If your original financial plan calls for you to sell certain securities once they have achieved a particular target price, be sure youâ€™re actually capturing the value you had originally intended to acquire. If all, or a large portion, of a particular holding is going to be taxed as ordinary income rather than as a long-term capital gain, your milestone may simply have been reached too early to accomplish its job. Equally important is evaluating where both your own financial situation, and the markets, are likely to be closer to April 15. Especially if tax-day is relatively far in the future, what seems like a pleasant windfall in July, might end up feeling more like a hard slap in the face next spring (and whatâ€™s true for selling, is every bit as true for buying). In the end, all that matters is the cash that actually STAYS in your pocket.