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"A Strange Loop" of Writing Discouragement


If you’ve been hanging around my blog long enough, you know that I’m a pretty serious theatre nerd. After all, last year I did back-to-back posts about the musicals of Jonathan Larson and a tribute to Stephen Sondheim and what both legends have to teach us about the art of storytelling.


Right now, I’m fixating on A Strange Loop, which won the Tony award for best musical this past Sunday night. The show tells the story of Usher, a down-on-his-luck, queer, black writer trying to create a musical that tells the story of his life as a queer, black writer trying to create a musical that tells the story of . . . you get the idea.


It’s called A Strange Loop for a reason, guys.


If that sounds like a lot to you, you’re not alone. But once I listened to the cast recording, I was blown away by how much the story resonates with me as a writer dealing with discouragement.


Throughout the show, Usher fights a fierce internal battle with himself, personified by the six actors that play his Thoughts. He’s an overthinker haunted by a toxic relationship with his parents, who are baffled by the direction his life has taken and try to fit their son into the box of their own expectations. He obsesses over his financial situation, sex life, whether there’s an audience for his play, and how the different aspects of his identity reinforce his art (or don’t reinforce it enough).


Does any of this sound familiar? My guess is that it does.


That’s the thing I love so much about A Strange Loop. It may depict Usher’s very particular life experience, but there is something in his story for everyone who has ever looked in the mirror and asked themselves if their work or even if they as individuals are enough.


And in particular, I think there’s something very special in his story for writers.


What Are Your Thoughts Like?


The minute I wake up, a million things start flying into my head.


I woke up too late. Again.


I need to let my dog out.


Gas prices are too high and I’m not making enough money.


Is what I’m doing worth it?


Does anyone actually care?


Then I go look in the mirror, and often, it’s like all the bullies in my head from when I was fourteen have slammed five pots of espresso and have just been waiting for me to show up.


Then I actually sit down to get to work and wonder, in Usher’s words, “Can I really write this?”


I don’t know what your mornings are like, but my guess is that there’s at least part of this that you can relate to.


(Note: If you have no idea what I’m talking about on any level, please email me, because I want to know your secret.)


Here’s a question . . . why are the thoughts creative people have about themselves and their work overwhelmingly negative?


We all have our own answers to that question and the purpose of this blog post isn’t to make you do psychotherapy on yourself.


But regardless of what your personal reasons are, creative people have a special ability to sabotage themselves into perpetual creative discouragement.


I think it happens for two reasons . . .


We make the mistake of finding our identities in our creative work


How often do you place your self-worth in your ability to consistently write good stories?


That’s a good goal to work toward. We all want to do the best we can with our creative gifts.


But how often do you berate and degrade yourself when you fail to meet your expectation of what “good writing” looks like?


This also happens when we’re given opportunities to share our work with people. A bad Amazon review or critical comment in a writing class can make us crater emotionally. A rejection letter can make us feel hopeless.


It’s normal to feel a little discouraged about your writing, but giving into despair is a sign that you have elevated your work to a point it was never meant to occupy.


Your worth as a human being is not based on performance. It’s not based on how good your writing is.

Your worth as a human being is actually not related to your writing at all.


The minute that you reduce yourself to only one aspect of your personality or identity, you deny that you are a unique person with a contribution only you can make.


This is what Usher does to himself. And it’s what we do, too.


If we get so discouraged with our writing that we transfer that frustration to the totality of who we are, what should be a creative and life-giving act instead deprives of us of vibrancy and life.


I’m not here to say this is easy or that I’ve mastered it. As a lifelong perfectionist who has a history of being hard on my own performance, I am here to say it’s hard. However, I speak from experience that becoming aware of this tendency is the first step in working to correct it.


We mistake other voices for our inner critic.


As I mentioned last week, I recently went to a writing retreat put on by my writing community, The Habit. At the event, our community leader, author Jonathan Rogers, spoke about the dangers of allowing the negative voices in our heads to be louder than our ability to objectively view our writing.


“The helpful voice of the inner critic isn't the only voice inside you,” Rogers writes in an email newsletter summing up the presentation. “There are who-knows-how-many other voices reverberating in there. Often we internalize the voices of harsh and/or shaming criticism so thoroughly that we mistake them for our own voice. What you think of as your inner critic may simply be the voices of outward critics that have taken up residence inside you.”


In A Strange Loop, Usher’s problem is not a lack of talent. That much is clear from the show-within-a-show that he produces by the play’s conclusion.


His problem is that he’s internalized a slew of voices that have leveled judgment against him at his core.


He’s consumed with guilt for letting down his well-meaning, but toxic parents, haunted by abuse, fighting shame, and facing a wide array of complex emotions toward his family, race, and sexual orientation.


As a result, he’s so plagued by self-loathing that he not only is creatively blocked, but regularly sabotages himself with self-destructive thoughts and behaviors.


I think that Usher offers another lesson for dealing with this kind of toxic writing discouragement: we need to confront the origins of the baggage itself and learn to make the voice of truth the only one that matters.


In one scene, Usher encounters a tourist who attends a performance of The Lion King at the theatre where he works as, well, an usher. He opens up about his struggles with his art and receives some unexpectedly poignant wisdom from her in response:

“So my advice, don't play nice Don't look back and don't think twice Don't let doubt get in the way of what you want
 Just roll the dice
 Stay the course, seize the day
 Ride your horse into the fray
 Live your life and tell your story
 In exactly the same way:
 Truthfully, and without fear
 In spite of those who wish you'd disappear
 Find joy inside your life while you're still here
 That's your challenge from a sympathetic ear.”

I won’t give any specific spoilers, but by the end of A Strange Loop, Usher has stared the source of his dysfunction in the face. He does exactly as the woman advises: he tells his story truthfully and fearlessly. It’s a painful process—but he is able to recognize that confronting the source of his obstacles is the only way out.


It’s the only way to not just create, but to live a meaningful life.


I know this is HARD stuff we’re talking about. But overcoming any source of discouragement about your writing is going to be.


Having gone through this process, though, I can say with certainty that there are good things waiting for your art and your life.


Oh, and one more thing . . .


Michael R. Jackson, the writer of A Strange Loop, first started creating the extensively autobiographical show 20 years ago.


On the show’s Broadway opening night, he gave a speech to the audience where he related his creative struggles along the journey toward his production’s success.


Watch the full video below. It’s proof that Usher’s story isn’t just something a writer dreamed up.


It’s a triumph that actually happened.


So, What Now?


I’m not a counselor and I can’t help you with the personal issues at the heart of your writing discouragement.


But I am a consultant and I can help you with your writing issues.


I might even be able to give you some ways to overcome your creative discouragement.


Click here to access my calendar. I’d love for you to book a completely free, no strings attached appointment to talk about any writing related questions you have.


I know that you want to reach your full creative potential so you can impact and inspire readers, and this is the easiest way to get on the path toward doing just that.


Hope to talk to you soon!

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