The protégé problem today
Issue 292: Knowledge flows downhill anymore
For the past three years I’ve been asking myself the same question at the end of each week: “Are things going to get crazier than they are now?” I stopped asking the question because the answer seems to be, “Yes” every single time. I keep going back to the tech shift being Multi-modal and Multi-generational as two key reasons why things are so unstable.
The first rewrite makes a lot of sense. Software development is changing before our eyes. A year ago, when Anthropic CEO Dario Amodei said 90% of code would be written by AI, the statement felt like lunacy. These past three months made me think he was right. The Multi-modal shift of sentient lobsters, more sophisticated toolchain access, and generative AI breakthroughs means every company has to re-write and re-imagine itself.
The Multi-generational shift is like plate tectonics; slower moving, quiet, but when it happens, it’ll be felt at immense scale. There are three generational shifts happening at the same time in one of the most tumultuous times in tech. One of the generations is getting squeezed in the middle with nowhere to go.
This is the protégé problem we’re facing.
The protégé, often mistakenly described as a mentee, is traditionally a talented prospect guided by a wiser mentor; the person who provides wisdom to help guide their careers. This relationship doesn’t look the same anymore. The first reason is careers are non-linear. The concept of climbing the ladder is not as rigid as it once was. The second factor, most relevant to the issues at hand today, is many people who often provided mentorship don’t know the new skills and way of working and their protégés are more advanced than them. This type of mentor can still offer some value, but it’s now limited because of the lack of foundational skills.
The generational landscape
Any time there is discussion about different generations, it can be generalized and a hasty generalization. However, it’s important to talk recognize the three groups and reflect on the situational challenges each face, and how to find a path forward together.
There’s a version of this essay that gives everyone a clean action item. I’m not sure that’s actually useful here, because the situation for each group is different enough that a single prescription would flatten what makes it interesting. But the move does look different depending on where you sit — so let’s be specific.
The Elder Millennial
The Elder Millennial (also known as Geriatric Milennial), born roughly from 1981 to 1989. These are the people who get excited about Justice’s “Genesis” being played in a Cadillac commercial. They are the one generation active in tech who grew up along with the internet; using dial-up connections to make GeoCities pages and self-taught HTML through Notepad.exe. They didn’t consume the internet as much as they tinkered with it like a toy. Each platform shift — web to social to mobile to cloud — required them to actively adapt to new interfaces.
The position you’re in right now is genuinely unusual. You span both paths in a way most people don’t — mentor on judgment, be mentored on tools, hold credibility in both directions without fully belonging to either. That’s a rare thing and worth taking seriously.
The thing worth being honest about is that it has a shelf life. The people who built during the mobile boom had a window of maybe three to five years where that particular fluency was differentiated before it just became normal and the advantage disappeared. Something similar is happening now. Spending that window waiting for things to settle is a way of watching it close.
You’re not running out of relevance. You’re running out of time to position yourself as the bridge before the bridge becomes the road.
The Squeezed Middle
Younger Millennials, early Gen Z, are people in their late twenties to mid-thirties. They are caught between two gravitational pulls of different generations; not enough seniority to coast on experience, not enough native fluency to be the person everyone’s suddenly paying attention to.
The tools they built are being deprecated faster than they can be replaced. The instinct is to manage that by staying current — reading, course-taking, keeping up — without fully committing to being a beginner again. That instinct is understandable, and it’s also the thing getting in the way. The obstacle is rarely the skill gap. It’s the ego that formed around the previous version of the skill.
The App Store is the meal kit you nuke. Convenient, reliable, completely abstracted from the making of it, which was fine until the moment required something different. Building with AI agents rewards people who at some point had to understand the material, not just use it. This is the challenge for many in The Squeezed Middle. They no-coded and auto-layout’d their way through the work.
The people navigating this well aren’t just consuming information about AI. They’re actually letting themselves be taught by tools, younger colleagues, and in situations that have no particular respect for what they already know. That’s the move. Not catching up.
The Young Builder
The young builder is late Gen Z and emerging Gen Alpha. They are born digital natives with what others call emerging tools as the baseline. They’re sitting on something that hasn’t been fully valued because the professional world is still figuring it out. The lag makes it frustrating for people who hold a title higher than them to “catch up” to their capability. They were the ones in school who worked on their own side projects because the professor was teaching out-of-date concepts.
The soft skills can feel like a tax on top of the work. A 21-year-old can ship what used to require a team of twelve. What’s harder is managing the fallout when it breaks, reading a room that’s operating on fear, navigating a board conversation where the subtext is more important than the text. Those things are learnable. They just require the same kind of humility that everyone else in this story is also being asked to find.
Two paths to the same breakpoint
The mentor and protégé relationship isn’t gone. However, it’s forked and completely changed in path. One version still looks recognizable — a young builder, an elder Millennial somewhere above them in the org chart or in their network. The exchange is real but the terms changed. The young person often knows more about the tools, what’s possible right now, what the current defaults are, where the interesting edges are. What the older person has is harder to name but not less valuable: judgment, pattern recognition, the ability to sit with an unresolved situation without panicking. Having watched hype cycles inflate and detonate, having been through acquisitions and pivots and the particular kind of organizational grief that follows a reorg — that experience doesn’t look like expertise in the traditional sense anymore. It looks more like weather prediction. You’ve seen enough systems fail in enough similar ways that you can sometimes feel the pressure changing before anyone else does.
The second version is harder. An experienced person submitting — genuinely submitting — to being taught by someone younger. The difficulty isn’t really about learning new tools. Most people can do that with enough time and motivation. The difficulty is what you have to put down first: the identity that formed around knowing things, the assumption that seniority means something in territory that’s unfamiliar to everyone, the specific discomfort of being uncertain in front of someone who used to report to you. The people who can move through that without making it a whole thing tend to be okay. The people who keep waiting for things to stabilize are going to wait a long time.
Both paths have the same requirement: you have to know who you are clearly enough that learning something new and not feel threatened.
What replaces it
The traditional format assumed knowledge had a fixed address. It lived in the most experienced person and traveled toward the least experienced one, and the whole architecture of professional development was built around managing that transfer. What’s been destabilized isn’t just who holds the knowledge — it’s the assumption that knowledge works that way at all right now.
The multi-modal AI rewrite and the multi-generational rewrite feel like separate phenomena but they’re doing the same thing. Both are dismantling the idea that expertise is located, stable, and moves in one direction. You don’t get to finish one before the other starts and need to face both at once.
Here is the opportunity for each group.
The Elder Millennials have a narrow window to do something that matters as they are towards the end of their careers. They’ve seen the patterns before and have the foundational tinkering skills; the reason adaptability to AI is familiar. These folks have the right amount of experience and capability to set up the next generation just like the original casts in sequel reboots.
The Young Builder has more to offer professionally than ever. They are the digital natives who know the tools, now with the direct distribution the Elder Millennials didn’t have as much. The ability to build in public is not at the speed of bringing your Iomega Zip drive to the computer lab so you can FTP your files to your personal website. It’s at the tap of a button to go live and share.
Finally, for the Squeezed Middle, you have to find a path by choosing a direction. Though it’s not their fault as many started careers during the Blitzscaling era; an era that isn’t valued or frankly exists. This cohort actually has the best advantage of holding both positions. It’s not too late to re-skill and they have a lot to offer. The key is acknowledging the tough situation they are in and moving forward.
That quality turns out to be the thing that transfers across all three situations. Not the tools, not the tenure, not the title. The willingness to keep learning without needing the learning to be finished.
The people who come through this well won’t have figured it out. They’ll have stayed curious long enough that figuring it out stopped being the point.
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