05/28/2026
A few weeks ago, I sat down with an executive who had done everything right.
Strong career. Growing income. Meaningful equity compensation.
But when we got into the details of his stock options, he paused and said:
"Honestly… I’ve just been waiting for the right time."
The challenge was - there wasn't a clear plan behind that “right time.”
He was holding a significant portion of his net worth in company stock, unsure when to exercise, concerned about taxes, and hoping the price would keep climbing.
We stepped back and reframed the conversation:
Not “What will the stock do?”
But “What role should this play in your overall financial picture?”
From there, the strategy became clearer:
• How much risk he was actually taking
• When exercising made sense from a tax standpoint
• How to turn concentrated equity into long-term financial security
Stock options can be an incredible wealth-building tool for executives.
But without a strategy, they can quietly become one of your largest unmanaged risks.
If equity compensation is a meaningful part of your picture, it’s worth taking a step back and asking:
👉 Is there a clear plan behind my decisions?
Happy to be a resource if you’re thinking through it.
https://bit.ly/4uIAtxE
