Selling Stock Without Blowing Up Your Tax Bill: Timing, Gifting, and Layering Strategies

Selling a large stock position sounds simple — until taxes enter the picture. Without a plan, you could lose 20–30% of your gains to capital gains tax and NIIT (net investment income tax).

Spread It Out Strategically

You don’t have to dump everything at once. A multi-year selling plan can help manage your tax brackets, reduce risk gradually, and preserve flexibility. Consider selling in lower-income years, spreading over multiple tax years, or pairing gains with losses elsewhere in your portfolio.

Add Some Giving to the Mix

Want to do good and do well? Gifting appreciated shares to a donor-advised fund (DAF) or charitable trust can help you avoid taxes entirely while locking in deductions. For family transfers, gifting shares directly (within annual exclusion limits) is another smart way to pass wealth without triggering a tax bill.

Need to unwind your stock position without a tax hangover?

Let’s design a smart, strategic exit plan based on your goals — not guesswork.