​
#206 - The Next Bend In The River 🌊

I first met Kevin Lee in 2013, just after moving to Singapore and joining Uber. At the time, he was working for a quirky Silicon Valley startup. Like me, he'd just come to Singapore from California.

We met through a friend, and I remember liking him off the bat. He was one of those rare leaders who really got recruiting. Its off-the-charts importance, yes, but also the effort and nuance it demands. Its long-term, compounding impact.

I know this because Kevin has recruited me. Three times now.
​
But looking back at our emails and WhatsApp pings, it was always subtle. It was invites to lunch and events. It was thoughtful check-ins. It was requests for help, and offers of the same.

So we stayed in loose touch. I went from Uber to Netflix to TalentStories. Kevin, from Palantir to Grab, and then DBS.

Then, late this summer -- 13 years after first meeting -- I found myself in Kevin’s office again for what I thought would be a casual catch-up.

He was someone I’d always enjoyed. I’d heard good things about the company he’d joined, Cognition. I was curious to hear what he was up to, learn about a cutting-edge company, and of course, geek out on its hiring challenges.

I’ve always pushed myself to take meetings like these. To get in front of good people, stay curious, and have conversations without an agenda. Most of these meetings end there with nothing more than conversation, connection and learning.

This one didn't.

I’m joining Cognition, an AI software engineering company, to lead talent acquisition in APAC. I’ll start in a couple of weeks. 🙌

Fertile ground

All the clichés apply here, folks: I wasn’t looking for a job, I didn't expect to take one, I didn't think it would move so quickly. In fact, I got back to Singapore in August, and immediately ran two community events, doubled down on career coaching, and set up the landing page for my next course.

Still, Cognition didn't appear in a vacuum. There were a few things -- personal and external -- that had been percolating for a while.

One is that I've missed being part of a team. The momentum and lift and learning you get when a group of people work hard together on something meaningful. Ditto the camaraderie.

Another is that I've missed the feeling of doing something I'm naturally good at. I've spent my career recruiting, building teams, and building cultures. There were times when I was apologetic about my affinity for those things. When I couldn't tell you why I was so drawn to them. That's not the case anymore.

TalentStories, by contrast, has made me a beginner, over and over again. I learned to write, tell stories and create content. To build community, coach, sell, and find distribution.

Being a beginner has been one of the best gifts of this phase. It's made these years transformative. But I do miss the confidence that comes from doing something I'm fundamentally competent at.

The third trend is less personal: AI is changing the way we work in a way I struggle to get my head around. I’ve spent the last few years observing it, writing about it, and trying to understand what it means for careers, organizations and work.

But the faster the change has come, the more it's felt like a weird time to opine from the sidelines. Do I want to spend the next few years analyzing a historic transformation? Or do I want to try to participate in some small part of it?

All this had been swirling around in my head. Then I had coffee with Kevin.

Careering in bets

As readers, you know I’m obsessed with the idea that a career is a series of bets made against uncertainty. You know I believe that with intent, we can learn to make better bets. And that today's rate of change demands we do that, and do it more often.

So I routinely ask myself: is what I'm doing the best possible use of my time and skills? And for the past many years, the answer has been yes.

I left Netflix to make my biggest career bet: on TalentStories. It gave me autonomy and flexibility. It gave me this community. It let me write and teach and coach and build things I didn't think I could.

But as with any good bet, you also have to figure out how long to keep placing it. The world changes, your opportunity set changes, your opportunity cost changes. You change.

So when something like Cognition appeared, I perked up.

And to be clear, this is also a practical and financial decision, not just a personal one about growth. I'm taking equity in a startup, and if Cognition does well, that upside could matter.

Why Cognition?

Cognition builds Devin, an autonomous AI software engineer, used by engineering teams at large companies like Citibank, Mercedes Benz and Nvidia. It sits at the intersection of AI, agents and work, which means a chance to be closer to trends I’ve spent years trying to understand.

