Simon Says... We're Back!

Welcome to the new weekly newsletter from Rachel Simon.

Welcome to Simon Says, a weekly newsletter from Rachel Simon all about freelance life—from the inside scoop on just-published stories to advice on how to pitch to what it’s *really* like to leave a cozy full-time gig for the chaotic, unpredictable world of invoicing (jk, freelancing, but IYKYK). Thanks for reading!

We’re back, baby! As it turns out, I really like talking about myself (who knew?) so after many months away, I’ve decided to make a return to Substack and my lil weekly newsletter.

This time around, though, we’re changing things up, as you might’ve seen from the description above. Instead of a newsletter that’s about, well, everything inside my brain, Simon Says 2.0. will focus on all things freelance—writing, pitching, promoting, you name it. And that doesn’t only include article writing, as I also now spend my time teaching classes (on writing, because if you couldn’t already tell, that is literally my only skill), giving 1:1 consulting sessions, editing college essays, and creating personalized crossword puzzles (okay I lied, I have *two* skills. Go me!)

If you’re a writer and/or freelancer yourself, I hope you’ll find this newsletter helpful, and even if you’re not, I hope you enjoy getting a peek into what life is like for those of us who’ve made the wise and/or foolish (it depends on the day) decisions to leave full-time editorial jobs to strike out on our own.

And perhaps I’ll pepper in some non-freelance related thoughts from time to time, like what I think of that Jeremy Strong profile (brilliant/incredible/five stars) or why I need everyone to watch Yellowjackets on Showtime right now (spoiler: it’s because I can’t be the only one having plane crash-related nightmares every night. You’re welcome!).

So without further ado, here’s what I got in store for you today:

Some Stories I Wrote Last Week

Normally, this section will probably mention just one or two articles, but I had a bunch of things go live this past week, so here they are!

I wrote about Billie Eilish’s fifth Vanity Fair annual interview, in which the 19-year-old is more honest and vulnerable than ever before, for Shondaland.

Also for Shondaland, I wrote an essay/feature on why I love making friends with people way older than me and why you should do it, too.

For W Magazine’s “Family” theme this month, I looked back at the emotional whammy that is Six Feet Under Season 5. That Claire scene!

In the Triangle-based Indy Week, I reviewed Christopher Marley’s stunning Exquisite Creatures exhibit at the North Carolina Museum of Natural Sciences.

Last but not least, I did some ecomm stories for People, Real Simple, and Travel + Leisure about, respectively: Amazon’s new room design feature, a super-soft cardigan I adore, and the best totes under $100 at Nordstrom right now. Happy shopping!

The Inside Scoop

Each week, I’ll pick one story I’ve written (new or old, if needed) and explain how it got from pitch/assignment to publication. This week, it’s the Billie Eilish story above.

I first wrote about Billie Eilish for Shondaland a year ago, when the 2020 edition of the Vanity Fair video came out. So when I saw in mid-November that the 2021 one was on the way, I reached out to my original editor and asked if she’d want me to update the piece with details from the new video. She considered it, but eventually decided that it’d be more worthwhile for me to write a totally new piece focusing on the biggest takeaway from the 2021 video. And that’s what I did!

Other Work Stuff Of Note

I did a couple 1:1 consulting sessions this past week, and I’d like to remind you that if you’re looking for help with sending pitches and/or general freelance life (finding editors, self-promoting, figuring out rates, etc.), I offer two types of consulting on my website. Message me if you have any qs!

Some Neat Things That Happened

I made a custom crossword puzzle for Hank Green (!). He found me on Twitter, of all places, and requested a puzzle full of inside jokes between him and his wife, for them to do together over the holidays. I’ve been a fan of Hank’s forever (seriously, watch his TikToks), and it was an honor to get to make him a puzzle. Best of all, he tweeted YourCrossword a shoutout that got me legit two dozen new customers, so let’s all give a big thanks to Hank!!

(And if you want your own personalized crossword puzzle, especially before the holidays, get your order in now via my Etsy page.)

Also, I went to Hawaii! But that’s a story (literally) for another time.

Coming Up…

I wrote a few fun pet-centric stories that should go live sometime this week, as well as a few other articles I’ll stay mum about for now, to maintain some ~suspense~.

And that’s all for now, folks! I hope you enjoyed this revamped newsletter, and if there’s anything you’d like to see in future issues (they’ll be out weekly on Wednesdays), don’t hesitate to shout it out. Thanks for reading!

-Rachel