“An expert is an expert on how the world used to be, not what it might become.”
That quote (or some variation of it) has been rattling around in my head for years. And the more I see the world tilting on its axis—especially with tech—the more I believe it.
See, expertise is a double-edged sword.
On one side: hard-earned knowledge, pattern recognition, deep intuition, frameworks built on evidence.
On the other: rigidity, overconfidence, blind spots, and a subtle but dangerous attachment to “what used to work.”
The world doesn’t stay still. And inflection points don’t ask permission.
The Nature of Expertise
Expertise is, by definition, retrospective. It’s about accumulated understanding from repeated exposure to a relatively stable system. The more you’ve seen, the more patterns you recognize, the better you can predict outcomes—within that system.
Experts thrive when things evolve linearly.
But inflection points?
They’re not linear.
They’re discontinuous.
They rewrite the rules of the system itself.
And that’s where the trouble begins.
When Expertise Gets in the Way
Most experts have their identity wrapped up in being right. That’s fine when the world is steady. But when the ground shifts—when a new wave crashes in—experts often become skeptics, not visionaries.
It’s not malicious. It’s just human. You can’t dedicate decades to mastering a domain and not feel resistance when something threatens to overturn it.
History’s full of examples:
- IBM laughed at personal computers.
- Blockbuster shrugged off Netflix.
- Newspapers ignored blogs and newsletters.
- Taxi companies dismissed Uber.
- Big banks overlooked crypto.
- Search engine giants downplayed generative AI.
Each time, the “experts” relied on what they knew—but what they knew had quietly expired.
Inflection Points are Pattern Breakers
Inflection points don’t politely knock on the door. They smash the frame and install a sliding glass panel instead. The very idea of how things work is up for grabs.
And this is the problem:
Experts often look for new patterns to fit old ones. But when the new pattern doesn’t play by the old rules, they label it incomplete, wrong, or unworkable.
This is why you see seasoned professionals dismiss disruptive ideas with phrases like:
- “That’s not how it works.”
- “There’s no demand for that.”
- “People won’t adopt it.”
- “It’s just a fad.”
Until it’s not. And by then, it’s too late.
Who Does Thrive at Inflection Points?
Ironically, it’s often not the experts. It’s the curious, the cross-pollinators, the tinkerers, the outsiders.
These are people who:
- Ask what if?, not just what is?
- Combine knowledge across fields.
- Value adaptability over certainty.
- Have less to lose if things change.
They’re not always “right,” but they’re often closer to the edge of what’s coming. And they’re not trapped by legacy thinking.
The Trap of Past Success
If you’ve been rewarded for doing things a certain way, it’s hard to let go. Why would you?
But clinging to past success is like gripping a map that doesn’t match the terrain anymore. You can follow it perfectly—and still walk off a cliff.
In tech, we’re seeing this right now with AI.
People trained on traditional machine learning paradigms are struggling to wrap their heads around LLMs, agents, and emergent behaviour. It’s not just a new tool—it’s a new frame of reference.
Same with people trying to apply 20th-century rules to 21st-century platforms.
Old playbooks don’t work in new games.
So, What Should You Do?
Here’s my take, based on years watching this dance play out:
1. Respect expertise, but interrogate it.
Ask: What assumptions is this advice built on? Are those assumptions still valid?
2. Look for first principles.
Don’t just copy tactics. Understand the underlying forces. What’s actually happening?
3. Stay curious and keep experimenting.
The best way to see the future is to build small versions of it and see what works.
4. Get comfortable with ambiguity.
Inflection points feel messy. The trick is not mistaking that mess for madness. It’s often just early-stage brilliance.
5. Diversify your inputs.
If everyone you listen to is an “expert,” your perspective is skewed. Add in voices from outside your bubble.
Final Thought
Experts are great at explaining how we got here.
But getting to what’s next?
That takes something else.
A beginner’s mind.
A flexible spirit.
A healthy dose of irreverence.
And maybe the courage to say, “I don’t know—but I’m willing to find out.”
#StayFrosty!
Q&A Summary:
Q: What is the double-edged sword of expertise?
A: On one side, expertise provides hard-earned knowledge, pattern recognition, deep intuition, and frameworks built on evidence. On the other, it can lead to rigidity, overconfidence, blind spots, and a dangerous attachment to 'what used to work.'
Q: Why do experts struggle at inflection points?
A: Experts often struggle at inflection points because these are not linear and they rewrite the rules of the system itself, which can contradict their accumulated understanding from experience. Experts can also be resistant to change as it threatens to overturn the domain they have spent years mastering.
Q: How does past success become a trap for experts?
A: If you've been rewarded for doing things a certain way, it's hard to let go. But clinging to past success is like gripping a map that doesn't match the terrain anymore. You can follow it perfectly—and still walk off a cliff.
Q: Who thrives at inflection points?
A: Ironically, it’s often not the experts. It’s the curious, the cross-pollinators, the tinkerers, the outsiders. These are people who ask what if?, not just what is?, combine knowledge across fields, value adaptability over certainty, and have less to lose if things change.
Q: What are the suggested strategies to handle inflection points?
A: Strategies include respecting but interrogating expertise, looking for first principles, remaining curious and experimenting, getting comfortable with ambiguity, and diversifying inputs. Add in voices from outside your bubble.
