When (if) I should consider cashing in (selling) shares to realize capital gains?
"The only general rule is ""If you would buy the stock at its current price, hold and possibly buy. If you wouldn't, sell and buy something you believe in more strongly."" Note that this rule applies no matter what the stock is doing. And that it leaves out the hard work of evaluating the stock and making those decisions. If you don't know how to do that evaluation to your own satisfaction, you probably shouldn't be buying individual stocks. Which is why I stick with index funds." You should know when to sell your shares before you buy them. This is most easily done by placing a stop loss conditional order at the same time you place your buy order. There are many ways to determine at what level to place your stop losses at. The easiest is to place a trailing stop loss at a percentage below the highest close price, so as the price reaches new highs the trailing stop will rise. If looking for short to medium term gains you might place your trailing stop at 10% below the highest close, whilst if you were looking for more longer term gains you should probably place a 20% trailing stop. Another way to place your stops for short to medium term gains is to keep moving your trailing stop up to just below the last trough in an existing uptrend. "In a perfect world of random stock returns (with a drift) there is no reason to ""take profit"" by exiting a position because there is no reason to think price appreciation will be followed by decline.   In our imperfect world, there are many rules of thumb that occasionally work but if any one of them works consistently over a long period of time, everyone starts to practice that rule and then it stops working.  Therefore, there are no such rules of thumb that work reliably and consistently over long periods of time and are expected to continue doing so.  Finding such a rule is and always has been a moving target. The rational, consistently sensible reasons to sell a stock are: These rules are very different from my interpretation of the ""walk with your chips"" behavior mentioned in your question." How about this rule? Sell 10% of your shares every time they double in price.  (of course, only buy stocks that repeatedly double in price)
"A mutual fund could make two different kinds of distributions to you: Capital gains: When the fund liquidates positions that it holds, it may realize a gain if it sells the assets for a greater price than the fund purchased them for. As an example, for an index fund, assets may get liquidated if the underlying index changes in composition, thus requiring the manager to sell some stocks and purchase others. Mutual funds are required to distribute most of their income that they generate in this way back to its shareholders; many often do this near the end of the calendar year.  When you receive the distribution, the gains will be categorized as either short-term (the asset was held for less than one year) or long-term (vice versa). Based upon the holding period, the gain is taxed differently. Currently in the United States, long-term capital gains are only taxed at 15%, regardless of your income tax bracket (you only pay the capital gains tax, not the income tax). Short-term capital gains are treated as ordinary income, so you will pay your (probably higher) tax rate on any cash that you are given by your mutual fund. You may also be subject to capital gains taxes when you decide to sell your holdings in the fund. Any profit that you made based on the difference between your purchase and sale price is treated as a capital gain. Based upon the period of time that you held the mutual fund shares, it is categorized as a short- or long-term gain and is taxed accordingly in the tax year that you sell the shares. Dividends: Many companies pay dividends to their stockholders as a way of returning a portion of their profits to their collective owners. When you invest in a mutual fund that owns dividend-paying stocks, the fund is the ""owner"" that receives the dividend payments. As with capital gains, mutual funds will redistribute these dividends to you periodically, often quarterly or annually. The main difference with dividends is that they are always taxed as ordinary income, no matter how long you (or the fund) have held the asset. I'm not aware of Texas state tax laws, so I can't comment on your other question." &gt; You also have to think about tax on dividends from these stock options, which is only 15%, which is paltry to regular incometax rate that the rich pay on their salaries  dividends is just cash being removed from companies and being paid out directly to the stockholder  if dividends get taxed at a higher rate, every company would just use that same cash to buy back shares since that would be more tax efficient - the stockholder would receive compensation in higher stock prices which they could then sell instead of receiving a dividend. Thus, they would pay capital gains rate instead of your new dividend rate.  The dividend rate must be the same as capital gains rate for this reason. They are not free money since the stock price gets decreased when a dividend is paid out - the company gets poorer when they pay out the dividend. Don't let tax considerations be the main driver. That's generally a bad idea. You should keep tax in mind when making the decision, but don't let it be the main reason for an action. selling the higher priced shares (possibly at a loss even) - I think   it's ok to do that, and it doesn't necessarily have to be FIFO? It is OK to do that, but consider also the term. Long term gain has much lower taxes than short term gain, and short term loss will be offsetting long term gain - means you can lose some of the potential tax benefit. any potential writeoffs related to buying a home that can offset capital gains? No, and anyway if you're buying a personal residence (a home for yourself) - there's nothing to write off (except for the mortgage interest and property taxes of course). selling other investments for a capital loss to offset this sale? Again - why sell at a loss? anything related to retirement accounts? e.g. I think I recall being able to take a loan from your retirement account in order to buy a home You can take a loan, and you can also withdraw up to 10K without a penalty (if conditions are met). Bottom line - be prepared to pay the tax on the gains, and check how much it is going to be roughly. You can apply previous year refund to the next year to mitigate the shock, you can put some money aside, and you can raise your salary withholding to make sure you're not hit with a high bill and penalties next April after you do that. As long as you keep in mind the tax bill and put aside an amount to pay