1. Stop the concentration from growing.

A big early win came through education. Kristen held on to vested restricted stock because it felt simpler, and selling felt like it might create extra tax consequences. Our team walked her through the reality: once stock vested, she had flexibility to sell without triggering additional income tax beyond what was already recognized at vesting. That insight alone helped change behavior and slow the accumulation.

2. Build a tax-smart exit plan for the legacy stock.

Reducing a large stock position is not as simple as “sell it.” The timing matters because the tax impact can swing dramatically based on income thresholds.

Using scenario modeling, our team stress-tested six scenarios with different sale timing/amounts to answer one question:

How much stock could Kristen sell each year to meaningfully reduce risk while staying in a more favorable capital gains range?

This mattered because the wrong move could push her into higher effective capital gains rates and trigger additional taxes that appear only after certain thresholds are crossed (including the Net Investment Income Tax).

The team’s plan focused on using Kristen's post-retirement “low-income window” — a two-year stretch where ordinary income dropped enough to make strategic sales far more efficient. The goal: reduce the concentration before distributions from qualified accounts begin, and do it with discipline instead of guesswork.