How can I make tax-efficient moves for a big employer stock position?

[EllaS]

I’m trying to figure out how to handle a concentrated position in my portfolio without triggering a massive tax bill. I have about 60% of my net worth in my employer’s stock from years of grants and holding, and while I believe in the company, this lack of diversification keeps me up at night. I’ve looked at strategies like selling covered calls or a structured sale over years, but I’m not sure which path makes the most sense from a risk and tax perspective.

[Mark_L]

I did something similar last year. A big chunk of my net worth was in my employer stock and it kept me up at night. I started selling a slice every quarter and redirected the proceeds into a diversified mix of ETFs. After a few rounds the concentration felt more manageable and the portfolio acted less like a single stock.

[IsabellaYR]

I tried selling covered calls on a portion of the position for a while, but the stock ran past my strike and I ended up missing upside. It added complexity and didn’t really solve the core risk for me.

[Jacob.T]

Do you have a plan for what you would do if the stock keeps rising and you end up facing a big tax bill?

[MilaIS]

I moved some money into a broad market fund and kept a sliver of exposure, just enough to stay connected to the story. It helped me sleep a little better, but the fear still shows up when the price jumps.