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

Hi Caryn, do you have some perspective or insight you can share with us on the question of when someone should give up versus when they should keep going?
I really like this question because I think it’s something that a lot of us struggle with. For a long time, it was hard for me to even admit to myself – let alone the world – that I was an actor. It’s scary going after your dreams! Especially when there are no guarantees of “success” and it’s just so much easier to get a “normal job” and not go for it at all. And then add to that all the rejection? You really have to be determined to keep going! I think a lot of people don’t want to talk about the struggle, they want to believe you just get discovered and then have a career – but that’s not reality. You have to do all the work and make things happen on your own – and that takes time. And a lot of “no”s.

There’s a saying that goes something like, “if you can do anything else besides a career in this industry, you should do that” and believe me, I tried! I’ve had plenty of “day jobs” over the years that I could’ve settled into, earned a decent living… if only they made me happy. The thing is, if nothing else makes you happy, you have to keep going! For me, even though it felt like I quit a number of times, I never really gave up, I just changed directions. Added new skillsets. Pivoted.

Put another way: “if at first you don’t succeed, try, try again.”

When I had a full-time day job and pursued acting at night and on weekends, I was mentioned in Backstage West for my performance as the comedic relief in a serious play, which helped me embrace my talent for comedy. So, I followed that path and traded acting classes for comedy classes. After graduating from The Second City Conservatory and The Groundlings, I “quit” acting to focus on creating my own content. Honestly, it was a huge relief to not be so stressed trying to leave work in the middle of the day to fight LA traffic to audition for uninspiring roles in low budget films and commercials for products I would never use.

After spending quite a bit of money making videos that I’m still super proud of, multiple live sketch shows and tours that only lead to a few “close calls,” it became challenging to keep a talented troupe together without a TV deal or a trust fund! But by then I was kind of addicted to the exhilaration of being on stage and making people laugh night after night, plus I really enjoyed the art of crafting jokes so I found an easy “pivot” to stand-up. I spent the next 6 years almost exclusively focused on that grind, and eventually toured across the country as a “feature act” and headlined the House of Blues Foundation Room in Chicago.

It was a big deal for me to achieve all the goals I had set with stand-up, but I knew I didn’t want to be a “road comic” for very long. I really missed the collaborative process of creating a show, so I decided my next big goal was to be a writer in a comedy writer’s room. In order to do that I felt it was necessary to “quit” stand-up for at least a while to focus on creating my half-hour writing samples and enrolled in some writing classes.

There are a few different ways to get “staffed,” but all require specific writing samples. Crafting several spec episodes and solid pilots along with all the personal essays and pitch decks that go along with it takes time – during which I also co-created the 15-episode web series, “Baked Goodes” with 4 awesome women and one man. The experience of co-writing, co-producing and co-starring on that series – along with spending so much of my time solely focused on writing – made me realize I was definitely on the right path, but 1) that I needed to find a job I could do between now and being “staffed” where I could be around performers and artists every day and 2) that actually, being on set is my happy place. So, in true pivot fashion, I refocused my energy and took classes and started building up my experience as a script supervisor.

Being a writer and comedian, I have found script supervising to be the perfect “day job.” And, I continue to write and perform – the sketch “Poverty Tourism,” which I co-created and starred in, played multiple festivals during the pandemic. I am truly living my dream. A dream that keeps evolving and changing. As long as you have the passion for it and you can’t not do it, don’t give up.

While I may not be a household name, I’ve been seen on “Good Morning America” and “The Wendy Williams Show,” fixed a pair of stilettos with a wad of gum on “Hack My Life,” got Zonked on “Let’s Make a Deal” and led my team to victory on “America Says.” Our web series “Baked Goodes,” was featured in Newsweek magazine and named Decider.com’s “Afternoon Delight.” I also co-hosted and wrote for the weekly late-night talk show “Midnight Parade” at Chicago’s Second City and performed in and had my work selected by multiple festivals including, Chicago SketchfestGilda’s Laugh Fest, and Houston Comedy Film Festival where my pilot won Best Dark Comedy Teleplay and the Independent Shorts Awards where “Vadgevertising” won Honorable Mention for Best Parody Short. I’ve told jokes on iconic comedy stages at The Comedy StoreZanie’s, and Jokes and Notes, did shows with big names like Tiffany Haddish and Donnell Rawlings, and script supervised alongside Oscar and Emmy Award-Winning crew on multiple projects, and was selected for BlackMagic Collective’s Filmmaker Advancement Initiative. Not bad for a “quitter.”

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 am really grateful for the opportunity to explore so many of my interests – from bodybuilding to stand-up comedy to writing and producing – and to have found my way to becoming a professional script supervisor and artist. I talk more about my windy path in the question about “should I quit?” but when I think about myself in grade school, it’s just crazy – I mean, even if I knew the answer, I would never raise my hand in class because I was too shy to speak. And now I’m a professional comedian!

To this day, one thing I still find challenging is the whole “jack of all trades, master of none” trap. I feel this pressure coming from everywhere to define myself as ONE THING. Am I an actor OR a writer OR a script supervisor OR stand-up comic OR producer? But really, I am all of those things. And while it’s nearly impossible to do them all on a film production, I’m basically doing it now for my new podcast, “Script Supervisors: Unsung Heroes of Film & TV.” Hopefully soon society will evolve to be more accepting of multi-hyphenates, because I know that people like me with diverse interests and experiences bring so much more to whatever job they are doing. Like, do you know another script supervisor who can help their director do a stretch that alleviates their back pain? Or how many writers look for potential continuity errors while they write?

