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I applied for a job for the first time in 20 years. Job seekers are in a whole new world now.

June 27, 2026
in News
I applied for a job for the first time in 20 years. Job seekers are in a whole new world now.
The author takes a selfie next to a row of lockers in a high school.
The author said applying for a job for the first time in more than 20 years had some unexpected challenges. She persevered and landed a job as a test proctor. Courtesy of Trisha Daab.
  • The last time I applied for a job was more than 20 years ago.
  • My résumé needed a major update, which led me to go through old paper files.
  • After a lot of work, I applied and landed a job.

Recently, I paid off my student loans ahead of schedule. Along with the joy of saying goodbye to 10 more years of payments, I unexpectedly felt open to doing something completely different.

I stepped away from my marketing career in 2023 to focus on something I was more passionate about, writing. I will continue to write, but I’ve realized that I crave more regular interaction with people in my day-to-day life.

I spotted a listing at a local high school for advanced placement (AP) test proctors — a job I hadn’t known existed. That’s how I found myself applying for a job for the first time in 20 years.

I had forgotten a lot

The last job I completed a traditional application for was in corporate America in 2004. Since then, my jobs have come through networking and recruiters, some of which didn’t even require a formal application.

Applying for a job in 2026 was a new experience. It started similarly with an online application requesting work experience, education, and references. The difference this time around was me, my priorities, and 20 years of work experience.

My résumé needed a major update

I was surprised to realize that I hadn’t updated my résumé since 2014. One of the biggest challenges was finding the dates I needed to include. When did I start grad school? Did I start that job in April? How old are those references? It was hard to know these things for sure.

Thank goodness for LinkedIn. I had kept that updated with my writing work, the marketing role I left in 2023, and many of the dates I hadn’t thought about in years.

A collection of old resumes rest on a laptop.
The author said she had to dig up old resumes, including one with her maiden name, to get dates and other important info from her work history. Courtesy of Trisha Daab.

As for the earlier part of my career, well, that took some digging. I found a few hard copies of outdated résumés from the early 2000s; one even had my maiden name on it. They were a good starting point, though, and a trip down memory lane.

These were crafted before AI, electronic résumé readers, and writing résumés tailored to job descriptions. They aren’t riddled with corporate speak and data. There are no budgets or sales figures to prove what I had achieved. They are, of course, one page.

The process was involved

Once dates and work experience were located and entered, I could move on. Now it was time for step two, verifying what I said in my application.

For starters, every job working with kids seems to be done through a system that requests the employer’s name, phone number, email, and a contact name. That’s a lot of information that I can admit I didn’t readily have at hand.

This even included my stint as a preschool teacher in high school, a children’s hospital in college, and volunteering at my kids’ schools this year.

Just thinking about the preschool I worked at in 1996 was an experience, let alone finding a phone number and remembering my manager’s name.

Next was fingerprinting. A process that the employer made super easy. It’s all electronic, no black ink involved.

The author sits at a laptop with a dog on her lap and coffee by her side while applying for a job.
The author landed a job as a test proctor and has since applied to be a substitute teacher. She said the application process went much faster the second time around. Courtesy of Trisha Daab.

I landed a job

My application was submitted successfully. Soon after,k I was hired, trained, and proctored multiple tests.

Being a proctor, I was in a high school, engaging with staff in a new way, not as a parent or volunteer, but as an employee. I was with students in a role of authority instead of feeding them dinner, and that felt like a good fit.

By day two of proctoring, I realized how much I loved being in the school and helping the students and staff.

Since then, I’ve obtained my substitute teaching license and completed another application with a local school district. It went much faster this time!

Read the original article on Business Insider

The post I applied for a job for the first time in 20 years. Job seekers are in a whole new world now. appeared first on Business Insider.

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