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The Wrong People Have Impostor Syndrome Part 2


This is gonna be a very different approach for me. In the previous post, I discussed the competence gap more in terms of my own personal experience and thought experiments and suggestions for how to avoid falling into the trap of letting confidence equate to competence. But today, we’re going to dive more into how this plays out in the real world using some very specific examples that are playing out in real time. I know that we’re focused on empathy and engineering, and in some of these examples we’re talking about technology, but in all of them we’re talking about specific public figures’ lack of empathy and lack of ability to see beyond their own perspective. Especially when that perspective is misguided, wrong, or just plain evil.

The three examples we’re going to cover today are:

  1. Bari Weiss and The Free Press Take Over CBS News
  2. The “AI Will Replace Programmers” Leaders
  3. The “Low/No Code Development” Evangelists

In all of these examples, what you’ll see is that the louder the voices, the less likely it is that it’s coming from a reliable resource. The more measured and caveated the response, the more likely it is coming from a reliable source.

With that… let’s get into it.

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Bari Weiss and The Free Press Take Over CBS News

Funny enough, I wanted to rant about this, and then all of a sudden John Oliver was way ahead of me and did an EXCELLENT job explaining all of the reasons she’s unfit to run CBS News.

After her foray into the New York Times as an op-ed writer, she left the NYT with a screed about bullying and everyone criticizing her and creating a hostile work environment as a result, and then started a new enterprise that she titled “The Free Press” (originally it was called “Common Sense” so you can see what she was trying to sell through the names she chose).

And of course, The Free Press is anything but - it’s just another opinion magazine, just rebranded as journalism. But the stated goals were to build a “new media company … built on the ideals that once were the bedrock of great American journalism: honesty, doggedness, and fierce independence.”

The deal is… SHE DOESN’T KNOW WHAT JOURNALISM IS. And it’s evident in those stated goals! The bedrock of American Journalism isn’t “honesty, doggedness, and fierce independence.”

The preamble to the code of ethics for The Society of Professional Journalists states: “[P]ublic enlightenment is the forerunner of justice and the foundation of democracy. The duty of the journalist is to further those ends by seeking truth and providing a fair and comprehensive account of events and issues. Conscientious journalists from all media and specialties strive to serve the public with thoroughness and honesty. Professional integrity is the cornerstone of a journalist’s credibility.”

Compare and contrast what Weiss says vs that statement above… her focus is independence, whereas the latter’s focus is public service. Journalism isn’t about your viewpoint. It’s about serving the people. It’s a check on power through providing a fair and comprehensive accounting of events and issues. It’s not about doggedness. What’s that even MEAN in this context?! You’re determined… to do what?! Be independent?! Honesty is great, but that’s not the same as truth!

Honesty is about your own personal integrity, whether you believe in the things that you’re saying. Whereas truth is meant to be an objective reality that anyone could agree with.

Even just parsing the words that she uses you can see that she’s not thinking journalistically - she’s thinking like an oped writer.


The consequences of this are minimal if it’s just a random person who thinks that they know things when they don’t. But it’s much more pernicious when you realize that The Free Press was acquired by CBS, and Bari Weiss was installed as the head of CBS News.

And this is where we start talking again about the wrong people having Imposter Syndrome. By all measures, Bari SHOULD feel like an imposter. Because in fact she is! She’s never been a journalist. She’s never run a journalistic endeavor. Even the statements on her values for her “journalism” site CLEARLY evoke the language of opinion and not objective truth.

And yet, people that should be smart to be in their roles, gave her ~$200 million to run CBS News. And how is that going so far you might ask?

Exactly as you would expect.

But, she puts on airs that give people with the right to make decisions the impression that she knows what she’s doing. She’s overly confident that she can “solve the problems” with journalism.

She claims she wants to serve people who “want to be surprised. People who want to learn. People who are open to changing their minds in the face of new facts. People who believe that curiosity is a virtue and who crave common sense in a world that feels upside down” and yet, look above.

The point isn’t that she’s unqualified, though she is. Nor is the point that she doesn’t REALIZE she’s unqualified, though she doesn’t.

The point is, that people put her into these roles because she ACTS like she is competent, not because she actually is. She uses big words, she names her newsletter “Common Sense”, then transforms it to pretend it’s journalism by calling it “The Free Press”, not because it’s any of those things, but because it SOUNDS smart without any of the intellectual rigor required to be either common sense or a true free press organization.

So just to recap… a person with no journalism experience and no network news experience… now runs a network news room and a journalistic online magazine.

And we all can see fairly easily that this is a mistake, the reason that she’s given the opportunity to run a news network is because she’s so ignorant of her inability, that she’s instead boasting that she can fix journalism.

The gap between competence and confidence creates a misalignment in skill and as a result, sets itself up for failure.


The “AI will replace programmers” leaders

Let’s get back into tech.

