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Meet Madeleine Chalk

Today we’d like to introduce you to Madeleine Chalk.

Thanks for sharing your story with us Madeleine. So, let’s start at the beginning and we can move on from there.
After I graduated from college in 2018, it was LA or bust. I’d dipped my toes in the entertainment industry here during my undergrad and fell in love. So, about a month after graduation, I headed back to the city of dreams— English B.A. and obligatory yoga mat in tow.

With exactly what objective, though, I wasn’t quite sure yet. I’d always been creative: I was the kid who drew, wrote stories, and sang all the time. A playdate at my house meant you would inevitably be cast in a Madeleine Chalk original musical (whether you liked it or not). I kept it up through high school and college, from musicals to choirs, to an opera-turned-literature degree. Although I’ve always tried to stay active in the things I loved, I think I really resolved to pursue a career in the creative world after receiving invaluable mentorship as an intern at Upbeat Productions in London, followed by Gidden Media in Beverly Hills (mentorship to which I still turn today). My respective experiences in those workplaces with such kind, involved leadership equipped me to take the leap into the professional world as soon as I could.

After quickly discovering that the corporate world was not for me early in my post-grad career, I saw my newfound freedom as an opportunity to go for what I really wanted, and I went crazy planting seeds to see what would grow: I took improv classes, acted for student films, made a podcast, braved stand-up open mic nights, sang for friends’ bands, and started a freelance digital illustration business.

Over the past year, I focused more on specific goals: I like to create things from scratch with others. This past August, I wrote, casted, directed, and produced my own sketch comedy show, “Kale, Caesar!” with a gaggle of wonderfully gifted friends. Since then, I’ve gotten more opportunities to write and perform on several other sketch teams and kickstarted several individual playwriting, songwriting, and video production projects. I hope never to restrict myself and to see as many of the seeds I’ve planted flourish as possible— hopefully into some Donald Glover or Steve Martin type of career: one day I’m a musician, the next an actor, and then, boom. I write a novel. Why not? If there’s a place to pursue that kind of multiplicity, it’s LA, baby. Of course, I’m still new to it all; I still have a lot to learn and plenty of mistakes to make, but I can’t wait.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Oh, boy. The road has certainly had its twists and turns, to say the least.

My first LA success ended up my first mistake: I got a corporate job. Don’t get me wrong, I was thrilled at first. I was an assistant at a talent agency, working 50-hour windowless workweeks for a boss who hated me, with no time to do what I loved (I now wish I’d tallied the number of times I called my parents crying). The decision to jump ship was a hard one, though—on one hand because I was grateful: I knew it was a coveted gig that would open a lot of doors (doors to other offices, it turns out). And of course, I was scared: was I cut out for the day-job-and-a-big-dream lifestyle? Ultimately, I realized that admitting I was a struggling artist would at least mean I was an artist, so I took the plunge and never looked back.

Transportation and housing have proven wild adventures of their own since moving here. I totaled my car my first month here. I’ve moved four times to four different neighborhoods, with experiences ranging from sharing a house with complete strangers to sharing a 350-square foot studio with a then-boyfriend. It took a long time—a year, give or take—for the dust to finally settle.

Through all that transience and uncertainty (not to mention being broke most of the time), the biggest struggle was probably finding a sense of home—of belonging—in LA. It’s hard not to feel like because you’re not rich and famous yet, LA doesn’t really want you; you have to earn your keep. This city doesn’t welcome you with open arms, it slaps you in the face with brutal taxation and obscene gas prices. Sink or swim, it seems to say. The way I’ve found home, though, is in community with other young hopefuls (read: scumbags) like me, making that same uphill climb in their respective creative fields. Working hard and swimming upstream together makes it easier, and makes this city feel like home.

We’d love to hear more about your work and what you are currently focused on. What else should we know?
I own and operate Chalkified, a freelance digital illustration business specializing in custom portraits I call “Chalkifications.” I love to draw people, and it’s gratifying to personally putting my skills to use for others.

Aside from that, I write and produce sketch comedy while acting and singing on the side.

What moment in your career do you look back most fondly on?
Seeing “Kale, Caesar!”, the sketch comedy show I’d created from scratch successfully come to life onstage was the most rewarding moment of my time in LA so far. It was my biggest, riskiest undertaking up until that point and I had absolutely no idea what I was doing (thankfully, I had help from some gifted collaborators). Its creation was a stressful, educational, deliriously joyful few months, the momentum of which has pushed me to continually take on new projects and (hopefully) grow as a writer and performer.

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