- Kevin Cash got laid off in late 2022 and has since applied for nearly 2,200 jobs.
- To get by, the Navy veteran with five degrees has been driving for Uber and doing Taskrabbit gigs.
- Despite networking through Uber, Cash has faced numerous rejections and financial struggles.
This as-told-to essay is based on an interview with Kevin Cash. Cash, who lives outside Portland, Oregon, has a background in business intelligence and working in semiconductor manufacturing facilities. Cash, 43, served in the Navy, is a member of the high-IQ society Mensa, and has five degrees, including an MBA. He's been looking for a full-time job since getting laid off in November 2022. Cash previously spoke to Business Insider about his approach to cover letters back when he'd applied for about 1,200 jobs. This essay has been edited for length and clarity.
I've been spending less time in front of my computer these days because I'm almost up to 2,200 job applications. With the results that I've gotten, my plan at this point is to give up on the search.
Lately, I've been doing a lot of Uber driving and Taskrabbit. I'm just grateful they exist because if it wasn't for those things, I probably would have moved in with a friend by now or something.
I have to grind sometimes 12 hours a day, but I keep a roof over my kid's head, and she's comfortable and a little bit protected from the reality of what's going on. It's important that she has stability.
With Taskrabbit, I've been hanging things for people, putting together Ikea furniture — whatever they hire me to do.
When I get back home after a job, I drop off my equipment and then eat lunch. Usually, it's a can of tuna with some mayonnaise — glamorous, I know. Then I'll jump back in the car. I'll drive from 3 or 4 p.m. until at least 10 or 11 p.m., but many nights I will drive later than that.
I've put, gosh, probably 20,000 miles on my car in the last three or four months.
When I get home, I'm tired and hungry. By the time I'm done eating, it's often midnight or later. I then want to eat, lay down on the floor, and stretch out from being in my car for so long. I haven't had a chance to get into the gym, and my fitness is suffering at this point.
'Do you do this full time?'
Almost inevitably, when I'm driving someone, the question comes up, "Do you do this full time?" Then I tell people, this is what I used to do — corporate strategy and whatever else. Then I tell them about my education. Then people say, "Oh, gosh. Why are you driving Uber now?" I tell them it's been almost two years and more than 2,000 applications. People can't believe it.
I tell people, for one, that a lot of posted jobs are fake. I did the math once I started researching how pervasive fake posts are on job boards, and it turns out that based on how long the average application takes me, I've spent a solid 12 and a half days applying to jobs that never existed.
There were a lot of people I've driven in Uber and friends of mine who said I should start a podcast about this, so that's what I'm doing.
I'm calling it "We're Moving Forward." It can apply to anything — as in self-improvement and becoming better in different aspects of life, entrepreneurship, or fitness. The verbiage comes from the boilerplate rejection letters I always get. You know, "We're moving forward with another candidate."
It's taking something negative and turning it around and owning it to make it positive.
Networking while driving for Uber
I've continued to try to network. What's surprising is there has been some good stuff that's come from driving for Uber — just from people being in my car. In my last full-time job, before I got laid off, I worked at a consultancy.
Not too long ago, I gave a ride to this guy in downtown Portland. It was about a five-minute trip, but he said he was in town for work. I asked him what he did and he said he worked for this big consulting company. Immediately, I was like, "Oh, my God, I've probably applied there a dozen times in the last year or two."
So I told him what I'd done in my prior work and gave him my card. He contacted me and said, "If you see any posted positions, let me know, and I'll give you a referral." I thought that was awesome. I saw one posting for a job that was a good fit. So I messaged him. He sent me a referral link, and I applied to it. I still got the automated rejection letter within a day or two.
I've also made connections at Adidas and FILA while driving. I recently had three people in my car from another top consultancy that I've applied to a handful of times. And I had a referral from someone who works at Amazon. It's been really weird that now these connectors are coming from Uber.
A futile search
Since I've been in this job search, I've had my résumé professionally reviewed nine times. It was sometimes through universities I've gone to or by recruiters who messaged me on LinkedIn and offered to help.
I have been doing some consulting work here and there around business intelligence. This is so I don't have a gap in my résumé because it's been almost two years since I've had a full-time job.
Looking at the spreadsheet I keep of my job search, I applied to 254 jobs in January. By May, it was down to 129. Then, in August, it was down to 41.
It's not because I'm being more thoughtful about it or targeting specific companies. It's because it's futile.
It's so frustrating to try to do this when the outcome is the same every time. I know that for every application I submit, I have a 0.55% chance of getting a phone screener and a 0.28% chance of getting an interview for each application that I submit, according to the database I've kept.
Even when I do get a screening call, some of them aren't legit. There was one woman who wanted 10 years of experience with a certain software program, but it had only been around for six years.
So, my job search is trending down. I'm at 2,181 applications. I've spent some time thinking while driving around, tried to do some meditation just to keep my sanity, and talked with close friends. I've decided I have 19 more applications left in me.
When I hit 2,200, I'm just going to stop applying for jobs. I just don't have it in me to continue to do it. It's either God or the universe or source energy or the Great Pumpkin or whatever telling me that I don't need to have a job. So, I'm just going to stop applying.
It's not like I'm shotgunning my résumé out. They're jobs I know I could do. I've been applying to everything from entry-level business analyst roles all the way up to director of business intelligence or market intelligence. I get more traction on the upper end and I've had a couple of phone screeners and interviews for roles like senior manager or director level.
I'm going broke
This isn't how I expected things would play out. I'm careful with money and finances. After my divorce was finalized more than two years ago, we sold the house. I had a good amount of money left over from that. And then I had my investments, my 401(k). For the first year and a half of being out of work, I was just applying to jobs nonstop and trying to hang on to that money. I thought I would use it to buy a house as soon as I got a job.
I didn't think that after almost two years, I'd still be looking. Rent is almost $3,000 a month here. Plus, I've got a kid. She wants back-to-school clothes and has other needs.
So, a couple of months ago, the money was gone. I was completely broke and starting from scratch at 43 years old. I had no other option but to go drive Uber and do Taskrabbit.
But one thing I'm looking forward to is my podcast. I've made the intro and am working on other episodes. I've had conversations with people I've met through Taskrabbit. And there are a couple of HR professionals who want to talk about their side of things, too. They're having a hard time finding people.