it - you'll be fine. I see no reason to sell at loss or pay extra interest to someone just to reduce the nominal amount of the tax. If you're selling at loss - you're losing money. If you're selling at gain and paying tax - you're earning money, even if the earnings are reduced by the tax. Stock awards by employers are treated and taxed as salary. I.e.: you pay ordinary rate income tax, FICA taxes, State taxes etc. The fact that you got your salary in shares and not cash is irrelevant for tax purposes. Once you got the shares and paid your taxes on them, the treatment is the same as if you got the salary and immediately bought the shares. Holding period for capital gains tax purposes starts at the time you paid your taxes on the award, which is the time at which you get full ownership (i.e.: vesting time, for the restricted stocks). When you sell these stocks - you treat the sale as any other stock sale: you check the holding period for capital gains tax rates, and you do not pay (or get refund) any FICA taxes on the sales transaction. So bottom line: You got $10K salary and you bought $10K worth of company stock, and you sold it at $8K half a year later. You have $10K wages income and $2K short term capital loss. In the real world, there are only two times you'll see that 5% become worth anything - ie, something you can exchange for cash - 1) if another company buys them; (2) if they go public. If neither of these things happen, you cannot do anything with the stock or stock options that you own. Ask yourself a better question: Under my current investment criteria would I buy the stock at this price? If the answer to that question is yes you need to work out at what price you would now sell out of the position. Think of these as totally separate decisions from your original decisions to buy and at what price to sell. If you would buy the stock now if you didn't already hold a position then you should keep that position as if you had sold out at the price that you had originally seen as your take profit level and bought a new position at the current price without incurring the costs. If you would not buy now by those criteria then you should sell out as planned. This is essentially netting off two investing decisions. Something to think about is that the world has changed and if you knew what you know now then you would probably have set your price limit higher. To be disciplined as an investor also means reviewing current positions frequently and without any sympathy for past decisions. "The process of borrowing shares and selling them is called shorting a stock, or ""going short.""  When you use money to buy shares, it is called ""going long."" In general, your strategy of going long and short in the same stock in the same amounts does not gain you anything.  Let's look at your two scenarios to see why. When you start, LOOT is trading at $20 per share.  You purchased 100 shares for $2000, and you borrowed and sold 100 shares for $2000.  You are both long and short in the stock for $2000.  At this point, you have invested $2000, and you got your $2000 back from the short proceeds.  You own and owe 100 shares. Under scenario A, the price goes up to $30 per share.  Your long shares have gone up in value by $1000.  However, you have lost $1000 on your short shares.  Your short is called, and you return your 100 shares, and have to pay interest.  Under this scenario, after it is all done, you have lost whatever the interest charges are. Under scenario B, the prices goes down to $10 per share.  Your long shares have lost $1000 in value.  However, your short has gained $1000 in value, because you can buy the 100 shares for only $1000 and return them, and you are left with the $1000 out of the $2000 you got when you first sold the shorted shares.  However, because your long shares have lost $1000, you still haven't gained anything.  Here again, you have lost whatever the interest charges are. As explained in the Traders Exclusive article that @RonJohn posted in the comments, there are investors that go long and short on the same stock at the same time.  However, this might be done if the investor believes that the stock will go down in a short-term time frame, but up in the long-term time frame.  The investor might buy and hold for the long term, but go short for a brief time while holding the long position. However, that is not what you are suggesting.  Your proposal makes no prediction on what the stock might do in different periods of time.  You are only attempting to hedge your bets.  And it doesn't work.  A long position and a short position are opposites to each other, and no matter which way the stock moves, you'll lose the same amount with one position that you have gained in the other position.  And you'll be out the interest charges from the borrowed shares every time. With your comment, you have stated that your scenario is that you believe that the stock will go up long term, but you also believe that the stock is at a short-term peak and will drop in the near future.  This, however, doesn't really change things much.  Let's look again at your possible scenarios. You believe that the stock is a long-term buy, but for some reason you are guessing that the stock will drop in the short-term.  Under scenario A, you were incorrect about your short-term guess.  And, although you might have been correct about the long-term prospects, you have missed this gain.  You are out the interest charges, and if you still think the stock is headed up over the long term, you'll need to buy back in at a higher price. Under scenario B, it turns out that you were correct about the short-term drop.  You pocket some cash, but there is no guarantee that the stock will rise anytime soon.  Your investment has lost value, and the gain that you made with your short is still tied up in stocks that are currently down. Your strategy does prevent the possibility of the unlimited loss inherent in the short.  However, it also prevents the possibility of the unlimited gain inherent in the long position.    And this is a shame, since you fundamentally believe that the stock is undervalued and is headed up.  You are sabotaging your long-term gains for a chance at a small short-term gain." This depends on the particular index, of course. Capital gains taxes occur when stock is sold (for a profit). This occurs less frequently in an index fund: Where an active manager frequently buys and sells stocks (after all, he wants to be active :-) ), the index fund only sells stocks when the particular stock leaves the index. For an index such as the S&P 500 this does not happen that often.  The more specific the criteria of the index fund, the more often the selling of stock and thus the need to pay capital gains taxes occurs.