William and Jennifer have company stocks which have become a dangerously large percentage of their overall portfolio. However, quickly selling out of these positions would be highly inefficient on a tax basis.
The agreed plan is to work out of concentrated positions using the tax calendar to predictably space out the tax liability, and when possible, tax loss harvest portfolio losses against realized gains.
Option writing strategies can also be designed to protect downside risks while at the same time systematically reducing shares. Premiums collected from covered calls could be used to offset and pay capital gains taxes.