<prompt> Human: Hi PF, looking for some sage advice here, on a great problem to have situation.At my previous job, I earned a large amount of stock and have foolishlyfortunately held it over the last few years as its grown rapidly in value. Its at past the point where I should diversify. So... what should I be considering while I set about doing this?For context, Im married with joint household income of 200Kyear. We own two homes, one paid for free and clear worth 800K, one were making payments on worth 450K, 250K left on a 30-year, fixed mortgage 4.037;. No other debt of note. I have another 600K that my financial planner manages, with some modest capital losses there that could be harvested, but not enough to significantly offset the 1.1M cap gains on this stock Im looking at.My current naive? idea is to just sell shares monthly over then next 3 tax years such that the harvested cap gains stay within the 1537; tax bracket for cap gains capped at 479Kyear.My question is this: What other strategiesoptions might I have for reducing my tax obligation? What am I not considering?Any feedback or other thoughts you folks might have will be much appreciated. Thanks!  <response>: Start by turning off reinvestment of any dividends. 