The observation of how the weekend effect is expected to work may be distorted by the decision to count or not count weekends in longer-term volatility analysis. For example, the CBOE’s VIX is calculated using 365 days, but most options analysts prefer limiting their studies to the 252 trading days in a year. This is a difference of about 30% in terms of the number of days used to study volatility (and time decay). The result is that the VIX tends to exaggerate market volatility because it counts weekends when volatility levels are lower than on weekdays. The difference between calendar days and market days should not be ignored because the assumed outcomes under each method can be vastly different. Markets are typically open for 6 ½ hours each trading day but closed for 17 ½ hours. Over the weekend, the hours closed add up to 65 ½ hours. This difference in time – 17 ½ versus 65 ½ -- may explain why weekend time decay should never be overlooked as a timing factor for short trading close to expiration. The use of weekends as part of time decay analysis is also distorted by the different timing between last trading day (Friday) and expiration day (Saturday). Should expiration Saturday be included in thew analysis, considering that trading ends the day before? Because of the difference in just which days are counted is substantial, volatility analysis and expected time decay are distorted. Short positions might not perform as expected by traders trying to take advantage of the weekend effect. There are many reasons for the disappointment, mostly related to timing of entry and exit, moneyness, and liquidity, A simplified assumption might be that “all options lose one-third of their value between Friday and Monday before expiration,” but this is not true. Toi truly benefit from this fact of time decay selection is the key. The option should be opened and closed at maximum timing (early Friday and late Monday); it should be as close as possible to the money; and it should be a liquid position, meaning the spread between bid and ask should be as narrow as possible. Michael C. Thomsett is a widely published author with over 80 business and investing books, including the best-selling Getting Started in Options, coming out in its 10th edition later this year. He also wrote the recently released The Mathematics of Options. Thomsett is a frequent speaker at trade shows and blogs on his website at Thomsett Publishing as well as on Seeking Alpha, LinkedIn, Twitter and Facebook. Related articles Options Expiration: 6 Things To Know Expiration Surprises To Avoid Assignment And Exercise: The Mental Block Should You Close Short Options On Expiration Friday? Day Before Expiration Trading

In cases when earnings and dividends are timed for this day, a range of separate risks and opportunities must be considered. The uncertainty of earnings surprises on expiration Thursday will be especially impactful. For example, Amazon (AMZN) has not announced its next earnings announcement date but is likely to be February 4, 2021. This company’s earnings have been notorious for earnings surprises. How will a post-close announcement on February 4 affect overnight option pricing for options with the last trading day of February 5? A true speculator will relish the opportunity to enter a position during trading hours on February 4. The potential gains will be substantial if any surprises appear that evenings, but the potential losses will be equally large if price moves in a direction opposite the one desired. A solution many traders have attempted is to enter one form or another of spread. A vertical spread with Friday expiration will be expensive, not only because Amazon trades (currently) near $3,200 per share, but also because of the potential for large earnings surprises. The last 4 quarters reveal how much surprise is possible: Sep 2020 + 64.25% Jun 2020 +543.08% Mar 2020 - 19.83% Dec 2019 + 62.82% These recent historical earnings surprises demonstrate the difficulty of selecting spreads likely to overcome many surprises in earnings. The more than 500% in June is the exception, but most other quarters present situations difficult to exploit, given the richness of short-term options for Amazon. For example, as of Wednesday, December 2, the options expiring December 4 (2 days away) could be used to set up vertical spreads, but at great expense. With only a 5-point spread in either direction, the ask on call at 3225 is 35.25, and on put at 3215 is 36.45, for a total premium of 71.70. That is a wide margin to overcome. Moving to a 50-point spread in either direction, the 3270 call reported ask of 19.35 and the 3170 put at 18.70, for a total cost of 38.05. Using these levels of premium as examples, long or short positions with only 2 days remaining are expensive, and the required point move may be insurmountable as well. For short spreads, the collateral requirement is substantial as well. For most traders, speculating on short-term price movement due to earnings surprises is a high-risk strategy. The alternative to the spread is to gamble on the direction of surprise, and with a comp any like Amazon, the temptation is to assume a