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#202 - Greenland, Not London

A few weeks ago, after a panel I joined, someone beelined for the stage.

Emboldened, I think, by the wine the venue was serving, this guy had something to share, and wanted my take. He laid it all out:

He was eight years into his career, in a good, stable job. The job paid him well. And, he reminded me, Singapore was not a cheap place to live.

The guy was nervous, but genuine and charming, and you knew there was a "but" coming.

When it came, it was a hairy one: as much as the job was nourishing his bank account, it was draining his soul. There was no lift, no spark anymore. He loved the stability and the lifestyle, but was scared of who he was becoming, and it was eating him up.

"Have you ever felt that? What should I do?"

Of course, I didn't tell him what to do. But I did give him something to think about. And it's been on my mind all week. Because that conversation wasn't really about his job or his career. It was about math.

What replaces the ladder?

I’ve been arguing for a while now that the career ladder is obsolete. That the linear playbook is out the window.

But it begs a pressing question: what replaces it?

The old ladder came with old career math: pick a lane, work hard, get promoted, retire. Someone else built the rungs. You climbed them.

But modern careers don't work like that anymore. Growth is diffuse and multi-dimensional. Outcomes are less predictable. Stability is lower. Agency is higher.

More and more, we create our own opportunities, projects, audiences, businesses, relationships, leverage.

What replaces the ladder is the need to make good bets against uncertainty. It's learning to place better and better bets in ways that compound unfairly in our favor over time.

That's the core TalentStories thesis: in a decentralized, fractionalized world of low job security, we can't keep all our eggs in one basket. Careers become portfolios of bets.

And we're already building those portfolios, whether intentionally or not. Every day, we allocate our time, energy, trust, and attention.

The question is whether we're doing it consciously. Whether we're learning to place smarter and smarter bets.

What I left out

Way back in issue #137, I wrote about how careers compound, using basketball superstar Kobe Bryant’s logic to make the case. Kobe trained at 4am, while his competitors were still sleeping:

That’s compounding. The early starts widen the gap. The competitors can’t close it.

The thing is, I left out half the equation:

The same math goes in the other direction, too.

Five years on the wrong training schedule. Five years on the wrong train. Five years in the wrong job, the wrong function -- the wrong loop -- and we can’t close the gap to where -- and who -- we should have been, either. The math works just as aggressively against us.

Because compounding doesn’t care which way it’s running. It just runs, and gets dramatically stronger as it goes.

What we fail to appreciate, though, isn't just that compounding cuts both ways. It's the distance between the two. The gap between a career compounding for you and one compounding on you isn't X. It's not 2X either. Over time, the math doesn't add, it multiplies:

The key point is that careers compound. Either for us. Or on us.

Watch it run

You can see this play out in real-time. There are many visible examples of careers compounding, but I'll cite Lenny Rachitsky, who many of you follow.

Lenny's loop is simple: Free content -- podcasts and a newsletter -- earns attention. Paid content and a paid community convert some of that attention into recurring revenue. Often, content produced by the community gets kicked back to the top of the loop, generating more content, which begets more community. 🔁

Meantime, more products leverage the same audience -- courses, a job board, software bundles -- each feeding the next. Attention compounds into audience. Audience compounds into revenue. Reach and revenue compound into the next thing Lenny offers.

The loop has been running, intentionally, for years. That's the unfair-in-his-favor version of the math.

I appreciate Lenny might look like a business template, not a career one. But that is a fundamental misunderstanding, because that gap is vanishing. Running an unpredictable, uncertain business like his and navigating a modern career are becoming the same activity: attracting opportunity, making smarter bets under uncertainty, and letting the right ones compound.

My loop, my bet

Up until this year, TalentStories monetized via B2B revenue. Startups hired me to advise, train, and build their talent function. It worked well; still does.

But I was writing this newsletter to individuals, and growing a community of readers. I was building a consumer audience, and then converting that energy back into business engagements. There was a loop. I just wasn't finishing it.

So I started building the back half of the loop. Now I offer paid coaching and courses; consumer products that leverage and feed the audience I'm building.

It's early days, but it feels like it's starting to compound: the course work is begetting good content. So are the events. The content feeds the newsletter and the community. Both feed the next cohort and event. The loop I'd been half-running is starting to run the whole way around.

The muscles are new and different. There's some fear involved. To be honest, I don't even know if I'm going to enjoy this loop, or can make it work. But it was the impact I wanted to have, and the bet I wanted to place. So I'm in it; building and testing the loop. 🤞

If you've seen what I've written on pivots, remixes, luck surface area, or borrowed-versus-built, this -- compounding -- is the engine underneath all of it. Compounding is what makes those things work. It's the math doing the thankless, herculean lift, while the frameworks get the credit.

We already know

I think most of us already know. We know which loops energize us and which drain us. We know which rooms lift us, and which drag us. We know whether the math is running for us, or on us.

The work isn’t gathering more signal. It's to pause and listen to the signals we have. To act on them before five years, or ten years, go by and the gap is wider than we want.

The questions aren't complicated. Pick a loop you're running right now, and ask:

• Is it energizing me, or draining me?
• In two years of running it, what would I have built? Who would I have become? In five?
• Would that gap be unfair in my favor, or would I be unfair to myself?

It boils down to one question that we keep not asking: Is my career compounding for me? Or compounding on me?

Greenland

Back for a moment to my over-served, under-nourished friend at the panel that night. He wanted an answer: what would I do? What should he do?

What I gave him instead was a visual: "Imagine you're on a flight from New York to London. But you go one degree off course. Just one. So by the time you cross the Atlantic, you don't land at Heathrow. You land in Greenland. No Big Ben. Just reindeer."

All of a sudden speechless, he nodded. Then nodded a few more times, like you do when something that was there the whole time gets surfaced.

I have no idea what he's going to do. But I think he already knew.

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

Aki