I’m a Retired Google Employee With $10M - Should I Be Doing Roth Conversions Right Now?

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:

Should we be doing Roth conversions?

With their current structure, their projected taxable income was landing in the low-to-mid 20% bracket range, before any Roth conversion.

And underneath that question, a few things they didn’t say directly.

Geopolitics.

Inflation.

Healthcare costs before Medicare.

 

But underneath all of it was a simpler question:

How much can we actually spend without breaking the plan?

That’s usually how these conversations go.

The instinct is to grab onto something actionable. In this case, Roth conversions.

 

“We’re in a lower tax bracket now. Should we convert aggressively?”

Reasonable instinct.

Coming out of high-income W-2 years, the shift from a federal tax bracket over 37% into the 22–24% range is real.

But most people asking about Roth conversions are really asking something else.

They’re asking whether they’re going to be okay.

And starting with the conversion question skips too much.

 

Start Higher Up The Chain 

The macro layer is already handled.

That’s what stress tests are for:

higher inflation,

market declines,

lower return assumptions...

The plan holds together at a high level.

 

That doesn’t eliminate risk.

It just tells us we don’t need to solve everything at once.

So the conversation moves down a level.

 

Before Roth conversions, before tax strategy, before any of that, we need to understand what the plan actually requires.

Start with inflation.

Not all expenses move the same way.

Living expenses and healthcare, especially pre-Medicare, are inflation-sensitive.

A fixed mortgage or car payment isn’t.

That distinction matters more than the headline number.

 

Then income.

In this case, there was a bond ladder covering a meaningful portion of annual distributions.

Not theoretical income.  Scheduled income.

That distinction matters more than most people realize, because it directly determines how much room you actually have for Roth conversions.

If that ladder needs adjusting, that decision happens here.

Change the structure, you change the income. 

Change the income, you change what gets reported.

Dividends. Interest. Realized gains.

That becomes the baseline.

 

Where Roth Conversions Actually Fit

Only then do Roth conversions come back into the conversation.

They’re elective.

They sit on top of everything else.

If income is low enough, there may be room to convert at 22–24%.

If income is higher, maybe not that year.

That decision follows the structure.

Not the other way around.

 

What Happens If You Do Nothing

There’s another layer most people don’t say out loud.

RSUs stop vesting- but the Google stock is still there.

 

Stock Concentration doesn’t fix itself.
It just sits.

The decisions that feel optional today become more constrained later, and your exposure becomes less intentional over time.

Doing nothing is still a decision.

It just feels easier in the moment.

Understand what your taxable income actually looks like before Roth conversions.

In most cases I see, once that number is clear, the question shifts from:

“Should we convert aggressively?”

to:

“Do we even have room to convert this year?”

Not easier.

But clearer.

 

In practice, most people don’t approach Roth conversions the same way every year.

They tend to:

Convert opportunistically in lower-income years.

Skip conversions when income runs higher than expected.

Revisit annually rather than forcing a fixed strategy.

The decision follows the structure and not the other way around.

 

This isn't about getting the Roth decision right in isolation.

It's about deciding in the right order.

Because when the order is right, the decision tends to take care of itself.

This is the kind of question we work through with fellow Googlers regularly, especially when RSUs, concentrated stock, and portfolio income all need to connect once the W-2 years are behind you.

If the concentration piece is still sitting in the background while you're thinking through conversions, this is worth reading next:

Why Selling Concentrated Stock Isn't the Decision You Think It Is

 

And if you want to see how all the RSU decisions fit together before the W-2 stops:

RSU Guide for Tech Employees: Start Here

 

If any of this feels familiar and you're ready to work through it, that's exactly the conversation worth having.

Schedule an Introductory Conversation

 

Disclaimer: This is general information, not individualized tax or investment advice. Outcomes depend on your specific situation,  please coordinate with your CPA or advisor.