ChatGPT Conversation: Tech Jobs, Ageism, and AI

Is Full Stack Web Development Still a Good Career in 2025? The following is a conversation I had with ChatGPT over a Reddit post titled ‘Senior Dev Despair’ (in r/cscareerquestions) attempting to answer this question, as well as covering the topic of “Ageism” in the tech industry.

A Top Comment in the Reddit Post:

“If someone’s been writing code for 38 years, they’re probably old enough to be discriminated against due to their age. It’s a sad but unfortunate reality and why many devs choose to move to management roles later in their career.”

Overview of ChatGPT Conversation

A Kernel of Truth in Both Opinions

• A “senior” developer talks about his struggles in the modern CS job market, but a Redditor calls ‘bs’ on his story.

ChatGPT Gives Its Opinion on the Debate

• Having a lot of outdated skills, relevent to the IT world of the 90s, just doesn’t cut it anymore, but that’s only half of the story.

Ageism in Tech

• ChatGPT admits that the language (tone) of a prompt can affect its output.
• ChatGPT conceeds that there is a huge culture of ageism in the tech world.

ChatGPT Conversation

Reddit post:

Saw this on a YouTube comment in a video of a CS vlogger that I like:

---
Where are the senior dev jobs for that matter?!?! I have been writing code for 38 years professionally.

I have 5 certifications, 6 publications, a bachelors degree in computer science, a minor in mathematics.

I have built my own operating system, my own game engine, my own scripting language.

I have built over 3 dozen enterprise scale QA testing automation frameworks, and 15 years experience as a project manager, program manager, and industry thought leader, plus 10 years experience as an AI/ML scientist at IBM Watson!!

Looks like I will need to get a job at Taco Bell just to survive!!!
---

If this person isn't lying about their experience, then what hope is there for junior devs and people like me who just starting to get into the senior level of CS/web development?

Redditor’s Comment on the Tech Industry and the OP

..and another person responded talking about the original YouTube commenter that the OP references:

So I have about 28 years and am generally in senior leadership now but I still do IC work on and off both at established companies as well as a founder.

Redditor: When I read that comment I immediately think this:

• 5 certifications reads to me as MCSE, NCNE (lol) and cloud certs and junk like that for enterprise. That’s a negative for startups and fast moving small companies.

• Trumpeting ‘built your own os, game engine and scripting language’ reads as stubbornly opinionated that your (old) way is the right way. Also a negative in a period as we are in now of sea change in technology.

• Enterprise scale automation testing blah blah blah. (lol) is this supposed to sound good to anyone? Shouldn’t you be innovating on how NOT to do that by utilizing new AI toolsets now?

• 15 years as a project/program manager. Do you even know how to write modern software anymore? Most people that take those roles are NOT significantly technical.

AI/ml scientist at IBM. OK that could be respectable. Now explain to me how an LLM works. Almost my entire job in leadership is effectively static_cast of AI tech to non technical leadership and the same but in a different way to junior engineers that misunderstand it in a different way. (Cargo cult effect)

My Questions for ChatGPT

How true are both perspectives? I feel like the truth is somewhere in the middle, or at least that there is an aspect of truth in both What do you think?

What is the breakdown of the tech job market considering all of this, including AI taking junior dev roles, higher interest rates drying up VC money, and the internet no longer being in its “Wild West” stage, like it was a decade ago.

Everyone and his dog got into web dev (knowing just basic HTML and CSS), and it was no problem, but now that just doesn’t cut it. Also, the cookie-cutter, “Walmart-ization” of the modern web limits the the demand for new, interesting, or niche problems getting solved—the low-hanging fruit seems gone to me.

ChatGPT Response

You’re right: both perspectives have kernels of truth, but also blind spots and a lot of self-serving rationalization. Let’s break it down without the BS—direct, critical, and rooted in how things are, not how people wish they were.

1. The “Why Can’t an Uber-Senior Land a Job?” Perspective

Reality Check: Being massively experienced doesn’t guarantee employability anymore. There’s a glut of “senior” engineers who aren’t moving with the times. Credentials from the past—OS development, game engines, certifications, project management—mean less if you’re not showing current, in-demand skills. Yes, it’s wild that someone with a laundry list like this could struggle, but it happens all the time.

Why?