positive surprise; but that can be dangerous as well. Without earnings in play on expiration Thursday, traders must consider the degree of price movement overnight, even without outside influences. When implied volatility is low, large time decay remains possible, and this should not be overlooked as a possibility. Expiration week trading on Thursday is perhaps the most uncertain of times for both long and short positions. It could make sense to select options the following week if preferring short positions, because time decay between Friday and Monday average a reduction of about 32%. Thursday is the best day to enter this position for ATM or slightly OTM positions, because of the large losses expected overnight, as well as further decay over the weekend. Historically, short trades entered on Thursday before expiration Friday will become profitable. If the underlying stock changes substantially, the analysis will be distorted due to movement in intrinsic value, but most traders recognize that although this is a risk, it is limited in terms of time, with only one day to Friday and four days to Monday. Based on knowledge about time decay and pricing behavior, it makes more sense to trade on Thursday for expiration 8 days ahead, rather than for 1 day ahead. The risk tolerance for one-day trades in options must be high, because even with superior analytics in hand, short-term underlying price movement can never be known. It is invariably erratic and, in that chaotic moment, both opportunity and risk are at their highest. It comes down to understanding the difference between calculated risk and speculative risk. In calculated risk, the prevailing knowledge about time decay between Thursday and Monday for options expiring the following Friday presents greater opportunity. In speculative risk, deciding to trade options expiring the next day is affected by unknown, outside forces, not to mention levels of implied volatility, selection of strikes and moneyness, underlying historical volatility, and premium of the option. Timing based on very short-term expiration is complex and, compared to other strategic timing of trades, the most interesting. Further complicating the decision is selection of long or short, or of single trades versus combinations. These may include ratios, synthetics, spreads, or straddles. When selecting both trade structure and time, recurring errors are based in most cases not only on wrong guesses about price movement and behavior, but also on a lack of consideration for the full range of possible influences. The understanding if risk and opportunity is never a simple matter, but even for the most experienced traders, it is often the case that the full range of risks is overlooked or discounted. This means it is not just a matter of risks traders understand that determines trade outcomes, but equally a matter of which elements are ignored or even unknown. One danger in being an experienced trader is in developing poor habits. These include focus on overly narrow analytics (such as pricing models, the Greeks, or implied volatility as points of decision), or selecting strategies base don past success even when those experiences do not reveal how future pricing will behave. This reality – the uncertainty of options trading – is the most important and defining feature of all trading decisions, especially when timed based on immediately expiration dates. Michael C. Thomsett is a widely published author with over 80 business and investing books, including the best-selling Getting Started in Options, coming out in its 10th edition later this year. He also wrote the recently released The Mathematics of Options. Thomsett is a frequent speaker at trade shows and blogs on his website at Thomsett Publishing as well as on Seeking Alpha, LinkedIn, Twitter and Facebook.

It is more profitable to sell extremely short-term contracts, whose time decay will be rapid and immediate. Another benefit of the short-term strategy is that it reduces exposure time from many months, down to only a few days. An example: Caterpillar (CAT) closed on October 16 at $168.75 per share. A trader looking for a short call yielding maximum value may consider the contracts of June 18, 2021, which expire in 244 days. The 170 call reported a closing bid of 16.15. Yield was: 16.15 ÷ 168.75 = 9.6% The annualized return is calculated by adjusting the yield to reflect its equivalent for one full year: 9.6% ÷ 244 * 365 = 14.4% This is a decent return without any doubt. However, this short position requires leaving the position open for longer than 8 months. It could be closed earlier, of course, and the true market risk depends on several factors. Is the call covered or naked? If covered, is the trader willing to give up 100 shares at the strike of 170? If naked, how is the outcome affected by tying up capital for collateral requirement? An alternative offering more profit is to sell the shortest possible contract. Time decay will be rapid and immediate, and annualized profits will be substantially higher as well. Returning to the example of Caterpillar, the 6-day contract is far more attractive. The 170 call closed with a bid of 