I Just Ended My Career

I am officially a full-time Substack writer after 13 mediocre years in tech. Please clap.

I’ll get into the story and the details of what happened, but first I’m letting you know that to celebrate this big milestone, I’m offering a 20% off discount on all annual subscriptions!

If you’ve been following this Substack for a while, you’ve probably figured out that I have a…uhhh…complicated relationship with work, in part because I get fired way more than your average person, which explains this reaction to the above tweet:

From an early age, I wanted to be a writer and a mom, and never had any plans to work a 9-5 (of course, most kids don’t—although there was a girl in my high school who was weirdly passionate about hotel administration.) My dreams continued into my teen years, and by the time I was in my twenties, I was faced with reality: I graduated in a recession, I didn’t have a trust fund or parents who were going to pay my rent, and there was no Comedic Novel Factory that would employ me as a full-time writer. Unrelated but equally devastating, bandage dresses were going out of style. Anyway, I had to get with the program and get a job.

Because my husband Nick (then boyfriend) was a year ahead of me in school, he was already working on his startup in San Francisco when I graduated college. I immediately moved out to be with him. I started working in tech (specifically sales and account management) mostly because that was the main industry there. Although I still had dreams to write (at that point I wanted to be a novelist and was working on an absolutely awful young adult novel called The Gilded) I knew how hard it was to make money that way, and I anticipated I would probably continue to work in tech for a while. And I did—for thirteen years. Up until yesterday.

Presenting, The Gilded

Obviously, I experienced many ups and downs in the tech industry, given that tech attracts very ambitious, type-A types, and I was only doing it for a paycheck. At times, I tried to “trick” myself into being excited about my work—usually by parlaying my writing or comedy abilities into things like leading live training sessions—but it never stuck. For one, I’m just not good at doing jobs. But also, I had pretty bad OCD, which centered around a fear of having to travel away from Nick, in case something happened to him. At multiple companies, despite confirming zero travel at the offer stage and going through the HR process of “reasonable accommodations,” I was more or less fired for having this limitation.

My issues at these tech companies weren’t just about my lack of interest and my OCD. My social skills or lack thereof were a major problem too. Remote work (which I’ve been doing since 2019) helped me a great deal in this area, because it put an end to mandatory socialization, which at one point included a field day with an inflatable obstacle course. Of course, I still found ways to alienate people over Zoom, but it took longer.

When I professionally published a novel in my late twenties—which I promise was better than The Gilded—I thought I might be looking at the end of my tech career, provided my book took off. And not only did my book not take off, it did so badly that my agent told me to “take a break from writing” for…a few years.

CHH—which started as webcomics drawn in my uniquely bad style—was a coping mechanism to deal with the book’s failure, among other unfortunate events in my life around that time. I’m writing about that in more detail on Monday, so stay tuned. But anyway, I didn’t anticipate that this hobby would become a full-time writing gig, or even involve writing at all.

Now, some of you following my job drama on Twitter might have noticed that earlier this year, I mentioned being at a company that I was certain would fire me, and then quitting that job to beat them to the punch. Those things are true, but what I failed to clarify was that I quit that job for another job, under the impression CHH wasn’t growing fast enough for me to do it full time.