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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.

Restricted Stock Units (RSUs) can be a powerful wealth-building tool for technology employees, but they can also create tax surprises if the rules are not understood upfront.

Many professionals assume RSUs work like a simple bonus. In reality, vesting can increase taxable income quickly, affect withholding, and influence later investment decisions.

For many employees at large technology companies, Restricted Stock Units (RSUs) can accumulate into a significant portion of their net worth over time.

Years of vesting schedules, refresh grants, and strong stock performance can gradually turn employer equity into one of the largest assets in an investor’s portfolio.