In this section, we’ll look at two different world builders, Mark Benioff and Mark Zuckerberg.

There’s already a whole movie about Zuck so let’s start with Benioff.

Benioff is obviously a very successful guy. He was the youngest VP ever at Oracle, was personally groomed by Larry Ellison, and of course started Salesforce. Like Bari Weiss, he has a very impressive background in his field and knows a lot.

A thing I need to call out that I think I missed with Bari is, none of these people are DUMB. What they are, is ignorant of their own ignorance.

Benioff isn’t an engineer; or rather he’s as much of an engineer as I am lol. Which is to say, he’s been in engineering orgs and likely has learned a lot from engineers but hasn’t been responsible for building, maintaining, or supporting enterprise software. Like me, he has been more in execution, sales, marketing and other various business roles, that had connections to engineering.

I know this is going to be a shocking statement… but he’s much more successful in those endeavors than I am lol. And if you wanted to get his opinion on building an empire, or selling enterprise CRM’s, I’d be all ears.

But, instead he dove directly into the AI will replace developers discourse by saying Salesforce “will not be hiring any more software engineers in 2025” and said “we have increased the productivity this year with Agentforce and with other AI technology that we’re using for engineering teams by more than 30%.

He even claimed that AI currently accounts for 30-50% of the companies current work. He even claims that AI is right 93% of the time!

But what evidence does he have to back that up? It’s startlingly lacking. Instead it’s all bluster. We’ll lay people off, we’ll say AI is doing everything, we’ll stop hiring engineers. No worries right?

And people will listen because of his success, but again… his success isn’t in transforming an enterprise from a human based one to an AI based one. He doesn’t know what level of efficiency AI is creating or whether it’s actually able to replace humans. He’s making conjectures and just saying it confidently!

I know that he doesn’t have real statistics, becasue of how difficult it is to quantify! And then saying a range like 30-50% is belying the truth of the matter: he’s just making shit up. And on top of that, not being an engineer himself, he doesn’t have the qualifications to make any of these claims. But he’s able to do it, and get the markets to trust in him, because of his background.

And this isn’t limited to Benioff — it also spills out to CEO’s that did have a software engineering background like Mark Zuckerberg.

But the Marks are both… well… marks lol. They’re high on their own supply and have no idea. They keep advocating for cuts to people to replace them with AI without having any AI tools that can adequately replace a human being, even as Zuck argues that AI will replace lots of middle management functions to make them less necessary (as a prolonged middle manager, and an advocate for empathy in the work place… that proposition is gonna fail HARD).

But once you get past the Marks and move into the real life experience of developers they’ll give you a very different story. AI can help with prototyping and with some levels of vibe coding, but engineers will tell you that tools like GPT are right 50% of the time or less. Even if they got some utility out of it (and I know a ton of people who do!) it’s not a 10x multiplier and it’s not removing the needs for humans today.

AND EVEN IF IT DID you still need software engineers to do fine tuning of responses and to train the models to keep getting things right. Because AI doesn’t work like a resource plan. It’s non linear. It’s not standard software where you program in a specific path, and then users are forced down that path. It’s meant to respond to whatever input you provide and then create the paths as it goes. It’s not inuitive to engineers let alone non engineers. So if you have a flow that isn’t working in a standard engineering environment you can trace the code and identify the failure point - but with AI you’re not debugging, you’re training. You have to encourage it to want to respond the way you want it to respond. Even once you get it deployed, it’s still needing more prompting to be more effective, so you have to build in the way the neural nets are firing and pinging off one another rather than just writing a line of code to execute a function.

Making assumptions based on the demos you’re seeing from your teams, or extrapolating based on reports from your subordinates, or even believing statistics being presented to you without showing the intellectual curiosity to delve deeper and identify what’s bullshit and what’s concrete, and whether what’s concrete is telling the story you think it’s telling… it’s a different skill.

These are brilliant people. I’m not saying that to blow smoke up their asses, I could give a shit what these guys think of me, but I’m saying it to acknowledge that they’re not doing or saying these things because they’re dumb. They’re doing it because they’re ignorant in these specific spaces, but don’t see it because of their success and brilliance in VERY specific ways.


The “Low/No Code Development” Evangelists

Similarly, we’re finally past the era of low code/no code development (granted that’s because we’ve effectively moved to “vibe coding” and thinking that we can just develop throught prompt engineering… but that’s a different topic lol).

These tools have been around forever - hell I remember being in high school and using BBEdit to try and build websites only to be so frustrated that I ended up just learning HTML. But that didn’t stop execs from once again claiming that tools they didn’t understand would democratize software development.

Satya Nadella, the CEO of Microsoft, is an advocate of the no code movement, citing that it’s a democratizing factor, and equating it to the enablement of tools like excel to do really complicated tasks without knowing how to code.

But that’s yet another example of a leader not understanding the underlying concepts of what they’re talking about and ending up showing their low skill high confidence selves.

