I showed up ready to learn something useful, something I might have overlooked under the burden of everyday survival. A hand up, not a handout. Others – close to a dozen of them – probably wanted to learn about possible careers in the fastest-growing sectors of the economy: technology, or specifically, AI. Or any sector, really, that might actually hire humans in the coming decade, and hopefully for a living wage. Instead, we were instructed by (very kind) staffers to take an Enneagram personality test and watch a playlist of inspirational videos, featuring a well-intentioned Gen Z narrator. She beamed with boundless enthusiasm but showed zero real-world experience when explaining job hunting to adults twice her age.

This would be darkly funny if the stakes were not food.

To be fair: the orientation, facilitated by an external contractor, was much less depressing than most of my interactions with notoriously understaffed and underfunded HRA. Over the years, I have been at this grim building numerous times, mostly as an interpreter for others, not a subject. But more than one thing bothered me, a product of free education focused on critical thinking, and to the point of sitting down to write this post.

I was also the only white person in the room. That is not a coincidence. The people being forced to prove they deserve food assistance while being offered outdated training were overwhelmingly the same people our labor market has historically excluded and continues to filter out first.

I suspect the personality test was to help us understand ourselves better… But for my money, the room already explained how the system works.

The Wrong Diagnosis

The way I see it, the message was subtle but unmistakable: “Your struggle is personal. Improve yourself. The system is fine.” It would be touching if it weren’t professionally irresponsible. Because as I learn first-hand the reality of job interviews in this day and age, here is who is actually deciding whether these people get interviews:

Automated résumé filters that reject formatting they don’t like.
Algorithmic matching that rewards insider language.
Video analytics that score affect and micro-expressions.
Dashboards that block humans from seeing certain applications at all.

Well-intentioned facilitators teach people to “present confidently” to interviewers who will never see their face. And keep teaching people how to impress human hiring managers in a market where human hiring managers are a dying species.

Digital Literacy Has Leveled Up

Digital inclusion used to mean things like: “Do you have internet access?”, or: “Can you use basic software?” As much as many of these questions remain painfully relevant – today, it means: Can you navigate the systems that judge you before a person knows you exist?

After that class, I realized the system would not modernize fast enough to matter.

So I started teaching myself:
• AI tools for communication
• How automated hiring works
• How digital bureaucracy filters people
• How to translate machine logic into human strategy

Not to “work in tech.” I am not a dude named Jared with a history of college lacrosse.
(Thank you, Heike Schiellmann!)
To survive the shift. And possibly tell others.

If you ask me, the real failure is structural. There is no serious retraining strategy for workers. Federal?Nonexistent. City/state: outdated and reactive. Vendors: still recommending personality quizzes. And the way I see it, digital illiteracy is being enforced, not caused by personal shortcomings. The people most impacted by automation receive the least education about it.

The Punchline & A Conversation Starter

AI is the new gatekeeper. If you cannot see how it works, you cannot see the door. If I survive the shutdown with my SNAP intact, this article will be the first in my series on digital inclusion as seen from the trenches.

(Maybe) Next: The Invisible Job Interview: How AI Judges Applicants Before a Human Does

If you’ve been through mandatory ‘readiness’ programs lately, I’d love to hear what you learned — or didn’t.

ABOUT ME

Autodidact in digital literacy and AI tools. Raised under authoritarian rule, fluent in reading between the lines. I share what I learn because staying quiet has never protected anyone — and because I’m a smart ass with a low tolerance for preventable confusion. Also, allergic to white savior tropes.