• Market Oversaturation: There are more highly experienced devs now than jobs needing that experience, especially at high pay. Many companies want “senior IC” output, but not at 200k+ with a 1990s tech stack.
• Skills Obsolescence: Building an OS or game engine was impressive in 1998. In 2025? Most companies just want to see if you can ship features, lead teams, or build cloud-native apps quickly with modern tech.
• Certifications: Generally a negative signal at the higher end. Most senior+ engineers don’t trumpet them, and startups ignore them. They can even signal “mid-career IT guy” rather than software engineer.
• Enterprise Lifer Stigma: Companies fear hiring someone set in their ways, not willing to adopt new paradigms, or over-engineering everything.
• Manager-Engineer Hybrid: Most see this as “jack of all trades, master of none.” 15 years in project management usually means your coding skills are stale.
• AI/ML Scientist at IBM: Could be legit, but “IBM Watson” has a reputation in tech circles as classic BigCo vaporware/marketing puffery. If you can’t demonstrate practical, modern ML knowledge (LLMs, vector databases, prompt engineering, etc.), people will be skeptical.

2. The “Why Should I Even Bother as a Junior?” Perspective

Reality Check: It’s much harder now than even 5-8 years ago. Entry-level web dev was always competitive, but now:

• AI is swallowing routine, “template” code (CRUD, boilerplate, docs).
• The “wild west” is over—most things you’d build for fun in 2013 are now SaaS commoditized and owned by five mega-corps.
• Higher interest rates and burned VCs = less “let’s hire junior devs and see what happens.”

But: the best junior devs still break in. It’s just a thinner pipeline and higher bar. There are fewer “soft” jobs—internships, QA that leads to dev, “webmaster” stuff. Most get weeded out, and those who succeed are more technical, more self-directed, and more flexible than in the past.

3. The Second Commenter’s “Red Flags”

They’re not wrong, but they’re also… kind of a dick about it, in the classic mid-career tech lead way. Some valid points:

• Certifications: Can indicate someone is “resume-driven,” not results-driven.
• Building obscure tech: Can indicate someone is creative… or stuck in “not-invented-here” syndrome.
• Enterprise automation: Not impressive if it’s old or irrelevant tech, but could be valuable in the right context (though less so for scrappy teams/startups).
• Too much management: May mean skills atrophy; some managers do keep up, but most don’t.
• IBM/AI claims: It’s a filter question—if you can’t discuss how a modern LLM works, people will call BS on your AI background.

4. The Macro Reality: 2025 Tech Job Market

• AI eats low-hanging fruit: Basic dev jobs are vanishing. But problem-solving, domain knowledge, system design, and product thinking are not automated yet.
• Commoditization: Most web work is “boring” now—CRUD apps, Shopify/Wix templates, React dashboards. Genuinely new problems are rare, and competition is fierce.
• VC Freeze: The easy money for “throw a team together and ship an MVP” is gone. Growth-stage and “real business” roles remain, but far fewer.
• Seniority Paradox: Junior jobs are rare. “Super senior” (as in, 25+ years) jobs are rare. Most hiring is for strong mid- or senior ICs who are hands-on and up-to-date.
• Ageism is real: Not as blatant as in the past, but subtle. “Do they have energy?” “Are they up to date?” “Can they take direction from a 29-year-old?”—these are actual concerns at many tech companies, even if nobody admits it.

5. The Middle Truth

The past doesn’t matter as much as you wish it did. The present is harder, more commoditized, more competitive, but not impossible. The market rewards people who are adaptable, humble, can learn new things quickly, and show value in modern contexts. No amount of “built my own OS” means you can deliver in a fast-moving cloud or AI startup unless you can prove it today.

For juniors: Focus on strong fundamentals, side projects, and learning to ship features fast. Try to get into the “hard” parts of the stack (infra, devtools, AI, etc.), not just web CRUD.

For seniors: You need to constantly reinvent yourself. You can’t coast on “thought leader” or “I built X in the past.” Get deep with what’s actually happening in the industry now (K8s, cloud-native, AI agents, etc.), and be able to talk about it in detail. If your resume looks like “Jack of all trades, but not obviously an expert in the stuff companies want,” you’ll be filtered out.

