Son Challenges Mom to Apply for Job Online—She Realizes How the Process Has Changed Since the 90s

Ally Perry • Writer and Editor

Jul 30, 2026 6:00 AM EDT

A lot of parents do not appreciate the struggles that their adult kids go through when they are looking for a job.

The world of work today is undeniably totally different from the one that Boomers and Gen X experienced when they took their first steps into the profession of choice. It feels like the jobs are fewer, the hoops you have to jump through to get them are even more difficult to reach, and the fact that almost everything is done online only seems to make things more difficult when they should be more accessible.

Nonetheless, many an out-of-work young person has suffered through some motivational speech from an older relative about how they should focus on handing out resumes directly, or work on perfecting their handshake. They simply don't understand how much things have changed and are not willing to concede that maybe things are harder even for those who are trying their best.

Arguably, the only way to appreciate the challenges of finding work today is to attempt it for yourself. Of course, most who are retired, nearly retired, or have otherwise put that particular life goal behind them rarely have much interest in doing that themselves.

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In this post, a son was frustrated with his mom's out-of-touch attitude toward the job market. Her frame of reference for what it was like to try to find a job was stuck in a time period of thirty years ago, and he wanted her to understand the kind of struggle that job seekers go through now.
As a result, he decided to challenge her to do her own job search, applying to roles online that matched the skills and experience she had as a clinical psychologist. It is safe to say that she found the process challenging in ways that she didn't expect.
I made my mom apply for a job. Here’s what happened
My mother is a lovely, lovely woman but she doesn’t quite grasp what the job market is like in 2026. She talks a lot about my dad’s “difficulties” finding a good job in the 90s, which mostly comes down to which Fortune 50 company he’d accept an offer from after graduating from a top tier business school. So to help her understand I had her apply for a job online.
She was a clinical psychologist back in the day but hasn’t worked for a long time, and never actually defended her doctorate dissertation for family reasons, so applying for any jobs with licensure requirements was out, as she’d have to provide a license number and stuff.
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So we got creative and decided to apply to five jobs that were looking for unlicensed counselors (e.g., people in grad school) or various non-patient facing jobs that required graduate education in psych. In broad strokes, she has five years of experience, an undergraduate double degree from a top 50 school, and clinical training from a well regarded program in a top five metro area. I spruced up her resume to reflect the modern market better, changed her dates of graduation and such, and let her rip.

Two hours later she called. “hi, I’m uploading my resume but it’s not populating correctly. The dates aren’t filling in and it keeps changing the line breaks at the bullet points.” So I had my brother help her with an extension, and went back to my day. An hour went by.
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“What do you need to put in a cover letter these days?” I rarely if ever apply for jobs with them, so I sent her some resources and moved on.
I kind of forgot about the project until midweek when she called. “I was rejected from two of the places because I didn’t meet the qualifications for the position, that doesn’t make sense.” Of course it didn’t make sense, I crafted the resume so it would hit every checkmark. But that’s job hunting in 2026, baby. She asked if she could get feedback from the recruiter. I told her she could try but they’d almost certainly refuse to respond, which is exactly what ended up happening. I told her to tailor her resume to match each job description even harder. „So I need to pay a 25 dollar subscription to even get a chance of getting an interview”? „Yes, yes you do”
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A few days later my mom gets an email from a recruiter excitedly emailing some follow up questions, ranging from salary expectations to experience with different patient populations. This job asked a lot about her experience working with trans youth, which according to her was a complete unicorn case when she was practicing. With her input we answered the questions and responded to the recruiter.
A week went by and the recruiter responded with a salary range and some other follow-up questions. My mom called. “What on earth is this salary offer? This is what I got paid in the 90s.” Of course, there are wildly differing salary expectations depending on the type of work, insurance reimbursement possibilities, etc etc but that simple data point was a serious “what the ****” moment for her.
The other two jobs never even bothered responding. Her conclusion was “this is a pain.”