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ChiTownScreenwriting with Kat O'Brien - Issue #6 | FOMO & Failure

Welcome back to ChiTown Screenwriting with Kat O'Brien!
In this week’s issue:
  • On Writing and Creating: Embracing the Rewrite
  • Tips and Tricks: How To Stand Out, Overcome Writers’ Woes
  • Wisdom & What I’m Loving: Nomadland & FOMO [#nomofomo?]
  • Workshops and Events: Diverse Representation & Adapting Books
  • Someone You Should Know: Industry Gurus Weigh In On “Failure”

A Letter From Kat
Wow, #chitownscreenwriting! We are growing and building a following around the country and around the world and I couldn’t be more excited about it! Thank you for reading, and for sharing with your communities!
This week’s issue is all about overcoming FOMO - the Fear Of Missing Out, reframing your notion of “failure”, and finding resilience. Enjoy!
On Writing and Creating: Embrace The Rewrite
Preparing your work for production or publication? Then you know, editing is everything, writing is rewriting, all the cliches abound. Whenever I’m getting work ready to show and submit, I tend to obsess over every detail, striving to perfect that which will never be so.
I know there’s wisdom in setting deadlines and letting go. As critical as it is to just get the draft on the page and not be precious about it, it’s even more critical to let the revisions be what they are, get feedback that it’s good enough, and hit send. This tricky two step of being okay with the imperfect version of our work and finding collaborators we can trust takes practice and patience to pull off effectively.
"The only kind of writing is rewriting." - Ernest Hemingway
"The only kind of writing is rewriting." - Ernest Hemingway
We know the first 10 pages can be critical for readers, they either hook us or they don’t. And as a writer, you have to find a way to trust yourself that you’ve crafted a compelling opening so you can get past the first 10 and keep going.
When I can’t stop obsessing over the first 10, or any scene, I find it helpful to annotate my drafts. I love using the Script Navigator function in Final Draft to add notes for moments and punch ups so I can tell myself that I’ll come back to this after I get someone else’s feedback, so I can dig into it more deeply with validated focus. This can be hard with comedy, but I try not to let landing the perfect joke slow me down. As I’ve matured into my comedic voice and become more confident in my craftsmanship and sense of humor, I realized that improv mindset can be really helpful in this regard. On stage, when you’re improvising – that’s it. You’re in the moment, you execute, and there’s no revision mode. Sometimes, I have to embrace that thought process when I’m revising scripts as well.
To be able do this well, I think it’s essential to find a punch-up posse – a group of friends and fellow writers (directors, producers, actors too!) that you can text, call, or add as a collaborator to your draft to help you punch up those moments in the rewrite process. I have a few that I know I can text whenever, about whatever, for a quick “get me through this moment” with an alt joke, or validation that the moment I scripted is as funny as I think it is, or a creative suggestion to take it in a different direction that’s still on brand for my voice and POV, and authentic to the story I’m trying to tell. What’s helpful about a punch-up posse is that you can all be working on your projects at once, and the creative bandwidth required to support and engage is rather minimal. One-offs. A text-thread. Anytime, anywhere, easy for the non-committal types. Raise your hand if you feel seen.
For the heavier lifting required in the story development process, I think it’s essential to find a stronger support system. Start, or join a writers’ group. So many writers I know have been exploring their sense of connection/isolation heightened by this pandemic and are navigating the writers’ group process for the first time, or anew, trying different approaches to building more sustainable creative communities that work with your creative workflow. For this, you want to think about – who will read your interim drafts when you get stuck and help with notes along the way?
And while peer groups of writers are phenomenally supportive, you should also be thinking about who can you go to for the critical feedback that helps you unlock the next level of your art/craft? If you’re not yet ready for a manager or producing partner, or exploring your skills in a new format or medium, find a mentor or coach to help you build the confidence you need to produce or publish your work on the platform you’re pursuing.
You'll see this one again, in more depth, not to worry.
You'll see this one again, in more depth, not to worry.
In upcoming issues, we’ll be taking deeper dives into advice from throughout our creative community from writers working in different formats and platforms for all of these topics. If you have any questions, or advice that you’d like to share with #chitownscreenwriting about forming writing groups, finding reps, mentors, coaches, getting published, or getting produced– please don’t hesitate to reach out!
On My Feed: Tips & Tricks
Some of this is new, some of this is review, and I’m putting all into one round-up context just for you.
How to Make Your Script Stand Out From The Pile
Confidence is key and shows up on the page in interesting ways. Here’s a round up of my fave tips to finding your confidence as a writer & creator.
You're ready for the room/zoom if you think you are
You're ready for the room/zoom if you think you are
Meetings are just opportunities to connect with other creatives! No sweat!
Meetings are just opportunities to connect with other creatives! No sweat!
This is everything IMO, when it comes to landing your Big Idea.
This is everything IMO, when it comes to landing your Big Idea.
Everyone's looking for your voice on the page. Here's how to own it.
Everyone's looking for your voice on the page. Here's how to own it.
Kat O'Brien
“hey, it’s a no pee zone”
“... or you’ll get your car TOWED!”
- convo between my young sons on the way to school today

