The Five "Whys" of Character Creation
Book Excerpt from "Playwriting With Purpose" by guest playwright Jacqueline Goldfinger
I wrote Playwriting with Purpose as the book I wished I had as a writer; a balance of art and craft, invigorating writing prompts, and advice from working writers who know what it’s like to be stuck on a third act break at 2AM.
As a book, it’s like a good night out at the pub with your playwright friends; talking, dreaming, drinking, swearing, and occasionally hitting on a transformative truth that you take home in your pocket. Welcome to the party!
Excerpt
The Specific Becomes the Universal and The Five “Whys”
The more specific your characters are, the more universal their stories become, even if that feels counterintuitive at first. Throughout the writing process, you’ll learn more specifics about your characters that will influence your writing. Get as specific as you can – never be afraid of being too specific. You can always revise, edit, and shape this specificity in your actual play later, but for now, dig as deep as you can get into your characters.
For example, in playwright Yasmina Reza’s Art, the very specific detail of one unique painting is key to understanding the relationship between the friends.
In Art, the relationship between three friends (Marc, Serge, and Yvan) is fractured when Serge buys a painting for a large amount of money that is an entirely white canvas with a few small white lines. Is this Art? Is it an enormous waste of money? What does this say about Serge? Through their disagreement over this one very specific painting, which is interpreted differently by each character, we watch their friendship spiral out of control. By the end of the play, we learn that Marc isn’t really upset over the painting, but over the fact that Serge made the purchase without him. We learn that Serge now feels Marc is too controlling. We learn that Yvan tries always to be agreeable to them both because he values their friendship even though it sometimes makes him uncomfortable. The three men gradually put their friendship back together, but all three are changed due to this disagreement over Art which – in the end – was about a specific piece of art (a painting we see) and, more powerfully, the art of friendship over a lifetime. It was Serge’s choosing that painting at that moment in time and sharing it with those friends that makes it a universal story of how friendships evolve and how art is realized in the world.
Even in plays that are set in fairytale, myth, or fable – which tend to have less defined time periods – characters and their worlds are highly specific.
For example, playwright David Harrower’s Knives in Hens is a fable set in a pre-industrial landscape, and features a character only known as Young Woman. However, at the beginning of the play, the playwright immediately begins defining who she is as a character and the world in which she lives very specifically. From the Young Woman and her Husband’s actions on page one we learn:
They live in a cottage at the end of a village in a rural place.
They work on a farm.
The farm requires hard labor with no modern equipment (like tractors).
The Young Woman is very curious and asks questions that are practical, spiritual, and theoretical.
Her husband does not care for her questions, and thinks he’s smarter than she is, even though we can see he is not smarter than she is.
There is a lot of tension in the marriage.
Immediately, the playwright centers the visceral specificity of the Young Woman and her world. Through that specificity, we begin to understand and connect with the characters, even though we don’t know exactly what the story is about yet.
Writing Prompt: The Five “Whys”
To understand the deeper truth as to “Why” your character is doing something, pick one important moment in their lives. If you already know one that will happen in the play, select that one. Otherwise, select any formative event.
Now, ask “Why” this character behaved this way in that specific moment. Write down an explanation quickly on your list, don’t over think it.
Now, ask “Why” four more times. Each time, go deeper within your character’s psyche.
This will help you write more complex, specific, and compelling characters. However, it won’t lead to days of overwriting where you get nowhere because you have an end point – after five “Whys” stop and take stock.
Ask yourself the questions: What have you learned that you did not know before? What connections have been made clear? Are any of these connections surprising to you? If so, how are they surprising and do they change the course of the character’s journey?
Once you answer these questions, you might chose to write more “Why”s or go on to something else, but it will give you a deeper understanding of your character and more specifics about their life to use within the play.
