You know that feeling when your phone updates,
like overnight? You wake up, you go to turn off
the alarm, and the button isn't where your thumb
thinks it is? Oh, yeah. It's moved like three
millimeters. And for the next week, every time
you try to turn on the flashlight, you're, I
don't know, opening the calculator? The phantom
tap. Yeah. It's a very real, very frustrating
thing. It's maddening. And look, that's just
a phone. That's just me before I've had coffee.
Now, imagine that same feeling, but you apply
it to an entire organization. a whole school
district, a whole hospital. Right. Suddenly the
upgrade that was supposed to make everything
more efficient is actually costing thousands
of hours because no one can find anything. Exactly.
The digital furniture has been rearranged. And
that's what we are getting into today. We've
got this really fascinating kind of contrarian
piece from Gary Ackerman at Hack Science Education.
It's a blog post titled Contingencies and Technology
Planning. Yeah. Published just this month, February
2nd, 2026. And, you know, don't let that title
scare you off. Right. Contingencies. It sounds
so dry. Like something you talk about with your
insurance agent. It does. But he isn't talking
about Plan B here. He's using it in the... the
engineering sense, the idea that everything that
exists now depends on this messy, complicated
web of things that happened before. It's like
the butterfly effect, but for an IT department.
That's a perfect way to put it. You can't just
change one thing without shaking the whole web.
And if you're a manager, a CEO, or even just
someone wondering why your office software is
so clunky, This is for you. OK, let's start with
a word he uses that I think is just perfect.
I hadn't heard it in this context before. The
Cluj. Ah, yes. The Cluj, K -L -U -G -E. That
sounds like a German pastry or something. Yeah,
or maybe a heavy boot. But no, it's in the computer
science world, a Cluj is a solution that's clumsy.
It's inelegant, inefficient. But, and this is
the most important part, it works. It's the duct
tape and chewing gum solution. Exactly. It's
the workaround that became permanent. But here's
where Ackerman really drops the bomb. He argues
that in most schools, the entire IT infrastructure
is basically one giant kluge. That sounds harsh.
I mean, surely these things were designed by
professionals, right? We spend millions on this
stuff. They were, yes. But they weren't designed
all at once. That's the key. Ackerman says school
IT systems aren't built from a single blueprint.
they evolve, more like a coral reef. Okay, I
like that image. Well, think about it. You had
a server put in, say, 2018. Then in 2021, you
bought a bunch of iPads. Then in 2024, the state
mandates some new security protocol. So you're
constantly just bolting new shiny parts onto
old rusty ones. Exactly. And to make them talk
to each other, to make the new 2025 software
work with the old 2018 server, you have to write
custom scripts. You create these weird configurations.
You create a Cluj. Which explains why the IT
department always looks terrified when you ask
to change something. I just thought they were
being difficult. No, it's because if you pull
the wrong thread, the whole sweater could unravel.
It's a house of cards. And that gets us to the
first big idea of this article. just dismantles.
The myth of the clean slate. Oh this is a huge
one. We've all had this fantasy right? You look
at your slow computer or the Wi -Fi that cuts
out and you just think let's burn it all down
throw it out and buy the new version. The whole
seal replacement dream. Let's just start over.
So why is that a myth? Is it just about the money?
Because hardware is getting cheaper isn't it?
The hardware is sure but the system is more expensive.
Ackerman talks about the iceberg of costs. He
says the sticker price of a new computer is like
a tiny fraction of the real cost. So what's the
rest of the iceberg? It's engineering the network.
Okay, break that down for me. If I replace a
server, what's the big engineering cost? Don't
I just plug it in? I wish. Remember the contingencies.
That old server you want to get rid of. It might
be running some custom script that lets the library
database work, or it might be the only machine
that knows how to talk to the ancient printers
in the science wing. So it's not just a box.
It's a box with a decade of handshakes and secret
agreements with all the other boxes. That's it,
exactly. And to replace the hardware, you have
to re -engineer every single one of those handshakes.
You might have to hire outside consultants because
the internal team doesn't even know how the old
Kludge was built. Because Dave, the guy who built
it 10 years ago, retired and didn't leave a manual.
