Media broke my heart

A special Valentines Day newsletter update

It’s been a little over a year since I started freelancing for the first time—albeit with a nice six-month break to go in-house and do app stuff at the Times—and there is nothing I like doing more in this newsletter than being completely candid about how things work in this here media industry, so I figured I would do a little retrospective about what it’s been like for me personally.

I think I should probably preface this with—I don’t know. Not a disclaimer, I guess, but a note unpacking how lucky and privileged I’ve been so far, in my first five years of quixotically attempting to be a journalist. I went to a good public high school, and then I got into a good private college with a journalism program, and even though I will die with my debt, and even though I could never do the unpaid summer internships in New York impressed upon us throughout college as all-important for our careers, just being there gave me an edge. I have other edges: I may have grown up working-class, but I’m a cis white woman, which comes with all of its own privileges. The first apartment I lived in in Brooklyn, which I found through a classmate from Syracuse, was a $450/month room, a godsend when I was making $13/hour as a post-grad intern. I worked at a media startup first, and I was there when it sold for a lot of money, and then I went to work for a legacy magazine, and when it looked like layoffs were looming, I left. My instincts may have been good, but maybe I was just lucky too. More than half of my friends have been laid off in their short careers already. I just opted to unemploy myself last January.

Last year, I made $21,000 freelancing, per my own book-keeping and tax-doing. This is the result of about four or five months of work, if you consider that I spent one month of 2019 working at and then leaving a media company, and then six months at the Times, full-time. $21,000 feels both like a lot (I made $0 freelancing in 2018, and I’m sort of in awe that I could sustain even part of myself on freelance income) and not a lot at all (in New York it’s simply not livable; my salary at Vanity Fair when I left was about $72,000 and my annual salary at the Times was about $120,000). That $21,000 I made last year from freelancing came from longform feature writing, shorter pieces, some editing work I did for Conde Nast, copywriting, and ghostwriting.

But here’s the thing. I don’t want to freelance—I never have. It’s not sustainable for me. I need to go to an office and work with people. It’s all I’ve ever done. I just know this about myself, and I know how bad I am at things like “saving money for taxes” and “getting out of bed every morning if I don’t need to” So starting last fall, when things were winding down at the Times, I started poking around, looking for work. A man at the New York Post even wrote a post letting everyone know I was looking for work. It must have been a slow news day! Who can say for sure. Anyway, in December I decided I would spend every day of January, February, and March applying for jobs. Initially I told myself I’d apply for a job a day, but are you familiar with the tedium of cover letters? Or the need to do other work? So I scaled back to a goal of 2-5 applications a week, and I’ve been applying to jobs in journalism and outside of journalism. I follow up on every lead someone sends me. Nothing has really stuck yet. On my worse days I’m sure that it’s personal and that there’s something very wrong with me, and that’s why I still don’t have a job. There’s no other way for me to personally justify why three different media companies over the past year extensively interviewed me for weeks and asked me to take long, considered edit tests for jobs, only to ghost me without explanation, or why HR departments on screening calls seem to think I’m being unreasonable when I say I’d maybe like a salary of more than $60,000, and no, I can’t go lower than that. On better days, I know rationally that this industry is still a mess, and HR departments are a mess, and hiring takes time, and it’s all an imperfect science, and I’m being impatient. I still feel bad those days, but less so.

Prior to this past year, I’d gotten my jobs by employers reaching out to me and rarely had to deal with the banal and inevitable sting of rejection. It’s a lesson I never had to learn early on: I got into nearly every college I applied to, and in college I acclimated easily because I didn’t try that hard. I interviewed for an editor job at an on-campus magazine after calculating how risky it was (not very), and I got it easily. This kind of repeated itself for four years: I never put myself too far out there to be rejected so I never got rejected, and I never got too disappointed. Now I feel like I have nothing to lose, and I’m more willing to put myself out there. That combined with the volume of qualified and talented writers applying for the same jobs I’m applying for, along with the sensation that media is always sort of consolidating even if everyone appears to be hiring just leads to a lot of nos—for me and for everyone else, too.

The bottom line is that I just need a job, and I’m getting less fussy over time about what that job is, and it’s new to me to be in a position where I’m at the mercy of an application process to get a job. Still, I’m not convinced anyone has ever gotten a media job by simply applying to it; I know from being in-house at different media companies that legally or to comply with union rules, companies post job listings all the time and already have an internal or external candidate in mind for the position, rendering the listing a formality. When you see a listing and then see someone get hired to that role a couple weeks later, it isn’t because they applied online and got hurried through the interview process, it’s because the company wanted to hire that person. Of course, this is cold comfort when you’re not the person they want, and it feels like all you can do is continue to feed your resume and a cover letter to an HR website, or the occasional well-intentioned acquaintance who knows you’re looking.

This is a long way of saying: I’m still freelancing a year later, though not entirely by choice. I’ve always known this to be true, but if you’re really determined to survive in an industry that’s constantly beating the shit out of you, you have to be sociopathically determined to stick out the bad parts and accepting of the premise that the good parts can disappear overnight (or you have to have generational wealth. Either one). I’ve always prided myself on having these qualities of adaptability, but now, I’m just kind of tired.

Still, I’ve been working on a number of features, and when those stories are published, I’ll be excited to share them with you. I’m not going anywhere quite yet.