Is there a simple strategy of selling stock over a period of time?
"The best strategy for RSU's, specifically, is to sell them as they vest. Usually, vesting is not all in one day, but rather spread over a period of time, which assures that you won't sell in one extremely unfortunate day when the stock dipped. For regular investments, there are two strategies I personally would follow: Sell when you need. If you need to cash out - cash out. Rebalance - if you need to rebalance your portfolio (i.e.: not cash out, but reallocate investments or move investment from one company to another) - do it periodically on schedule. For example, every 13 months (in the US, where the long term cap. gains tax rates kick in after 1 year of holding) - rebalance. You wouldn't care about specific price drops on that day, because they also affect the new investments. Speculative strategies trying to ""sell high buy low"" usually bring to the opposite results: you end up selling low and buying high. But if you want to try and do that - you'll have to get way more technical than just ""dollar cost averaging"" or similar strategies. Most people don't have neither time nor the knowledge for that, and even those who do rarely can beat the market (and never can, in the long run)." Yes, there is an analogous strategy for selling: it's to sell a fixed number of shares per period of time.
If so, are there ways to reduce the amount of taxes owed? Given that it's currently December, I suppose I could sell half of what I want now, and the other half in January and it would split the tax burden over 2 years instead, but beyond that, are there any strategies for tax reduction in this scenario? One possibility is to also sell stocks that have gone down since you bought them.  Of course, you would only do this if you have changed your mind about the stock's prospects since you bought it -- that is, it has gone down and you no longer think it will go up enough to be worth holding it.  When you sell stocks, any losses you take can offset any gains, so if you sell one stock for a gain of $10,000 and another for a loss of $5,000, you will only be taxed on your net gain of $5,000. Even if you think your down stock could go back up, you could sell it to realize the loss, and then buy it back later at the lower price (as long as you're not worried it will go up in the meantime).  However, you need to wait at least 30 days before rebuying the stock to avoid wash sale rules.  This practice is known as tax loss harvesting. Some financial planners would not advise one way or the other on a specific stock without knowing your investment strategy... if you didn't have one, their goal would be to help you develop one and introduce you to a portfolio management framework like Asset Allocation. Is a two of clubs a good card?  Well, that all depends on what is in your hand (diversification) and what game you are playing(investing strategy). One possibility to reduce your basis over time if you would like to hold the stock is to sell calls against it, known as a 'covered-call'.  It can be an intermediate-term (30-60+ months depending on option pricing) trading strategy that may require you to upgrade your brokerage account to allow option trades.  Personally I like this strategy because it makes me feel proactive about my portfolio rather than sitting on the side lines and watching stocks move. "Remind yourself that markets recover, usually within a few years. If you believe this and can remind yourself of this, you will be able to see the down cycles of the market as an opportunity to buy stock ""on sale"". No one knows the future, so many people have found investing on a regular schedule to be helpful. By putting in the same amount of money each period, you will end up buying fewer shares when the market is up, and more when it is down. As long as your time horizon is appropriate, you should be able to wait out the ups and downs. Stocks are volatile by their very nature, so if you find that you are very concerned by this, you might want to consider whether you should adjust the amount of risk in your investments, since over time, most people lose money by trying to ""time"" the market. However, if your investment goals and requirements haven't changed, there likely isn't any need to change the types of assets you are investing in, as what you are choosing to invest in should depend on your personal situation. Edit: I am assuming you want to be a long-term investor and owner, making money by owning a portion of companies' profits, and not by trading stocks and/or speculation." A specific strategy to make money on a potentially moderately decreasing stock price on a dividend paying stock is to write covered calls.  There is a category on Money.SE about covered call writing, but in summary, a covered call is a contract to sell the shares at a set price within a defined time range; you gain a premium (called the time value) which, when I've done it, can be up to an additional 1%-3% return on the position.  