Meet Cindy Whitehead | Author, Skateboarder, Sports Stylist

We had the good fortune of connecting with Cindy Whitehead and we’ve shared our conversation below.

Hi Cindy, why did you decide to pursue a creative path?
I’ve always been a person who gravitates toward artistic endeavors. When I was growing up, I was an avid skateboarder – skating pools and half-pipes and ended up turning pro as a teenager. Skateboarding is all about creating lines, finding your flow, having your own style, and being creative. There were no rules to follow, and it encouraged me to push my creativity. Later on, as an adult, I became a fashion stylist for advertising shoots, commercials, and editorial spreads. I tapped into my creativity to put looks together that were interesting and different. I still work as a stylist on sports-related shoots, and I love what I do. But in the back of my mind, I always knew that I would branch out and have a career as a writer at some point. I loved creative writing in school and absolutely love reading, so I just knew that this was another creative outlet I wanted to pursue.

I can not imagine a day where I am not being artistic or creative – it fuels me, and it’s what I love. I feel very fortunate to be able to be creative in all the career paths I have chosen.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
I started by writing every day – for myself. I’d be on planes in-between jobs, and I’d write for hours working on story lines. Later I did an outline of my biography as a female skateboarder in the 70s and what the scene was like. I signed with a literary agent who pushed me toward writing YA (Young Adult) books, and I loved creating the storylines and thinking about where I wanted each character to go. The industry was tough, and in those years, it probably wasn’t ready for me, and maybe I wasn’t ready for it. So, I parted ways with the lit agent and shelved my passion for writing yet again.

In 2013 I started a blog for female skateboarders, writing about what I knew, especially my thoughts and observations on this still male-dominated industry. I did interviews with female skateboarders, covered contests, and more. At times my articles would be picked up by other publications. I knew I was doing something for myself that I loved, but that also resonated with other people as well.

In 2017 I self-published the first hardback book on women’s skateboarding, “It’s Not About Pretty: A Book About Radical Skater Girls.”, That led to me writing about the underground scene of girls skateboarding in India for Vogue, and numerous articles for skate publications. I also feel honored that I was asked to write the forward for two skateboard books, and articles on women’s sports for espnW.

During the pandemic, I had the idea to pitch articles on what was happening here in Los Angeles – so I wrote for Los Angeles Magazine and Los Angelino Magazine about the empty streets of LA due to the stay-at-home orders, pop-up fridges across Los Angeles where people could help themselves to any food they needed, the Black Lives Matter movement and more.

During this crazy pandemic, I felt it was the perfect time to focus even more on my writing career, and Rockridge Press published my books “The Self-Love Journal for Teen Girls” and “Girl Power: A Journal”. Both books are about empowering young women and girls.

I just finished writing two chapters on women’s skateboarding in the 70s and 80s for Smithsonian Books, “Four Wheels and a Board,” which will be released in November.

Being a writer, it is challenging to learn to work with various editors who have different styles of working and sometimes meeting crazy deadlines, but the tradeoff for making my own schedule most days and being creative is well worth it.

I’d like for people to read what I write and be so immersed in the story that they are transported to another place and feel like they are a part of it. Or, even learn something new from what I have written. It’s most important to me that I am authentic and “me” when I write, and I hope people enjoy reading it.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
I’d have them stay at the Proper Hotel in Santa Monica so they’d be near Venice Becah and the skatepark. We’d hit the skatepark up for sure, then ride the rides on Santa Monica Pier. Drive up the coast to Malibu and have sushi at Nobu. Do some shopping at Cross Creek. Later I’d make a stop at Arcana Books in Culver City for the best photography and art book selection in town. Hollywood Forever Cemetary has a great movie night under the stars. And they’d have to come down to the South Bay and shop at Beach and Beverly and get a custom hat made by Bone by Dawn. While they were here, we’d swing by Hook & Plow for a yummy lunch and pick up a great book to read while lounging on the beach at Pages Bookstore in Manhattan Beach. There is also a semi-secret spot I love high in the Hollywood Hills, where rows of palm trees flank a windy road, and it’s a great skate spot! Whew!

Who else deserves some credit and recognition?
If I hadn’t had access to the brilliant photography of women’s skateboarding over a long span of time from photographer Ian Logan and the added bonus of epic design work from Elise Crigar, the “It’s Not About Pretty” book never would have happened – they say it takes a village and it really does. I have received so much encouragement from day one from a writer I really respect, Staci Greason, so shout out to her! Illustrator Jim Rugg who created the brilliant “Street Angel” graphic novels, introduced me to comic book editor Shelly Bond who has hired me numerous times to write about everything from skateboarding to elder care. I have learned so much about the comic book industry and graphic novels from both of these amazing humans! Zach Moldof for bringing me in to write for his skate magazine and write the forward for his book “Skate Bud”. The team at Callisto Media and Rockridge Press have been so supportive and encouraging about my writing pre-teen and teen books on female empowerment. Also, a big thank you to Jane Rogers and Betsy Gordon for having me write a couple of chapters of the new Smithsonian Book, “Four Wheels and a Board,” And a big thanks to every single person who reads what I write – I wouldn’t be here doing this without all of you!

Website: https://www.cindywhitehead.com/

Instagram: https://www.instagram.com/sportsstylist/

Linkedin: https://www.linkedin.com/in/sportsstylist/

Twitter: https://twitter.com/SportsStylist

Image Credits
Ian Logan Smithsonian Books