1.81, and a yield of: 1.81 ÷ 168.75 = 1.1% This is not as impressive before it is itemized. However, itemizing reveals the true comparative yield for this short-term call: 1.16% ÷ 6 * 365 = 66.9% This return as far more attractive than the longer-term call. Selling for 6 days and repeating it over and over, will end up with a greater yield. Based on the first example of 244 days, it would be possible to sell as many as 40 calls, one each week in the same time period. If the 6-day premium remained the same week after week, the weekly 1.81 would grow to: 1.81 * 40 = $72.40 Compared to the 244-day premium of 16.15, the repetitive weekly strategy is over four times more profitable. The maximum benefit from this strategy is gained by opening the trade on the Friday one week prior to expiration. When this occurs, the time decay between Friday and Monday absorbs three days (because time decay occurs even on days when the market is closed). However, only one trading day has passed. According to author and options expert Jeff Augen, [Augen, Jeff (2009). Trading Options at Expiration. Upper Saddle River NJ: FT Press, p. 41], one third of time value is lost in the final week, most of it between Friday and Monday. This means the strategy could involve a sell to open on Friday and a buy to close on Monday, week after week, with a high likelihood of profits most of the time. (In cases where the option value does not decline, a loss may be accepted, the trader can wait to see what happens next, or it can be rolled forward). Another key date in this final week occurs on expiration Thursday, the day immediately before last trading day. Between Thursday and expiration Friday, another 31% of remaining time value disappears (and the rest will be gone the next day). These two days (Friday one week prior, and Thursday one day prior) are the keys to profitability is the short-term strategy. The other is to recognize the massive difference between short-term profitability and long-term profitability. Looking only at the dollar value of premium is misleading. With annualization, traders can realize the true potential yield and a preference for repetitive short-term trades, over single longer-term trades. This comparison is complicated by the existence of LEAPS contracts, which may last as long as 30 months. Strategies based on LEAPS trading are popular among some traders, but the high time value is not always advantageous, even for short positions. Traders have no doubt observed that longer-term contracts are less responsive to underlying price movement, than shorter-term contracts. The time element adds greater risk to a position than the analysis of moneyness. For example, an ATM contract with little remaining time is likely to see premium movement close to point-for-point changes in the underlying. The contract with the same strike expiring many months in the future will tend to have much less response. Changes in intrinsic value often are offset by adjustments in implied volatility, even for ITM contracts. This occurs because the longer time involved adds uncertainty about the future and where the moneyness will end up moving as expiration draws closer. Some traders have viewed LEAPS straddles or spreads as offering great potential for dollar value, even when yields are lower than those for short-term contracts. For example, a straddle expiring in 8 months will yield an attractive dollar value. However, annualization proves that the same comparison as that for single calls or puts is dismal compared to short-term combinations. The same rules apply when looking beyond the dollar amount and analyzing annualized yield. In the example of Caterpillar calls, the longer-term dollar value was $16.15, versus shorter-term $1.81. A preliminary analysis seems to indicate that longer-term contracts are better, just based on the dollar amount. The same trader may reject a return of less than $2 per contract due to this analysis. But in fact, this indicates that the trader’s experience does not extend to the more accurate comparison in which annualized yield (which makes the two truly comparative) is more accurate and revealing. For some traders, selling a long-term contract in a single trade is preferable, because going through the same process every week is a lot of work. However, the far better yield more than justifies what really is a matter of a few minutes each week, all to accomplish a much higher annualized yield from the short trade. And market risks are lower as well. Michael C. Thomsett is a widely published author with over 80 business and investing books, including the best-selling Getting Started in Options, coming out in its 10th edition later this year. He also wrote the recently released The Mathematics of Options. Thomsett is a frequent speaker at trade shows and blogs on his website at Thomsett Publishing as well as on Seeking Alpha, LinkedIn, Twitter and Facebook. Related articles Options Trading Greeks: Theta For Time Decay Why You Should Not Ignore Negative Gamma Options Expiration: 6 Things To Know Should You Close Short Options On Expiration Friday? Fear Of Options Assignment Are Covered Calls a ‘Sure Thing?’