With this strategy you're collecting dividends and come out with the best return if the stock price stays in the middle: if the price does not shoot up high enough that your option is called, you still own the stock and made extra return; if the price drops moderately, you may still be positive. "You don't seem to be a big fan of trading as you may think it may be too risky or too time consuming being in front of your computer all day long. You also don't seem to be a fan of buy and hold as you don't know what your investments will be worth when you need the funds. How about a combination of the two, sometimes called trend trading or active investing. With this type of trading/investing you may hold a stock from a couple of months to many years. Once you buy a stock that is up-trending or starting to up-trend you hold onto it until it stops up-trending. You can use a combination of fundamental analysis (to find out what to buy) and technical analysis (to tell you when to buy and when to sell). So these are some topics you can start reading up on. Using a technique like this will enable you to invest in healthy stocks when they are moving up in price and get out of them when they start moving down in price. There are many techniques you can use to get out of a stock, but the simplest has to be using stop losses. And once you learn and set up your system it should not take up much of your time when you actually do start trading/investing - 2 to 3 hours per week, and you can set yourself up that you analyse the market after the close and place any order so they get executed the next trading day without you being in front or the screen all day. Other areas you might want to read and learn about are writing up a Trading Plan, using Position Sizing and Money Management so you don't overtrade in any one single trade, and Risk Management. A good book I quite liked is ""Trade Your Way to Financial Freedom"" by Van Tharp. Good luck." "You should establish a strategy -- eg a specific mix of investments/funds which has the long-term tradeofv of risk, returns, and diversification you want -- and stick to that strategy, rebalancing periodically to maintain your strategic ratios betwedn those investments.  Yes, that means you will somettimes sell things that have been doing well and buy others that have been doing less well -- but that's to be expected; it's exactly what happens when you ""buy low, sell high""." What you are suggesting would be the correct strategy, if you knew exactly when the market was going to go back up. This is called market timing.  Since it has been shown that no one can do this consistently, the best strategy is to just keep your money where it is.  The market tends to make large jumps, especially lately.  Missing just a few of these in a year can greatly impact your returns.  It doesn't really matter what the market does while you hold investments.  The important part is how much you bought for and how much you sold for.  This assumes that the reasons that you selected those particular investments are still valid.  If this is not the case, by all means sell them and pick something that does meet your needs. "By definition, there are no guaranteed profits. There are sometimes arbitrage opportunities, which are more accessible to some investors than others. In this case, I'm not referring to HFT as that is covered elsewhere on this site already.  At certain times, in certain equity markets, candlestick charts were used for profitable trading, though more for trades set up for weeks or months, not day trading. I am referring specifically to Nikkei 225 equities, in the 1980's and 1990's. I don't know why it was effective, and it hasn't worked for me since then. I recommend reading and heeding this answer. Some people DO use technical analysis (see ""TA is not..."" section) as a primary trading strategy, but they are not going to divulge their methods, not here nor anywhere else." Why wouldn't you expect a long-term profit?  Say you buy 100 shares of company X, selling for$1/share today.  You hold it for 20 years, after which it's worth $10/share (in inflation-adjusted dollars).  So you've made a profit, only making two trades (buy & sell).  What the algorithmic traders have done with short-term trades during those 20 years is irrelevant to you. Now expand the idea.  You want some diversification, so instead of one stock, you buy a bit of all the stocks on whatever index interests you, and you just hold them for the same 20 years.  