Job Search Exhaustion: After 2,200 Applications, Is It Time to Quit?

• Kevin Cash experienced a layoff in late 2022, prompting him to submit nearly 2,200 job applications in his quest for new employment.
• A Navy veteran armed with five degrees, including an MBA, Kevin has turned to driving for Uber and taking on Taskrabbit gigs to make ends meet.
• Despite his relentless networking and countless interviews, Kevin has faced a wave of rejections and financial hardships.

This poignant narrative, based on an interview with Kevin Cash, 43, who resides near Portland, Oregon, dives deep into his relentless journey of job hunting. With a rich background in business intelligence and semiconductor manufacturing, Kevin also boasts membership in the high-IQ society Mensa. Since his layoff in November 2022, his story highlights the trials of applying for jobs, navigating rejection letters, and maintaining hope.

I’ve been living my life behind the wheel lately, clocking in nearly 2,200 job applications. To be honest, at this point, I’m ready to throw in the towel on the job search. The reality of it all? It’s overwhelming.

During the day, you’ll find me driving for Uber and tackling odd jobs on Taskrabbit. Thank goodness for these gigs! Without them, I might have been forced to crash at a friend’s place just to get by.

Some days, I’m hustling for up to 12 hours straight, but I’m committed to keeping a roof over my daughter’s head. Her comfort and sense of security matter most during these turbulent times.

With Taskrabbit, I’m taking on everything from hanging pictures to assembling Ikea furniture—whatever I can do to make an extra buck.

After each gig, I rush back home, drop off my tools, and grab a quick lunch—usually a can of tuna with a dollop of mayo. Not exactly gourmet, but it’s sustenance. Then it’s back to driving, typically from late afternoon until well past midnight, often until 11 p.m. or later.

In just a few months, I’ve racked up around 20,000 miles on my car. By the time I finally crawl into bed, I’m utterly exhausted and starving. It’s often past midnight by then, and I find myself longing to stretch out on the floor after being cooped up in my car for so long. Fitness? What’s that? I haven’t seen the inside of a gym in ages.

‘Do you do this full time?’

It’s like clockwork; every time I pick up a passenger, they ask, “Do you do this full time?” I share my past—I used to work in corporate strategy, and oh, the degrees! Then the inevitable question comes up: “Why are you driving for Uber now?” I explain about the two years and 2,000 applications, and they’re usually taken aback.

I tell them, for one, many job postings are just smoke and mirrors. Once I dove into research about fake job listings, I realized I’ve wasted a staggering 12.5 days on applications for positions that don’t even exist.

Friends and riders have suggested I start a podcast about my journey. So, I’m doing it! I’m calling it “We’re Moving Forward.” This podcast will touch on self-improvement, entrepreneurship, and fitness. The name stems from those boilerplate rejection letters—the ones that say we’re “moving forward with another candidate.”

It’s about flipping the script and transforming a negative experience into something empowering.

Networking while driving for Uber

Believe it or not, I’ve managed to network while behind the wheel. Some surprising connections have come out of my rides. Just the other day, I drove a guy who turned out to work for a major consulting firm. After we chatted, I handed him my card, and he offered to refer me if I spotted any roles.

I’ve made connections with folks from Adidas and Fila, and even scored a referral from someone at Amazon. It’s wild how networking opportunities arise during rides.

A futile search

Throughout this job hunt, I’ve had my résumé reviewed by professionals nine times, from university advisors to LinkedIn recruiters.

I’ve picked up some consulting gigs in business intelligence to fill the glaring gaps in my résumé since it’s been almost two years since my last full-time role.

My job application spreadsheet tells a disheartening story: I applied to 254 positions in January, only to see that number dwindle to 129 by May, and just 41 by August. It’s not that I’m being more selective; it’s the stark realization that this feels utterly futile.

It’s incredibly disheartening to see the same result over and over. Statistically, I have a mere 0.55% chance of landing a screening call and a 0.28% shot at an interview. Even those rare screening calls can be bizarre; I once spoke to someone who wanted 10 years of experience with software that’s only been around for six!

As I hit 2,181 applications, I find myself reflecting while I drive. I’ve tried meditating to keep my sanity intact and have confided in close friends. I’ve come to a significant decision—I have 19 more applications in me.

Once I reach 2,200, I’m throwing in the towel. It feels like a sign from the universe, telling me that maybe it’s time to stop forcing it.

And it’s not like I’m randomly sending out résumés. I’m applying for positions I know I’m qualified for, from entry-level roles to senior management. The upper-tier positions have garnered the most responses, with a few phone interviews and even some in-person meetings.

I’m going broke

This isn’t how I envisioned my life unfolding. I’ve always been prudent with money. After my divorce over two years ago, I sold the house and had some savings to fall back on. Initially, I thought I’d find a job soon enough and be back on my feet in no time.

Fast forward to now, and here I am, still searching. Rent is nearly $3,000 a month, and I have a child to care for with her own needs and wants.

A couple of months ago, my savings ran dry. It’s a harsh reality check, starting from scratch at 43. Driving for Uber and doing Taskrabbit were my only options left.

But I’m excited about my podcast. I’m in the process of producing episodes and have had enriching conversations with people I’ve met through Taskrabbit. Some HR professionals are also interested in sharing their insights—they’re struggling to find quality candidates, too.

Do you have a story to share about your experiences in the job market? We want to hear from you! Reach out to our workplace team from a non-work device at [email protected] with your insights or to connect with one of our reporters.