#POV #knowyouraudience #MagicMondays #TheKOBMagicIdea #comingsoon
... and here's how to sell that your voice belongs to you. How do you observe the world?
... and here's how to sell that your voice belongs to you. How do you observe the world?
How To Solve Some Of Our Biggest Writers’ Woes
In addition to embracing the rewrite and finding collaborators, here are two more of my fave tricks for keeping it real, and staying resilient in the writing and creating process.
Stealing is going to be a theme. Keep reading.
Stealing is going to be a theme. Keep reading.
For realz.
For realz.
Steal This Advice
In this advice column, someone once told me… some hot advice that you should steal, too. See what I did there? Feeling hot hot hot like Michael Scott. I’ll be dropping hints as to who I’m stealing from on twitter, insta, and facebook. Have fun, super sleuths! Catch me if you can.
*Someone* once told me...
*Someone* once told me...
Follow me @uknowkatobrien for #MagicMondays, #TuesdayTips, #Wednesday #Writing #Wisdom [aka Steal This Advice] and some #ThursdayThreads for pithy bits to keep you motivated and mindful throughout the week.
Writers' Wisdom: What I've Been Loving
First, this:
althea 🌈💖
i really wish people would give more support to indie/self-pub authors because that niche book with a queer/poc/disabled mc that you've been waiting to read is already out there, you just need to stop judging how good a book is by if it's published by a big publisher or not!
We’re celebrating indie publishers 24-7 in our #chitownscreenwriting community, as well as indie distribution and financing entities to help our community connect and collaborate to publishing and production opportunities. It can be tough to navigate this space, and we’re actively seeking to redesign it right now (more on that soon, too!) so keep an eye out for upcoming issues: our network of rockstar sages to bring you advice from all corners of this indie universe (including wisdom from the studio, prod co, and bigger publishing world, too).
The Nomadic Now
I’m getting a lot of queries from clients, colleagues, and my soon-to-be-graduating students alike about what to apply to, when, and how. Some of the best advice I’ve been given about this by the folks running fests, contests, fellowships, labs, my managers, and fellow colleagues is to really do your research and submit your project for the fests, labs, contests, and fellowships for which it’s best suited. Seems obvious, but I always hear about Fear Of Missing Out like, maybe I should submit this to [Sundance deadline is today, so let’s say Sundance] anyway even if…
…it doesn’t seem like the right fit. But who knows?
…I’m not done writing it but I can rush to make this deadline.
…I should make this deadline because… everyone else is? and if they get in they’ll move on without me? I’ll feel like I wasted an opportunity because I need to before I’m… 25, 30, 40, 50, 60, 70, 80–?
One of the most sage bits of advice I ever received I’m going to full on credit to Ron Friedman, comedy writer and professor extraordinaire, who helped cure me of my FOMO which gave me the courage to follow my heart by telling me–
There is no train coming. You are not tied to the tracks.
Lightbulb. I wasn’t a damsel in distress. I didn’t need saving. I could save myself, dammit, and I did. Time and again. It wasn’t easy. I’ve turned down opportunities to work on films and TV shows that were really awesome and hilarious and with good people so I know the experiences could have been magical but–
It wasn’t the right opportunity for me at the right time.
And there are choices I’ve made to take opportunities that proved devastatingly stressful to pursue – taking a toll on my health mentally and physically. But I love doing All The Things, and I was too afraid to say no.
Too often, we push ourselves to make it the right time, for fear that the opportunity won’t come around again, or that life is short, so we should carpe diem
– but I’m realizing now that this pressure we put on ourselves to take an opportunity even if the cost to pursue it (financially, logistically, psychologically, spiritually) feels like it could be too high is the source of much of our existential creative struggle between who we are, could be, should be, would be if only…
