Simon Says... Here's The Ugly Side Of Freelance Life

On *not* setting yourself up for success.

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).

You know those times when your schedule is lighter than usual because you did a lot of prep work to help yourself and so you look back at your past self all proud like, “wow, thanks past self, you really set me up for success”? Yeah, this is not one of those weeks for me. In fact, it’s the opposite. Past Rachel somehow thought it was perfectly fine to put a ton of story deadlines over the same upcoming three-day window, meaning that I’ve spent the first portion of this week working at warp-speed to get things done on time and may still have to ask editors if I can push a few deadlines, which I really hate doing and try to avoid as much as possible. Bad, Past Rachel. BAD.

As a freelancer, one of the things I pride myself on is organization. I’m generally (note: generally) very, very good at keeping track of all my deadlines and spreading them out far enough apart to not cause any stress. Not this time, though, Maybe I was distracted with wedding stuff, or maybe I just said yes to too many things, or maybe I simply had a brain freeze and couldn’t read a calendar. Whatever the reason, I messed up, simple as that, and now I gotta deal with the mess I made.

There’s so nice bow to wrap up this story—I’m stressed about all the assignments I still have to get done, and annoyed at myself for causing this avoidable situation. But I’m sharing it with you all because it’s a real, not-pretty side of freelance life; when you’re in charge of making your own hours and choosing your own workload, you don’t always get it right.

But ya live and you learn, friends. At least, I’m trying to, so Future Rachel doesn’t kill me.

Anyhow, onward:

Some Stories I Wrote Last Week

For NBC News THINK, I wrote a pretty personal op-ed about the importance of Amy Schumer revealing she has trichotillomania, aka compulsive hair-pulling disorder—more on that in the next section.

In less serious news, I spotlighted Amazon’s Mother’s Day jewelry sale that’s ongoing until the holiday and has big deals on rings, earrings, and so on for People.

Also for People, I made a list of some of the best items from Amazon’s cottagecore home decor section, ranging from lamps to throw pillows to picture frames.

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 NBC News THINK op-ed on Amy Schumer’s trichotillomania reveal.

I haven’t watched Amy Schumer’s autobiographical Hulu series Life & Beth, but when I read that there was a scene in which the comedian’s younger self was diagnosed with trichotillomania, I was immediately intrigued. Like millions of others, I’ve pulled out my own hair (eyebrows, in my case) for years, yet have rarely talked publicly about it due to the stigma and shame around the super under-discussed condition. A celeb with as big a profile as Schumer opening up about the disorder is a very big deal, and after reading more about her experiences, I was inspired to write an essay about why her comments matter so much. I pitched it to my editors at NBC News THINK, and we went through a few rounds of edits to tighten up the wording and add more context in before the piece went live.

I don’t often write things as personal as this op-ed, but I’m really glad I did. I’ve heard from several readers who also have trichotillomania about how glad they are that more light is being shined on the condition, and how grateful they are for both Schumer’s show and my story. I’m happy I could do my part.

Other Work/Life Stuff Of Note

Here’s your weekly reminder that you can pre-order my book Pickleball For All right now from Amazon, Target, Barnes & Noble, and tons of other places! Even if you’re not a player yourself, get it for your pickleball-loving friends, relatives, and neighbors. There are so many of us!

Also, I met a corgi this past weekend named Butters. He is perfect.

rsimon113

A post shared by Rachel Simon (@rsimon113)

Coming Up…

Just a few more weeks until my next Creative Nonfiction class starts on May 18! You can sign up here if you live in the Raleigh area.

Also, if you’re in need of Mother’s Day present ideas, I have a few gift guides going live in the coming days! I’ll share those on my socials and in next week’s newsletter.

Alright, friends. Thanks as always for reading, and reach out with any questions, comments, complaints, etc!

-Rachel