When is an option a certain number of strikes in the money? e.g. “two strikes in”?
"I have traded options, but not professionally. I hadn't come across this terminology, but I expect it counts how far in-the-money, as an ordinal, an option is relative to the distinct strike prices offered for the option series — a series being the combination of underlying symbol, expiration date, and option type (call/put); e.g., all January 2015 XYZ calls, no matter the strike. For instance, if stock XYZ trades today at $11 and the available January 2015 XYZ calls have strike prices of $6, $8, $10, $12, $14, and $16, then I would expect the $10 call could be called one strike in the money, the $8 two strikes in the money, etc. Similarly, the $12 and $14 calls would be one and two strikes out of the money, respectively. However, if tomorrow XYZ moves to $13, then the $10 previously known as one strike in the money would now be two strikes in the money, and the $12 would be the new one strike in the money. Perhaps this terminology arose because many option strategies frequently involve using options that are at- or near-the-money, so the ""one strike in"" (or out) of the money contracts would tend to be those employed frequently? Perhaps it makes it easier for people to describe strategies in a more general sense, without citing specific examples. However, the software developer in me dislikes it, given that the measurement is relative to both the current underlying price (which changes quickly), and the strike prices available in the given option series. Hence, I wouldn't use this terminology myself and I suggest you eschew it, too, in favor of something concrete; e.g. specify your contract strikes in dollar terms — especially when it matters."
When your options vest, you will have the option to buy your company's stock at a particular price (the strike price). A big part of the value of the option is the difference between the price that your company's stock is trading at, and the strike price of the option. If the price of the company stock in the market is lower than the strike price of the option, they are almost worthless.  I say 'almost' because there is still the possibility that the stock price could go up before the options expire. If your company is big enough that their stock is not only listed on an exchange, but there is an active options market in your company's stock, you could get a feel for what they are worth by seeing what the market is willing to buy or sell similar exchange listed options. Once the options have vested, you now have the right to purchase your company's stock at the specified strike price until the options expire.  When you use that right, you are exercising the option.  You don't have to do that until you think it is worthwhile buying company stock at that price. If the company pays a dividend, it would probably be worth exercising the options sooner, (options don't receive a dividend).  Ultimately you are buying your company's stock (albeit at a discount).  You need to see if your company's stock is still a good investment. If you think your company has growth prospects, you might want to hold onto the stock.  If you think you'd be better off putting your money elsewhere in the market, sell the stock you acquired at a discount and use the money to invest in something else. If there are any additional benefits to holding on to the stock for a period of time (e.g. selling part to fit within your capital gain allowance for that year) you should factor that into your investment decision, but it shouldn't force you to invest in, or remain invested in something you would otherwise view as too risky to invest in. A reminder of that fact is that some employees of Enron invested their entire retirement plans into Enron stock, so when Enron went bankrupt, these employees not only lost their job but their savings for retirement as well... It definitely depends on your risk appetite as Joe Taxpayer pointed out in his answer. Covered calls are a good choice for someone who already own's the stock, because the premium collected reduces the cost basis for the position. The downside is that if the calls are exercised, there is a good chance that you are missing out on additional upside in the stock price (because the strike is obviously below the market value for the stocks).  Another good option trade is the spread option. This would allow you to capture the difference between the two strikes of the options in the spread. This is also one of the less risky choices because your initial cost an potential profit/loss are known in advance of entering the position. "When the buyout happens, the $30 strike is worth $10, as it's in the money, you get $10 ($1000 per contract). Yes, the $40 strike is pretty worthless, it actually dropped in value today. Some deals are worded as an offer or intention, so a new offer can come in. This appears to be a done deal. From Chapter 8 of CHARACTERISTICS AND RISKS OF STANDARDIZED OPTIONS - FEB 1994 with supplemental updates 1997 through 2012; ""In certain unusual circumstances, it might not be possible for uncovered call writers of physical delivery stock and stock index options to obtain the underlying equity securities in order to meet their settlement obligations following exercise. This could happen, for example, in the event of a successful tender offer for all or substantially all of the outstanding shares of an underlying security or if trading in an underlying security were enjoined or suspended. In situations of that type, OCC may impose special exercise settlement procedures. These special procedures, applicable only to calls and only when an assigned writer is unable to obtain the underlying security, may involve the suspension of the settlement obligations of the holder and