How I Became My Own Hype Woman

When loved ones were less than helpful.

The first time it happened was during a family get-together. I had just returned to freelance writing after a disheartening track record of 30 rejections from editors. The publication that accepted my first pitch wanted me to write a personal essay about how I  — a millennial with high-functioning anxiety and childhood fears of joining in on the ‘fun’ of kids screaming for their turn to skip rope — had rented an online stranger as a friend for 50 dollars per hour. 

Typically, aunts and uncles in my Kikuyu community are over-eager to catch up with their nieces and nephews and this event was no exception. As my cousins mentioned schools they were teaching at and corporate jobs they’d landed, I started getting anxious. The thought of saying I was a freelance writer who worked from home suddenly didn’t seem like a great accomplishment. When it was eventually my turn, I hesitated—despite the recent success of landing an assignment with a dream publication, for a story I was excited to write. 

“So you’re doing it before you get a real job,” stated one of my uncles. Before I had time to explain that actually, I had quit my corporate job to pursue freelance writing, he moved on to my cousin Ken who worked with a taxation company, wanting to hear more about the changing corporate world. 

Suddenly, writing my personal essay on renting a friend didn’t seem so exciting anymore. And that insecurity crept into my writing as I started to work on the assignment. If my own family didn’t want to hear my stories, why would anyone? Eventually, I submitted a draft that was so vague and poorly thought out that not even five revisions could salvage the story. After the sixth revision, my editor killed the piece.

Even though the story never got published, my greatest regret wasn’t the lost compensation or byline. It was knowing that I had failed to become my own source of motivation when I needed it the most. As more of my pitches eventually got accepted and published, I bumped into more friends who would urge me to venture into something more serious than writing. 

My turning point—realizing that I had to stop relying on friends’ and relatives’ approval of my freelance writing career—was when a high school teacher privately messaged me on Facebook and asked why I was pursuing a career for the jobless when I had always been extra smart in school. After that, I knew I had to start focusing on how I could motivate myself, without relying on the approval of others.

Photo by Kyle Glenn on Unsplash

The first thing I did was to start accumulating any praise or kind words that editors or writers had ever offered  me. Whenever an editor acknowledged how good my story was, how I had made their work easier or how they couldn’t wait to work with me again, I started capturing those messages in sticky notes and posting them to my work desk. Revisiting such comments, like one from a Reader's Digest editor who said my piece had exceeded her expectations (which were quite high!) reminded me of the progress I had made as a freelance writer, especially thinking back to when an editor once called my story uneditable. 

I also made it a habit to constantly read positive comments from Twitter posts I shared about my published work. Just recently, a post I shared about a book roundup I had written got multiple writers thanking me for capturing different subgenres, which made my editor want to work with me again!

Motivating myself as a freelancer also meant learning how to brush off ignorant comments from friends about my career. I once had to cut ties with a close friend who kept insisting that she could connect me to jobs related to my major since she didn't know of any successful writers. This was despite me telling her that I was happy with my career and was even earning three times more than what I was getting in my previous banking job. 

For most writers, pursuing freelance writing is already a challenge, but for freelance writers in African countries, it's even harder.  One has to deal with the extra hurdles of late payments due to  compensation passing through various channels. And then there’s the fear that editors may not want to work with writers from certain demographics. 

A few months ago, a pitch I had been really excited to write got accepted. As I was discussing the angle of the story with the assigning editor, he realized where I lived and cut the piece because the publication does not deal with African writers. Safe to say that I have never pitched a story to that publication again.

 Learning to ask a lot of questions before I begin working on a story has helped me avoid similar scenarios. That rejection is discouraging, but I’ve managed to establish a steady flow of editors who are willing to work with writers in any location. 

Fellow writer Soila Kenya told me that her way of hyping herself up to continue freelance writing is by reminding herself of past wins. “Just the thought of those pitches that took forever to find a home but ended up finding the best place to be published motivates me to not give up,” Soila said. 

One year into freelance writing has taught me that the greatest skill in my freelance writing journey isn’t pitching, writing or editing. It’s becoming my own hype person, and ignoring the skepticism from those who think this is just a hobby. Sometimes I think about this quote from Tom Paulin: “I always feel freelance writers are leading a heroic life. I think that is the real writer's life. On the other hand, it's good to have another job. It gives you something to do.” And briefly I’ll consider applying for 'real' jobs. But then I’ll return to my conviction, thanks to those notes I’ve collected, like an email from a reader about how my story resonated with them. And I’ll remember why I got into freelance writing in the first place. Just like Soila, I too have learnt to schedule a day of journaling all my past wins as a freelance writer, which gives me the energy to send those pitches that I've been putting off. So far, it's working!