This whole post is about launching a paid tier. So, if you want to cut right to the chase, you can subscribe below. Monthly subscriptions are $5; yearly subscriptions get a 17% discount and are $50. All the deets and a whole lot of feelings are below.
I left my last full-time job in 2018. I’d worked in marketing for three startups back-to-back and was burnt out. My color-coded calendar was crammed with meetings, such that I needed to schedule things like eating lunch. I created more “fake meetings” to steal fifteen or thirty minutes to complete any actual task. Anything that took longer needed to be done after hours. I checked my work email first thing in the morning and last thing at night. I drank the #girlboss Kool-Aid.
I knew I wanted to leave that job but was overwhelmed by the prospect of figuring out what was next. I decided I’d take some time off: travel a bit, then try to pick up some freelance work until I was un-burnt-out, whatever that meant. I booked a bucket list trip that I wouldn’t actually take. I got a call the afternoon I was due to leave that my uncle was in the hospital. He’d had a low-grade, controlled cancer since I was in high school. The good kind, if there was a such a thing. But now, he’d taken a turn for the worst.
Instead of going to southeast Asia, I went to suburban Florida—alone—to watch him die. For a month and a half, I sat in plasticky chairs, first at the hospital and then at a hospice, reading on my kindle while listening to monitors ping, silently crying into my knuckles in public bathrooms, eating takeout from chain restaurants to self-soothe, before doing it all over again the next day.
By the time I got back to New York, I’d all but exhausted the time I planned to live off savings. Worse, many of my trip expenses were non-refundable, so I was paying for a ghost-trip I didn’t take. Luckily, before I left my full-time job, I had the foresight to send an email to my professional contacts telling them I was going freelance and had a couple leads in my inbox. I took the first two projects offered to me.
At first, freelancing was glorious. I could sleep until nine! I could grocery shop in the middle of the day! Any weekend could be a long weekend if I wanted! If my bosses wanted to invite me to pointless meetings, that was fine. They were paying me by the hour, they could feel free to waste my time!
2018 slipped into 2019, and I never revisited the idea of getting a full-time job. Plus, by then, Bad on Paper, the podcast I started with
and now co-host with was growing. Grace and I started touring the country doing live shows. The shows weren’t huge moneymakers when you accounted for travel expenses, but I had a blast doing them! In order to do this, I needed the flexibility freelance offered. I couldn’t be in Charleston on a Tuesday, Nashville on a Thursday, and Philly on a Saturday with a full-time job.But by the end of 2019, freelance had started to chafe. I complained to friends over drinks that I felt like a mercenary. I had a crew of work besties at every other job I’d had. Work was where I’d met some of my best friends (including my then podcast co-host). There was a sense of camaraderie. Sure, the hours were long, but we were in it together. But freelancing, junior employees I managed were wary of me; my bosses were drowning, hence why I was brought on in the first place. The flip side of getting paid by the hour was that there wasn’t much water-cooler chitchat, everything was straight down to business.
In January 2020, my friend Rachael and I started working on RomComPods—a series of audio fiction podcasts—as a creative lark. She’d long suggested we write a romcom, and I was deeply in need of a creative outlet. By the time quarantine happened, we were halfway through a script. Suddenly, I felt very lucky to have a steady-enough income via my freelance projects along with a new creative hobby that was lighting me up and proving a great distraction from the chaos of the world.
Writing scripts for RomComPods was my own personal story laboratory. I devoured craft books (Save The Cat! Story Genius!) and examined TV and movie scripts, picking them apart to see how they worked. I had a writing partner (who was much funnier than me!), so there was always someone to punch up my bad jokes and help brainstorm the plot problems I couldn’t solve alone. We’d work in tandem in Google Docs, writing and editing until the scripts shined.
By the end of 2020, I had the idea to tackle something I’d long dreamt about, but had always lacked the confidence and drive to pursue: writing a book.
I spent 2021 and the first three-quarters of 2022 writing and polishing what would become THE CHRISTMAS ORPHANS CLUB, all the while maintaining 20 – 30 hours a week of freelance work. There were so many times I was convinced the book would end up in a drawer, never to see the light of day. We took the book out on submission in October of 2022. I did back of the envelope math and told myself that if we sold the book for a certain amount, I could quit freelancing, which I was desperate to do.
I was sure it would never happen.
But lo and behold, things went better than I expected, and I did the thing they tell you not to do… I quit my day job. Do I regret it? Yes. No. Depends on the day.
Interestingly, the second I quit my day job, the leads on freelance projects completely dried up. And my freelance business was always very separate from my social media presence, so I don’t think it’s because they knew about the book. For five years, I coasted from project to project, working purely on a referral basis. But then… nothing. So, I’m not sure there’s a whole lot to go back to even if I wanted to.
2023 was a whirlwind of change, professionally-speaking. I edited my first book, started my second, learned about the book production process, and sat in the anxiety-ridden waiting period between finishing your book and it’s release. Then my book did come out! I promoted it. It didn’t make any best-seller lists or get any particularly positive trade reviews, but I’m still so incredibly proud of it. I got to experience the absolute thrill and joy of connecting with readers—MY PEOPLE—who enjoyed something I cooked up in my silly little brain. Truly, the rush!
But coming into 2024, I’ve been thinking a lot about work and money and social media and how I spend my time. I can say for certain that quitting my day job has put a lot more *STUFF* on writing my second book. I was incredibly mean to myself when the first draft didn’t come together easily (which, duh… it’s a first draft). I put a metric-ton of pressure on myself to start and finish a book in a year because that’s what other successful commercial authors do (some even do two or more! Witchcraft?). Spoiler: I didn’t make the year deadline.
(“Get to the point, Becca,” the hecklers yells. Oh, I’ve also started having a lot of conversations in my head with fake detractors.)
I’ve also been thinking a lot about how much time I spend on my phone and on social media, specifically. Metrics I do not feel great about. Coming into 2024, one of my goals was to put more time and effort into this here newsletter. For the past month, without any formal announcement, I’ve kicked up my posting frequency to weekly to see how it feels, and I’ve really enjoyed it. But the reality is that going from a haphazard cadence (bi-weekly, at best… sometimes nothing at all for months at a time) to weekly has taken some effort. So, I’ve been thinking about launching a paid Substack tier to help compensate me for that time.
Scratch that, I’ve been TERRIFIED about the idea of launching a paid tier. After all, what value am I creating that is worth your hard-earned dollars? You know what, I haven’t really figured that out either (but I’d love to hear your thoughts about what paid content you’d like to see in the comments).
So, this is a leap of faith. I’m going to flip this switch and see what happens. I’m going to try my best, but know I won’t be perfect. I’m going to stop overthinking.
There will still be free posts, too. Book rec posts will always be free. So, will any news about future books and occasional general updates.
I’m thinking of launching a monthly roundup for paid subs (I loved
and ‘s last month), more personal essays like this and last week’s. Maybe more frequent Q&A’s? Curated inspo posts? We’ll figure it out together.So, despite the jitters, I’m pressing send. Welcome to a new chapter.
Becca
I am more than happy to support your writing and work here on Substack! I've followed you for years (IG/the podcast) and your time and work DESERVE to be compensated for! Never second guess that! And as someone who has dreams (however far off they may seem!) to write more and maybe even a book someday (!!??), I'd love to hear more about your writing and publishing experiences, journey, insights, advice, etc! And I'm ALWAYS here for book recs! Congrats on this paid tier move!
Best of luck with this new venture! I am excited for you.