We caught up with the brilliant and insightful Ali Keller a few weeks ago and have shared our conversation below.

Ali, thanks for taking the time to share your stories with us today It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.

There’s a lot of answers to this question. The most recent career risk I’ve taken was participating in the Soho Playhouse Lighthouse Series last year. It was both an artistic and a financial risk.

Soho Playhouse does a great festival every spring/summer where writers can showcase sections of their full length shows to audiences who will then vote on their favorites. If a show gets voted through to the next round, the theater will pick one to produce the following season.

I had been developing and rewriting my play (un)conditional for a long time. People were always interested in the show, if I could get them into the room with it, but getting that to happen was an uphill battle. Still – it’s the play I kept taking out of the drawer and changing and working on. I wanted it to have a life.

After getting accepted into the festival, I was really nervous. It was both an artistic and financial risk. It costs a lot to put something up, even within a festival. Obviously, if the play won the festival, the cost would feel worth it, but I had to ask myself, “If I didn’t win, would spending the money still feel worth it?” I thought about it and decided that I loved this show and any opportunity to share it with people would be worth it.

Britt, the managing director of the company, gave the festival participants great advice. “Don’t try to tell your entire play in 15-20 minutes. Make it clear and get people hooked.” I decided to do two scenes from the middle of the show, which felt RISKY because the audience wouldn’t be seeing the set up of the play, how these two couples know each other, it just dumped them mid-conflict, mid-reveal, into the story. And in order for the audience to understand what was happening, I did something I almost never do: I wrote a monologue. (Typically I avoid writing them in shows.) But I figured the best way to get the understand the things they were missing was to have them explained in a monologue within the context of the show but the child character in the show. (Even typing that out now, the idea still feels insane to me.) But I went ahead with what felt right and the monologue became a highlight of the excerpt. And people keep asking me about it and when I said it was just a part of the festival presentation and not in the script, they were shocked.

I realized through the festival process and the support from Soho Playhouse that the full script needed the monologue. and not only that, but it needed others. So I wrote two more for the adult female characters in the piece and it’s completely changed the script for the better.

We ended up winning the festival and our Off-Broadway premiere will be in the fall of this year. In this case, the risk paid off big-time. But even if it hadn’t, I was able to see an audience’s response to the piece, which informed the show’s development and that alone would have made the whole experience worth it.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

My parents and my brother don’t watch TV unless it’s sports or the news. I grew up hearing that narrative shows were useless because they didn’t reflect reality, were very one-sided, and a waste of time. “There were more important things to do in life.” That confused me. Narrative stories seemed like a great way to understand being human. And trying to understand why my family didn’t understand that was what sparked my initial obsession with theater and film. The arts exposed me to people and beliefs that my Italian-Irish-Catholic-Conservative neighborhood was never going to. And my upbringing exposed me to thoughts and behaviors that growing up in an arts filled, Democratic and diverse neighborhood would have never shown me either. I see the beauty, humanity, and the horror in both. That’s why I write.

Whether I’m writing about fraternity girlfriends about to graduate and face the real world, a group of male friends who are trying to maintain their childhood friendships as adults with no emotional intelligence, a film crew working towards a deadline on their b-horror movie with no resources, a customer service agent who uses their love of wrestling to navigate everyday triggers, or married couples navigating their changing sexual fetishes, my characters are like the people I’d find in my neighborhood growing up exploring and pursuing topics and themes that their environments haven’t really prepared them for – like unconditional love, shame, reproductive rights, mental health, elitism in the arts and the relationships between feminism, racism and capitalism. I ferociously mine dark subjects by revealing the humanity and comedy beneath them. I write about and for people who aren’t typically interested in attending theater or film because typically the arts “aren’t for them”.

I write for people who feel the arts just want to lecture, scold or make fun of them. Those are the people who can be surprised that a story is empathetic towards who they are, rather than blame them for problems – which inspires discussion. No minds have ever been changed by winning an argument. But minds can be changed by listening, understanding, and trying to come to an agreement. I know because I started as a conservative, catholic, antifeminist, who didn’t believe in therapy and didn’t know they were neurodivergent. Now I am a diagnosed neurodivergent feminist catholic democrat who’s been in therapy for a decade. I don’t write for people who grew up identifying with the culture they were in, I write for the people who had to grow out of their culture to see the good and the bad in it and move forward.

I write to help people (and myself) better understand and radically empathize with the world around them. The question my work pursues is: how can our opposition be an access point to grow together rather than something drives us apart? And because I ask audiences to confront this idea through challenging subjects, I often partner with charities and organizations related to the shows’ subjects so anyone inspired to help or who’s in need can find assistance immediately.

My play (un)conditional (the show from my previous answer) is about two married couples who are navigating sexual fantasies in their relationships without a ton of experience navigating boundaries and/or advocating for themselves. The show is about the boundaries of compromise, communication, and unconditional in heterosexual relationships, grooming, and the messages our sexual identity and relationships kids are learning by existing in the same world as adults. And I’m very proud to say we are talking with RAINN to work together to make sure there are resources available to audiences after the show, representatives available from the organizations at our talkbacks, and incorporate their expertise into our creative process so that the creative team, actors, and audiences feel safe while facing these difficult issues.

Are there any resources you wish you knew about earlier in your creative journey?

Therapy. And exercise.

These might seem like obvious resources for everything in life. But I don’t think I realized how much they can be used to improve my creative journey until a few years in. Being mentally and physically healthy makes me more functional in my day to day life which helps me show up better to write, be in rehearsal and attend production meetings. But they also taught me how to use rest, pushing through things, and resilience.

Going through rough patches in my mental health in therapy has helped me grow stronger in the face of criticism and to believe in and trust myself, which are essential tools to work professionally as an artist. It’s not always easy, but committing to helping myself through hard times has made the commitment to my writing career almost effortless in the face of the ups and downs of theater and film. It’s hard to know when to rest when everyone is rushing. Or when to push through because you need to. And to keep going. It also has made me a more empathetic producer and dramaturg for the other artists I work with because I have the foundation to show up that way.

To me, athletic training has always felt like a parallel to working in entertainment. Audiences see your work on game days/performances/readings – the final product. But to get to that point, you need to show up and do the work: write, rewrite, pitch, edit, organize, promote, face critics, advocate for yourself and your work, rehearse, meet etc. So while personal training and soul cycle helps my physical health, it also helps me practice “pushing through” when I’m tired and harnessing the energy to keep going while checking in with my body to not blow past my limits. All of that puts me in a headspace every day to know how I need to show up for my career every day. I work out 3-5 times a week and most of my breakthroughs on drafts happen when my body and mind are focused on the weight I’m holding rather than my script.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

I had the incredible opportunity to do some producing for Paul Rizzo, who’s an author and award-winning TV producer. I learned so much from working with her in general, but she’s got great advice on her websites, live-stream show Inside Scoop and Linkedin courses, and books about productivity, lists, and media training. https://paularizzo.com https://listproducer.com

Contact Info:

• Website: https://www.alikellerplaywright.com
• Instagram: @alikeller47
• Facebook: https://www.facebook.com/ali.keller.315
• Linkedin: https://www.linkedin.com/in/ali-keller-b9b72635/

Image Credits

My headshot was taken by Chris Comfort, the photo of me standing in the colorful art installation was taken at the Ucross Residency, and the black and white photo was taken during rehearsals for my play Christen the Place, which was at IRT in NY and toured Norway. The cast picture was also about that show, which was an exploration of men’s mental health.