I’ve spent years talking to job seekers. Their stories have gotten sadder — and stranger.
One former accountant woke up at 3 a.m. every day to apply for jobs. Eventually, he applied to be the Chick-fil-A cow mascot.
A laid-off Gen Zer used an AI tool to submit more than 1,300 job applications in a month before landing a job.
A third job seeker took an interview from his car while waiting in line at a food pantry. Over the course of a 16-month search, he applied to more than 6,000 roles.
Looking back through more than 100 conversations, I realized these aren’t isolated anecdotes. Together, they paint a picture of how job searching in this low-hire, low-fire environment has become more time-consuming, financially stressful, technology-driven, and, at times, downright bizarre.
Here are some themes that stood out.
Planning for unemployment
When Michael Permana was put on a performance improvement plan, he worried his days at Amazon were numbered. So he used his paternity leave to look for another job, figuring it could take a while to land one.
“I was desperate,” he said. “I took the opportunity while I could.”
I was struck by how many people began planning for unemployment before it happened. Some cut back on spending, while others secretly took on multiple jobs.
A quality assurance professional was on track to earn about $800,000 last year by secretly working six remote jobs, until he lost four of them in a matter of weeks. He soon rebuilt his income to roughly $900,000 across five remote roles — but kept applying for more to hedge against future layoffs.
“Even if you have two or three jobs, they could be gone tomorrow before your coffee’s cold,” he said.
Searching for an edge
Many job seekers said looking for work felt like walking a tightrope. They worried that one false step in an application or interview could cost them the job. Nearly everyone I interviewed had pieced together their own job search playbook from online advice, networking conversations, AI tools, and plenty of trial and error.
While some strategies — like applying as soon as a job is posted — were backed by career experts, others blurred the line between proven advice and lore. Job seekers debated everything from whether to apply through LinkedIn or a company’s website to the value of AI tools and whether referrals really mattered. A persistent debate was over résumés — how to write them, and what belongs on them.
When Malhar Shah began looking for work, he repeatedly asked ChatGPT and Gemini to grade his résumé on a scale of one to 10, revising it until both gave it at least a nine. He credits the process with helping him land a six-figure role.
One San Francisco millennial struggled to find work after his roughly $120,000-a-year contract role in communications at Amazon ended. After a year of unemployment and food stamps, he broadened his search, eventually finding work as a ghost tour guide and a US Postal Service mail carrier, earning a combined roughly $55,000 a year.
He’s still searching for communications roles, but you won’t find his tour guide or mail carrier gigs on his résumé. Instead, he lists a comms consulting business that generates little income because he worries employers will judge him for working outside his field.
“I have to keep this charade up that my independent comms company business is healthy and successful and that I’m not hustling as a letter carrier,” he said.
When the money runs out
Eventually, many conversations stopped being about résumés and interviews, and turned to money. Some job seekers had enough savings or severance to buy themselves time. Others drained emergency funds, worried about losing their homes, and feared they’d never be able to retire.
After a year of unemployment, Jesse Jashinsky was supporting his family with SNAP benefits, help from their church, and mounting credit card debt. After their car broke down and they couldn’t afford the repair, he created a GoFundMe and shared it on LinkedIn, writing: “I don’t know if this is the right thing to do on LinkedIn, but I’m kind of desperate.” Jashinsky said the post helped his fundraiser collect more than $3,800.
Others worried less about next month’s bills than whether they’d ever be able to retire. After being laid off from her management role at Wells Fargo, Robin Peppers Daniel struggled to find full-time work and eventually turned to substitute teaching to earn income.
“In a perfect world, I would retire and get out of this work rat race, but right now, I unfortunately can’t afford to,” said Daniel, who’s in her 60s.
For some, the stakes are bigger than just finances. After being laid off while working in the US on an F-1 visa, Aman Goyal had just 90 days to find a new employer or leave the country.
One of his first moves was spending $50 on an interview-prep book — not so much for the book itself, but because it unlocked access to a 20,000-member Slack community where he completed dozens of mock interviews. He credited the community and interview practice with helping him land his dream role at T-Mobile.
What’s stayed with me
If there’s one thing every job seeker I spoke with could agree on, it’s that looking for work sucks. It’s often lonely, financially stressful, and full of uncertainty — with much of it outside your control. A tough job market has only heightened those feelings.
But one theme that surfaced repeatedly in my interviews was how many people leaned on others during their job search — whether online communities, professional networks, or even strangers. Some believed it gave them a competitive edge. Others felt they had no choice.
At the end of nearly every interview, I asked job seekers what advice they’d give someone in the same position. One answer has stayed with me. It came from Oscar Cecena Fujigaki, who spent three months finishing a science-fiction novel after losing his job at LinkedIn.
His answer wasn’t another job-search hack. It was about living with uncertainty.
“The past is gone,” he said. “The future you’re stressing about will likely unfold differently than you imagine. Focus on what you can control today, whether that’s your project, applying for jobs, or networking. The present is all that really matters.”
Do you have a story to share about looking for work? Reach out to the reporter via email at [email protected] or on Signal at jzinkula.29.
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