My AI Sloppy Job Hunt

My AI Sloppy Job Hunt

I’m still on the job hunt, and finding it tough in this market. Prospects were really dry at the end of last year. I’ve seen a bit of a pick-up now that 2026 is moving along, but still no offer, and only two interviews in front of hiring managers so far, though I apply to a dozen or so jobs a week.

It’s a striking contrast to how I was able to quickly land a position after being laid off in 2023, just three years ago.

Anyone else out there who’s looking having the same problem? Or is it just me?

Here’s a couple of observations if you’re wondering what it’s like to be on the job hunt these days. On the applications, companies still ask all the EEO DEI-type questions – gender, race, veteran and disability status. Sometimes pronouns. The private sector did not get the memo that we’ve gone MAGA now, and woke is out.

A few times I’ve even been been asked about my sexual orientation! That’s one question to which I always answer “I prefer not to say.” What business is that of yours, I’m trying to get a job at your company, not have sex with it!

One thing that has become prevalent on the job search is AI. For one thing, there are a lot of postings for jobs where you are training AIs. They don’t promise you a lot of hours, and the rates they offer have a wide range, sometimes seeming too good to be true. I have ignored these kinds of postings. I’m not there (yet).

Sometimes when applying for a job, an AI chatbot will intervene as part of the process. Annoying. I have also been requested to do AI interviews as a next screening step. I started one once, and when I realized that it was supposed to be on camera, I bagged. But then a little later, I was requested to do an AI-driven “assessment,” also on camera, and since they were going to present my resume to a client, I acquiesced. It was a bit unnerving to be interviewed by a bot, but at least I have some experience at it, for later.

You know, for when the AIs take over. Gonna have to be able to appear compliant.

But seriously, I won’t deny it, I have leaned a little on ChatGPT for advice, and for help tailoring my resume. I’m no Luddite, I’m down with the AI revolution! ChatGPT even made me this inspiring image:

But I also won’t deny I feel a greater sense of uncertainty than I have in past periods of unemployment. There are a lot of factors that could be hampering my job search, as I enter what is probably the last decade of my life where I am in the workforce.

  • I was laid off in the midst of a shrinking job market, one that still hasn’t recovered. How could it with a gonzo administration in charge and WWIII looming over our heads? It’s just a bad time to be looking for work.
  • I am facing discrimination because of my age. Companies would rather have younger, more energetic workers that can be paid less. I can’t afford to backtrack on my rate at this stage of my life, though, with “retirement” coming around the corner.
  • Related to the above, my experience is too specialized. This is only natural for a late stage career, as it makes sense over time to focus on our strengths and area of expertise. But this could be also be understood as carving ourselves into a rut that is hard to get out of when that specialized expertise is in less demand.
  • I’m not trying hard enough. In the past, I have enjoyed periods of “funemployent,” but always bounced back into the workforce with relative ease. Maybe that’s not a realistic expectation deep in middle age.
  • AI really is taking over. My whole sector of the workforce – Information Technology – simply needs fewer humans, now that “agentic AI” is smart enough to do our jobs.

Oh no!

5 thoughts on “My AI Sloppy Job Hunt

  1. Hi Steve,
    I’m 76, retired, so my experience is Boooooomer style, not your culture. However, I have had success learning how to use Claude AI, paying $20 a month. I use Chat and CoWork, but not Code yet. Claude builds articles for me to edit, I have a CoWork folder on my computer that Claude accesses to save and read files. Basically Claude is now my AI writing and research assistant. I’m not trying to make money, I just like learning, so my situation does not align with your goals. I’ve progressed from my first uninformed prompts, to uploading a Style Sheet and having Claude do version control for me. AI will wipe out the job market for entry level jobs, even if applicants are tech savvy. I’ve had Claude build me a dashboard for tracking a complex financial measurement. Claude has built graphs, charts, tables and helped me organize a complex, multi-layered Meta-framework. I recommend Claude AI to help you with your job search also. just realize there is a multi-month learning curve.

    1. Hey Richard!
      Sounds like Claude is having better luck in the job market than me. 🙂 Of course, I can’t afford to work for $20 a month. I’m glad to hear you are having fun and learning with Claude, though.

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