Episode 10 - Playwright, Director, Actress Sheila Kelleher

(Trusting that it will work out)

When I first learned that local actress and director Sheila Kelleher had written and staged her own original musical, I thought, “Wow, she did all of that by herself?” But talking with Sheila made it clear that her story is one of following detours, listening to herself, and trusting that things will turn out the way they’re supposed to be. We chatted about her musical, losing and regaining her creativity amidst an annulment and motherhood, the role of a director, and finding value in all of your life experiences.

Sheila Kelleher

In this episode, we talk about:

  • The role of the director as the eyes of the audience
  • Trusting the detours in life, because they are rarely mistakes
  • Giving yourself deadlines and support from others
  • Telling the best story you can, without worrying about what others think
  • Everything has value because it teaches you something
  • Follow your interests to find what you love


Where to find Sheila:

Sheila is an active performer around the South Shore in Massachusetts, and you can find her on Facebook to see what she’s working on.

Prefer to read instead of listen? Here’s the longer version of what we talked about:

Sheila Kelleher is an actress, director, playwright. Been performing for 20 years and directing for 8. She has a masters in theatre education and wrote a short musical called “The Annulment” which was produced by Hingham Civic Music Theatre in 2019.

She’s one of 10 children, who used to do shows in the basement. Grew up with cast recordings of the big musicals in the 60s, like My Fair Lady, Camelot, etc. That’s what they did because they had no TV. Her six sisters and she would listen and then go outside on the swingset and hum the overture and perform the entire album, with skips, because that’s how they learned it! When people would come over they would copy skits they saw or got from the library, and were always singing.

She went to an all-girls high school, and their brother school had a massive auditorium where they did a major musical every year with full orchestra, so she got to see those shows. Theatre has always been a part of her life.

Not all of her siblings wanted to do theatre. Her brother did in high school. One sister plays the piano and sang with a band. But Sheila’s the only one who really pursued it.

Playwriting started with The Bay Players in Duxbury. She got back on stage as an adult with Hingham Cabaret, and someone there asked her to audition for a play at Bay Players. During this show, she was backstage listening and pointed out that another cast member always said the wrong line in the same spot. The person she was talking to said she should be a director because she remembered everyone else’s lines.

Her first directing experience was “Five Women Wearing the Same Dress.” She loved it so much.

“The role of the director is to be the eyes of the audience.”

In one show, a pamphlet was a very important prop. She knew the audience needed to see a character put it down in a specific place, and it wasn’t happening, so she explained that the audience needed to see that moment clearly. Pauses in some shows are really important, too, because they are conveying things about what the characters are feeling. The actors can’t see how things are coming across to the audience, so that’s her job as a director to notice those things and make sure all of the important moments are working and that the story is told correctly. Little things make such a difference.

She wrote and directed her musical, “The Annulment” a few years back. It’s autobiographical! She always wanted to write the story of her early married life. She was working with someone who was doing a new works festival for new playwrights, who asked her whether she was submitting anything. Sheila had never written anything at this point, so she thought it was weird that she would ask that. The next day at work, a coworker who writes screenplays asked why wouldn’t she try to write a play? At this time, her ex-husband who she had divorced 13 years ago wanted an annulment so he could get remarried in the church, and the questions in the paperwork really brought back all of the pain of why things didn’t work between them. Her coworker said this would be the perfect framework for a 10-minute play (which would be 10 pages).

So she wrote a 10-minute play about a woman who gets the paperwork at her home, asks her friend to bring over a bottle of wine to go through it with her, and as she looks at each question, her younger self and ex-husband act out the truth of each situation. This play was the overall winner of the festival in 2013l! She was then asked to expand it to an hour, where she added in her neighbors and their relationships.

Then the play sat for a few years. Watching the musical “title of show,” she started thinking about songs that might be good for it. She gave herself a deadline to submit her script with songs to another festival. She started writing the songs and submitted to the festival, but they closed. This got her to finish the show and it was then brought to life on stage at Hingham Civic Music Theatre.

