Fearless & Careerless (Episode 2): The Agile Almost-Academic
Meet Sarah. She's the embodiment of a scrappy millennial side hustler looking to make it as a writer (of all things).
INTRODUCTION:
I’m back with another over-educated, underemployed, independent woman that you’re going to love to meet.
Sarah is a kind, patient person that will go out of her way to help the most desperate job seekers out there. She responded to her layoff last year by starting a job-search group with friends and colleagues. If you don’t know what a “job-search group” is, consider yourself old or one lucky young fucker.
How do I know her? Well, I confused her with one of the many soulless gatekeepers conspiring to keep me unemployed. Since she got laid off, though, we’ve become kindred spirits. Millennial misery loves company.
MMM: Welcome, Sarah.
Sarah: Good to be here. I’m glad I didn’t write you off when I first got your random email about how everything job-search related is a massive fraud. You’re more reasonable in large doses.
MMM: Yes, I’ve gotten into a lot of trouble for writing ill-advised emails—starting in college when email became popular. This whole Substack is a consequence of writing while angry (or WWA). But let’s talk about you.
Sarah: Sure. What do you want to know?
MMM: Well, first, I heard you got a new gig. Tell me about that.
Sarah: So, I started contracting full time for a startup I'd been freelancing for over the years. It’s a good fit.
MMM: Excellent. What I really find interesting, though, is that, like me, you’ve been dabbling into writing. Is that a new interest?
Sarah: No, I’ve always been a writer. When I was at UC Santa Cruz for undergrad 15 years ago, I taught writing as a TA and tutored ESL students. I was interested in teaching writing as a professor, which I (mistakenly) thought would give me tons of free time to write novels, but I had a lot of self-doubt. I didn’t think a graduate program would accept me right away, so I went off course a little and got an editorial assistant job at a magazine.
MMM: That’s still writing at least. I was a journalism major but never worked in journalism after college—unless you include what we’re doing now. Which I don’t.
Sarah: Well, it didn’t feel like much for me either. I started at $10 an hour and was living with my mom in San Francisco, which is a very expensive city. I didn’t have a car, so it took me over an hour and multiple buses to get to my editorial assistant job . And I wouldn’t have landed the role at all if it wasn’t for my stepmom, who had a connection to the magazine. I had been searching for a long time before that.
But I wanted to be a writer, so I kept at it for a while. Even after a raise, the pay was too low for me to support myself, so I moved with my then-boyfriend—who had just gotten laid off—to New York, where I thought the job market would be better.
MMM: New York?! How could you think that? Was it better?
Sarah: No, it was worse. I had to start a whole new professional network and string together freelancing work. For one job, I had to write more than 500 descriptions of hotels for Priceline.com. I was always broke and had to borrow money from my mom.
MMM: This is sounding more and more like the millennial curse. Sucks ass.
Sarah: Yep, so I ended up finding my way back to grad school. I started a PhD program at the University of Texas and picked back up on the dream of being a professor. However, it became clear that academia is basically a cult.
MMM: Did you have to give up all your earthly possessions?
Sarah: Not quite. But I knew I’d have to accept 50k a year after spending ten years in school making nothing. I applied for roles that paid better, but they didn’t work out. I didn’t do that bad with interviews, given that most academics apply for hundreds of roles across the country before landing one. But it felt like a dead end.
I took up freelancing once again—for low pay (once again). I did that until I got laid off last year (once again).
MMM: Gotcha. Before we get too far off the subject, what would you say to those thinking about getting a PhD?
Sarah: I have a lot of friends still trying to find jobs as a professor, taking on adjunct stuff, and barely scraping by. People like me got out when they realized it wasn’t going to happen.
I studied rhetoric, which is teaching writing and argumentation. I did that because I thought it was going to be a more practical choice. I really wanted to do French translation and surrealism. I wish I had just gone that route because any way you go is a crapshoot. It’s a lottery. There are so many smart people who are really into what they’re studying. The people who do well get lucky but also are all in on their thing. But some people who are all in on their thing still don’t succeed.
MMM: Sounds pretty bleak. You’re making me proud that I didn’t go the PhD route. I strongly considered it six years ago. I was trying to study in New Zealand but didn’t get a scholarship. And the program was in peace and conflict studies, so I said “fuck that”—not literally. Even then it felt naive as hell. I think going into tech was the better choice, even though I mostly regret it now.
Sarah: We both gave up on our dreams and went into tech.
MMM: Indeed. We suck. Or I’ll speak for myself at least. People say I was brave for quitting tech, but I was a coward for getting into it.
I’m curious to hear more about your relationship to work in general and if it’s evolved over the years.
Sarah: For a long time, it was “live to work.” I have always been a worker and an achiever. I remember in college my friends were all working in retail. One of my friends told me that her dad always said, “You’re not supposed to love your job. That’s why they call it work.” I thought that was crazy at the time.
You spend so much of your life working, so the concept of decoupling your identity from work was initially difficult, but it’s become more and more necessary as I’ve gotten older. I think academia is similar to tech in that people ARE their jobs. I feel a little bit “live to work,” but I’m getting fed up.
MMM: But not fed up enough to give up entirely and just write I assume?
Sarah: Not yet, but if money weren’t an issue that’s what I would do. I have support from my family, but I can’t afford to just quit and write a novel.
MMM: Yeah, I wish we lived in a country that gave a shit about creative types. It would feel great to get paid an hourly wage to produce meaningful words. I’d do it all the goddam time if that were the case.
As we wrap up, though, I’d be curious to hear an unemployment-related horror story. Whadaya got?
Sarah: It’s hard to pinpoint one story. My whole life after undergrad has been so underemployed and stressful. I’ve never felt comfortable with just one job, etc.
Two things come to mind. The first is I once tried to buy a couple cans of soup in New York when I was underemployed, and my card bounced. I opened my wallet to get cash, and all I found was a button. This story is completely true. I called my mom crying a lot those days.
Second, more recently, the unemployment people in Texas took five months just to respond to my initial claim when I got laid off. It was so fucking convoluted. They had to send a letter to my employer confirming I had been employed and claimed my employer responded late—which I’m sure is true because they sent a letter in the actual mail. I can’t imagine how anyone who doesn’t speak English as a first language could navigate that process. I didn’t end up needing the money, but otherwise I would have been screwed.
MMM: Ooh, I hate those unemployment insurance bastards and their retrograde ways with a passion. I wrote about them a while ago. I wouldn’t be surprised if they’re still using floppy discs in some states. Even when they call it sounds like they’re on a pay phone. One time I emailed to complain that the system was down, and I couldn’t submit my “weekly job search report” as a result. I got a response about two weeks later saying, “Sometimes it works, sometimes it doesn’t.” No fucks given.
Sarah: Gotta love that.
MMM: Yeah, I was thinking I should stop paying my state taxes. Fuck Virginia. It’s not for “lovers,” it’s for technically challenged, unhelpful asshats.
But on that note, money is time. I should give you back yours.
Sarah: Thank you. This was fun.
CONCLUSION:
Sarah is indeed a kindred spirit. Her story is the same as mine except that she’s better educated and grittier. (I mix with freelancing and job precarity about as well as oil and water.) I told her that if she ever decides to write her novel, I will give her as many free critiques as she wants—in the form of long, rambling, ill-advised emails. Write on!
If you’re wondering why this isn’t in audio form, I’m (still) working on it. Stop wondering and start helping—goddam it.
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