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If you've worked with a financial advisor for any length of time, you've probably brought something up that you read about or heard about; be it a trend, an asset, or a strategy that caught your attention.

What happens next tells you a lot about the relationship.

In Jurassic Park, the scientists didn’t fail because they lacked intelligence.

They solved every problem in front of them. The system worked exactly as designed.

And then the problem showed up all at once.

What Actually Matters When the Charts Are Saying "Stay"

If you're a Google employee with RSUs or a concentrated stock position, this is the decision you're actually facing.

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.

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.

Every spring, the financial industry publishes its version of what you should be worried about. This year the list includes geopolitical conflict, oil prices, tariff shifts, inflation that will not fully settle, and an AI investment cycle that is reshaping entire sectors,  including the ones many of you work in every day.

The data behind all of it is real.

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.

I want to walk you through a real scenario.

Not a hypothetical.

Not a headline.

A real household.

(Prompted by a sharp observation from Afrina M. on high-income pressure— this is what the math looks like inside a real household.)

A family of four.

Two kids.

If you work in tech, there’s a good chance a meaningful part of your wealth isn’t coming from your salary.

It’s coming from RSUs.

And in my experience, most people don’t struggle because RSUs are complicated…

They struggle because no one ever shows them how the pieces fit together.