How can I find ISIN numbers for stock options?
"Because an equity option can be constructed at essentially any price by two willing counterparties on an exchange, there are not enough ISINs to represent the entire (i.e. infinite) option chain for even a single stock on a single expiration date.  As a result, ISINs are not generated for each individual possible options contract.  Instead the ISIN is used only to refer to the ""underlying"" symbol, and a separate formula is used to refer to the specific option contract for that symbol: So that code you pasted is not an ISIN but rather the standard US equity option naming scheme that you need to provide in addition to the ISIN when talking to your broker. Note that ISINs and formulas for referring to option contracts in other countries can behave quite differently.  Also, there are many countries and markets that don't need ISINs because the products in question only exist on a single exchange.  In those cases the exchange is pretty much free to make up whatever ID scheme it wants. P.S. Now I'm curious how option chains are identified for strike prices above $99,999.  I looked up the only stock I can think of that trades above that price (BRK.A), but it doesn't seem to have an option chain (or at least Google doesn't show it) ..." Go to http://www.isincodes.net/, and enter your data. For example entering Alphabet gives you the ISIN US02079K1079 (for standard US shares). If you want to understand the number format (and build them yourself), check wikipedia: https://en.wikipedia.org/wiki/International_Securities_Identification_Number
I can understand your fears, and there is nothing wrong with taking action to protect yourself from them. How much income do you need in retirement?  For arguments sake, lets say you need to pull 36K per year from your 401K or 3K per month.  Lets also assume that you current contribute (with any match) 1,000 per month.  Please adjust to your actual numbers accordingly. One option would be to pull out 48K right now and put it in a money market.  With your contributions, I would then put half into the money market and half into more aggressive investments.  In 10 years, you would have about 110K in your money market account.  You could live off of that for three years.  If the market does crash, this should give you plenty of time to recover. Taking this option opens you to another risk, which is being beat up by inflation or lack of growth on a nice pile of cash.  My time frame is not that different then yours (I am about 12 years away), but am still all in stocks.  Having 48K and more with not opportunity for growth frightens me more than any temporary stock market crash. Having said that I think it would be a horrible mistake to get completely out of stocks.  Many of those destroyed in 2008 also missed 2012 through 2014 which were awesome years.  So do some.  Set aside a year or three of income in something nice and safe.  Maybe one year of income in money market, one in bonds and preferred stocks, and one in blue chips. "It includes whatever you want to do with your investment.  At least initially, it's not so much a matter of calculating numbers as of introspective soul-searching.  Identifying your investment objectives means asking yourself, ""Why do I want to invest?""  Then you gradually ask yourself more and more specific questions to narrow down your goals.  (For instance, if your answer is something very general like ""To make money"", then you may start to ask yourself, ""How much money do I want?"", ""What will I want to use that money for?"", ""When will I want to use that money?"", etc.)  Of course, not all objectives are realistic, so identifying objectives can also involve whittling down plans that are too grandiose. One thing that can be helpful is to first identify your financial objectives: that is, money you want to be able to have, and things you want to do with that money.  Investment (in the sense of purchasing investment vehicles likes stocks or bonds) is only one way of achieving financial goals; other ways include working for a paycheck, starting your own business, etc.  Once you identify your financial goals, you have a number of options for how to get that money, and you should consider how well suited each strategy is for each goal. For instance, for a financial goal like paying relatively small short-term expenses (e.g., your electric bill), investing would probably not be the first choice for how to do that, because: a) there may be easier ways to achieve that goal (e.g., ask for a raise, eat out less); and b) the kinds of investment that could achieve that goal may not be the best use of your money (e.g., because they have lower returns)." You also need to remember that stock options usually become valueless if not exercised while an employee of the company.  So if there is any chance that you will leave the company before an IPO, the effective value of the stock options is zero.  That is the safest and least risky valuation of the stock options.   With a Google or Facebook, stock options can be exercised and immediately sold, as they are publicly traded.  In fact, they may give stock grants where you sell part of the grant to pay tax withholding.  You can then sell the remainder of the grant for money at any time, even after you leave the company.  You only need the option/grant to vest to take advantage of it.  Valuing these at face value (current stock price) makes sense.  That's at least a reasonable guess of future value.   