I recently came across a profile of Jeff Dean that made me think about something beyond Google.

Dean joined Google in 1999, when the company still had fewer than 100 employees.

Over the next 27 years, he helped build some of the systems that made Google what it became. He and Sanjay Ghemawat helped build MapReduce and Bigtable, two of the technologies that allowed Google to handle enormous amounts of information as the company grew. Later, Dean led Google Brain and helped make Google an early leader in artificial intelligence. TensorFlow, one of the tools that came out of that work, went on to be used by developers around the world.

By almost any definition, Dean had already won professionally.

But what I found interesting was that he never seemed to act like he was finished.

Despite becoming one of the most respected engineers in the world, Dean apparently remained curious.

He reviewed code.

He spent time with younger engineers.

He asked questions.

He stayed close to difficult problems.

His colleagues described a leadership style that was more invitation than command.

Now, after 27 years at Google, Dean is leaving to help start Discovery Loop, a new company focused on using AI to accelerate scientific and engineering discovery.

Think about that for a moment.

After everything he accomplished at Google, he isn’t simply walking away from work.

He’s choosing what he wants to work on next.

There’s something worth thinking about there, especially if you’re well into a successful career yourself.

At some point, you may no longer need to prove that you can succeed.

The more interesting question becomes:

What do you want to do with the success you’ve already created?

One More Year

I’ve worked with Googlers since 2008.

I’ve seen careers grow, work culture evolve, Google stock rise and fall, families grow up, and people’s priorities change.

One pattern comes up again and again.

One more year.

One more year for the next vest.

One more year for the RSU refresh grant.

One more year because the promotion might be close.

One more year because walking away from a great income feels irresponsible.

And sometimes one more year is absolutely the right answer.

But it should probably be an answer.

Not a default.

If you’ve spent ten, fifteen, or twenty years building a career, you’ve accumulated considerably more than investments along the way.

You’ve accumulated skills.

Relationships.

Experience.

Credibility.

Maybe a house.

Maybe a substantial 401(k).

Maybe years of vested RSUs with a cost basis so low the IRS is practically rooting for you to sell.

Most importantly, you’ve accumulated choices.

The problem is that those choices can be difficult to see when you’re still running the same race.

What Does the Next Dollar Actually Do?

This is one of my favorite questions in financial planning.

Not:

How much more can you accumulate?

But:

What does more actually change?

For a Googler, that question can get complicated quickly.

Your RSU vesting schedule may be keeping you anchored to the next vest. An upcoming RSU refresh grant might make another year look particularly attractive. And after years of vesting, you may also have concentrated Google stock sitting alongside the rest of your investments.

None of those things automatically means you should stay.

And none of them means you should leave.

They simply belong in the same conversation.

Suppose another year of work allows you to save another $100,000.

That’s meaningful.

But relative to what?

If you have $300,000 invested, that additional savings could materially change your future.

If you already have several million dollars, a manageable mortgage, healthy retirement accounts, and relatively modest spending, the answer may be different.

The next dollar still has value.

But its value may be smaller than the value of the next year.

That’s the trade-off.

Money can compound.

So can experiences.

So can relationships.

So can time with your children.

And unlike money, some of those opportunities don’t wait for you.

What Happens If Everything Works?

Most financial planning starts with things going wrong.

What if the market falls?

What if Google stock drops?

What if you lose your job?

What if there’s a recession?

Those are reasonable questions.

But there’s another scenario I think successful people should spend more time considering.

What happens if everything works?

Your investments grow.

Your RSUs do what you hoped they would do.

You save consistently.

Your house appreciates.

Your retirement accounts are healthy.

You have enough liquidity.

Your family is okay.

Then what?

Do you keep accumulating simply because you’re good at accumulating?

Or does the purpose of the money begin to change?

Maybe you stay at Google because you genuinely love the work.

Great.

Maybe you stop pursuing the next level.

Maybe you take the sabbatical.

Maybe you spend a summer with your kids.

Maybe you help your parents.

Maybe you work less.

Maybe you teach.

Maybe you finally start the company you’ve been thinking about for six years.

Maybe you do absolutely nothing dramatic and simply create more room in your life.

There isn’t one correct answer.

That’s the point.

Your Career Doesn’t Have to End for Work to Change

That’s what I like about the Jeff Dean story.

He didn’t simply stop.

He chose something else.

Financial independence doesn’t have to mean retirement.

It can mean having enough financial strength to become more selective about what deserves your time.

You can continue doing ambitious things.

You can continue making money.

You can continue building.

But perhaps you no longer have to make every decision based on the paycheck attached to it.

That’s a very different relationship with work.

And you certainly don’t need Jeff Dean’s career or financial resources to begin thinking this way.

You need to understand your own life.

What do you actually spend?

What do you own?

What do you owe?

Who are you taking care of?

What needs to happen?

How much is enough?

And underneath all of those questions:

In service of what?

You Don’t Have to Know What Happens Next

I hope things work out exactly the way you’d like them to.

But what happens if life changes?

Nobody knows exactly what markets will do.

Nobody knows where Google stock will be five years from now.

Nobody knows what AI ultimately does to your career.

You don’t need to know.

You need enough structure around your financial life that more than one future can work.

That’s what optionality really is.

Not predicting the future.

Being prepared to choose when the future arrives.

If there’s one thing my experience working with Googlers has reinforced for me, it’s this:

The finish line keeps moving if you never decide where it is.

There will always be another vest.

Another promotion.

Another market milestone.

Another reason to wait.

At some point, the question isn’t whether you can accumulate more.

Of course you can.

The question is whether more is still in service of the life you actually want.

Because money is in service of life.

And sometimes enough is greater than more.

Continue Learning

If this has you thinking about what your own financial position gives you the freedom to do, here are a few places to start.

Thinking about life after Google?

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

What changes when the paycheck and regular RSU vesting stop, and how to prepare before they do.

Not ready to leave, but want to know if you’re making the right financial decisions?

The Right Order of Financial Decisions for Google Employees

A framework for deciding what should happen first, what can wait, and how the pieces of your financial life fit together.

Have a significant amount of Google stock?

Managing Concentrated Stock Positions

How to think about the trade-offs between holding, diversifying, and managing the tax consequences along the way.

Want to Know What Your Numbers Say?

You don’t need to know exactly what you want to do next.

But it helps to know what your finances already give you the freedom to do.

If you’d like to understand what your own numbers say, schedule an introductory conversation.

Disclosure

This article is provided for general informational and educational purposes only and should not be construed as personalized investment, tax, legal, or accounting advice, or as a recommendation to buy or sell any security. The planning concepts discussed are illustrative and may not be appropriate for every investor. All investing involves risk, including the possible loss of principal. Any planning scenarios referenced are generalized illustrations based on common planning situations and are not intended to represent any specific client or actual client experience. Past performance is not indicative of future results. Investment decisions should be made based on your own objectives, financial circumstances, and risk tolerance in consultation with your financial advisor, CPA, and attorney.

Hilpan Moxie Wealth Management, LLC is an investment adviser registered with the U.S. Securities and Exchange Commission (“SEC”). Registration with the SEC does not imply a certain level of skill or training. This communication does not constitute an offer to provide advisory services in any jurisdiction where the firm is not registered or exempt from registration.