What is the Truth? Is it true? Do 80% of all options REALLY expire worthless? Are 80% of all options buyers automatically losers which makes 80% of all options writers automatically winners in the options market without any risk? According to The Chicago Board Options Exchange (CBOE) here are the facts: Approximately 10% of options are exercised (The trader takes advantage of their right to buy or sell the stock). Around 55%-60% of option positions are closed prior to expiration. Approximately 30%-35% of options expire worthless. The CBOE goes on to point out that having an option expire worthless says nothing about the profitability of the strategy that it may have been part of: Multi-legged strategies can often require that one leg or more expire worthless although the strategy as a whole is profitable. Option positions closed prior to expiration may be profitable or unprofitable. Options that expire worthless may not be unprofitable if they were part of a strategy that involved other securities such as covered call writing. Only About 30% of Options Expire Worthless? What does it mean? ABSOLUTELY NOTHING! It doesn't mean that when you buy options, you automatically have 70% chance of winning, it also doesn't mean that if you write options, you only have 30% chance of winning. Here are some of the arguments used by different options gurus in order to separate you from your hard earned money: BE THE HOUSE – Not the Gambler! Be the insurance company and win 90% of the time! Get stable and consistent monthly income! Get 90% winning ratio with our strategy! Those arguments have no basis in reality. Insurance companies can lose significant amounts of money during periods of national disasters. Monthly income can become monthly loss during periods of high volatility. And so on.. If you are not a member yet, you can join our forum discussions for answers to all your options questions. Advantages of Options Selling Opportunity for monthly cash flow with high annualized returns. Opportunity to buy stocks at lower prices via naked puts strategy. Over the long term, Implied Volatility tends to be higher than Historical Volatility. Downside protection for put sellers or covered calls sellers. Options sellers tend to have a higher win rate (but a lower rate of return). Covered call writers may also capture dividends. Opportunities to trade in self-directed IRA accounts, especially covered call writing. Disadvantages of Options Selling Money can be lost is stock price dips below the breakeven. Profit potential is limited by the strike price. Assignment risk (may have to buy or sell shares). There is a learning curve and time commitment. In many cases, risk/reward is not favorable (you risk much more than you can gain). When using strategies like Iron Condors, one bad month can wipe out months of good gains. Why it doesn't matter Those who suggest that 80% of options expire worthless assume that if an option expires in the money, it automatically means a win for options buyers, which isn't true. If you buy a deep in the money option and the underlying stock moves against you, your options would still end up losing money even if it is still in the money by expiration! Ultimately, it is the direction of the underlying stock that determines if you end up profitable. How about hedging? If you bought options as part of overall portfolio using strategy like Protective Put, and your options expired worthless, is it necessarily a bad thing? Not if you stock doubled in value while you held those protective puts. And one final example: consider a strangle seller who sells options (both puts and calls) on high volatility stocks before earnings. He can gain $100 four times in a raw when the stock doesn't move in the money, but lose $1,000 during a cycle when the stock moved big time and one of the options became deep in the money. In this case, 9 out of 10 of the options expired worthless, but he still lost money. Even if the "80% expire worthless" myth was true, it doesn't matter - if you gain little when options expire worthless but lose big when they go in the money, your bottom line is still negative. But the most important thing is that most options are not held till expiration. Conclusion Percentage of options expiring worthless is completely useless to options traders. This is NOT what should impact your decision to become an options buyer or options seller. The only way to determine which options strategy suits you is by really learning about them, their reward risk ratios, practicing them and understanding which approach best conforms to your investment objectives, trading style and risk appetite. Options is risky no matter if you are an options buyer or seller, don't let anyone tell you otherwise. There is no such thing as becoming "banker" in the options market. Understand the risks of options trading and you will be profitable. Related Articles: Are Debit Spreads Better Than Credit Spreads? Selling Naked Put Options What Is The Best Options Strategy? The Road Not Taken Are You Ready For The Learning Curve? Can you double your account every six months? If you are ready to start your journey AND make a long term commitment to be a student of the markets: Start Your Free Trial