There's also the stage: it's a startup, its business is growing fast, and its team in Asia is small. That’s a combination I tend to enjoy: strong product momentum, with a lot of team to build.

Then there was the nature of this recruiting challenge, which surprised me. 😮

Before my conversation with the global head of talent, I assumed we'd discuss how to build a hiring machine: "What did you do to scale hiring at Google and Uber and Netflix in Asia? What do the levers and repeatability look like, Aki?"

Instead, we spent a lot of time talking about "spearfishing".

How do you find and hire truly exceptional people in tiny talent pools? How do you build relationships with people before they’re looking, and stay close over time? What does it mean to flip the entire mindset from "get the best person you can find right now" -- to everyone is gettable?

Maybe not today. Maybe this isn’t the right role, or the right timing. But great people are great people. And they're not static. Circumstances change, relationships compound, and great recruiting is a long-term game.

Cognition has lots of hiring to do. But its focus on finding extraordinary people, getting to know them and playing that long game complements the scaling-driven challenges I’ve tackled, even at companies with high bars. It's a problem that intrigues me. It was the hook.

Then I kept meeting people at Cognition.

Every company talks about its talent density. I've worked for companies I considered talent dense, and got to experience that lift.

Suffice to say, the signals I saw through Cognition's hiring process made me think it would deliver too. As I progressed, the prospect of working with such ambitious, talented people became intoxicating, in the best possible way.

But talent density alone wasn't enough. As the process went along, I started to notice more subtle signals.

I stumbled onto this exchange, for instance, between tech analyst Ben Thompson and profiler Jeremy Stern, about Stern’s profile of Cognition CEO Scott Wu:

It was signals like these, of warmth behind the intensity. Of groundedness, alongside the competitiveness. Of people at the top demanding a lot, while also caring about their people.

That combination felt unique, and was important to me.

Who will you become?

Early on in the hiring process, just before visiting the Cognition team in San Francisco, I called my best friend. He's also a talented coach, and knows me like the back of his hand. So he listened as I walked him through the contours of the opportunity.

Then, when we signed off, he wished me luck, and urged me to keep in mind one question as I explored:

Who will you become?

I’ve thought a lot about that question since he asked it.

We evaluate career opportunities through the standard lenses: the job, company, compensation, people, trajectory, etc. And we should.

But our jobs -- our work -- also shape us.

I know, for instance, who TalentStories has helped me become. And that helped me see this opportunity through another lens.

Four years ago, I knew recruiting. I knew talent. I knew working at tech companies. Then came this period of divergence.

I’ve written a lot about the concept and benefits of divergence and convergence as a career framework.

The idea comes from creative work: when you’re writing, designing, sculpting or solving a problem, you start by expanding possibilities. You generate, explore and experiment. Then you narrow, choose and commit. You diverge -- then converge.

I really believe careers work the same way.

They’re inherently uncertain, but they’re also creative. We can’t know which skills, experiences or relationships will matter five or ten years from now. So sometimes the right response to that uncertainty is to diverge: explore, experiment, and accumulate.​
​
​I’ve come to think of that divergence as raising human capital. And TalentStories has felt like a giant capital raise for me: Writing. Content marketing. Community. Coaching. Speaking. Entrepreneurship. AI.

It’s changed me, as the best experiences do, in ways I could not have known or predicted when I started.

But convergence is when you commit. You take what you’ve accumulated and combine and remix it with what you already have. You deploy and concentrate your capital on something.

This feels like a good time -- personally and externally -- to converge. And this opportunity feels like a bet worth converging on.

The contours of the work are familiar: relationships, judgment, influence, business thinking, culture, team building, Asia. But I'm coming back to them with a broader skillset.

And I’ll be working in a different technological moment, at a different type of organization, with a different business model. I’ll bring what I’ve learned about story, community, and content.

Through that lens, TalentStories wasn’t time away from my craft. It allowed me to expand it. And Cognition allows me to "go back", without going backwards.

Betting ≠ eliminating risk

Notice my language today: Bets. Signals. Intuition. Startups!

