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#190 - I Almost Never Left Google

Last year, a friend interviewed me for his newsletter. We spoke about portfolio careers and divergence and convergence: how alternating between exploration and intense focus can help tame career uncertainty.

The conversation eventually spilled onto LinkedIn, where he asked me a great question:

After writing issue #189 last week, on why going deep matters as much as exploration, I came back to Dexter's question. How do you actually know when to diverge and when to converge?

I thought a lot about it, as I had when he first asked me. And the honest answer is: I don’t have a formula.

There’s no spreadsheet or decision matrix. You can't plug your variables into a quiz, hit enter and spit out "the answer". If that’s your need, I'm not your guy.

What I can offer, though, is real examples. Career choices I've made, and the lessons they've imparted.

But the stories are useful beyond just lessons. They also allow us to tease out questions. Questions we can apply to understand decisions we've made, and guide decisions we'll make in future.

Today, we’ll look at two choices I made to diverge. What happened? What did they teach me? What questions do they prompt? Next week: two stories of convergence offer us different lessons and questions.

Writing these stories -- trying to understand my experiences for what they were, and were not -- has been one of the most empowering exercises I've undertaken in years.

But the goal isn't just reflection. It's also an invitation: I hope they nudge you to start your own journey: toward awareness of where you sit, grace for your past, and more clarity for what's ahead.

That's the exercise.

Know when to fold 'em

I wrote last week about my years at Otec, a recruiting firm in San Francisco. It was one of the best jobs I’ve had. The experience was convergent -- prolonged and focused -- so it returned real career capital: growth, skills, network, savings, story; fun.

But at some point, those returns started to flatten. And a new signal started tugging at me.

I felt pulled toward international work. I spoke languages I wasn't using. There were parts of my identity I was neglecting. I wanted to do something more global, with more social impact. So I went after it.

I went to a recruiting event for a French non-profit, and finagled an interview for a role I had no background for. Somehow, they placed me into a volunteer pool.

Then I sat in that pool for almost a year, waiting to be placed. All while friends worked through promotions and applied to graduate schools. Still, I felt so aligned with this organization's work that I waited it out.

I ended up in Guatemala, doing finance for medical projects. And it was fantastic. Not just the experience itself, but the divergence it offered me: a compounding set of new skills that would remix with what I had for years to come.

It turned out that the pull I felt -- the curiosity I couldn’t shut off -- "knew" the whole time. My mind had moved on. I just had to catch up to it.

Startup curious

Leaving Otec was a pull; it was personal curiosity.

Google was also curiosity, but it was professional.

As with Otec, my time at Google was convergent -- focused and concentrated -- over the course of many years. I deployed languages, recruiting experience, and cross-cultural chops. The culture was a natural fit; I performed well, earned well, felt the growth, and the return of career capital you expect in a focused phase.

But as we crossed from 10 to 15 to 20,000 people, the vibe shifted. I was an HR Business Partner in the sales organization by this point. It meant navigating egos, and reorgs, and the politics of bonus payouts.

The bigger Google became, the more I pined for the days when it was "just" a few thousand people. Not exactly tiny, but much smaller and faster than it had become.

Meantime, being in Silicon Valley but not working for a startup felt like living in a lottery game without a ticket. I was startup curious. That curiosity, and my hunch that I might enjoy a smaller company, had me antsy.

It must have been a constant angst, because at one point, my exasperated girlfriend, now my wife, said to me: "If you're so curious about a small company, why don't you just...join one? If you don't like it, you can always go back to a big company, right?".
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She was right, and I needed to hear it. Google proved a hard place to leave, especially in 2010. And if it wasn't for my her pep talk, I don't know if I would have ever pried myself out. 🙏🏻

So I began to talk to startups. I came within inches of joining one. But before I did, a headhunter called about a unique opportunity: a venture capital firm, Greylock Partners, was hiring for a newly created talent role.

Greylock had an incredible portfolio of startup investments: Facebook, LinkedIn, Airbnb, Workday (all private companies at this point). It would be new, and divergent for how it would expose me to startups and their people challenges.

But I wouldn't have to check my status at the door to join. I would still be well paid. Going there wouldn't raise colleagues' eyebrows.

The thinking was: "Why choose a startup from the outside? This puts me in the ecosystem; closer to startups, better able to choose the right one in future."

So, I leapt.

The lessons

Both decisions, in poker terms, were me folding my cards. The return had flattened; the pot wasn't worth it, so investing more of my time and energy wasn’t either.

I could have folded and just played another hand; deployed my chips (my career capital) into the next logical opportunity.

But in both cases, I chose to explore again after periods of intense focus.

Joining an NGO in Guatemala was completely new. Joining a small investment firm from big, public Google was new too.

Why diverge?

Because I was following an internal signal. I was listening inwards, and choosing to heed my curiosity.

That curiosity pulled me toward new environments where I could see and learn new things: a different part of the world in one case, and the inside of startups in the other.

In hindsight, that’s what divergence often looks like: folding a hand because the return has flattened, and the environment no longer fits; then using curiosity to guide you toward what to do next.

Questions I've learned to ask

Looking back, the signals have always been there. And over the years, I’ve learned to ask questions to better surface them:

• Is my career capital still returning? Am I learning, growing, and having impact with my time?
• Is this work draining or energizing me?
• What might someone who knows me well say I'm neglecting?
• If I left a good thing and it didn't work out, would that really be irreversible?

These are the questions I now come back to. Hard-earned, from years of not having them.

Learning to trust the signal

So, back to Dexter's question: how do you know?

The honest answer is: you never fully know. You make the call with the signals you’ve got. And you offer yourself grace over the fact that sometimes it goes well -- and sometimes it doesn't.

What helps isn't crystal balls. It's the kind of awareness I’ve been writing about. It's better questions, posed with more intent.

Next week, we'll look at the other type of decision: two moments I chose to hold my cards and converge. With complementary stories, lessons, and questions.

But underneath all the language and frameworks, the real skill is even simpler: self-trust.

Trusting your curiosity when it won’t shut up. Trusting the signal even when it raises peers' eyebrows. Trusting that you’ve navigated this before and have come out the other side; often, changed for the better.

Over time, you learn to trust. You build judgement, and learn to spot patterns and opportunities.

You remember that nothing is irrecoverable. That we make so many of these bets, over such a long career. That the goal isn’t to get every one right. But to de-risk, trust yourself, learn, and keep betting.
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So I'll ask you what I still ask myself:
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​Has your curiosity already moved somewhere you haven't followed?

Thanks for reading and exploring with me – and have a great end of the week! 🙏

Aki