For example, in my play Backwards Forwards Back, an American soldier returns home from the war in Iraq with Post-Traumatic Stress Disorder (PTSD). At a Fourth of July Parade, he has a violent PTSD episode during which he confuses his young nephew for a young Iraqi boy who saw his innocent family get killed by the Soldier’s squad. The Soldier is convinced the Iraqi child is coming to avenge his family, and the Soldier almost beats his nephew to death by mistake. Part of understanding the Soldier’s journey was discovering “Why” this moment at the Parade with his nephew triggered his episode.
Why? Because the Iraqi child and his nephew are the same age and are physically similar.
Why? Because the Soldier’s squad made a deadly mistake, killing the child’s family in front of him, and the Soldier is paranoid the child will come after him for revenge.
Why? Because the Soldier joined up after 9/11 to exact his own revenge, and he can’t imagine how much angrier and vengeful he would be if he saw his own family killed.
Why? Because the Soldier feels like he needs to protect everything and everyone around him.
Why? Because the Soldier was never protected as a small child and was hurt. As he grew up, he lifted weights, bulked up, and vowed always to stand up for those who can’t for themselves. And the young Iraqi boy is someone he wished he would have protected rather than harmed; that makes him the abuser, which is something he vowed he would never be. By creating this fiction in his mind that the child is coming after him, he turns himself back into a victim and so the beating, when he is triggered, is him trying to absolve himself of guilt by “defending” the Fourth of July party-goers from danger.
Understanding why his PTSD is triggered at exactly this moment gave me a much deeper understanding of the character. This deeper understanding enriched the scene of losing control and beating the nephew because the scene wasn’t just about him “flipping out.” Instead, it was about a core truth that connected with his journey from harm to healing. In the play itself, the Soldier never told the story of his “Why” but it informed my writing, and the Soldier became more complex and compelling because of it.
Overview
The more specificity you can bring to the characters and – by extension your play – the more universal it will become. Asking “Why” a character is doing something, then moving beyond the obvious explanation helps you reach deeper into their psyche, learn more about them, and have more specifics to use when writing your play.
Playwriting with Purpose is available wherever books are sold (https://a.co/d/hs5lau4). In the summer of 2025, an Expanded Second Edition will be released with more writing prompts, short craft lessons, and playwright interviews. However, the current edition has more than enough tips, prompts, and lessons to keep you busy writing until next summer.
Upcoming Event
Join me at Drama Book Shop October 1 for a preview of Playwriting With Purpose. I’ll be joined by Adam Szymkowicz, author of Letters to a Young Playwright. We’ll have a Question and Answer. EVENT INFO: https://www.eventbrite.com/e/playwritingmaking-art-and-making-a-living-tickets-907170540507
Jacqueline Goldfinger (she/they) is a playwright and librettist. Her awards include the Yale Drama Prize, Smith Prize, Glaspell Prize, Generations Award, and Opera America Discovery Award (with Composer Melissa Dunphy). Her plays and libretti have been produced by The Kennedy Center, BBC 3 Radio (UK), Contemporary American Theatre Festival, Sydney Opera House (Australia), Urbanite Theatre, Voces8 (UK), Capital Stage, Gate Theatre (New Zealand), École Nationale de Théâtre du Canada (Canada), Perseverance Theatre, and others. Her work has been supported by YADDO, National Endowment for the Arts, Millay Colony, among others. She has two Amazon bestselling playwriting books: Playwriting with Purpose and Writing Adaptations and Translations for the Stage (Routledge). www.jacquelinegoldfinger.com
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Audrey Cefaly's plays (Alabaster, Maytag Virgin, The Gulf, The Last Wide Open, Trouble) have garnered the Lammy Award, the Calicchio Prize, the NNPN Goldman Prize, the Edgerton, and a Pulitzer nomination. Her works have been produced at Signature Theatre, Cincinnati Playhouse, Barter Theatre, Merrimack Rep, Florida Studio, Florida Rep, Gulfshore Playhouse, and countless others. Cefaly is a Dramatist Guild Foundation "Traveling Master," an Arena Stage playwright cohort, and a recipient of the Walter E. Dakin Fellowship from the Sewanee Writers Conference. She is published by Concord Theatricals, Applause Books, Smith & Kraus and TRW
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