If you are absolutely sure that you will stay with the company until the IPO, then valuing the stock based on earnings can make sense.  A ten million dollar profit can justify a hundred million dollar IPO market capitalization easily.  Divide that by the number of shares outstanding and multiply by how many you get.  If anything, that gives you a conservative estimate.   I would still favor the big company offers though.  As I said, they are immediately tradeable while this offer is effectively contingent on the IPO.  If you leave before then, you get nothing.  If they delay the IPO, you're stuck.  You can't leave the company until then without sacrificing that portion of your compensation.  That seems a big commitment to make. "This answer is somewhat incomplete as I don't have definitive conclusions about some parts of your question.  Your question includes some very specific subquestions that may best be answered by contacting the investment companies you're considering. I don't see any explicit statement of fees for TIAA-CREF either.  I suggest you contact them and ask. There is mention on the site of no-transaction-fee funds (NTF), but I wasn't able to find a list of such funds.  Again, you might have to ask. Vanguard also offers some non-Vanguard funds without transaction fees.  If you go the Vanguard page on other mutual funds you can use the dropdown on the right to select other fund companies.  Those with ""NTF"" by the name have no transaction fees. Scottrade also offers NTF funds.  You can use their screener and select ""no load"" and ""no transaction fee"" as some of your filters. You are correct that you want to choose an option that will offer a good lineup of funds that you can buy without transaction fees.  However, as the links above show, Vanguard and TIAA-CREF are not the only such options.  My impression is that almost any firm that has their own funds will sell them (or at least some of them) to you without a transaction fee.  Also, as shown above, many places will sell you other companies' funds for free too.  You have plenty of options as far as free trades, so it really depends on what funds you like. If you google for IRA providers you will find more than you can shake a stick at.  If you're interested in low-cost index funds, Vanguard is pretty clearly the leader in that area as their entire business is built around that concept.  TIAA-CREF is another option, as is Fideltiy (which you didn't mention), and innumerable others.  Realistically, though, you probably don't need a gigantic lineup of funds.  If you're juggling money between more than a handful of funds, your investment scheme is probably needlessly complex.  The standard advice is to decide on a broad allocation of money into different asset classes (e.g., US stocks, US bonds, international stocks, international bonds), find a place that offers funds in those areas with low fees and forget about all the other funds." Today SPY (The S&P ETF) trades at $128. The option to buy at $140 (this is a Jan '13 call) trades for $5.  I buy the call, for $500 as they trade in 100 lots.  The S&P skyrockets to 1500 and SPY to $150. The call trades for $11, as it still has a month or two before expiring, so I sell it, and get $1100. The S&P rose 17%, but I doubled my money. If it 'only' rose 9%, to less than $140, I'd lose my investment. No, I don't need to buy the SPY I can sell the call any time before expiration. In fact, most options are not exercised, they are sold between purchase and expiration date. Thanks for your reply. I’m not familiar with the term “Held-For-Trading Security”. My securities are generally held as collateral against my shorts. To clarify, I am just trying to track the “money in” and “money out” entries in my account for the shorts I write. The transaction is relatively straight forward, except there is a ton of information attached! In simple terms, for the ticker CSR and short contract CSRUQ8, the relevant entries look something like this: There are no entries for expiries. I need to ensure that funds are available for future margin calls and assignments. The sale side using covered calls is as involved. "if you buy back the now ITM calls, then you will have a short term loss. That pair of transactions is independent, from a tax perspective, of your long position (which was being used as ""collateral"" in the very case that occurred). I can see your tax situation and can see the logic of taking a short term loss to balance a short term gain.  Referring to D Stanley's answer, #2 and #3 are not the same because you are paying intrinsic value in the options and the skew in #2, whereas #3 has no intrinsic value. Of course, because you can't know the future, the stock price could move higher or lower between #2 and #3. #1 presumes the stock continues to climb." I'll just copypasta out of the book for the sake of clarity:   * If you think about it, you see that the only brokers who touch the switch for light bulb number 64 are those whose numbers are divisors of 64. That is, light bulb 64 has its state changed by brokers whose numbers are factors of 64. This means brokers 1, 2, 4, 8, 16, 32, 64. Because light bulb 64 is originally off, it must be after this odd number of switches that it is on.   * You want to be short a put if you expect a price rise. In this case, you expect to keep the option premium when the option expires worthless.   There are a few pages worth of questions for the options, so the explanation for the IBM one is somewhat limited.