Here are six situations that should be of special concern when expiration day draws nigh. 1) Position Size When trading options, the most effective method for controlling risk is paying attention to position size (number of options or spreads bought/sold). Smaller size translates into less profit and less reward. However, successful traders understand: minimizing losses is the key to success. When options expiration approaches, an option's value can change dramatically. The effect of time is far less on longer-term options. Gamma measures the rate at which an option's delta changes. When gamma is high – and it increases as expiration approaches – delta can move from near zero (OTM option) to almost 100 (ITM option) quickly. Option owners can earn a bunch of money in a hurry, and option shorts can get hammered. However, those short-lived options often become worthless. These are the conflicting dreams of option sellers and buyers. The point is that having a position in ATM (or not far OTM) options is treacherous, and reducing the size of your position is a healthy and simple method for reducing risk. Consider reducing position size when playing the higher risk/higher reward game of trading options near expiration. 2) Margin Calls Receiving an unexpected margin call is one of those unpleasant experiences that traders must avoid. At best, margin calls are inconvenient. Most margin calls result in a monetary loss, even if it's only from extra commissions. Think of it as punishment for not being prepared When you hold any ITM short option position, there is the possibility of being assigned (and converting an option position to stock) an exercise notice. Early exercise is unlikely unless the option is deep ITM. However, you already know that any option that finishes ITM is subject to automatic exercise. Exiting the trade prior to expiration makes it likely (there is still the chance of being assigned before you exit) that you can avoid the margin call. Most put sellers (conservatively) sell puts only when cash secured. That means: cash to buy shares is already in the account. When cash is available, there is no margin call. Those who write call options are subject to the same assignment risk. If the trader is covered, there is no problem. Upon assignment, the shares already owned are sold to honor the option seller's obligations. When you receive a margin call, many brokers (no warning) sell enough securities (to generate cash) to meet that call. Other brokers automatically repurchase your short options (with no advance warning) before expiration arrives. Bottom line: When you cannot meet the margin requirement, do not hold a position that is subject to early exercise. And never hold that position through expiration (when assignment is guaranteed). Find a way to exit the trade to avoid possible margin calls. For clarity: If margin is not a problem, none of this applies to you. 3) Increased Volatility Pay attention to volatility – both volatility of the underlying stock or index as well as the implied volatility of the options themselves. For option owners volatility is your friend. The fact that stocks are more volatile is enough to raise implied volatility, and that in turn increases the value of your options – sometimes by more than its daily time decay. If you get lucky twice, and the volatile market moves your way, the option's price may increase many-fold. That's nirvana for option owners. However, if you are looking at increased market volatility from the perspective of an option seller, volatility translates into fear. Whether a trader has naked short options (essentially unlimited risk) or short spreads (limited loss potential), he/she must recognize that the market (the underlying asset) can undergo a large, rapid price change. Options that seemed safely out of the money and a 'sure thing' to expire worthless are suddenly in the money and trading at hundreds (or thousands) of dollars apiece. When an index moves 5% in one day (as it did frequently during late 2008), SPX options that were 40 points OTM in the morning were 10 points ITM by day's end. When that happens with an increase in implied volatility, losses (and gains) can be staggering. There is good reason for the shorts to be afraid. One good risk management technique is to buy back those shorts – whenever you get a chance to do so at a low price. Remaining short, with the hope of collecting every last penny of premium, is a high risk game. 4) Reward vs. Risk Expiration plays come with higher risk and higher reward. That's the nature of the game. In return for paying a relatively low price for an option, buyers have but a short time for the market to do its magic. Otherwise the option disappears into oblivion. Most new traders believe they are locked into the trade once it has been made. Not true. You should consider selling those options any time that you no longer believe they can make money. Don't sell them for a tiny premium, such as $0.05. For that price, take your chances. But when real cash is at stake, perhaps when the option is priced near $1, then it's a difficult choice: hold vs. sell. Make a reasoned decision. Although it seems to be an obvious warning, when buying options near expiration day, please be aware of what must occur to earn a profit. Then consider the likelihood of that happening. The same warning applies to option sellers. Time may be short, but when the unlikely occurs, the loss can wipe out years of profits. When there's just too little premium, cover the short position and leave the last bit of cash on the table. 5) Option Greeks – Delta and Gamma The Options Greeks are used to measure risk. Once measured, it is up to the trader to decide whether risk is acceptable or must be reduced. It's important to understand the greeks of your position and how they change when the underlying moves. It's not necessary to spend hours studying the data. Use the greeks to get a look at the big picture and decide whether your position is ok as is, should be adjusted, or closed. As has already been mentioned, delta and gamma change more rapidly near expiration (if the option is anywhere near the money). Stay alert to these changes. 6) News Events When news is released, the underlying stock often undergoes a substantial change in price. If you have a position, or are considering opening a new position, be certain that you know whether news is pending. Such news is most often a quarterly earnings report. If you are a risk avoider, don't hold short options with negative gamma in the face of earnings releases. Summary Expiration is an exciting time for traders who are either long or short options. If you want to play in that arena, understand what you are doing. If you are a more conservative trader, it's easy to exit all trades before options expiration draws too near. Related articles: How Index Options Settlement Works Can Options Assignment Cause Margin Call? Options Expiration: Six Things To Know The Right To Exercise An Option? Early Exercise: Call Options Want to learn more? Start Your Free Trial