Simon Says... Let's Talk Money.

Having a successful freelance career is hard, but not impossible.

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).

When I first decided to go freelance, I knew the biggest risk I’d be taking was no longer having a set income. How much (or how little) money I made was totally up to me, which meant that if I slacked a bit here or there or had trouble getting pitches accepted some weeks, it could make a real, not-so-fun difference in my bank account. So, I picked a number that I wanted to hit by the end of the year, and set it as my goal. It was an ambitious number—higher than what I was making full-time at Meredith—especially for my first year, when I was still going to be gaining my footing and figuring out a regular workflow. Nonetheless, I was determined to reach it.

The first few months of freelance life, I made way less than I hoped. Although I sold some big stories, I had trouble connecting with editors and garnering higher rates for time-consuming articles. I wasn’t in any immediate financial trouble (I had plenty of savings, and Kurt’s job, too), but the slow start made me panic that I was never going to even come close to hitting that number I’d set. That going freelance was a mistake, that I’d always have to work overtime just to make half of my old salary.

Slowly but surely, though, things started to change. By winter, I’d managed to score multiple consistent assignments each week and sell numerous stories to high-paying outlets. Plus, my Etsy puzzle side business had started to gain more traction, and I’d lined up a few classes to teach, too. One particularly good month, I surprised myself by matching my previous monthly income. The next month, I overtook it.

By early this year, hitting that Big Number didn’t just seem possible, but likely (selling a book certainly didn’t hurt, but it wasn’t the primary factor). I was writing more stories than ever, teaching frequently, offering 1:1 workshops, and creating several custom puzzles a week. Now, halfway through the year, it’s looking like I’ll reach the number by October, maybe even September—months earlier than expected.

I’m sharing this all not to brag, but to say that while having a successful freelance career is hard, no question, it’s not impossible. For me, it’s been largely about pitching outlets I knew paid well, forming reliable relationships with editors, and marketing my skills outside of writing. I’ve put in a lot of hard work, but I’ve also stayed true to myself and known my worth. If I take on a story on a topic I don’t care much about, I make sure I’m getting paid well for it; similarly, if I agree to write an article that does pay crap, I only do it if it’s a story I’m truly passionate about.

If you’re thinking about taking the freelance plunge but are worried that it won’t pay off, trust me: It takes time, but it can. And it feels damn good when it does.

Some Stories I Wrote Last Week

Two stories for People, one on a limited-edition Supergoop SPF kit and another on all the major grill sales happening at Amazon, Target, and more retailers right now.

For Travel + Leisure, I wrote about the workout sneakers Jennifer Garner (and many others) are obsessed with for their comfort and support.

And over at Daily Paws, I made a fun little list of signs that your dog is seriously spoiled (#guilty).

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 People story about the Supergoop SPF kit.

A lot of the time when it comes to ecomm, I’m assigned to write about products that I don’t have any particularly vested interest in. This is fine! I do my research, look at tons of reviews, and come up with enough things to say about the item to use in the story. But sometimes, I get the chance to pitch a story about a product I really do love, such as Supergoop’s SPF kit.

I’ve been a fan of the brand for a few years now (their face sunscreen is the best), and when they sent me a sample of their limited edition summer skincare kit, I was super excited to try it out. As expected, all the products work and feel great, plus they came in a super cute, well-designed package. I decided to pitch a piece about the kit to my editor at People, and she was immediately on-board. It was so satisfying to be able to highlight products I really do use and love, and encourage others to check them out, too!

Other Work/Life Stuff Of Note

Just over two months until my book, Pickleball for All, comes out. Pre-order your copy here and look at how pretty some of the promo images are!

Coming Up…

Reminder that I’m teaching a six-week Creative Nonfiction class via Zoom and a four-week personal essay course in Raleigh, both starting in July. Let me know if you have any questions!

Also, I am *very* excited that Season 2 of Only Murders in the Building is back, and I plan to binge the first two eps this weekend. This show is perfect, as are all of Selena Gomez’s sweaters.

Alright, gang, that’s all for this week. Until next time!

-Rachel