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Exercising stock options capital gains tax

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exercising stock options capital gains tax

Tax planning and compliance for investors Free Newsletter. Should you exercise a nonqualified stock option before you're ready to sell the stock? What's the best time to exercise a nonqualified stock option? Should you wait until you're ready to sell the stock? Or should you exercise earlier and hold the stock for at least a year stock a day, so that part options your gain is taxed as long-term capital gain? The answer to this question may be surprising. Let's consider three different guys: Able, Baker and Charlie. Able's strategy was to hold onto the option until he was ready to cash out. Baker's strategy was to hold the option for a while but then exercise and hold the stock tax it went up some more. Charlie didn't want to report any compensation income. Charlie came out the best in terms of dollars in his pocket, but actually used a very foolish strategy. If he did this, he would have taken exactly the same risk, and had exactly the same result, with one difference: Charlie's strategy produced what looks like a good result, but in reality he simply threw away the value of his option for no reason. Baker didn't make this mistake. But Baker had to come up with some money at the time he exercised the option: These comments apply to situations where the option holder has freedom of choice that isn't always available. In other situations the strategies of Baker and Charlie may turn out exercising make good sense. The thing that is most surprising, though, is that in the situation where the option holder has complete freedom of choice, the strategy that works best is generally the one that results in paying the most tax! That doesn't seem possible, but the logic is inescapable. A publication of Fairmark Tax Inc. Thomas - WordPress Entries RSS and Comments RSS. Home Our Books News Tax Help Message Board About Contact. Gains Forum Reference Room Our books Free Newsletter RSS feed. About our website About our author Contact us Privacy. Compensation in Stock and Options. Related Consider Your Options book for gains who receive stock options Equity Compensation Strategies book for professional advisors Options Minimum Tax free online guide AMT gains Equity Compensation forum for questions and comments on this topic Special Taxes capital access to forms for AMT or AMT credit. Our books That Thing Rich People Do Capital fastest, easiest way to learn the principles of investing. Our complete guide to Roth IRAs and Roth accounts in k and similar plans: Consider Your Options A plain-language guide for people who receive stock options or other forms of equity compensation. Equity Compensation Options A text for financial advisors and other professionals tax offer advice on how to handle equity compensation including stock options. Capital Gains, Minimal Taxes Tax rules and strategies for people who buy, own and sell stocks, mutual funds and stock options. That Thing Rich Exercising Do. Stock plain-language guide stock people who receive stock options or exercising forms of equity compensation. A text for financial advisors and other professionals who offer advice on how to handle equity compensation including stock options. Capital Gains, Minimal Taxes. Tax rules and strategies for people who buy, own and sell stocks, mutual funds and stock options. exercising stock options capital gains tax

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