Failing My Way To Success - Jennifer Lieberman

Nobody likes to fail, that’s pretty evident, but as kids we all understood it was a natural part of the process of learning new skills or becoming excellent at something. Somehow as adults we expect to automatically be proficient in things even if we’ve never done them before. It’s kind of silly when you think about it.

One of the major things that gymnastics taught me was discipline through repetition. Just because I landed a flip on the balance beam once didn’t mean I could execute it all the time. Many times in the gym we would get excited about landing a new move once, then for weeks go on trying to repeat that same skill unsuccessfully. During warm ups we would have to stick our tricks perfectly upwards or ten times before we could move onto the next one, and if we stumbled or fell we would have to start the count back at zero. When learning new moves we would work on progressions for weeks to get the right set up, height, body position and rotation before even attempting the move, and when we finally did, it was with spotters and crash mats for the first few dozen attempts.

Why is it as adults we expect our success to come more easily?

I had been working in theatre in New York for a couple of years before I started producing; the first play I produced was a complete disaster. I was so hard on myself at the time, but years later looking back, of course it was! At 22, still figuring out how to adult on my own; I knew nothing about business or marketing and had never managed people before. I was flying blind learning as I went - It’s absurd to think I actually expected myself to succeed and for the show to be a hit. It took at least half a dozen productions before I became a proficient theatre producer and several more until I became a successful one. Each mistake I made, each challenge I encountered as a producer pushed me to get better at it. I had to put in the reps and clock my 10,000 hours to become an expert at independent production.

Each failure in my career has pushed me to adapt and pivot into new roles and learn new skills with each one. As an actor I got frustrated waiting for other people to choose me, so I started writing and producing my own material. The first time I performed my solo show Year of the Slut it was a relative failure, but after working on the show for a couple of years, developing the writing and refining the acting, the show went on to win the Audience Choice Award and the Frigid Festival in New York City. If I would have accepted the failure of that first production, I might have quit acting, writing and producing altogether. Instead, that disappointment pushed me to work harder and now that show is not only an award-winning play, it’s the 5-time-award-winning and #1 Amazon Best Selling novel Year of the What?. My ‘failed’ acting career led me to become an award-winning actor & writer as well as a #1 Best Selling author. Pretty crazy right?

After my solo show, my friend Rebecca and I created the web-series Dumpwater Divas, a wacky 80’s dance spoof on YouTube. We made it for pennies and no one really got it. It’s what others would consider a total commercial failure, even a decade later we haven’t even hit 5000 views between all the episodes. For me, I LOVE this project, it was the most fun I ever had and I’m so proud of what we created and what all the actors brought to the writing. Was it completely unrealistic to think that my first project would be a hit? Yes, but of course I did. I think that’s part of the creative process, the delusional hopefulness - it’s a necessary element of being a creative. If we’re not consumed by our passion and willing to put all we have into it, and willing to risk failure, then what are we doing?

Once again the failure with Dumpwater Divas didn’t deter me, it only fueled my fire to keep creating. I didn’t focus on the failure, I was driven by my love affair with the creative process. I kept making stuff, and after a few projects I started to get some traction. My short films started getting into major international festivals like the Cannes Film Festival Short Film Corner, they were nominated for awards and finally my last short won Best Comedy at the Culver City Film Festival in LA and Best Screenplay at the Hollywood Short Film Festival.

As a writer I’ve learned that the first draft of anything is only ready for one thing - rewrites. As an actor I’ve learned the first choice I make for a character or a delivery is simply the first attempt in a focused exploration of many different choices. As a filmmaker I’ve learned that my first project is not my masterpiece. And, as a theatre producer I’ve learned that the first mounting of a play is simply the first of several productions before recognition.

The key to success in any endeavor is falling in love with the process, the exploration and the failures. That's what pushes us to get better, dig deeper and go further - or perhaps realize it’s not for us and pivot to something where we are willing to sustain the ups and downs. It doesn’t matter where your focus is, you must be willing to fail your way to success if you ever expect to get there.

Jennifer Lieberman is an actor/writer/producer from Maple, Canada. Her award-winning Solo Show YEAR OF THE SLUT is now the 5-time-award-winning and Amazon #1 Best Selling Novel YEAR OF THE WHAT? Lieberman's short films have screened at several international festivals including the Festival De Cannes Court Métrage; DETAILS, her directorial debut was a semi-finalist for Best Female Director at The Art House Festival of Beverly Hills in 2022 and her latest short film THE PENIS FAIRY won Best Comedy Short at the Culver City Film Festival in 2023 & Best Screenplay at the Hollywood Short Film Festival 2024. Jennifer founded Make Your Own Break Ltd. to help emerging actors and writers to create opportunities for themselves (like she did). Find out more at jenniferliebermanactor.com & @iamjenlieberman.

Article published in The Relatable Voice Magazine - August 2026. Download the full magazine at https://www.relatable-media.com/the-relatable-voice-magazine.