Back when I graduated college, I thought landing my first job would be cake. My assumption was that part of the deal of attending a “good” university was that it’d be easy to find a job. I was very naive. 

I remember taking it easy the summer after I graduated. I’ll let the companies start competing for my services in the fall, I thought. When September 2000 rolled around, I began poring over the LA Times classified section, circling jobs, and applying digitally on this new thing called Monster.com. When I didn’t get any callbacks, I began to realize the gravity of my situation. I was an English major without a post-graduate plan that didn’t even know what jobs to look for. 

I interviewed at Entrepreneur magazine. They gave me a writing assignment to craft an article from a brief. I was very intimidated. As an English major, you’re taught Shakespeare, Milton, and Chaucer, not the finer points of journalism. 

In other words, I didn’t know what a lede was or where I shouldn’t bury it. 

I did my best to mimic the sports recaps I saw in newspapers and ESPN.com. I didn’t land an offer, but I distinctly remember the hiring manager calling me to say she was very impressed by my writing. She was shocked that I’d never done anything like that before. This wouldn’t be the last time I got poor results with a side of good feedback.

I eventually landed a job at a magazine publisher in glamorous Beverly Hills. My salary was a glamorous $25,000 a year with no benefits, no healthcare, no dental. Raises were frozen my entire two-year tenure.

Despite all that glamor, the lack of healthcare was an issue. Eventually I found my way to a magazine publisher in Orange County via staffing agency. Look, I’d love to tell you that partnering with a staffing agency is a great way to find a job. I’m sure it works for some people. This, however, would be the first and only time in my 20-year career a staffing agency came through for me, and I’ve had accounts with several agencies for more than a decade that specialized in placing creatives. I’m not the only one with a few horror stories.

Anyway, with health benefits secured, I spent the next 11 years mostly, kinda, sorta content. But in 2009 I got married, and in 2011, we had our first child. We jammed the baby’s crib between the wall and our queen-sized bed in the only bedroom in our apartment. The $40,000 a year I’d worked my way up to wasn’t cutting it anymore. It’d been more than a decade since I’d seriously explored the job market, and the landscape had changed dramatically. Circling classified ads had long since become extinct.

I applied for publishing jobs, but print was already on its death march. I came up with a plan that fit my desperation: spray and pray. Indeed.com allowed me to quickly apply to dozens of jobs in a variety of industries. I applied to anything for which I was remotely qualified. I remember being out to lunch with a coworker when I received a call from Experian. Never heard of them. Didn’t even remember applying. My coworker clued me in.

“Dude, that’s a legit company.”

Oh, word?

I eventually landed the job. I was hoping for $45,000 a year. They offered 60. I’d just won the lottery.

The job merry-go-round begins

I assumed this would be my next 10, 20 years. Then they changed CEOs. No big deal, I thought. Then the CMO left and wasn’t replaced. We didn’t talk anyway, I figured. Then my boss was let go. I knew back in magazine publishing that it was no good when the person that hired you fell out of the picture. I didn’t sense good chemistry with my new boss, so I put the spray-and-pray plan back into action. 

A place in San Clemente called. It sounded far away and sketchy. When I went to interview, the marketing department was housed in a darkly lit conference room. One guy was wearing a throwback Pittsburgh Pirates jersey. It felt like home.

I became their content writer, and it was the first time writing was my primary function. I had to learn to create, not just edit other people’s copy, and how to do so for an inbound audience. I went through some growing pains, but by year two, I’d figured some things out. My confidence grew.

Though I’d pictured myself at this place for the next 20 years, they switched CEOs. Uh oh. The CMO left. Shit. I knew where this was going. 

I entered another exhausting round of spray-and-pray applications. One opportunity brokered through a staffing agency seemed promising. I was asked to complete a writing assignment. The recruiter said I was the only applicant that aced it. This is in the bag, I thought. Oddly, he asked how I aced it. I explained my approach. I didn’t hear from him again. I have long histories of acing writing assignments and getting ghosted by recruiters. I’m not trying to hate on recruiters, but WTF?

Next, I finally got with the times by creating my own professional website and portfolio. It was easier than scrounging up PDFs of writing samples every time a company asked. I eventually landed a new gig. 

I intended to stay at this next place longer, but after a year, the CMO left and management changed — notice a pattern developing? Fortunately, I got solicited by another company. I wasn’t eager to upend my career again. My company matched the offer, so I stayed put. However, a few months later, they called again offering a larger payday. I had two kids and the chance to crack $100K. I couldn’t refuse. 

A few of us were hired because of success we had at a previous company, but the next six months were rocky. The execs wanted plug-and-play results. The head of marketing bolted within two months. I recognized the bad signs, but they were happening in fast forward. By month six, a little something called COVID-19 presented an opportunity for unhappy executives to cut bait on the whole marketing department. This was the first time I’d ever been laid off.