Dave is a legend. But Dave kept it all in his
head. So you end up paying for forensic engineering
just to get back to where you started. That's
the legacy trap. You're a prisoner of past decisions.
And that brings us to the real core of the article,
I think. Because Ackerman says, even if you had
unlimited money for the hardware and you paid
all the engineers, you still haven't paid the
biggest bill. The greatest hidden cost. Right.
He pivots from the wires to the people. He says,
and I'm... Quoting here, perhaps the greatest
hidden cost of upgrading is the habits of users.
It's such a profound point. We tend to treat
users, employees, teachers like they're just
software, like they can just download new instructions
to their brains. Just read the memo, you'll be
fine. Exactly. But people don't work that way.
And he uses this perfect example. The learning
management system, the LMS. So that's your digital
classroom. The Blackboard, Canvas, Google Classroom,
things like that. It's where the homework lives.
It's the teacher's office. Now imagine an instructor.
They have spent years building their online classroom
in the current system. It's a ton of work. I
have friends who teach. They spend summers on
this. They're not just uploading PDFs. They're
designing a whole workflow. That's it. It becomes
muscle memory, cognitive automation. They're
not thinking about the software anymore. They're
thinking about teaching. The tool becomes invisible.
Precisely. Now the administration comes along
and says, great news, we're switching to LMS
2 .0. It's got a fresh new logo. And you just
hear this collective groan from the entire factory.
They panic. And for good reason. Ackerman calls
out the export import lie. The IT team always
promises you can just export your old class and
import it into the new one. It's seamless. It's
the cloud. And it is never seamless. He points
out that the formatting always breaks, the links
are broken, the images don't load right, the
quiz answers get scrambled. So the teacher is
basically digging their course out of the rubble
of a digital earthquake. Perfect analogy. And
while they're spending hours fixing links and
reuploading photos, what are they not doing?
They're not teaching. Not giving feedback. Not
improving their lessons. That is the hidden cost.
productivity just plummets and you have these
highly skilled professionals spending their days
trying to figure out where the submit button
went instead of doing their actual jobs. You
know, we usually see resistance to change as
some kind of character flaw, like, oh, they're
just being stubborn. But he's saying it's not
laziness. It's a rational economic calculation.
Yes. They've optimized their life for the clues
they have. When you break the clues, you break
their workflow. The frustration isn't about being
anti -tech. It's about being anti -inefficiency.
OK, so if the costs are this high financially
and in terms of morale, Why do we keep doing
it? Why are organizations constantly churning
through these massive system overhauls? And this
is where you get into the psychology of it all.
Ackerman identifies what he calls or what we
can call the new sheriff in town syndrome. OK,
set the scene. A school district hires a new
technology director or a company hires a new
CIO. This person comes from a different organization,
one that ran on, say, Microsoft, and now they're
in a Google based place. And as we've established.
Every Cluj is unique. Exactly. So the new leader
walks in. They look at this messy, complicated
system. The one that actually works, by the way.
And they feel uncomfortable. They feel lost?
Right. They don't know the shortcuts. They don't
know why the main server is named Gandalf and
why it can never be turned off. They feel like
they're driving a car with a steering wheel on
the wrong side. So they have choice. Option A,
learn the messy history of the new place. Or
option B, make the new place look just like their
old place. And human nature almost always prefers
option B. Ackerman says they will quote, prefer
the systems they have recent experience using.
But here's the line that really hit me. He writes,
the familiarity that comes from recent experience
cannot be confused with better performance. That's
the whole argument in a nutshell. Just because
the new leader is personally faster with system
X doesn't mean system X is objectively better.
for the thousand other people who have to use
it. It's a massive conflict of interest, isn't
it? The leader is basically prioritizing their
own comfort over the productivity of the entire
organization. It might be unintentional, but
yes, they frame it as modernization. They use
buzzwords. But really, it's often just them seeking
their own comfort zone. They're shifting the
burden of learning from themselves, one person
to the entire staff. Wow, when you put it like
that. I don't want to learn your system. So all
thousand of you have to learn mine. It's a huge
source of friction and cynicism because the teachers,
the staff, they know the new system isn't really
better. It's just different. It's just the new
box's favorite toy. And that cynicism just destroys
trust. Exactly. You burn all your political capital
on a software swap. So let's talk about the solution
because Ackerman doesn't just complain. He has
a very specific warning for the people at the
top. the CEOs, the superintendents. He does,
a very stern one. He says you need to be very
cautious of any new hire who comes in with a
demolition plan on day one. The I'm going to
fix everything immediately candidate. Right.
