The Second Curve of Expertise

Most weeks, what I write here begins as a conversation. This newsletter is my way of  extending those - exploring ideas a little further and thinking out loud. That's how I learn. My hope is you’ll learn something too.

If you know anyone else who might enjoy these reflections, share your favorite issue and invite them to join the conversation.

Last week in Narrative Myopia, I wrote about how company stories drift quietly from reality — how leaders must keep listening to realign. This week, I want to look at how the same thing happens to people.

What worked before may not be working as well now. Things change and so must we.

Expertise drifts, too. Not because we forget what we know, but because we stop testing whether it still works.

Most skills come with an invisible expiration date. You just don’t notice it until something stops working. Most of us build our reputations on what we’ve mastered - the frameworks, playbooks, and instincts that made us reliable. That’s the first curve of expertise: knowing how things work.

Even as you get better at something, there's a risk you fail to notice when the rules change.

That's where the second curve comes in. Where the first curve is a journey to mastery, the second curve begins when that mastery starts to get in your way — when what used to make you effective quietly becomes what keeps you from evolving.

The Trap of Certainty

The first curve rewards certainty. You learn the pattern, trust your instincts, and execute with confidence. It feels good. Predictable. Effective. 

Then the terrain shifts. The same instincts that once signaled mastery now steer you into blind spots.

I’ve seen this everywhere:

• A sales leader still swearing by cold calls.

• A founder clinging to the early scrappiness that built traction.

• A consultant defending an outdated framework

They’re not wrong. They’re early-version right.

And that’s the trap. The first curve trains us to double down. The second demands that we step back and ask: What changed? 

The Shelf Life of Expertise

Knowledge decays. Markets shift. Tools evolve. Culture redefines what “good” looks like.

The problem? Our confidence decays much slower. That’s how we end up defending old truths long after the world has moved on. The work isn’t just learning new things. It’s pruning the old ones.

When Expertise Expires in Real Time

In 1992, long before the cloud era, I worked on Wall Street, as a database administrator — the person who kept the systems breathing. 

Back then, everything was physical - metal racks, tangled cables, humming servers in chilled rooms. For every new application, we bought and built database servers ourselves — usually a pair of Sun servers to host Sybase databases. It involved weeks of capacity planning, performance tuning, and redundancy setups. 

Every detail mattered: how was data split across disks, how many disks were being used, which controller handled what, how fast would recovery be if something failed and so on. It was exacting, high-pressure work. 

One wrong move, and the markets would be affected. Downtime wasn’t an error - it was a million-dollar event. 

Fast-forward twenty years. 

At an AWS re:Invent demo, an engineer spun up a fully replicated, cached, and redundant database in fifteen minutes. 

Need more memory? Allocate it. 
More disk? Allocate it. 
More servers? Spin them up.

In that moment, I watched years of hard-won expertise evaporate. 

My story ended there because I left infrastructure. Others stayed and climbed the  second curve — translating their thinking, not their tasks, to a new reality.

That’s when I learned: What I’d thought of as expertise was really context. My real value wasn’t the commands I knew — it was how I thought about systems under pressure. The second curve meant learning to separate those.

And that’s the challenge every expert faces when technology changes the rules. AI is doing to knowledge work what AWS did to infrastructure — collapsing the mechanics so the real craft moves to judgment, context, and meaning.

But this isn’t new. It’s the same pattern that’s repeated for centuries — from the Industrial Revolution to the Digital age. Each wave of progress automates a layer of mastery and forces the people who built it to redefine their value. It was factory floors, then server rooms. Now it’s presentations, strategies, and stories.

If you’ve ever watched the ground shift under your expertise, you already know this feeling. The question isn’t whether it will happen again — it’s how you’ll recognize it sooner next time.

Because the harder you worked to build the first curve, the more you want it to last. That’s what makes the second one so hard to climb.

From Defending to Sensing

One measure of an expert is noticing when you might be wrong.

That’s what separates authority from adaptability.

The first curve teaches you to say, “I know.”
The second teaches you to ask, “Does this still hold?”

The shift — from knowing to sensing — is how you move from mastery (first curve) to the renewal (second curve).

The Real Marker of Mastery

The second curve isn’t about reinvention. It’s about release. Expertise isn’t a monument; it’s a renewable resource. Letting go of what used to work doesn’t erase your mastery — it refines it. The tools will keep changing. The pace will keep accelerating. But the deeper skill — the enduring one — is learning to separate what you know from how you think.

My real value wasn’t the commands I knew — it was how I thought about systems under pressure.

The second curve meant learning to separate those.

The world never stops changing, and neither can we. The second curve isn’t about chasing the new; it’s about paying attention.

Keep noticing when what you know stops working — and start again.

Berkson's Bits

As long as customers have choices, they will need help making sense of them. 

The website is not going away - its form may evolve, but its  purpose remains: to build trust through clarity. 

It's the place to show your company point of view. It started as a brochure, then evolved into a place for deeper exploration. The brochure and explore functions are being gobbled up by answer engines.

So now it's about authority and proof. It's the place to build trust, one layer feeding the answer engines, and the other is a proof layer customers seek when they’re uncertain.

What I'm Listening To...

I have a deep interest in the entertainment space, especially the future of live performance and Broadway. This two episode series on the Plain English podcast on the Future of Entertainment is worth a listen. Reinvention is a never-ending process.

• Part 1: Is Hollywood's Business Model Broken?

• Part 2: What's The Matter With Broadway?

The second curve is where awareness becomes a practice. 

The challenge isn’t keeping up — it’s staying open. Because every time you test what you know, you create space for what’s next.

If this resonated, share it with someone who’s been rethinking what expertise means to them.

Looking forward to continuing the conversation...

Alan