Out came the spray-and-pray playbook once again, but it felt like I could be doing more. I threw my spare energy into my professional website, which had gone mostly neglected. I wrote stuff I liked into existence: sports, video games, technology. Then I wrote a more personal post about the pains of being laid off. It got a lot of traffic, for me. One reader offered me a job. After applying to 74 jobs over three months with little traction, it was my blog that landed me my next opportunity. 

Though their intentions were good, the circumstances were unfortunate. After another six months, this company went belly-up and me with it. Bummer.

And now here I am again. 

I’ve applied to 105 jobs the past two-plus months: 14 interviews, zero offers. I wrote another modestly popular post, but no CEOs in shining armor have come to my rescue this time. Everything considered — a flooded job market, trapped at home with my family, and hundreds of thousands dead — it all feels insurmountable.

An audition too?

I made it deep into a hiring process recently and was asked yet again for the dreaded writing assignment. By now, I feel like Daniel Day Lewis having to audition for a role in a Hallmark Christmas movie. I don’t mean to be pompous, but if you have my resume, my portfolio, these blog posts, and we’ve video conferenced, why this hoop too? Is it really necessary for me to sink several hours into a written assignment that I won’t be compensated for and could result in a “Thanks, but no thanks”? I’ve gone through it dozens of times before and it sucks.

After toying with the idea of opting out of the assignment, I decided to play ball. I have no leverage, and I can’t afford to say no. Because this assignment was extremely light on detail, I decided instead to submit an outline of content pieces I’d pursue and how I’d go about obtaining the detail I’d need to actually write them. It ended up being a nine-page document. A couple of days later, they complimented me on the outline, but asked if I could still provide an example of the content I’d write anyway. Without any substantive information at my disposal, I was irked that they were essentially asking me to write a fluff piece. Easy enough, but what would that prove to them except that I’d roll over when pressed?

So I submitted their pretend blog post about nothing in particular. That landed me another interview but within a few days, I was informed they would not be moving forward with my candidacy despite feeling my “written work was particularly impressive.” 

If you’re scoring at home, my strategy outline and writing were “impressive” for this strategy and writing job, but they passed. That’s after I put something like 16 hours into interviews and labor. I’d love to tell you that I didn’t write this entire blog post just to complain about this one incident, but I mean, just look at the title.

You may want to give hirers like this the benefit of the doubt.

You didn’t give them the fluff piece they requested in the first place.

True. Then just cut me loose. Don’t ask for more.

They were probably letting you down easy by complimenting your writing.

Could be. But this was far from the first time a hirer went out of their way to compliment my writing while concluding our business.

Maybe you didn’t perform well in your interviews.

That’s my conclusion too. It still doesn’t sit well with me that I did good at writing for a writing job but didn’t get it. It’s like vetting then rejecting a heart surgeon because you didn’t like his golf handicap.

Self help

Despite landing a steady amount of interviews, I haven’t been able to close. A couple of week ago I decided improve my interview skills. I identified two opportunities for improvement.

Tell better stories

You’d think as a professional writer, I’d be better at this. Following the advice of Madeline Mann, YouTube’s “Self Made Millennial,” I have stories of my experiences preloaded for each interview. 

I start by tearing apart each job listing in search of pain points. Most hirers repeat what they’re looking for several times in their post. For the jobs I apply to, they’re often looking for prolific writers of compelling content who incorporate metrics. Mann recommends preparing several stories from your career that address the hirer’s needs. I’m still working on my delivery — ironing out awkward transitions and lots of rambling — but practice makes perfect.

Show measurable results

Most jobs I’ve had measured success chiefly through internal approval. Does the boss agree with the spirit of the piece I wrote? If the answer is yes, job well done. On to the next one.

My work is rarely tied to objective results. Objectivity, however, is the language of the world we live in. Moneyball brought objective analysis (and a fun Jonah Hill gif) to baseball. Daryl Morey brought a similar sensibility to the NBA. Objectivity is what makes stat-heavy think pieces and infographics so appealing. It’s why we’re drawn to the election analysis of CNN’s John King like beatniks snapping their fingers at a poetry slam.

I reached out to a couple of former colleagues to recover some measurable results of my work. Most of it is anecdotal, but being able to say pageviews increased by 6,340 percent on web copy I wrote during my tenure is far better than offering nothing (that’s a real stat by the way). The end result, hopefully, is the interviewer noting, “Applicant claimed responsibility for big success.” Box: checked.

…

I’ve had six interviews since I began incorporating more storytelling and metrics in my responses. I’m still in the running for five of them. Fingers crossed that things will turn around soon. Although, two have said if I make it far enough, I will be asked to submit to a writing assignment.

---