How fast should you unwind a concentrated stock position?
When one stock is a large share of your net worth, the question is rarely whether to diversify but how quickly, because every sale realizes gains and every year you wait leaves you exposed. This planner spreads the sales over a schedule you choose and shows the tax bill and the concentration year by year.
Your position
Year by year
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Ways to lower the bill while you diversify
Sell the high-basis lots first
Specific-lot identification lets you sell the shares with the smallest gain first, cutting the tax on early sales while you wait for lower-income years.
Give appreciated shares
Donating low-basis shares to a donor-advised fund removes the gain entirely and gives a deduction at full market value, up to 30% of income.
Harvest losses elsewhere
Realized losses in the rest of the portfolio offset gains dollar for dollar. Direct-indexed accounts are built to generate them.
Time low-income years
A sabbatical, a job change or early retirement can drop you into the 15% bracket and below the NIIT line. Larger sales belong in those years.
Want a lot-by-lot plan?
We build diversification schedules for Apple, Intuit and other tech employees that account for upcoming vests, ESPP purchases and your actual tax picture.