Sinclair: What’s your three word bio?

Kara: Connecting the dots!

Sinclair: I love your Brass Ring Daily newsletter and I think everyone should subscribe. How many days have you done it for and how do you keep up with it so well?

Kara: I’m grateful to have carved out a little corner of your inbox every weekday! I’ve written around 375 editions so far, which, now that I think about it, is the longest project I’ve worked on in my life. My trick to keeping it going is figuring out what worked best for my brain. I knew if it was weekly, I would find a reason to skip here and there. Writing it daily incorporated it into my life much more organically. It feels like something I just *do* and not something I have to do.

Sinclair: What’s the Brass Ring Summit and how can folks be a part of it?

Kara: The Summit is a casual monthly get-together for people to talk about what they’re working on and what they’re excited about, whether that’s a big new magazine assignment or an amazing play they’ve seen. A few years ago, I was feeling a little isolated as a freelancer and wanted a space to see my old friends and make new ones, but scheduling coffee dates and meet-ups is always a challenge, so I thought…why not invite a bunch of people over so they could all meet and find value from each other?

Sinclair: I see. What type of response do you get from readers?

Kara: Originally, I thought my newsletter would only be interesting to writers, editors, freelancers, etc, but I’m surprised and happy to have made new reader friends who work as accountants, yoga teachers, real estate agents, and more. I guess it’s not only for people who self-identify as “creative” or people who are writing. I just want to give people some little nuggets to think about and apply to their work and personal lives.


“Be kind and do your best work. That’s all you need.” – Kara Cutruzzula


Sinclair: You’ve been published in Esquire, The New York Times, Daily Beast, and more. How did you get to be the writer you are today?

Kara: I still feel like a first draft, in many ways. Wonderful editors help you become a better writer. I’d follow a good editor to the moon. Reading books about writing helped me develop my style and craft. On Writing by Stephen King and Bird by Bird by Anne Lamott are two longtime favorites. And everyone attempting to work on something creative should read The War of Art by Steven Pressfield. Plus, I will read anything: plays, screenplays, poetry, longform journalism, captions, museum plaques, cereal boxes. Ideas and inspiration are everywhere.

Sinclair: What’s one tip you have for other writers looking to be published like you are?

Kara: Write pitches that sound like you, and talk to editors as if they’re human. (They are!) Also, don’t be afraid to follow-up. An editor’s inbox is as deep and labyrinthine as a cave in Thailand, and no one gets mad if you gently resurface your story idea.

Sinclair: Tell us about a play you’ve written that was a challenge to write.

Kara: I’m writing a play right now that is much more experimental than my usual work, and pushing the boundaries of what I can do on stage and what makes a play especially theatrical is thrilling and challenging.

Sinclair: What project are you working on right now that you’re both excited about and a little anxious about as well?

Kara: I’m working on writing my first musical! Six months ago I had never written a song. But then I thought, “Why not?” So I took a lyrics writing class and found some collaborators and here we are.

“I still feel like a first draft, in many ways.” – Kara Cutruzzula

Sinclair: What’s the best part about going to work each day?

Kara: Knowing I have choices about how I spend my time. Not saying I always make the best choices, but knowing I have the ability to say “yes” or “no” or pitch new work or think about the long game or take a midday nap is very important to me in my attempt to find some balance.

Sinclair: How would a friend describe you on your best day?

Kara: Oh goodness. I didn’t know how to answer this so asked my brother Eric, and this is how he described me on my best day:
Always there to motivate and give encouragement and to think about the long game of life with perspective.


“Write pitches that sound like you, and talk to editors as if they’re human.” Kara Cutruzzula


Sinclair: On your worst day?

Kara: Again, from brother: Difficult to make decisions usually from a lack of sleep, caffeine, exercise or a combination of all three.

This is very accurate! *chugs third cup of coffee*

Sinclair: What’s something you wish you could say to your 16 year old self?

Kara: The Backstreet Boys will still be together 15 years from now. You are on the right side of history.

Sinclair: What’s something you’re working to unlearn?

Kara: Being interested in a bunch of different avenues, whether that’s journalism, theater, advertising, or entrepreneurship, isn’t a bad thing. Every discipline feeds and informs the other.

Sinclair: Who do you go to when you’re needing support and guidance?

Kara: My brother Eric and my brilliant network of friends.

Sinclair: What’s one challenge you face in your work that you’re still working on navigating?

Kara: Picking one project and seeing it through to the end. I’m addicted to starting new things!

Sinclair: When was the last time you practiced self-care? What did you do?

Kara: This isn’t your typical “pour a bubble bath” version of self-care, but I made a dentist appointment after a long (five-year!) delay. It was always on the back of my mind. Of course, actually making the appointment and going took no time at all. And now my teeth feel so clean!

Sinclair: What’s something that’s been bringing you joy lately?

Kara: Seeing as much theater as possible.

Sinclair: What’s something that’s been pissing you off lately?

Kara: I try really hard not to be pissed off!

Sinclair: When was a time that self-doubt was at its worst for you while on your career and life journey?

Kara: I’ve been laid off (twice!). I’ve had freelance clients and editors disappear. I’ve had to chase down checks. But these situations are all out of my control. I just have to trust in my abilities and my—dare I say it?—intuition. I know when something doesn’t feel right, whether that’s a new gig or assignment or project or collaborator, and as long as I trust that feeling and do what feels right, I’m good.

Sinclair: What are your unshakable values and when did you become clear on them?

Kara: I’ve learned these lessons especially over the last five years:

  • Be magnanimous
  • Always make the more interesting choice.
  • Always take the meeting.
  • Always ask for more money.
  • Everything happens for the best.

Sinclair: What is one piece of advice you’d give to an up and coming playwright/writer struggling with self-doubt and feeling like giving up on their dreams?

Kara: What is the next smallest action you can take today to get a little closer to your goal? I’m all about laying a foundation brick by brick. Write one line of dialogue in a notebook. Set a timer for 20 minutes to come up with a story idea. Email that person who said they’d like to read your writing. There are so many concrete things you can do. Focus on those.

Sinclair: It’s years in the future. You’re on stage to accept an award for your life’s work. What’s your five word acceptance speech?

Kara: I grabbed the brass ring.

Sinclair: Imagine that all your life’s work disappeared and you only had 1 minute to tell the world what you truly believe to be true. What would you say?

Kara: Be kind and do your best work. That’s all you need.


Kara Cutruzzula is a playwright, journalist, and newsletter writer. She splits her brain equally among her written endeavors, with her articles and essays featured in The New York Times, Newsweek, Esquire, The Daily Beast, and other venues. Her work has been seen onstage in New York at Cherry Lane Theatre, Manhattan Rep, Secret Theatre, and The Wild Project. Her newsletter Brass Ring Daily covers work, life, creativity—and usually her unadulterated love of Moviepass. She also holds a monthly gathering called the Brass Ring Summit for writers and creatives to discuss their most exciting projects.

Learn more about Kara and connect: Instagram | Twitter | Website

Featured Awesomeness: Kara says, “My newsletter Brass Ring Daily is where you can find me and my work every day!”



Published by Sinclair P Ceasar III

Sinclair Ceasar is a speaker, podcaster, and higher ed professional committed to helping people live a better story, and be more hopeful. He sends weekly inspirational emails to over 1K readers each Monday. Email him at or connect with him via Twitter @Sinclair_Ceasar

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