You Don’t Need a Crystal Ball to Make Smart Decisions With Your Company Stock

One thing I regularly tell clients is that “I don’t have a crystal ball.”

I’m still waiting on my Hogwarts letter and like Harry, I probably wouldn’t be much good at Divination anyway.

This comes up a lot when I’m helping clients with equity compensation. The truth is, no one knows what will happen to your company’s stock price. Not you. Not your employer. Not your co-worker who seems to have it all figured out. And definitely not me.

The reality is: no one knows.

That can feel pretty scary—especially when you’re facing big decisions involving your company stock. The uncertainty can be overwhelming. But the truth is we can’t make a perfectly optimal decision with a single stock. There are too many unknowns. And the “right” answer often isn’t clear until years, maybe even decades, later.

So how do you make the best decision when the outcome is uncertain?

You change the equation.

Once you accept that perfection isn’t possible, you’re free to make choices that align with your goals, values, and vision for your future. Instead of trying to optimize your equity compensation in a vacuum, focus on how your stock can support the life you actually want to live.

That could mean:

• Creating a strategy to exercise ISOs gradually to manage your tax liability

• Selling RSUs as they vest to free up time (and cash) for travel

• Exercising and selling NSOs to build savings for a future sabbatical

• Strategically cashing out stock to pivot to a less demanding, more fulfilling career

When you stop chasing optimization and start planning around what matters to you, everything changes. You take the pressure off yourself to predict the future and start using your equity to build a life that feels meaningful today.

Because at the end of the day, your company stock should serve your life, not the other way around.