If someone says in an interview, I see you're
using system A, that's garbage. We're migrating
to system B in the first quarter. That should
be a massive red flag. Isn't that what we hire
leaders for? Vision. Decisiveness. Not with IT
planning. Not when there's a clues involved.
Yeah. Because that candidate doesn't know the
contingencies. They don't know why the system
is the way it is. It's that idea of Chesterton's
fence. Oh, that's a perfect fit. Remind us what
that is. It's a principle. If you find a fence
in the middle of a road and you don't see why
it's there, you can't just tear it down. You're
not allowed to tear it down until you first understand
why it was put up in the first place. Right.
Maybe it's keeping a bull out of the road. Maybe
it marks a property line you can't see. And Ackerman
is applying that to IT. That clunky old server
might be the fence keeping the payroll system
from crashing. So the advice for the CEO is don't
let them swing the hammer until they've read
the blueprints of the old house. Ackerman literally
says a new leader should not be authorized to
make big changes until they fully get the existing
systems. That requires so much patience, though.
We tend to reward action, right? We reward the
person who shakes things up. We do, but in this
case, shaking things up is just breaking things.
True leadership, he's implying, is the humility
to learn the system before you try to change
it. It's asking why before you ask what's next.
It's about respecting the history of the place,
respecting the clues, and respecting the people
who have built their entire professional lives
around it. Exactly. And understanding that the
total cost isn't just a number on a spreadsheet.
It's the stress level of your staff. It's the
hours of lost productivity. It's the phantom
tap times 1 ,000. This is really compelling.
It makes me look at every update now button with
deep suspicion. As you should. So let's zoom
out. We've been talking about schools, but this
supplies everywhere, doesn't it? Oh, absolutely.
Think about a new manager taking over a sales
team. The team tracks leads on this weird color
-coded spreadsheet instead of a fancy CRM. Then
the new manager hates it. They want dashboards.
Right. But maybe that spreadsheet captures some
nuance the CRM can't. Maybe the team's speed
relies on that clues. If the manager forces the
switch without understanding the why, sales could
just tank. It's the same exact pattern. Familiarity
versus actual performance. Yep. It happens everywhere.
We try to impose this clean, logical order on
a messy reality, and we just end up making a
different kind of mess. A new mess that we then
have to maintain. And the cycle starts all over
again. So what's the big takeaway for someone
listening, whether you're the employee suffering
through an upgrade or the leader planning one?
If you're the leader, my advice would be slow
down. Hunt for the contingencies. Before you
announce the big change, ask your team, if I
change this, what breaks? And actually listen
to the answer. And if you're the employee, the
one staring at all the broken links. Validate
your frustration. It's not just you being bad
at tech. You are feeling the real cost of a system
that wasn't designed around your habits. And
if you can, try to articulate that hidden cost
to your boss. How do you do that without just
sounding like you're complaining? You speak their
language. Don't say, I don't like it. Say, this
change will cost me 10 hours of project time,
or rebuilding this workflow will delay our client
report by two weeks. You put a price tag on your
habits, you make the hidden cost visible. Make
the hidden cost visible. That's really powerful.
It is. You know, I want to leave our listeners
with one final thought. We live in a culture
that worships disruption. We love the story of
the innovator who comes in and just smashes the
status quo. The modern genius archetype, right?
Right. But based on what Gary Ackerman's laid
out here, is that disruption always innovation?
Or is it sometimes just ego? That's the really
uncomfortable question. If a new leader proposes
a massive overhaul on day one, are they truly
serving the organization or are they just trying
to make their new world look a little more like
the one they just left? Are they building a better
future or just a more comfortable mirror for
themselves? A mirror that everyone else is forced
to polish. That lands hard. On that note, good
luck with your next system update. May your links
stay unbroken. Thanks for exploring the Cluj
with us. My pleasure. See you on the next deep
dive.