How has what the short-term traders done in the intervening time affected you? High frequency trades are intra day. The would buy a stock for 100 and sell for 100.10 multiple times. So If you start with 100 in your broker account, you buy something [it takes 2-3 days to settle], you sell for 100.10 [it takes 2-3 days to settle]. You again buy something for 100. It is the net value of both buys and sells that you need to look at. Trading on Margin Accounts. Most brokers offer Margin Accounts. The exact leverage ratios varies. What this means is that if you start with 10 [or 15 or 25] in your broker you can buy stock of 100. Of course legally you wont own the stock unless you pay the broker balance, etc. "It's impossibly difficult to time the market. Generally speaking, you should buy low and sell high. Picking 25% as an arbitrary ceiling on your gains seems incorrect to me because sometimes you'll want to hold a stock for longer or sell it sooner, and those decisions should be based on your research (or if you need the money), not an arbitrary number. To answer your questions: If the reasons you still bought a stock in the first place are still valid, then you should hold and/or buy more. If something has changed and you can't find a reason to buy more, then consider selling. Keep in mind you'll pay capital gains taxes on anything you sell that is not in a tax-deferred (e.g. retirement) account. No, it does not make sense to do a wash sale where you sell and buy the same stock. Capital gains taxes are one reason. I'm not sure why you would ever want to do this -- what reasons were you considering? You can always sell just some of the shares. See above (and link) regarding wash sales. Buying more of a stock you already own is called ""dollar cost averaging"". It's an effective method when the reasons are right. DCA minimizes variance due to buying or selling a large amount of shares at an arbitrary single-day price and instead spreads the cost or sale basis out over time. All that said, there's nothing wrong with locking in a gain by selling all or some shares of a winner. Buy low, sell high!" "Edited: Pub 550 says 30 days before or after so the example is ok - but still a gain by average share basis.  On sale your basis is likely defaulted to ""average price"" (in the example 9.67 so there was a gain selling at 10), but can be named shares at your election to your brokerage,  and supported by record keeping. A Pub 550 wash might be buy 2000 @ 10 with basis 20000, sell 1000 @9 (nominally a loss of 1000 for now and remaining basis 10000), buy 1000 @ 8 within 30 days.   Because of the wash sale rule the basis is 10000+8000 paid + 1000 disallowed loss from wash sale with a final position of 2000 shares at 19000 basis.  I think I have the link at the example:  http://www.irs.gov/publications/p550/ch04.html#en_US_2014_publink100010601" You can execute block trades on the options market and get exercised for shares to create a very large position in Energy Transfer Partners LP without moving the stock market. You can then place limit sell orders, after selling directly into the market and keep an overhang of low priced shares (the technical analysis traders won't know what you specifically are doing, and will call this 'resistance'). If you hit nice even numbers (multiples of 5, multiples of 10) with your sell orders, you can exacerbate selling as many market participants will have their own stop loss orders at those numbers, causing other people to sell at lower and lower prices automatically, and simultaneously keep your massive ask in effect. If your position is bigger than the demand then you can keep a stock lower. The secondary market doesn't inherently affect a company in any way. But many companies have borrowed against the price of their shares, and if you get the share price low enough they can get suddenly margin called and be unable to service their existing debt. You will also lose a lot of money doing this, so you can also buy puts along the way or attempt to execute a collar to lower your own losses. The collar strategy is nice because it is unlikely that other traders and analysts will notice what you are doing, since there are calls, puts and share orders involved in creating it. One person may notice the block trade for the calls initially, but nobody will notice it is part of a larger strategy with multiple legs. With the share position, you may also be able to vote on some things, but that solely depends on the conditions of the shares. "I've traded covered calls now and then. This is a recent trade. Bought 1000 shares of RSH (Radio Shack) and sold 10 calls. So, I own the stock at a cost of $6.05, but have to let it go for $7.50. There's a 50c dividend in November, so the call buyer will call it away even if the stock trades below the strike. So, I'm expecting this is a 10 month trade for a 24% return.  This is one strategy where options clearly take down the risk (of course, I did not say 'remove', just lessens). The stock can be 10% lower a year out, and I'm still ahead by 8% plus the dividend if it's not canceled.  Note - it's a rare case for a one year trade to return 20% or more at a flat stock price. More common is 10-12%.  (I hope this example is acceptable as an example of this type of trade. If not, I can edit to ""XYZ corp"" to remove the stock name. (So if anyone comments, please do not repeat name in case I need to remove)" I don't believe in letting the tax tail wag the investing dog. You have a stock you no longer wish to hold for whatever reason? Sell it. But to sell a loser, hoping it doesn't rise by the time you wish to re-buy it in 30 days is folly.  This effort may gain you $50 if done right. No, it's not worth it either way.