Taxes, Puts and the Wash Rule
"There are different schools of thought. You can ask the IRS - and it would not surprise me if you got different answers on different phone calls. One interpretation is that a put is not ""substantially identical"" to the disposed stock, therefore no wash is triggered by that sale. However if that put is exercised, then you automatically purchase the security, and that is identical. As to whether the IRS (or your brokerage firm) recognizes the identical security when it falls out of an option, I can't say; but technically they could enforce it because the rule is based on 30 days and a ""substantially identical"" stock or security. In this interpretation (your investor) would probably at least want to stay out of the money in choosing a strike price, to avoid exercise; however, options are normally either held or sold, rather than be exercised, until at or very close to the expiration date (because time value is left on the table otherwise). So the key driver in this interpretation would be expiration date, which should be at least 31 days out from the stock sale; and it would be prudent to sell an out of the money put as well, in order to avoid the wash sale trigger. However there is also a more unfavorable opinion - see fairmark.com/capgain/wash/wsoption.htm where they hold that a ""deep in the money"" option is an immediate trigger (regardless of exercise). This article is sage, in that they say that the Treasury (IRS) may interpret an option transaction as a wash if it's ballpark to being exercisable. And, if the IRS throws paper, it always beats each of paper, rock and scissors :( A Schwab article (""A Primer on Wash Sales"") says, if the CUSIPs match, bang, wash. This is the one that they may interpret unfavorably on in any case, supporting Schwab's ""play it safe"" position: ""3. Acquire a contract or option to buy substantially identical stock or securities..."" . This certainly nails buying a call. As to selling a put, well, it is at least conceivable that an IRS official would call that a contract to buy! SO it's simply not a slam dunk; there are varying opinions that you might describe as ranging from ""hell no"" to ""only if blatant."" If you can get an ""official"" predetermination, or you like to go aggressive in your tax strategy, there's that; they may act adversely, so Caveat Taxfiler!"
You need to report the income from any work as income, regardless of if you invest it, spend it, or put it in your mattress (ignoring tax advantaged accounts like 401ks).  You then also need to report any realized gains or losses from non-tax advantaged accounts, as well as any dividends received.  Gains and losses are realized when you actually sell, and is the difference between the price you bought for, and the price you sold for.  Gains are taxed at the capital gains rate, either short-term or long-term depending on how long you owned the stock.   The tax system is complex, and these are just the general rules.  There are lots of complications and special situations, some things are different depending on how much you make, etc.  The IRS has all of the forms and rules online.  You might also consider having a professional do you taxes the first time, just to ensure that they are done correctly.  You can then use that as an example in future years. "This is the best tl;dr I could make, [original](http://www.dailymail.co.uk/news/article-4742712/Why-chickens-washed-chlorine.html) reduced by 93%. (I'm a bot) ***** &gt; There is no legal requirement to wash US chickens in chlorine or other disinfectants, but 97 per cent of its birds are cleaned in this way after slaughter.  &gt; Jim Sumner, president of the US Poultry &amp; Egg Export Council, said US chickens are treated humanely and are only washed with chlorine to make them &amp;#039;extra safe&amp;#039; for consumers because it guards against food poisoning bugs.  &gt; Supporters of chlorine-washed chicken point out both the US and European food safety authorities have declared the chemicals used to wash chickens in the States do not pose any risk to human health.   ***** [**Extended Summary**](http://np.reddit.com/r/autotldr/comments/6qi0kj/too_fat_to_stand_and_their_flesh_rots_while/) | [FAQ](http://np.reddit.com/r/autotldr/comments/31b9fm/faq_autotldr_bot/ ""Version 1.65, ~179191 tl;drs so far."") | [Feedback](http://np.reddit.com/message/compose?to=%23autotldr ""PM's and comments are monitored, constructive feedback is welcome."") | *Top* *keywords*: **chicken**^#1 **farm**^#2 **poultry**^#3 **birds**^#4 **food**^#5" In my opinion it depends on the type of product. I would get a warranty for a washing machine or tumble dryer or other product with lots of moving parts that is liable to break down. I also take into account my luck, the one washing machine I didn't get covered broke down 2 weeks outside the normal warranty period... I would not get a warranty for a consumer electronics product like a TV, PC, or iPod because they devalue so quickly. As a rule of thumb, if the model you buy today is going to be on sale for the next few years for around the same price and has moving parts, it is worth considering a warranty. If it will be worth a small percentage of its value because newer faster shinier models come along to replace it don't bother. I would also not get the warranty from the shop I bought the product from. You can get warranties for consumer products from specialist third parties that will allow you to cover multiple products for a discount. These work out a lot cheaper than the one the shop will give you. For example in the UK, DomGen will cover 3 appliances for £14.99/month and 6 for £20.99/month In a comment on this answer you asked  It's not clear to me why the ability to defer the gains would matter (since you never materially benefit until you actually sell) but the estate step up in basis is a great point! Could you describe a hypothetical exploitive scenario (utilizing a wash sale) in a little more detail?  This sounds like you still have the same question as originally, so I'll take a stab at answering with an example.   I sell some security for a $10,000 profit.  I then sell another security at a $10,000 loss and immediately rebuy.  So pay no taxes (without the rule).  Assuming a 15% rate, that's $1500 in savings which I realize immediately.  Next year, I sell that same security for a $20,000 profit over the $10,000 loss basis (so a $10,000 profit over my original purchase).  I sell and buy another security to pay no taxes.  