“I wasn’t planning to leave work yet—but now my paycheck is gone, and most of my net worth is riding on one stock,” he shared after a recent layoff.
The Challenge:
Protect a highly concentrated stock position without being forced into a fire sale or a massive one year tax bill.
The Solution:
Rather than sell everything at once, we put structure around uncertainty. We created room for some appreciation and guardrails from a market correction. We implemented an options overlay strategy to help define downside protection, giving him breathing room in a volatile market. That protection allowed us to be patient instead of reactive.
As volatility spiked, we were able to opportunistically sell portions of the stock at prices above recentmarket levels with a put contract, without abandoning the position all at once. The remaining shares stayed protected, allowing future decisions to be made on his timeline, not the market’s.
This phased approach respected both sides of the equation: managing tax exposure over time while protecting the portfolio from a sharp downturn.
The Outcome:
The relief was immediate. What felt like a forced ending became a controlled transition, turning uncertainty into a plan.
💡If a single stock plays an outsized role in your financial life, especially during career transitions, a structured strategy can help you protect what you’ve built while keeping your options open.
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