She hadn’t written a play or a song for a musical before doing this project, and those things came about because other people told her she should try them. Having the deadline and goal to write one song a month really kept her on task. She’s been playing the piano since she was little so that helped.

She was nervous about writing the music. She went to the Broadway Teacher’s Workshop in New York and there was a session for directors. An older gentlemen next to her said he taught orchestra at Berklee, and she mentioned she was nervous about writing the music. He told her to write the lyrics and then get a Berklee student to write the music for her. “Even Carol King didn’t do both,” he said.

Then she thought that a student would interpret the feel of the songs differently than she would, so she tried it herself after all. She laid on her floor and sang her lyrics, then called a friend who knows music to make sure her melody wasn’t copying anything, and then she just finished it.

She remembered more about music theory than she thought she did, and had the help of Sarah Troxler (former podcast guest!) to make sure it came out correctly.

She was really lucky to have the cast she did for staging her original musical, especially the main character played by Carol Shannon. She wanted to get it done and wasn’t very worried about the reaction, she just wanted to flesh it out to make it a better story to tell. Some people liked it and some didn’t. She feels what she feels about the subject matter and the content – she can’t worry about what everyone thinks.

“It’s my story – I don’t need that validated, it is what it is.”

It’s more important to her that people love the end result, or say things like “I loved when they did this,” or “This part was so funny.” Then she feels like she did her job as a director or a playwright. It’s important that it was cast properly and that it serves the story. It’s all about the audience.

Her creativity disappeared for a long time. When she went away to school, the albums she grew up with stayed at home, so she wasn’t singing all the time anymore. She got married right out of college and had three kids in three and a half years, and stopped singing. She didn’t really realize it happened, it was a gradual change in her life. She was the wife to someone who wasn’t really into that stuff.

Columbia Record and Tape Club – she looked at this magazine one day and saw all the albums of her childhood. She got all of them for a dollar and was so excited to listen to them all again, especially “West Side Story.” There was a great moment when she finally heard the line that the album of her childhood had skipped through.

Her daughter was taking piano and playing by ear really well. She wasn’t reading the music because she was doing it by ear, and wanted to quit. Sheila didn’t want to lose the spot with her teacher, so the teacher suggested she take piano lessons instead. She started teaching her all of the new and modern musicals that were out, and Sheila’s love for theatre really came back.

This was one problem in her marriage – her husband didn’t want her going out to do other things like theatre.

“One of the things he said to me was, I don’t even know you anymore. And I said, that’s so funny because I’m more me than I ever was. That’s the truth. If I hadn’t left, I wouldn’t be where I am today. That’s me.”

Her daughter Cat is an actress, dancer, choreographer, and more. She is more disciplined than her mom and a perfectionist. She was 8 when she watched her mother do Hingham Cabaret, and called out the people who didn’t keep their final poses or were looking the wrong way.

Sheila thinks Cat has surpassed her already, but hopes she learns that not everything will always be perfect. Sometimes things work out for the best, even if they’re not what you wanted.

“Perfection is one thing, but you have to trust that things will work out. And if they don’t, then it wasn’t the right thing. Everything has value, because everything teaches you something, good or bad. Something the detour is what takes you to…where you’re supposed to go. You have to let things happen that you think are mistakes because they generally aren’t.”

She read a great book called “Big Magic” by Elizabeth Gilbert. She makes a great suggestion about just being curious.

“If something peaks your interest, just find out more about that thing. And that’s what will drive you to find what you love. You have to keep learning and exploring the world. Find the things that spark your interest, and then follow them.”

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Want more? You can find all episodes of the Let’s Get Real Creative podcast on Spotify, iTunes, Amazon Music/Audible, Google Podcasts, iHeartRadio, and more!

And trust me when I say I know my audio quality is not quite as stellar as I’d like, as I recorded this season in like .2 seconds while 6-8 months pregnant. (Anyone else a podcaster out there with inexpensive mic and Zoom recording recommendations?)

One Response

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