Of course, choosing a direction doesn’t eliminate uncertainty. I’ve spent time trying to de-risk this decision. But the reality is, this is inherently risky.

I met a lot of people. I asked a lot of questions and did a lot of diligence. I spoke with friends I trust, played out worst case scenarios, and asked them to help keep my excitement honest.

After all, what if we’re in an AI bubble that bursts? What if the frontier labs "move up the stack" and devour Cognition? What if new compounding technologies eat its lunch? What if Cognition doesn’t become what I think it can become?

I also don’t know what it’s really going to be like to work there. Interviews signal a lot about a culture, but they can't tell you what another late Tuesday night feels like, six months in.

That's the nature of a career bet though: if you knew how it would turn out, it wouldn’t be a bet.

At some point, you realize you can never eliminate risk. Your job, instead, is to make the best choice you can, with the information you have, knowing things can go either way.

Here, the upside ultimately feels worth the risk. So away we go. 🚀

What about TalentStories?

This was one of my biggest questions throughout the process.

TalentStories isn’t going away. In fact, Cognition was super supportive of me continuing it. Even of finding ways to support it.

So some parts will pause now: I won’t be taking on new coaching or consulting work, or running courses.

But the TalentStories community will continue apace, on WhatsApp and through live events. ❤️

And I'll have plenty to share as I go from talking about the future of work, to working in a small part of it. So the newsletter won't be weekly, but I'll still be keen to write and make sense of the journey with you.

The people in the raft

This summer, my family and I went whitewater rafting in Montana. My wife and kids, along with some of our in-laws and cousins. It was pretty tame stuff as far as rapids go.

But at one point we did hit a tough stretch:

After the rush of getting tossed and drenched, I looked up and saw my nephew and son treading water in the river. We did what the guide just trained us to do: reached over the front of the raft and hauled the boys back in.

A few seconds later, I turned and saw a waterproof shoe -- bright pink, unmistakably my wife's -- floating in the water. It turned out she and my daughter had also gone over! (They were plucked out, safe and sound, by the guide. 🙃)

So last week, after I shared in the family chat that I’d decided to join Cognition, my brother-in-law replied:

It meant so much to me.

Partly because we'd just been in Montana together at the front of that raft. But also because I’ve spent years arguing that careers are not ladders. That they're messier; full of rapids you don’t expect, and bends you can’t see around. That the better analogy, now, is navigating your own whitewater raft.

And what really matters is who's in that raft with you.

I’ve spent these years as a "solopreneur", working for myself, a business of one. But the truth is, none of it was alone. Not one day of it.

My wife and kids have been in my raft, for every twist and turn. My parents, sister, and in-laws have been there, too. So have my friends, the people I’ve called when I was excited, stuck, or trying to figure out what the heck to do.

The TalentStories community has been in my raft. It's supported me, encouraged me, lifted me, introduced me, and hired me.

Then there's all of you.

You’ve opened these emails and replied to them. You’ve forwarded them, and told others they should join. You've kept reading. In some cases, for years.

Attention is such an extraordinary gift to bestow on someone. You've gifted me yours, and I'm so grateful for it.

So, sure, I may have been the one holding the paddle at the front of the S.S. TalentStories. But I never paddled it alone. 🙏

Who will I become?

The more I think about my friend's question, the more I appreciate that I don't know how to answer it.

I know who TalentStories has helped me become. And I know this next phase will change me.

But what lies around the next bend -- much less who I will become? That I cannot tell you.

And that’s the whole point, isn’t it? To enter the uncertainty with curiosity and optimism. To be excited about what’s ahead, and about the person I might become along the way. And to know that, whatever's around the bend, I’m lucky to have people in the raft with me.

For now, that feels like plenty.

Thanks for reading -- and have a great end of the week! 🙏

Aki

P.S. If you want to join the TalentStories WhatsApp group, and/or are free this coming Wednesday night in Singapore for a casual hangout with some of the community members, reply here, or DM me!