Navigating our dreams and our realities is always going to be hard as we juggle the myriad responsibilities we have as members of our respective communities – family, friends, neighbors, citizens – and seek to align those priorities with our highest truths, and finding joy.
This is what Chloé Zhao’s Nomadland made me think about, and it’s still with me. #zeitgeist #nomofomo
Kat O'Brien
#Screenwriters, with @sundanceorg fellowships due soon, many of us are #writing about why our stories are relevant. Struggling with it? Here’s my tips on how to unpack that, and a 🧵 reflection on how #Sundance alum Chloé Zhao does it in #Nomadland
#TheKOBMagicIdea #MagicMonday
Now streaming on @hulu ICYMI.
What did #Nomadland make you think about?
NOMADLAND | Official Trailer | Searchlight Pictures
NOMADLAND | Official Trailer | Searchlight Pictures
For me, this introspective film broadly touched on themes of pervasive isolation in an increasingly connected world.
Made me reflect the ways in which we have all been isolated this past year, how many of us will continue to distance ourselves from connecting with each other, balancing the need to be needed with the need to not be/as much.
Bigger picture: made me think about what we need, how much we need, and how remembering connects us to what we don’t need – only when we can let that go can we truly live in the moment, being fully present. And how nature has a magical way of helping us realize that.
Multi-layered on all levels of craftsmanship, the artistic brilliance of this film, for me, was its incredible connection to the zeitgeist, rapturously even moreso as we navigate life during and beyond this pandemic.
Francis McDormand’s performance, thoughtfully directed and captured by the moody cinematography, exposes us to this notion of dispensability in the workforce, especially at a certain age, and examines the idea of sustainable relationships between humans and nature, on this planet, now.
Our anti-hero Nomad’s restlessness, elusive grasp on Belonging, and her connection to her family, her expatriated-from-Empire and fellow nomadic friends, her sense of home, sense of purpose rippling out from the micro-cosmic personal level to the cosmic universal captures THE NOW–
– with haunting reflections in the visual storytelling from intimate close shots of her most personal moments to the wider, epic lens through which we see her (in)significance against the wild Western landscape, carried along by the sweeping piano score.
Like Zhao’s Nomad (McDormand), we are collectively in a moment *right now* of recalibrating our connection to the lives we know, the lives we lived and the lives we hope to live going forward.
So, that said– what are you observing re: your story and the world? And how are you capturing that in your written words?
On My Calendar: Workshops & Events
We are in a unique time for unprecedented virtual access to amazing workshops and opportunities to continue to learn and engage as a community of content creators and collaborators. Thanks to my creative partner Tamika J. Spaulding @tjmadeafunny for curating this wonderful list for us!
  • Tuesday, 5/18 @ 11 am PT
  • Women’s Weekend Film Challenge
  • Thursday, 5/20 @ 3 pm CT
  • Amazon Studios & PGA
  • Thursday, 5/20 @ 9:30 am PT
  • CAAMFest & Comcast NBCUniversal
  • Sunday, 5/22 @ 1 pm PT
  • Seed & Spark
  • Monday, 5/24 @ 3 PM CT
Writers' Spotlight: Someone You Should Know
I found it really hard to handle my FOMO when I was constantly comparing my successes to others. It wasn’t until my friend’s mom posted something on facebook about why would an apple want to be an orange that it finally clicked, and then I became obsessed with all my characters talking about being kumquats for like, the next 10 years.
I’m not saying I’m over it yet, either. The kumquat thing I mean.
Embracing this idea of being the best version of *you* that you can be is something that I’m getting better at the more I teach my kids about it, and as such, realize that I ought to practice what I preach.
Which brings me to this issue’s spotlight. For those of you in the #screenwriting twitter #WritingCommunity space, following folks whose shares are vulnerable and candid about FOMO and the idea of success/failure can be really helpful for normalizing a healthy, and less competitive mindset when it comes to creativity. I think competition in the creative space is one of the most difficult challenges to fostering true collaboration – which is one reason that I found Chicago to be such a supportive creative community. It’s all about the collaboration culture.
