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#198 - Being Good Isn't Good Enough Anymore
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By the time I got to him, Clint Eastwood was in the mature, reflective stage of his career. He'd grown soulful. Perfect World. In the Line of Fire. Million Dollar Baby. Great movies, all of them.

But my dad, after moving to the US, fell in love with Clint Eastwood 1.0. That Clint did many things. Ruminate was not one of them. No, dad's Clint was all squint, swagger, and cigarillo.

To this day, in my folks' kitchen, if you rip a hunk of bread from a loaf, you're doing it "Eastwood style": mean, rough, raw. Who's got time for knives when there's justice to mete out?

So, it was a steady stream of The Outlaw Josey Wales. The Good, the Bad and the Ugly. Dirty Harry. Years of iconic movies, characters, and lines. None more so than Harry's: Do I feel lucky?

Only it turns out, Harry was asking the wrong question all along.

The wrong question

My beef with Do I feel lucky? is that it treats luck as a coin flip. Something that happens to you, or doesn't. You feel it, or you don't.

For most of my career, I thought about luck the same way.

I was lucky to have grown up with two loving parents, in a good postal code. ❤️ Lucky to have graduated into a strong job market. Lucky to have stumbled into tech in time to ride a bull market. Lucky to have made some good career bets.

I still feel all that. That kind of luck is real.

But it's all backward-looking.

The forward-looking question is different. And it's more important than ever.

The better question

Most career advice treats luck as purely random. It's not. Luck is also downstream of our behaviors. And those behaviors, in turn, flow from concrete strategies.

In a work world that's become so unpredictable -- where careers have gone from ladders to portfolios of bets; where outcomes are more hit-driven and binary -- those strategies are our edge. They're the whole game.

But you don't engineer outcomes. You engineer exposure.
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More specifically: you create more ways for opportunity to find you. In 2010, Jason Roberts coined a term for this: luck surface area. He even gave it a tidy equation:

You've got two levers: doing work that matters, and telling the right people about it. Do more of both, and you get more surface area. You max out your chance of bumping into opportunity, i.e. of getting lucky.
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But both sides matter. Doing gives you something real to share. Telling helps the signal spread.

I was late to Jason's math. But looking back, I can find stories of manufacturing my own career luck. We all can.
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So today, let's explore one bet on writing; and one relationship that resurfaced at just the right time. Both about telling; just to different audiences.

Telling strangers​
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​Starting to write this newsletter was a bet.

When I started TalentStories, I didn't know how I'd monetize. I just knew I wanted to write -- and that writing in public was a way to put a signal into the world. To say, "This is what I think about; this is how I think about it."

I went at it for about six months before I decided -- informed by years of explosive hiring in tech -- "OK, I'm going to consult to high-growth startups."

But right then -- and I mean right then -- the techpocalypse kicked off: Google laid 12,000 people off in early 2023. Meta cut 11,000. Amazon, Salesforce, Microsoft, startups -- the whole industry started to heave and hemmorhage. Just as I was going to market.

But here's what happened: before I'd built any decks, or approached any venture capital firms, or told my network what I was going to do -- a founder reached out.

He'd been reading the newsletter. He found a mutual friend, and asked for an intro. We met up at a co-working space here in Singapore, and hit it off.

He was building a startup. His team was dying for clarity. He needed help defining values and behaviors, tying those to hiring and performance, and communicating everything thing to a team that was doing too much, without knowing why it mattered.

That was TalentStories' first invoice. 💵 🙏

Most of my work since has come the typical way, through network, ex-colleagues, and people who know my work. But the first engagement came cold, through writing, from a stranger.

I didn't do traditional BD, or reach out, or wine and dine. I put a signal out, and a stranger tuned into it. It was networking, but in reverse. ⬅️

In traditional networking, you go looking for opportunity. You go to people, and the arrow points out. ➡️ Reverse networking is when your work goes out and gives opportunity a way to find you.

Both increase luck surface area. Both work. But the reverse version is the one I wish I'd started much earlier. Because it works across time zones, while you sleep, and in ways you can't predict.

It's been hard, and it's been slow. Sometimes I feel like I'm shouting into a void. But every so often, a message starts with "I've been reading your stuff for a while,"...and makes it all worth it.

Telling friends

A few years before the writing bet, I made a different one, leaving Google to join a venture capital firm. The bet was that the brand would open doors, and give me a startup network that I lacked.

I got to spend time with leaders at then-startups Facebook, LinkedIn, and Airbnb. I also befriended a talented startup recruiter at a real estate startup in Seattle, Redfin.

A few years later, I made another bet -- this time with my wife, and baby daughter in tow -- on Singapore. As a trailing spouse, I split my time between setting up visas, cable service and cell phones, and trying to get in front of any startup that would meet me.

Then I posted on Facebook: "We moved to Singapore! Get in touch if you're around!" It was a 10-second life update with an awkward family selfie. Not some grand strategy framework.

"You're in Singapore?! We need to talk."

The next day I woke up to a message from my friend at Redfin, who'd done what startup recruiters do: joined another startup; made another bet. This one, on Uber.

She was now its head of recruiting. She'd seen my post. Uber was about to expand into Asia, and they needed to hire.

Two days later, I was interviewing. A week after that I was working from our closet of a Singapore office, explaining to everyone I met what it meant to call a car using a mobile app.

That whole sequence -- Google to VC to Uber -- sounds linear. It wasn't. Each step was a bet. Each bet expanded my surface area. And the most consequential one, Uber, happened because of a social post and a relationship I'd forged.

That's traditional networking, right? You build the relationships -- you nurture, you reciprocate without expectation -- and you keep your signal out there enough for luck to strike.

Both these stories are about telling. To different audiences, via different channels. But it's the same mechanism.

The writing magnetized opportunity from someone I'd never met. The Facebook post magnetized opportunity from someone I already knew, but didn't know what I was up to. We have to do both.

​Zara Zhang put it in one line:

That seeing is the multiplier.
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Luck isn't a single roll of the dice. It's a practice you build over time -- strengthened by doing and the telling -- that bends the distribution of outcomes in your favor.

This matters more now than it used to. For a long time, many of us were taught that telling was "bad", and separate from the work. Maybe even beneath the work. Just do good work. Keep your head down. Let the results speak for themselves.

That bargain made more sense when careers were linear, companies were more stable, and institutions did more signaling for us. A school, a title, a logo, a manager’s endorsement, those things all gave more automatic trust. They made us legible.

But in the new career game, trust is more scarce. There's more noise. Institutions are less trusted. Credentials are less trusted. Titles and logos matter, but have less weight than they used to. So visibility becomes part of the work. We need to show proof.

The new bargain

You can't make yourself feel lucky. You can make yourself findable.

That doesn't mean posting on LinkedIn every day for six months. Or quitting your job, or becoming a creator. It means not letting your work become invisible.

You can do real work, and then make sure that work has somewhere to go. You can write a post, or share a project. You can ask for a meeting, close a loop, or show up where your people are. You can keep relationships warm. You can let people know what you’re building, learning, or seeing. Sometimes it’s as simple as telling someone, clearly, what chapter you’re in now.

None of that guarantees outcomes. That’s the point: you can't control the roll. It's about expanding the surface.

It's about understanding that the heads-down, work-hard-and-the-rest-will-follow math doesn’t add up the way it used to.

It’s about seeing that the surface is wider than we think. Most of the moves don’t require a platform. They require intent.

Most of all, it's about internalizing that the question -- Do I feel lucky? -- is the wrong one. That it always was.

Dirty Harry would still tell you to ask yourself a question.

But he'd tweak it:

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