What drives me is a passion to collaborate with women, POC & gender non-conforming folx to tell diverse stories and share “non-traditional” perspectives. That’s both what I write and create, and the types of projects I prefer to script supervise. I’m really proud that most productions I script supervise are directed by women, a majority of those being women of color.

As a writer, I am drawn to deeply broken characters whose sadness manifests in self harm and/or a desperate need for belonging or quest for fame. Super funny stuff, right? Lol But my favorite genre is comedy, and I love using dark humor, mockumentary and satire to shed light on uncomfortable truths in our society. Drawing from my personal experience with disgusting men, I was able to transform into Leo Mann, the misogynistic ad-man who wasn’t content “just using ‘tits’ to advertise products” for the short “Vadgevertising” that I co-wrote, produced, and starred in – in drag. My co-creator and I were outraged by Tom Ford’s sexually exploitative perfume ads that we burst out, “what’s next? Advertising INSIDE vaginas??!” Then we laughed and knew we had to make it! And I’m thrilled that it just won “Honorable Mention” for Best Parody Short at the Independent Shorts Awards, and premiered last year at the All the Laughs film festival in Atlanta.

Of course I love when the audience laughs, but I get really excited when my jokes make people cringe or even groan(!) at an unflinching look at our society and how we value (or don’t) women and girls. Sometimes comedy is the only way to talk about the truth. Ideally, I want my work to spark conversation that fosters empathy and understanding.

My happy place is collaborating with other comedians and artists. When we’re spitballing ideas in a writer’s room or helping solve problems on set – I love that whatever we create together is always better than what any one person could envision alone. And being a part of these unique once-in-a-lifetime artistic discoveries is what feeds my soul.

Besides graduating from The Second City Conservatory and The Groundlings “Lab”, I’m probably most proud of co-creating and co-starring in the 15-episode web series, “Baked Goodes” as the “older” stoner neighbor Jan (pronounced “John”). It’s still hard to believe the five of us met, wrote, produced, and released the entire first season of 13 episodes in under 2 years. The thing about our process that was the most special – and maybe it’s because we were a group of women – was that everything was decided by consensus. EVERYTHING. We had no showrunner, we were all co-showrunners and staff writers. And our hard work really paid off. After we launched, we were featured in Newsweek and Decider.com, and were sponsored by Hempire who put us on a billboard inside their game!

I’m still really impressed by what we did, and how we all worked together so well. Unfortunately, many collaborations never make it to the end for one reason or another. It’s really hard to find one person, let alone a group that can all maintain their passion for one project every single week for over a year – especially when you’re not being paid.

Speaking of being paid, when I’m not writing and creating comedy you can find me behind the camera doing my other passion – script supervising. I love this work so much and am grateful that I get to collaborate with so many wonderful creatives on a varitety of sets while utilizing all my skillets in this role that is really integral to filmmaking.

In addition to writing and creating comedy, I also enjoy expressing myself through photography, drawing, painting and occasionally, poetry. Fun fact, my paintings were featured in an episode of a web series as the character’s artistic works.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
Oh wow! I LOVE LA so much and appreciate the opportunity to share how great it is!

Since there are too many amazing places to see in any single visit, I would design a tour to show them the best of what LA offers that they would love. (I have a secret desire to get all of my favorite people that live somewhere else to move here haha)

For my comedy friends we would definitely go to shows at all the iconic spots – The Comedy Store, The Groundlings, catch a TV show taping or two, something at the Dynasty Typewriter, and of course an underground comedy show.

My vegan friends would get to eat at Gracias Madre, Sage Bistro, Vegan Glory, Crossroads and Shojin (scratch that – my non vegan friends will like these restaurants too!), filmmakers and movie buffs will get to see the Cinerama dome, the Dresden, the Frolic Room, the “piano stairs,” tour the Paramount Lot, and take a drive along Mulholland.

If they are visiting in the winter from a cold climate, we will eat every meal outside lol & check out the piers & shopping in Manhattan Beach during the day and the Hermosa Beach bars at night, as well as Santa Monica’s 3rd Street Promenade and the Grove. I’ll bring my workout buddies to the Santa Monica Stairs, the “love stairs,” Temescal and Runyon Canyons, and if it’s their first time here, we have to walk Hollywood Blvd & Melrose Ave. and drive up Beachwood Canyon to see the Hollywood sign.

Finally, for the people who’ve been here a million times and/or moved away, depending on the season, we’ll go to Pershing Square for a free concert or ice skating, splurge on box seats at the Hollywood Bowl, check out some new restaurants and hit up as many of their old faves that are still here.

Who else deserves some credit and recognition?
Without question, master Career Strategy Coach and all-around amazing human, Sandra Lord. I recently learned that some of her past students refer to her as “THE Lord” which I think is hilarious and not entirely wrong. I took her career strategy course a few years ago followed by private coaching, and although I already had some solid credits under my belt, it wasn’t until I started working with Sandra that I actually began to believe in myself. With her tools and guidance, I learned to better utilize networking opportunities and communicate more effectively by leveraging my credits in a way I had never considered. This led to more success, which led to more confidence and to doing things I had always dreamed of but never knew how to manifest. I am truly grateful for her deep industry knowledge, experience, and vision of what I could create for myself and my career. She helped me to become – and see myself as – the accomplished professional multi-hyphenate that I am.

Website: http://carynruby.com

Instagram: https://www.instagram.com/caryn_ruby/ AND https://www.instagram.com/the.script.supervisor.podcast/

Twitter: https://twitter.com/carynruby

Facebook: https://www.facebook.com/carynruby/

Youtube: https://www.youtube.com/user/carynruby?feature=mhee

Other: https://medium.com/@carynruby https://womennmedia.com/profile/caryn-ruby/

Image Credits
Ashly Covington

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