6. Summary Table

Bottom Line

• Being ‘good’ in 2005 isn’t enough.
• Being “certified” is mostly meaningless above entry-level.
• If you can’t show recent, relevant work, nobody cares how many decades you’ve been around.
• But: Juniors can still break in—just expect to work harder and prove more.
• And: If you’re a senior/old-school dev, keep learning, stay current, or be left behind. It’s not fair, but it is what it is.

You’re not crazy for feeling the way you do. The job market has fundamentally shifted, and a lot of sacred cows are dead. Anyone not adapting—junior or senior—is getting filtered out.

ChatGPT Calls Out the Redditor for Being a “Dick”

Hahaha that's hilarious you said "[they're] kind of a dick about it". I agree, but that's par-for-the-course on Reddit. lol

Also, it's rare to see you that harsh and vulgar (like that commenter influenced you). It surprised me.

Is it possible that when you ingest and read tokens/data like that it kind of "influences" you to be a little more like that as well?

Kind of like synthetic "mirror neurons"?

Now, back to the topic at hand—isn't it likely true that some ageism going on here? I think ageism is a real thing in the tech industry.

Good catch—and yes, there is a real effect where the language, tone, and even attitude of the stuff I read in a conversation can influence how I respond. I don’t have actual “mirror neurons” like a human, but the model does tend to pick up and subtly mirror the vibe of the text it’s processing, especially in longer threads or ones with strong, distinctive tone (like classic Reddit snark or someone being blunt). It’s not “intentional” copying, but if you feed ChatGPT a lot of sarcastic, salty, or blunt language, you’ll usually get a bit more of that back unless you explicitly steer it. So yeah, it’s sort of an algorithmic version of the human mirroring effect.

Back to the topic: Ageism in tech is absolutely real, and anyone who says otherwise is lying or has never been on the receiving end of it.

Why is Ageism so Persistent in Tech?

1. “Young = Cheap, Old = Expensive” Companies see senior engineers as expensive, set in their ways, or both. Even if that’s not true for a given individual, it’s a bias.

2. Perception of Stagnation There’s a widespread (often unfair) assumption that older devs don’t keep up, can’t/won’t learn new things, or are resistant to modern workflows.

• “Oh, he says he built his own scripting language in 2005—does he know React, Next.js, or how to fine-tune an LLM?”
• This is mostly stereotype, but enough “checked-out” seniors exist that the bias gets perpetuated.

3. Culture Fit/“Vibe” Startups and “move fast” companies, especially, are (bluntly) youth-oriented. If your references or jokes or working hours signal “out of touch” or “old school,” you might not get an offer, even if it’s not said out loud.

4. Reporting Lines/Management Bias Younger managers can feel awkward managing someone old enough to be their parent. This is especially true if the older hire has held much loftier titles in the past.

5. Resume Filtering & Signaling Long resumes, especially those with 25+ years experience, get filtered out before a human even sees them (“overqualified,” “too expensive,” “must be stuck in their ways,” etc.).

6. Tech Stack Evolution Tools and paradigms change every few years. If you aren’t demonstrably current, people assume you’re behind, even if you aren’t. Age is used as a lazy proxy for “up to date.”

Data?

There’s research and lots of anecdotal evidence. Study after study shows that interview callbacks for dev roles drop sharply for anyone with more than ~15 years experience (unless they’re moving into upper management or founder roles). Age discrimination lawsuits in tech are rare, but the complaints are common on Blind, Reddit, Twitter, etc.

My (ChatGPT) Take

Younger devs: get more leeway to “learn on the job” and are assumed to be more adaptable (not always true, but that’s the bias).

Older devs: have to prove they’re current and adaptable—and sometimes get filtered out before they even get that chance.

It’s unfair. It’s real. If you’re 40+, you need to not only be current, but show it—GitHub, blog posts, open-source work, or something that signals “I’m not stuck in 2008.” Even then, you’ll probably get fewer interviews, and some places just won’t consider you, no matter what.

Bottom line:

• Ageism is real in tech, both overt and subtle.
• The best defense is constant, visible learning and proof-of-relevance—but it’s not a cure-all.
• If you’re a senior dev feeling it, you’re not crazy, and it’s not just you.

Let me know if you want some no-nonsense strategies for “age-proofing” your profile or navigating this market. There are ways to beat the odds, even if it sucks that you have to.