It’s always refreshing to me, when folks use their platform and following to lead by example and look for ways to support other writers.
David H. Steinberg
We went out with a pitch for feature animation last summer and it didn’t sell. So this year we retooled it for an animated series and guess what? It still didn’t sell! Man, this business is tough, but let’s #NormalizeFailure
David H. Steinberg
All tv projects end in failure. Scripts don't sell, sold scripts don't get pilot orders, pilots don't get picked up to series, and series gets cancelled. My heart goes out to all the creatives getting their hearts broken this week.
David H. Steinberg
That being said, most of these failures feel like getting dumped by a s.o. but getting a show cancelled, that's like losing a loved one. Sometimes they've led a long life, sometimes they were gone way too soon.
David H. Steinberg
But it's the showrunner who calls the actors and tell them we’re not coming back and they cry and you watch them tear down your sets and throw them in a dumpster. So yeah, you made it further than most, your show was alive, but that just makes the heartache that much worse.
There Really Is No Such Thing As “Failure”
Interestingly, the same topic came up with Jeanne Veillette Bowerman @jeannevb with Pipeline Artists. For writers that aren’t yet following this community on twitter, I recommend engaging. Friday night #pipelinewriters chat about the writing life, and Jeanne moderates a Sunday evening #scriptchat on industry trips, tricks, and strategies as well.
Jeanne Veillette Bowerman
For me, there really is no such thing as "failure." Sure, I've fallen. Been beaten up. But every single time I learn from it. When I do NOT learn from it, then THAT is the failure. #scriptchat
Connect with #chitownscreenwriting
Writers and creators, in Chicago and around the world, please share ChiTown Screenwriting with anyone you think might enjoy it, and be sure to let us know how ChiTown Screenwriting can uplift or support you and your projects.
Upcoming Issues | Call for submissions!
We’re looking for feature essays, random thoughts, creative pieces, images and/or videos exploring the following topics:
  • Getting published
  • Getting produced
  • How to land financing or distribution
  • Starting and engaging in writers’ groups
  • Increasing visibility of (intersectional) identities (race + gender + sexual orientation + ability) and cultures in film, TV, and other media
Ongoing Call for Submissions!
As this grassroots movement finds its voice and expands our reach, we’ll continue to solicit content contributions in the areas of:
  • advice on writing and creating
  • tips and tricks on twitter (tag me @uknowkatobrien if you got some!)
  • wisdom, think: self care, mindfulness, changemaking and more
  • workshops and events to continue our professional development, and foster opportunities for connection, and collaboration
  • as well as writers and creators you should know
  • cool projects launching that we should spotlight
Who’s someone that I should know, ChiTown Screenwriting creators? Ping me @uknowkatobrien.
If you enjoyed this, or have writing/creative life questions I can unpack and answer, or are looking for support to promote your work and projects, reach out and let me know? And please share widely! #grassroots #letsgo
Thanks for reading, and see you next week #chitownscreenwriting!
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Kat O'Brien
Kat O'Brien @uknowKatOBrien

ChiTown Screenwriting is a publication that I write and edit, for writers and creators to find community on their journey to getting published and produced.

More ambitiously, ChiTown Screenwriting is a movement, and a mindset. Global and local, we're a community connected by creative collaboration, and we're all about connecting collaborators to creative opportunities!

Each issue shares the wisdom and advice from storytellers and changemakers, with the goal of demystifying some of the more elusive processes and strategies for navigating the business, art and craft of getting our stories to our audiences.

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