celebrating six months of full-time freelancing!

Plus, an upcoming webinar for my fellow freelancers

#WednesdayWisdom

“I am my best work—a series of roadmaps, reports, recipes, doodles and prayers from the front lines.” ~ Audre Lorde

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Morning Musings

On my vision board, which is taped to the wall behind my desk, I have the word “entrepreneurship” in bold black letters. I cut out the word during my friend Aisha’s virtual vision board party as a visual reminder me for me to keep going.

On September 1, 2023, I quit my full-time reporter role at Fortune. The truth is I was burned out, depressed and highly anxious. Something had to give. I’ve also found myself in this pattern before: start a new job; bust my ass for a promotion that will never come; become obsessed with getting said promotion; burn out. Wash. Rinse. Repeat.

As some of you may recall, this isn’t my first rodeo with full-time freelancing. I quit my nonprofit PR job in December 2020 in the midst of a global pandemic and IVF cycles. I’ve never considered myself much of a risk-taker, but that’s definitely been one of my riskiest moves to date (though for full disclosure I had $30,000 in savings at the time and joined Jeff’s health insurance).

But barely a month later, I panicked and started a part-time role as the senior mental health editor for YR Media (a fab media nonprofit for young people). It remains the most diverse newsroom I’ve ever worked in and I’m super proud of the work I did while I was there, and yet I couldn’t help but feel like I wasn’t fully walking in my purpose (despite simultaneously writing a book encouraging other people to trust their dopeness).

I quit…again (are you starting to notice a pattern here?) and went back to full-time freelancing. Until I went on maternity leave. And we decided to move back to Chicago. And we needed two full-time incomes. Which is when I joined Fortune six months later.

This time around, however, I’m determined to do things differently. This time I’m determined to give full-time freelancing my all. At least for a year, then we’ll reassess. Which is why “entrepreneurship” is on my vision board and why this six-month milestone is a BFD.

I’ll be the first to admit the first three months were pretty rough (hello, Target meltdown). But these last three months I’ve started to find my footing and make the mental shift from freelancer to entrepreneur, thanks in large part to my coach

Jenni Gritters

, therapy and Zoloft (more on that in a future newsletter).

The biggest difference is freelancing used to my side-hustle…something I did in addition to my full-time job. Being an entrepreneur requires me to think of myself and my brand as a business…and build and move accordingly. The shift has been a slow one, but a shift nonetheless. And I’m grateful I get to pay my bills and contribute to our household doing work I love (most of the time).

Now I’m going to share how I do it. Later this month I’ll be hosting a webinar all about pitching. Pitch Clinic: Level Up Your Freelance Writing Skills is perfect for those new to freelancing. Using my 16 years of editorial experience, I’ll teach you how to craft compelling pitches; build relationships with editors; negotiate rates and so much more. Plus, you’ll receive a personalized pitch review with yours truly. As a reminder, paid subscribers get 20% off ticketed events (feel free to email me if you can’t find your promo code). Are you in?

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ICYMI

I had the pleasure of first meeting John Caleb Pendleton, founder and creative director of the Chicago-based floral company Planks & Pistils, at a coffee shop back when Jeff and I lived in Rogers Park. I came for the quiche (baked by his lovely wife, Kari) and stayed for the camaraderie. I interviewed John back in 2022 for a Fortune article about Black men and mental health, but this time around, in my first story for Design Observer, the focus is all on him, his artistry and Black joy.

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Upcoming Events

• March 10: Yoga for Fertility Community Class. If you’re curious about my Yoga for Fertility series, but missed the last one you can join me this Sunday for a free community class at Pulling Down the Moon in Chicago.

• March 19: Embracing Imperfection Workshop. In this interactive, virtual event, I’ll join Lauren Strayhorn of

  Notedd
  and certified mindset + leadership coach Sam Cartagena for a candid conversation about redefining success and reaching your full potential through self-acceptance and compassion.

• March 27: Pitch Clinic: Level Up Your Freelance Writing Skills. If you’re ready to kickstart your freelance writing career and land your dream bylines, join me for this hourlong webinar.

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Links I Love

• The complex battle between Black hairstylists and their clients (NBC News)

• Issa Rae’s Rap Sh!t made the grit of Florida girls gleam onscreen (Teen Vogue)

• How ‘Supernova Momma’ is using her platform to center disability in Black History Month (The 19th)

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Now Hiring

1. Communications Manager for Slate

2. Speakers Bureau Manager for Represent Justice

3. Director, Marketing and Communications for Youth Guidance

4. Part-Time Writer for Lit Hub

5. Staff Writer for Washingtonian Magazine

6. Grant Writer for The Mariam Foundation

7. Project Manager, Community Engagement & Diversity, Equity, and Inclusion for WTTW

8. Director, PR & Social for Babylist

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Get Your Official SWFP Merch!

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Thank You

A special thank-you to April, Jeff, Carol, Cait, Amanda, Harleen, Megan, Najja, Jessica, Priti, Cat, Jenna, Mallory, Rachel, Angel, Sarah, Camesha, Vix, Anna, Stephanie, Dominique, Tiffany, Emily, Mabinty, Lindsey, Casey, Lynnae, Dani, Amanda, Raina, Abigail, Sharon, Kristen, Heather, Renae, Jennie, Brittaney, Kyndall, Sarah and Cecilia for becoming paid subscribers and helping to fuel this newsletter. I truly appreciate your support! 💜

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