I have a significant amount of my portfolio tied up in my company's stock. The opportunity to take some profits (~200% gain from my options) presented itself last month and I passed to wait out the capital gains period which would have taken around 6 more months. The money wasn't desperately needed, but I've been tucking it away in a nest egg for my own startup one day.<p>Long story short, tech recently got hammered and even with the bounce back I lost far more than I would have saved in a preferential tax rate. Normally I'm pretty objective about my stocks and will take profits without being greedy. In hindsight, I think I didn't make the "a dollar saved is a dollar made" connection: not making the right play simply because of taxes is still a form of greed. Are there any good rules of thumb for incorporating tax scenarios into your trades?