writer and/or the fixing of cash settlement prices in lieu of delivery of the underlying security. In such circumstances, OCC might also prohibit the exercise of puts by holders who would be unable to deliver the underlying security on the exercise settlement date. When special exercise settlement procedures are imposed, OCC will announce to its Clearing Members how settlements are to be handled. Investors may obtain that information from their brokerage firms."" I believe this confirms my observation. Happy to discuss if a reader feels otherwise." "Simple answer: Breakeven is when the security being traded reaches a price equal to the cost of the option plus the option's strike price, assuming you choose to exercise it. So for example, if you paid $1.00 for,say, a call option with a strike price of $19.00, breakeven would be when the security itself reaches $20.00.  That being said, I can't imagine why you'd ""close out a position"" at the breakeven point.  You wouldn't make or lose money doing that, so it wouldn't be rational. Now, as the option approaches expiration, you may make adjustments to the position to reflect shifts in momentum of the stock.  So, if it looks as though the stock may not reach the option strike price, you could close out the position and take your lumps.  But if the stock has momentum that will carry it past the strike price by expiration, you may choose to augment your position with additional contracts, although this would obviously mean the new contracts would be priced higher, which raises your dollar cost basis, and this may not make much sense. Another option in this scenario is that if the stock is going to surpass strike price, it might be a good opportunity to buy additional calls with either later expiration dates or with higher strike prices, depending on how much higher you speculate the stock will climb.  I've managed to make some money doing this, buying options with strike prices just a dollar or two higher (or lower when playing puts), because the premiums were (in my opinion) underpriced to the potential peak of the stock by the expiration date.  Sometimes the new options were actually slightly cheaper than my original positions, so my dollar cost basis overall dropped somewhat, improving my profit percentages." "That's the way the markets work in THEORY. In actual fact, markets are subject to ""real world"" pressures. That is, there are so many things going on in the market that the end of the ""Lined In"" lock up is just one of many. To produce the result you describe, traders would have to hold cash in reserve for this so-called ""contingency"" to buy at the end of the lock-up. In most cases, they wouldn't want to because of everything else that is going on.  To use a real world analogy, would you want to wait until the last possible moment before going to the bathroom? Or would you go now while you had the chance? That's what the decision about ""holding cash in reserve for a contingency"" is like." Someone entering a casino with $15 could employ a very simple strategy and have a better-than-90% chance of walking out with $16.  Unfortunately, the person would have a non-trivial chance (about one in 14) of walking out with $0. If after losing $15 the person withdrew $240 from the bank and tried to win $16, the person would have a better-than-90% chance of succeeding and ending up ahead (holding the original $15, plus the additional $240, plus $1) but would have at that point about a one in 14 chance from that point of losing the $240 along with the original $15.  Measured from the starting point, you'd have about a 199 out of 200 chance of gaining $1, and a one out of 200 chance of losing $240. Market-timing bets are like that.  You can arrange things so you have a significant chance of making a small profit, but at the risk of a large downside.  If you haven't firmly decided exactly how much downside you are willing to accept, it's very easy to simultaneously believe you don't have much money at risk, but that you'll be able to win back anything you lose.  The only way you can hope to win back anything you lose is by bringing a lot more money to the table, which will of course greatly increase your downside risk. The probability of making money for the person willing to accept $15 of downside risk to earn $1 is about 93%.  The probability of making money for the person willing to accept $255 worth of risk is about 99.5%.  It's easy to see that there are ways of playing which have a 99.5% chance of winning, and that there are ways of playing that only have a 15:1 downside risk.  Unfortunately, the ways of playing that have the smaller risk don't have anything near a 99.9% chance of winning, and those that have a better chance of winning have a much larger downside risk. If you sold bought a call option then as you stated sold it to someone else what you are doing is selling the call you bought. That leaves you with no position.  This is the case if you are talking about the same strike, same expiration. I have an example of a trade I made some time ago.  By entering the position as a covered call, I was out of pocket $5.10, and if the stock traded flat, i.e. closed at the same $7.10 16 months hence, I was up 39% or nearly 30%/yr. As compared to the stock holder, if the stock fell 28%, I'd still break even, vs his loss of 28%. Last, if the stock shot up, I'd get 7.50/5.10 or a 47% return, vs the shareholder who would need a price of $10.44 to reflect that return. Of course, a huge jump in the shares, say to $15, would benefit the option buyer, and I would have left money on the table. But this didn't happen. The stock was at $8 at expiration, and I got my 47% return. The option buyer got 50 cents for his $2 bet.  Note, the $2 option price reflected a very high implied volatility.