Using excel as the example is incredibly rich. Do you know an excel wizard? Are they an excel wizard because of how easy it is to use excel? OF COURSE NOT. They are a wizard because they had to do a painstaking amount of learning and essentially learn how to code inside of excel. You don’t just figure out how to create and use a pivot table, or a formula, or a nest of formulas in excel. You have to learn how to use it! Just like with any tool.

There are plenty of other examples from executives at Appian and Salesforce and it’s granted that some of this is just corporate bluster to sell a product… but that’s also the point I’m making here. It’s bluster.

These are demo tools, that show the happy path for the simplest workflow and sell the dream of creating software without needing to understand the underpinnings that make it work. And you CAN make some simple things with no code tools. But the second you want to do anything bespoke, or beyond the scope of the tool, you’re not just signing up for the licensing fee to the tool but you’re ALSO signing up for all the maintenance and services you’ll need to get it to do what you need it to do!

And on top of that, you’re locking yourself into an ecosystem that you’re not in control of! I worked at a company that bought into the idea of a tool that could take your code and recompile it for multiple different operating systems, and guess what happened? We had to hire developers to write the original code, then more developers to customize the code per platform, then pay the services fees for the tool, then also write custom code for the tool to bypass some of the bullshit that was in that we couldn’t use AND when there were late breaking updates to operating systems… we had to wait for weeks while the vendor fixed the tool!

Low code/No code tools all fall into the category of “this is still a development tool that requires a developer” no matter what the sales pitch is, and these leaders are out here with their bluster to say that it’s democratizing software development NOT out of a malcious intent… but because they fundamentally are ignorant yet confident.


This isn’t a new phenomenon. And it’s not that it’s even necessarily WRONG that sometimes the people who are telling you they can solve a problem actually can! Sometimes there are folks that can blend the competence with the bravado, but the point is more that 1) it’s rare and 2) it’s incredibly impactful to ALL of us.

The Free Press sold for nearly 200 million dollars despite not having any journalistic integrity. The economy is resting on the edge of a knife due to AI investment. Software engineers are struggling to find good opportunities becasue we’ve commoditized development in the market, even though the skill required for it isn’t a commodity!

And the problem is that as power is consolidated in fewer and fewer hands the feedback loops become smaller and smaller and allow for confidence to appear as competence and continue to spiral creating more powerful yet less competent leaders and organizations.

This isn’t the end of the story either — as the media landscape continues to go down this spiral we’re not just going to lose track of competence, but we’re going to lose track of objective reality. You can see it already with CBS, and you can see it on Fox News, and OANN, and whatever they’re calling MSNBC now, and countless other media outlets where opinion is being laundered as “news”. (and yes, I get that MSNBC isn’t engaging in propoganda which is just a different problem, but my point is about the transition from “news” to “opinion” not about the content or quality of those opinions)


To bring this back to the framing of Imposter Syndrome vs Dunning Kruger — it’s so much easier to live in the Dunning Kruger world. It’s so easy to assume you already have all the knowledge that you need. And it’s so much more work to continue to learn and grow and realize that there is always going to be something to learn even in fields where you’re an expert.

Why is it that we don’t optimize society differently to make it easier to learn instead then? Because we’ve focused on the wrong values. Our values are instead on efficiency, monetization, and individuality. And I’m not here to claim that I’m NOT doing those things either, hell I put a paywall on this article. I’m monetizing this blog or substack or whatever we’re calling this thing these days, not becasue I’m desperate for more money, but because I want people to have skin in the game if they’re going to hear me rant about things that I think are important but controversial. And because I’m spending my time doing this and… until we can get to something like a universal basic income, then we have to put a value on our time.

But I don’t like it. I want to change the way we work. I would love to frame leaders as teachers. I would love to frame employees as students. I would rather stop grading people well after school. You got a 2 on your annual review, good work. How do you get to a 1? Oh don’t worry it’s all made up and the only reason you didn’t get a 1 is because we have a quota and we can’t go over it.

We’ve systemitized the idea that competence doesn’t matter but confidence does. Knowing the bosses boss is more important than doing good work. And it’s bullshit and we all know it.

I know I like to surround myself with people who want to buck these trends, and it’s reassuring to see others live the values that I want to live and want to see in the world… but every one of them pays the empathy tax for it. All while they are surround by “successful” people who couldn’t do a lick of work if they didn’t take advantage of their employees and treat them like numbers on a page instead of people.

And in the end, the solution isn’t to say “do away with confident leaders”. Sometimes they’re great leaders! Nor is the answer “make the quietest person the leader!” They probably don’t WANT to be a leader! In the end, the solution is to move away from the focus on efficiency and always needing to grind to create value, and instead work on growing people. Because people that are growing create value.

And if we’re being honest about striving to always provide value, it starts with… you guessed it - empathy for people.