If you’re a retired Google employee with a meaningful portfolio and no W-2 coming in, this is probably a question you’ve asked. Or will ask.

I was in a conversation recently with a retired Xoogler and their spouse.

Both retired.

Roughly $10M across accounts.

RSUs had done their job over the years, and even with diversification efforts, there was still a meaningful Google position, one they were comfortable with, but aware of.

They came in with one question:

Most retirement plans don’t fail because people are too aggressive.

They fail because they’re just reasonable enough to go unquestioned.

A Googler asked me this week whether 3% was a solid COLA projection for retirement planning.

It’s a reasonable assumption.

It’s also doing more work than most people realize.

She had a significant position in Google stock, a clear number in her head for what retirement looked like, and a plan built on the idea that prices would rise about 3% a year for the next 25 years.

In the 1985 film Real Genius, a group of brilliant students spend months building a powerful laser. They solve every technical problem. The physics is flawless. The execution is perfect.

And then someone else points it at a house and fills it with popcorn.

The laser wasn’t the problem. The sequence was.

The biggest tax mistake I see isn’t people doing something reckless.

It’s people doing exactly what they’re supposed to do.

And getting hit with a six-figure tax bill they never saw coming.

A few weeks ago, I was sitting across from someone who had just left a large tech company.

No panic. No chaos.

They had already done what most people never get around to doing.

They opened everything up. Looked at the accounts. Thought it through.

And they said, very calmly: