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ChiTownScreenwriting with Kat O'Brien - *RE-ISSUE* #3 | Take 2: Ted Lasso & #SelfCare

Welcome back to ChiTown Screenwriting with Kat O'Brien!
In this week’s issue, a lot about Ted Lasso and #SelfCare. Not gonna lie.
  • Writing Advice for Finding The Time (Part 2)
  • Tips and Tricks: On Being Ready To Take Creative Risks, Fellowships
  • Workshops & Wisdom: Can’t Miss Opps & Design Thinking
  • Writer Spotlights: The Oscars & My Fave Recommenders

A Letter From Kat. The RE-ISSUE or Take 2
OMG. So, a good lesson in being okay with imperfection. I’m experimenting with Revue as a newsletter platform, and apparently, the version that you were all sent yesterday was wonky. I’m super paranoid about smooth operating and am definitely a bit of a perfectionist. I don’t love looking like a hot mess but I’ll be real with you – I’m still figuring out this platform and I clearly goofed somehow. A partial draft for my advice section On Writing & Creating: Finding the Time (Pt 2) was somehow scheduled instead of the version I *thought* I drafted, saved and sent out to all subscribers. So here’s re-issue, Take 2. Thanks for understanding, ChiTown Screenwriting!
On Writing and Creating: Finding the Time (Pt 2)
How do we know which project to focus on creatively at any given time?
Last week, we unpacked the why now and how approach to prioritizing what we pitch, draft, and refine. This week, I’ll share my time management tips and work/life balance tricks to getting it done while still having fun.
Pitching: Keep Those Irons in the Fire
Getting It Done | Keep an Idea Journal. Organize those fleeting what ifs. Ideas don’t have to be fully formed, but it can be helpful to categorize them by type, genre, and what it will take to execute them. Brainstorm a list of events, contests, fests, residencies you want to attend, fellowships and opportunities you hope to land, and meetings you’re eager to get on your calendar. Checking in with ourselves whenever - daily, weekly, monthly, quarterly, whenever you get stuck - and writing down our raw ideas and goals *at the same time* can help us to see new ways to position ourselves for the right opportunity at the right time. Whether you make a habit of doing this for 10 minutes at a time, or binging every so often– do make the habit of organizing your ideas. You’ll be more ready to pitch whomever, on whatever, whenever the opportunity arises.
Having Fun | Turn Pitching Into Happy Hour. There’s a reason why the Hollywood exec and agent scene is dominated by coffees and breakfasts, power lunches, drinks, dinners, desserts… all work and no play can be really draining, so take a page from the pros and multi-task. It’s really easy to get discouraged, lose momentum, or focus when we’re brainstorming ideas in a vacuum. Even if you’re not taking your pitches out to parties, or if this extrovert’s approach to self-promotion kinda makes you want to throw up, by reaching out to your crew of friends and family, you can low-key beta test early ideas to see how sticky they are. Go to your collaborators to see if you can pitch someone to get excited about executing your idea with you and making something happen with it. Test out early concepts on a bigger audience on social media – be as anonymous as you need to be– and see what kind of traction you might get. We need to know our ideas can live somewhere besides our own heads. That’s the first part. The second part is – sometimes, to make time, we need to feel like it’s worthwhile. It’s important to nurture connections with your creative support team or fans who believe in you. Bonus if you can do something else you love while you’re at it: lose yourself in nature, go workout, grab a post-vax bite to eat.
Drafting: Which Project Do I Write?
Getting It Done | Write in Shifts. Throughout film school and in my early 20s, I thought I needed to clock 12-14 hour writing weekends or all nighters to get my writing done. As I transitioned to more freelance work for myself, I found that my writing schedule stayed the same: I never had time to hang out, have fun, do the things I wanted to do. I told myself it was “self-discipline” but the reality was – I began to resent my writing like it was more of a chore than my passion. I started investigating how other writers managed their time and realized it was far more common than I realized for pro writers to write in shifts. 5-6 hours a day. Today, I write in 3-6 hour daily shifts. I still love a good binge-writing weekend, but to keep my projects moving forward and balance everything else I got going on– I have to schedule my writing in shifts. Limiting my time helps me stay focused, and I also feel great about having time to do all the fun things I want to do with my friends and family.
Having Fun | Schedule Shifts to Minimize FOMO. Sometimes, it’s just not possible to limit my time. I have to meet a deadline, and the writing has to get done. I’ve hit my shift ceiling and it’s still unfinished. This is when I pull the all-nighter, or have to miss out on something. But I have legit FOMO, especially when it comes to be a present mom and spending time with my kids and husband or doing something super fun with friends. So to minimize that, I try and schedule my writing windows for times that I know they will be otherwise engaged. I try and ensure our meal times align and try to exercise during outdoor play, so that when we all come home and need to unwind, everyone can do their own thing quietly, while I finish writing in a shared space that is hopefully somewhat chaos-free.
Refining: Knowing When It’s Ready To Show
Getting It Done | Stick to a Deadline Schedule. Set a limited window to complete your revisions, and shift creative priorities (pitching, drafting) accordingly. Once you refine and hit send, be done with it for now, and move on to something new. Remember, you don’t have to limit yourself to working on and completing one project at a time. Many writers and creatives I know have a slate of projects in various stages of development and production so they can stay fresh and challenged thinking about storytelling in different ways. Shifting from draft mode to refining mode within a specific deadline window is a great way to balance your project slate and still get things done.
Having Fun | Celebrate! It is a big deal to finish a draft. First draft, revised draft. You put in the time, no doubt made sacrifices, battled some FOMO and got something ready to show. Celebrate! My introverted celebration is having a fun or fancy dinner and something delicious to drink. My extroverted celebration is inviting everyone I know to join me! Or doing a table reading. Live on stage. Virtually on Zoom. Gathering fam and friends to pull up a cushion in my living room. We can’t rely on others to validate our work, so we need to find ways to validate both the process and the product for ourselves.
On My Feed
When asked what advice Amy Poehler had for young female directors she said: “Do it even if you don’t think you’re ready... a lot of women wait until they think they’re really really ready for something. And I’ve worked with a lot of guys who aren’t ready for what they’re doing.”
Kat O'Brien
#pipelinewriters re: authentic character quirks, R U 👀 the biscuit storyline in @TedLasso? Gr8 ex. of an action-driven [bakes, delivers] character reveal [so thoughtful] that subverts tropes [competitive coach] and leads to memorable moments. Who else has a fave 💎 discovery?
SIDEBAR | Steal This Writing Trick
Warning. Ted Lasso Spoiler Alert.
This is a quick trick (micro-lesson) for writers, directors, producers, execs. It’s a solid punch up strategy for comedy and/or for extracting more emotional resonance out of a given scene, regardless of genre.
Are you feeling fired up and ready to take some creative risks? Great. Here’s a quick hack to writing “the memorable moment”. Let’s go!
Ted Lasso does it so well and we’ll use this show as our model example. Make a list of some verbs [e.g: bakes, delivers]. Make a list of personality traits [super thoughtful, extra]. Make a list of jobs or hobbies, edified by a descriptor [competitive coach, destructive dentist]yes, I love alliteration. Mix those up. Shake and Bake! You’re ready to roll.
This ideation strategy for brainstorming character quirks that can lead to memorable moments on the page is my go-to for getting unstuck creatively. Let’s break it down with Ted Lasso. This is how you get a competitive coach being super thoughtful, extra all the way, in that he bakes and delivers cookies for “Biscuits with the Boss”, creating some tension with a little lie that he doesn’t admit (at first) that he bakes them himself– which becomes a running joke and leads to multiple memorable moments throughout the show. Why? Tension and Emotion. The recurring exchange allows Ted and Rebecca an opportunity for some awkward comedic tension and also vulnerability. The repetition of these scenes gives us a structure to map their relationship arc. The premise is a great scene set up [they’re active, they’ve got scene goals] for any exposition or storyline-driven dialogue they need to get out, and *bonus* it’s also a metaphor for what Ted’s doing with the team. Brilliant.
The ideation exercise of generating random responses to the prompts is something that anyone can do that at anytime. To apply this to your own scripts whenever you’re stuck follow the same basic formula: action verbs + what you want to reveal about your character + describe who they are leveraging the specifics about *your* character and your story. Have fun!
Ready for Fellowships?
My colleague, fellow professor Scott Myers at DePaul University, writes Go Into The Story, which is an awesome writing blog that you should be following if you are not already doing so. He also put together this great round up of upcoming (mostly TV) fellowship deadlines.
Hollywood Writing Fellowships | by Scott Myers | Go Into The Story
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 rad creative partner, comedian, filmmaker, and fellow changemaker Tamika J. Spaulding @tjmadeafunny for these curated recs below!
This Week’s Curated Workshops & Events by Tamika J. Spaulding
No. More. Zooms.
If that’s how you’re feeling these days, I completely understand. But, now more than ever, it’s important to push past Zoom fatigue and show up for the amazing workshops & events that wouldn’t typically be available to creators outside of L.A. and NYC. Even if you have a packed schedule, sign up. Most events will send you a video recording when the event has concluded. All will keep you on a distribution list for events in the future. This is the kind of access and opportunity that #ChiTownScreenwriters need in order to help build a robust writing community here in Chicago.
And, when you’re participating in these workshops and events, be sure to visit the chat where attendees are sure to be exchanging contact information or creating lists for future reference. Drop your reel. Reach out to others to form a writers group. Tell people what you’re working on, and where you may need help. I had the pleasure of meeting an animator in Chicago that I would have never met otherwise if we hadn’t been in the same workshop hosted by an L.A.-based organization. We’re now collaborating on a project! 
Now is the time to show up in any way that you can. And, of course, be sure to let everyone know to sign up for ChiTown Screenwriting to stay connected to more can’t-miss events and advice for writers.  Feel free to tag us @tjmadeafunny and @uknowkatobrien and bring our community into the convo using the #chitownscreenwriting hashtag!
Got an event that should be on our calendar? Drop us a line!  
Creators Writing Room
Tuesday, 4/27 @ 6 pm PT
PBS Kids
Wednesday, 4/28 @ 2:30 pm AND May 3 @ 1:30 pm ET
Women in Film
Thursday, 4/29 @ 6pm PT
Final Draft & Seed & Spark
Friday, 4/30 @ 2pm CT
Creators Writing Room
Friday, 4/30 @ 6pm-7pm PT
Chicago/Midwest Emmys
Saturday, May 1 @ 11am CT
Writers' Wisdom: What I've Been Loving
Feeling Overwhelmed? #SelfCare
Obvi, I’m obsessed with #SelfCare.
And this article in the Harvard Business Review, written by fellow DePaul University professor Alyssa Westring is one of the most resonant deconstructions of #SelfCare I’ve heard in awhile. As I’m studying mindfulness and applying it to the creative process, I think it’s super relevant for our community of creators and collaborators. Check it out!
DePaul Newsroom
.@alyssawestring (@driehausbus) writes in @HarvardBiz about self-care and how it can look different for each person. "To figure out what you need, start by simply noticing when you feel invigorated and when you feel drained. Look for patterns," she writes.
#SelfCare Space
What Does Your Ideal Writers’ Room Feel Like? How Does It Look?
I love design thinking, and I love the art of designing a space. I think #SelfCare is going to become one of the hottest ideas in reshaping industries and the return to work post-pandemic. My friends, Design Team Huili Feng and Ross Barney of @TumuStudio and I have been discussing how, after a year of working remotely, many commuters are eager for more of a work/life balance and this is going to show up as a trend in redesigned workspaces. Check out a thread we started here and let’s make this a bigger conversation. We’d love for ChiTown Screenwriting to have pop-up writers’ rooms and a designated collaborative space to access for free. Co-working spaces and membership clubs can be prohibitively expensive for self-employed freelancers and so for many, it’s just cheaper and easier to go to cafes. How would you redesign your workspace? What’s your ideal writers’ room?
Kat O'Brien
Looks like it's gonna be rainy & cold in Chicago this weekend. Perfect writing weather. #Pipelinewriters, what's your ideal writing space when the world totally reopens? Design team @tumustudio & I were just talking about this yest. I ♥️ space w #highceilings & #historicaldetails
#SelfCare Saturday and Sunday
Making Time For Weekend Reads, Weekend Watch
One of my business students asked a brilliant question last week - how do writers make time for all the books, movies, shows we’re supposed to be watching while still having time to write? I don’t, really. It’s hit or miss. I take the advice of my kids’ kindergarten teacher “Do your best and forget the rest” – and mix it up with a little senior exec mindset. The prod co and studio development game relies upon a hierarchy of content consumption. The lower you are on the food chain, the more content you should be consuming and curating for the boss. So, I’m sometimes late to the party but I also have friends that are literally watching and reading everything who can curate and recommend to me what I can and should be adding to me Weekend Reads or Weekend Watch lists. You can do the same!