In fact, I pay no taxes like this for fifty years as I live off my investments (and a pension or social security that uses up my tax deductions).  Then I die.  All my securities step up in basis to their current market value.  So I completely evade taxes on $500,000 in profits.  That's $75,000 in tax savings to make my heirs richer.  And they're already getting at least $500,000 worth of securities.   Especially consider the case where I sell a privately held security to a private buyer who then sells me back the same shares at the same price.   Don't think that $10,000 is enough?  Remember that you also get the original value.  But this also scales.  It could be $100,000 in gains as well, for $750,000 in tax savings over the fifty years.  That's at least $5 million of securities.   The effective result of this would be to make a 0% tax on capital gains for many rich people.   Worse, a poorer person can't do the same thing.  You need to have many investments to take advantage of this.  If a relatively poor person with two $500 investments tried this, that person would lose all the benefit in trading fees.  And of course such a person would run out of investments quickly.   Really poor people have $0 in investments, so this is totally impractical. A Section 1256 contract is any: Non-equity options include debt options, commodity futures options, currency options, and broad-based stock index options. A broad-based stock index is based upon the value of a group of diversified stocks or securities (such as the Standard and Poor's 500 index). 60% of the capital gain or loss from Section 1256 Contracts is deemed to be long-term capital gain or loss and 40% is deemed to be short-term capital gain or loss. What this means is a more favorable tax treatment of 60% of your gains. http://www.tradelogsoftware.com/tax-topics/futures/ It's a really wierd rule (arbitraty 60% designation, so broad, etc), but section 1256 contracts get preferential tax treatment and that's what Buffett's talking about. "The question you are asking concerns the exercise of a short option position.  The other replies do not appear to address this situation. Suppose that Apple is trading at $96 and you sell a put option with a strike price of $95 for some future delivery date - say August 2016.  The option contract is for 100 shares and you sell the contract for a premium of $3.20. When you sell the option your account will be credited with the premium and debited with the broker commission.  The premium you receive will be $320 = 100 x $3.20.  The commission you pay will depend on you broker. Now suppose that the price of Apple drops to $90 and your option is exercised, either on expiry or prior to expiry.  Then you would be obliged to take delivery of 100 Apple shares at the contracted option strike price of $95 costing you $9,500 plus broker commission.  If you immediately sell the Apple shares you have purchased under your contract obligations, then assuming you sell the shares at the current market price of $90 you would realise a loss of $500 ( = 100x($95-$90) )plus commission.  Since you received a premium of $320 when you sold the put option, your net loss would be $500-$320 = $180 plus any commissions paid to your broker. Now let's look at the case of selling a call option.  Again assume that the price of Apple is $96 and you sell a call option for 100 shares with a strike price of $97 for a premium of $3.60.  The premium you receive would be $360 = 100 x $3.60.  You would also be debited for commission by your broker. Now suppose that the price of Apple shares rises to $101 and your option is exercised.  Then you would be obliged to deliver 100 Apple shares to the party exercising the option at the contracted strike price of $97.  If you did not own the shares to effect delivery, then you would need to purchase those shares in the market at the current market price of $101, and then sell them to the party exercising the option at the strike price of $97.  This would realise an immediate loss of $400 = 100 x ($101-$97) plus any  commission payable.  If you did own the shares, then you would simply deliver them and possibly pay some commission or a delivery fee to your broker.  Since you received $360 when you sold the option, your net loss would be $40 = $400-$360 plus any commission and fees payable to the broker. It is important to understand that in addition to these accounting items, short option positions carry with them a ""margin"" requirement.  You will need to maintain a margin deposit to show ""good faith"" so long as the short option position is open.  If the option you have sold moves against you, then you will be called upon to put up extra margin to cover any potential losses." So I don't have any problems with your analysis or the comments associated with it. I just wanted to mention that no one is talking about taxes. Your answer....Figure out new portfolio breakdown and sell to 1.) Get money I need and 2.) re-balance the portfolio to my new target allocations is completely correct.  (Unimpeachable in my opinion.) However, when you calculate what you need to sell to meet your current cash needs make sure to include in that analysis money to pay taxes on anything you sell for a gain, or keep some invested to account for the tax money you would save by selling things for a loss.  The actual mechanics of calculating what these amounts are are fairly involved but not difficult to understand. (IE every situation is different.) Best of luck to you, and I hope your cashflow gets back up to its previous level soon. Your question is missing too much to be answered directly. Instead - here are some points to consider. Short term gains taxed at your marginal rates, whereas long term gains have preferable capital gains rates (up to 20% tax rate, instead of your marginal rate). So if you're selling at gain, you might want to consider to sell FIFO and pay lower capital gains tax rate instead of the short term marginal rate. If you're selling at loss and have other short term gains, you would probably be better selling LIFO, so that the loss could offset other short term gains that you might have.  If you're selling at loss and don't have short term gains to offset, you can still offset your long term gains with short term losses, but the tax benefit will be lower. In this case - FIFO might be a better choice again. If you're selling at loss, beware of the wash sale rules, as you might not be able to deduct the loss if you buy/sell within too short a window.