We caught up with the brilliant and insightful Sean O’Connor a few weeks ago and have shared our conversation below.

Sean, looking forward to hearing all of your stories 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.

This is a great question. First, I just want to emphasize the importance of risk-taking. Both as an artist, and as someone building a career. As an artist, your work grows through the risks you take. If you’re a writer, you can use your talent and write according to all the rules you learned in school…and those rules are helpful…but you’re never going to break down a wall and venture into new and perhaps uncharted area. But it’s that area where writers find their true and unique voice, and it’s that area that raises their work above the fray. You might sometimes fail. And that’s fine. Failure is part and parcel of a vital creative process. But, when you succeed, the rewards are many. Especially in the growth of your artistic vision: understanding what it is that you see and want to express, and creating a bigger and more robust arsenal of creative tools.

And it is just as crucial for your career. It’s very easy to sit back, and be shy, and insecure, and say who am I to feel I can pursue that contact? Be it a renowned person, a renowned theatre, publisher, agent, film company, etc. But the risk you didn’t take, is the chance for success you never let yourself have. Just do it. The worst they can say is the old one-syllable “No.” And who cares? Every artist gets that one-syllable pest thrown at them all the time. Laugh at it. The brilliant playwright and TV writer Rod Serling (“Twilight Zone”) said he wanted to paper his entire apartment with rejection slips. They’re just rungs on the ladder to success. Some people won’t take to your work because they have a different feel for what work in your realm should accomplish, and that’s fine, a mere difference of opinion. But others…and they could be few, nothing wrong with that…might well share and be excited by your work. It’s those that will make your career. If you hadn’t taken the risk, your career doesn’t happen.

My biggest risk? It was career-wise. I was acting a lot in NYC throughout my 20s. Mostly theatre and TV, and I was doing well, but….writing…the art of writing was lassoing me from behind big time. I’d be in a soap opera dressing room, reading Tolstoy and writing poems, bits of stories, and one day, a play snuck up on me. And for a year and a half, all I wanted to do was write that play. I did and it did very well. It won awards, had real good productions, Got published. I wrote another, then another. I couldn’t get away. And I realized hey, this is what I’m supposed to be doing. I directed my energies into it fully. Still acted, but it was more “this thing I’d do once in a while…but I’m mainly a writer.” It was a big risk. I’d had real acting success, I was destined for more (although you never know in this biz), and how could I presume I could also make it as a writer? It was risky. But it paid off, in the ways that were important to me. Sometimes in life, you have to just follow your heart. It’s always risky. But it well might be leading you into your deepest calling.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m a Writer/Actor/Director. The emphasis being on playwriting and film writing, but acting and directing are what I also do. I got into it for the reason many others get into it, and other art disciplines. There’d been some problems when I was a kid, family problems, that left a big scar. I’m sure many of you reading this have your own scar. Scars are great, but the big ones don’t quite heal all the way. And it was that “rest of the way” that sparked my creative pursuits. The hope that through the knowledge and comfort one gains creating art, I’d one day make the pain disappear. That never happened but it healed more, and the desire to keep healing became the jet fuel of my creativity. It had its origins in this one moment: After years of family turmoil, I was walking past my Mom’s room one day, and Richard Burton and Elizabeth Taylor were screaming at each other from inside our little black and white TV. I stopped dead in my tracks. All I had known till then were 1960s sitcoms. “Leave it to Beaver,”” “My Favorite Martian”…strange, alien worlds I couldn’t relate to. But this…”Who’s Afraid of Virginia Woolf?”…made sense. It had been happening in my living room for years.

That was the beginning. The realization that my life stories were not entirely unfathomable to the public, and that the creation of these stories and putting them in front of the public, might be important for two reasons. 1, perhaps the audience could glean something from these stories that would help them understand their own lives better. And 2, perhaps I could create a career out of this stuff. That began a cascade of writing and acting (and playing music, and exploring photography and drawing) all through college, then all over NYC, and later, far outside. I write plays and films, and I act in both, plus a lot of television when I was younger. My writing deals with family relationships but there’s always other socio-cultural themes i’m exploring: war, sexism, racism, random violence, addiction, and on and on. There’s a lot of comedy in my work, poetry also, and I know how to keep an audience on the edge of their seats. Which is very important. It’s all the things I just listed that perhaps sets my work apart from others. Especially the desire/need to have the stage and/or screen reflect life in some way that is true, and unadorned. Even if it’s a surreal or expressionist piece. If it happens in life, it’ll find a way into my work.

I am most proud of two things. The first being that I never balked due to fear that I wouldn’t be good at something. The fears were all there. But I focused on my work, and rose above the fear. Becoming a bit of an all-purpose artisan in my craft. The second is, simply, my plays. I’m very, very proud of what I’ve written. I think they’ve reached a very high level of artistry and that they’ve made audiences think about their lives, and the world in which those lives journey through, a bit differently. In a way that, maybe…helps them heal also.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

I had to unlearn the desire to burn bridges when I was younger. I did it a number of times. Part of it was confidence, real or feigned. But…much of it was negative: arrogance, insecurity, unresolved anger from earlier in life…and probably a few other less than noble things. As I tell my two daughters, one of the most important lessons I can give you is to finish well. Whatever it is, a relationship, a project, ride it nobly to its completion, and finish that completion with dignity and respect for it and all else involved.

An example from my life occurred when I was in my early 30s. After acting a lot in NYC and doing a couple of leads on TV, my writing began having some real success, I foolishly dissed my acting agents when they wanted me to audition for more TV roles. I actually turned down a role, thinking hey, I’m a real artist, not some TV clown! I’m a playwright!

Don’t do what I did. Keep all your options and relationships as open and healthy as possible. My writing has done very well, but I never regained the presence I had as an actor, and the ability to get high paying roles, after that. And I should have.

Is there mission driving your creative journey?

Yeah, definitely. It’s the desire to create excellence again and again and again, and it’s also the desire to surpass excellence and move my work into an arena that only the greatest artists who work in that arena have been allowed to enter. I’m not there. But I’m not that far away. And I keep working on all my projects, seriously and joyfully, in an attempt to one day be invited into that club.

Part and parcel of this is the old Dylan song, “When I Paint My Masterpiece.” I thought I’d created a few masterpieces but, despite them doing great, the invite didn’t quite arrive. A few of my works I actually think might have achieved that invite under different circumstances, but if it doesn’t arrive, you can’t enter the club. So…I’m hoping to create that “masterpiece” as yet unborn, or that one of my past creations will be given a forum where its “masterpiece-ness” gets the recognition it perhaps deserves. (You gotta keep hoping…and creating.)

Contact Info:

• Website: https://writersean.com
• Linkedin: https://www.linkedin.com/in/sean-o-connor-4aaa077/

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