Because I teach night classes am a mom of two young kids, and have discovered that I do actually need to sleep, I only have time to watch 1-2 episodes of something before I go to bed at night, and that’s not always long enough to watch a movie from start to finish. Sometimes, I watch movies in “chapters”. Sometimes I stay up too late. Sometimes I binge and write very little in a given period of weeks or months, and other times I write a lot and watch nothing and then when I’m done, it’s like I’m coming out from hibernation.
The amazing thing we’re realizing about immediate premium content access as a result of the pandemic is that viewing habits are changing, and I think that as a result, we’re going to increasingly see tighter release windows for bingeable content and more of a shift to the Netflix model of 3 season series. What I’m wondering is if and how this might eventually start to impact the structure of feature length movies. What do you think?
So many good movies and shows to catch up on, but meanwhile, my current Weekend Watch has been finishing Ted Lasso and now I’m going to finish taking down the full Oscar line up.
Women and Hollywood
History made.

Chloé Zhao is the first woman of color to win Best Director

Directing - @nomadlandfilm: Chloé Zhao #Oscars
Writers' Spotlight: Someone You Should Know
A lot of the dialogue around yesterday’s Oscars was related to the historic elevation of under represented voices, primarily, what felt like persistent shock and awe that we’re not seeing a more diverse Hollywood yet. Still. Kathryn Bigelow was the first woman to ever win an Oscar for Best Director. Last night, Chloé Zhao was the second-ever, and first woman of color. And Emerald Fennell’s win for Best Original Screenplay for Promising Young Woman last night was the first for a woman in 13 years: last one was Diablo Cody for Juno.
I’ve been reading and consulting for a long time, acting as a gatekeeper of sorts for major production companies and studios and I think one of the reasons I’ve been valued is for my eye for intersectional diversity in story telling and its potential for that representation to carryover on screen. One thing I’ve noticed is that representation has a powerful trickledown effect.
There are so many creators in the margins of intersectionally under represented identities that are obviously not winning Oscars and one way we’ll see more of these artists in the mainstream for prime time recognition is by consuming and recommending content by all the other writers and directors out there telling the stories representing these perspectives, characters, and experiences on screen. That doesn’t mean that there isn’t room for Ted Lasso anymore– clearly, there is. Notably, this show driven by and starring [cis het white] male creators is elevating complexly flawed co-starring female characters in the show. Although it’s set in England, we’re diving into the internationally diverse world of football and experiencing moments on the show through the perspectives of more racially and ethnically diverse characters, too.
So where do we go to support more high profile, diverse content to consume to really push through that glass ceiling… and where do we go to support everything else that needs to get into that pipeline?
Today’s Writers’ Spotlight is focused on entertainment journalists @kylebuchanan, pop culture reporter and The Projectionist for The New York Times and Rebecca Martin, founder of Cinema Femme @cinema_femme; as well as filmmaker and Professor John Rangel @parksidefilms.
Why I Love Kyle’s Reporting | I’ve known Kyle since our days at USC together, where his taste and pulse for the zeitgeist was always impeccable. He’s so savvy to the pop culture scene and is intentional about elevating under represented creators and perspectives in his reporting. As The Projectionist, Kyle’s my go-to for what’s a must-see in the acclaimed space and if he says it’s good, you know it’s good.
Why I Love #FemaleFilmmakerFriday | Connected with Rebecca for an early feature when she first launched Cinema Femme, and since then, I’ve been loving how she spotlights intersectional feminist talent from up-and-comers to those on the scene for decades. Check out her Friday newsletter and #FemaleFilmmakerFriday.
Why I Love Following Rangel’s Recs | I’ve known Rangel for years as a teaching partner. He is a brilliant filmmaker and tapped into the indie scene and Criterion Collection history like no one else I know. As a filmmaker and teacher, John Rangel is so brilliant at finding and elevating the up and coming can’t-miss indie films and shows. Following him on twitter, you’ll also see gems on diverse storytelling throughout film history as he frequently unpacks his love for the Criterion Collection.
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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