Sunday, October 9, 2016 marked a full year since I quit my day job to focus on freelancing full-time. I figured I should talk about my experiences, any lessons I’ve learned, and what I hope is next.

The Fantastic

I’ve loved the freedom freelance provides. I’ve loved not having to go into a predominantly white workspace the day after the news explodes with another black death and having to tap down the anger, resentment, hurt, and helplessness so no one would feel uncomfortable.

It’s been great building relationships with writers and critics I admire. I’ve tried my best to learn from those same people by studying their work and the work they praise.

People have blessed me with tremendous opportunities, like appearing on Another Round (twice) and Vulture’s TV Podcast.

I’ve been able to apply for fellowships and residencies I would’ve been afraid to go after while working my day job because of worrying about time-off or who would cover my responsibilities. As such, I was able to make a long-held dream come true and became a Callaloo fellow. I attended the 2016 Callaloo Creative Writing Workshop at Oxford University in Oxford, England where I worked with poet Vievee Francis. It was an amazing experience, and I finally got to add another stamp to my passport. Becoming a Callaloo Fellow helped remind me that I’m more than a recapper, that I’m still a creative writer and can do more than write personal essays or interview celebrities. All those things are fine and are dreams come true, as well. I remember when I was in high school, talking about Martin, A Different World, Frasier, and Living Single, I used to wish I could get paid to watch television, and now I do.

My freelance career began about 3 years ago when Shani O. Hilton of BuzzFeed asked me to write up a Twitter rant about how Olivia Pope and Abbie Mills were breaking down the Strong Black Woman myth on Scandal and Sleepy Hollow, respectively. Since then, I’ve written more for BuzzFeed, and The Toast, Vulture, Rolling Stone, Elle, and more. Some work I’m more proud of than others, but I’m always grateful for the people who allow my byline to join those who are far more experienced than I.

The Money

I was only 2 years into freelancing before I went full-time, and I was very nervous about the decision. Most people who freelance exclusively have a spouse or partner to help support them or a juicy nest egg, but it was just me. Living with my sister helped with expenses, but about 4 months in, I had to give up my car because there were already times I didn’t make enough to cover my car note, insurance, gas, and other maintenance plus cell phone and my household contributions. I live in Nashville. Our public transportation sucks. Not having a car is a pain, and I feel like a burden on family and friends. I often feel trapped, and when I have the means, I just order what I need from Amazon instead of trying to wait to borrow a car or tagging along when someone runs errands.

Hustling is key to freelancing. I still haven’t figured out all the etiquette. When I pitch something, I don’t know how long I should wait before I pitch somewhere else. I’ve had people respond the same day and other people respond after a month. Do I wait for a response or do I pitch multiple sites and whoever bites first, gets me? Do I pitch after I already have a full draft or pitch the idea and then write a draft? I’m still learning.

Right now, I’m waiting to be paid for a July invoice. This late payment has had such an effect on my bank accounts that even when I do get paid, I’m still in the red. There have been times I’ve had to ask repeatedly about a late payment. I hate having to do that because I don’t want to seem greedy, and I don’t want my contacts at the site to think “boy, she sure wants to get paid. Maybe we shouldn’t work with her any more.” It seems silly to think that people would get upset with you for wanting them to honor their part of the contract, but it’s a real frustration.

People don’t turn to freelancing to get rich, as far as I can tell, and that was never the goal for me. I said earlier I was doing this by myself, but that’s not true. I don’t know where I would be without my family and friends looking out for me, but I’m tired of being a burden.

The Fuck-Ups

Whew. I’ve had plenty. Missed deadlines. Panic attacks. Self-sabotage.

Artist’s self-doubt leads to anxiety and depression, and there are some months where I’m constantly fighting to avoid sinking beneath it all. I’m treading water right now, but unlike when I was younger and didn’t know how to deal with the overwhelming sensations, I know I can make it through all of this. I try to be more honest about what I’m feeling and reach out when I need help.

Where does the self-doubt come from? Oh, so many places. Fear that what I’m writing isn’t good, that I’ll be stuck freelancing forever, that I’m too old for anyone to hire, that sites won’t let me have certain assignments I know I would kill because I’m freelance, that I won’t get other kinds of assignments because sites only want me to cover “the black stuff…” I worry that writing about pop culture stuff is making me less creative. There’s a short story that’s bubbling in my brain but every time I sit to write it, I end up thinking about ideas to pitch. I’m afraid I’ll never get an agent or a book deal or sell a script. I’m scared I’ll have to return to my previous field of work, and I’m not a spring chicken any more. I worry I’ll never be able to afford living by myself again, that my missed deadlines have sabotaged various working relationships.

There’s a constant hum of anxiety. Some days are better than others, but, ironically, I’ve never been more professionally satisfied. I’m making a living, no matter how tight, as a writer. This is what I’ve wanted since I was 7 years old.

The Future

With film and television becoming increasingly diverse, I want to contribute to pop culture criticism as staff. I’ve been doing all this pop culture stuff from Nashville, and I think it’s time I moved to New York for whatever’s next. I worry about that because I’m far past the point of wanting to live with 10 people in order to survive. Regardless, New York is on the agenda. I’m not sure how it’ll happen, but I’d love to join a media company full-time to write about pop culture, sex, and/or relationships.

Freelancing has given me the chance to work on various creative projects, like a collection of personal essays that I’ve been sending out a book proposal for. Some agents have expressed interest but it doesn’t go far. That’s okay. I was prepared for this to take a long time. There’s also a novel and 2 screenplays that are stuck in ideas-and-outline mode. I have a poetry manuscript that’s ready for review, but that costs money and I’m waiting for a(nother late) payment to make that happen. I need to build my website, but that costs money, too.

I have a Kindle Single available via Amazon. It’s called Romance Novels Ruined Me. It’s a long-form essay about how reading romance novels affected my expectations about relationships. It’s a part of that collection of personal essays I’d like to publish one day. The collection is about the ways pop culture and growing up southern influenced my relationships. Ultimately, I want to showcase the diversity of black womanhood and let the world know our lives aren’t all about trauma and misery.

Buy “Romance Novels Ruined Me.” If you’d like to leave a love offering, I’d appreciate that as well.

Thank you to everyone who’s supported me throughout the years. I hope you stick around.