Best Results Organizing

Welcome back to another installment of our rare Paper Doll series of interviews with colleagues and special guests. I’ve interviewed productivity specialist Melissa Gratias, academic/life coach and inventor Leslie Josel, genealogy organizers Janine Adams, Jennifer Lava, and Hazel Thornton, and life coach/author Allison Task.

Today, I’m excited to introduce you to journalist/writer/editor/playwright/lyricist/librettist Kara Cutruzzula (rhymes with Methuselah!), friend-of-the-blog and purveyor of motivational oxygen.

We met when I subscribed to Kara’s newsletter Brass Ring Daily in 2019. She’d provided a link to a spec script she’d written for Gilmore Girls, one of my all-time favorite TV shows, and I wrote a fan-girling email to tell her how brilliant and talented she was, the subject line of which was, “My neighbor was awakened by my raucous laughter thanks to your Gilmore Girls script!” Kara’s ear for dialogue and how she made secondary and tertiary characters like Michel and Lane absolutely shine were impressive.  

Paper Doll readers may initially wonder what Kara’s talent for capturing the distinct voices of characters on a hit television show has to do with organizing and productivity, the bread-and-butter topics here on this blog. But you’ll soon see — and it all started with that get-to-know-you chain of emails where Kara and I traded our insights about the process of getting things done — and the frustration of not getting things done.

it’s OK to archive that email you never responded to back in August 2021.

it’s also OK to respond! yes, today!

less OK is staring at in your inbox for another six months.

free yourself. one or the other.

— Kara Cutruzzula (@karacut) February 22, 2022

We kept finding ways to work together and support one another’s efforts. I interviewed Kara about newsletter writing and magazine editing for a monthly meeting of the NAPO Authorship & Publishing Special Interest Group and then she interviewed me for a great feature for Forge, Medium’s personal development outlet. Readers, that piece, Now Is the Right Time to Declare Bankruptcy on Your Projects, is so good, you should open it in another tab right now so you don’t forget to read it.

And Kara just interviewed me for the soon-to-premiere season #2 of her Do It Today podcast! If you find productivity compelling, or you could use a little motivation to turn your dreams into reality, get to know Kara!

EVERY SUPERHERO HAS AN ORIGIN STORY

Paper Doll: Could you tell Paper Doll readers about your early life and college years? I know you majored in English at UCLA. What did you plan to do when you finished school?

Kara Cutruzzula: Hearing this question makes me laugh because…I didn’t have a solid plan! My Big Idea was to move to New York and find a job “working with words.” (So cute!) I was applying for internships and editorial assistant jobs every day. Book publishers, magazines, websites, university presses, you name it.

A few weeks after graduating I bought a plane ticket and took advantage of the generosity of my aunts Gina and Jo by crashing on a pull-out couch in their apartment (we called it “the nook”) and crossed my fingers I would find something to do. Then I did.

This highlights something that’s come up over and over again in my career: First you leap, then you figure it out.

You have used your words to craft a set of interlocking and parallel careers. Basically, you’re a polymath (a fancy-pants way of saying Renaissance Woman). Your fascinating and diverse experience includes work as an editor, writer, newsletter creator, playwright, lyricist, and podcaster.

Did (or how did) your internships in film and TV prepare you for the career path you’ve had? How did you get your start in writing for online outlets? 

In hindsight these unpaid college internships (at a film development company, at a publicity firm working on Oscar campaigns, and a B2B travel magazine) laid stepping stones for the future. I loved taking the bus (yes, I was the rare LA bus rider) to the 20th Century Fox lot to work at the film development company.

Sure, I picked up chopped salads for the executives, but I also read and wrote coverage of screenplays and TV pilots, and covered assistants’ desks when they were out of the room. (To this day, there’s still nothing scarier to me than “rolling calls” — placing and returning phone calls to intimidating execs at a lightning-fast pace!)

Working at the travel magazine was a great stroke of luck, too. The editor-in-chief, Ken, kindly set me up on an informational interview with a magazine editor when I moved to New York. No job came from that interview, but even a short getting-to-know-you meeting is a huge lift to your spirits when you’re 21 and don’t know anyone in the industry.

As for writing, if you caught me during the first five years of my career, I wouldn’t have called myself a writer at all! In 2008, I was hired as a culture intern at The Daily Beast, a then two-month-old website founded by editor Tina Brown. The team was small, maybe 15 people, and that was my real education. I helped the culture editor plan out culture coverage — what was the site going to cover and how were we going to cover it? — and transcribed interviews and contacted publicists and all sorts of other tasks. 

Then I became a homepage editor. Remember, this was back in 2008. We weren’t getting traffic from social media. People actually visited a website’s homepage. As a homepage editor, you were responsible for story placement, headlines, photos, and deciding what needed coverage on the Cheat Sheet — basically “the mix,” as Tina called it. What did people want to read? (Actually, being a homepage editor was scarier than rolling calls!) But there was a real sense that what you were doing was important. You were covering the news. Everyone was incredibly invested, and the team was brilliant.

After The Daily Beast merged with Newsweek in 2010, I moved over to the magazine side to edit and assign stories for the back-of-book section covering film, TV, theater, fashion, and a back-page feature called “My Favorite Mistake,” where I interviewed James Earl Jones, Barbara Corcoran, Richard Branson, and other fun folks. But I got a crash course in magazine editing. Very different from editing for a website! You can only fit so many words on a page. I loved it.

This is a very long way of saying I was primarily an editor for four years. It was fun and rewarding and also exhausting. Newsweek published its Last Print Issue in 2012 (it’s since been resurrected) and I was laid off.

I didn’t want to work full-time at another magazine or website. (This was 2012; freelancing was a little less common than it is now.) So I thought: What else is out there?

Over the next 10 years, I became a writer. 

GRABBING THE BRASS RING

You launched Brass Ring Daily in 2017. What caught my eye in those daily emails and the (now) 1000+ newsletter archive was the fact that while you were writing about disparate aspects of your own life, theater, and things that were going on in the world, you were blending motivational quotes, advice about productivity and self-empowerment, and doing it all without trying to sell anything. And Vanity Fair called it, “A life coach in your inbox.”

What prompted you to start the Brass Ring Daily? What has meant the most to you about the experience?

I became a freelance writer and editor — I even spent a solid three years as a travel writer — but I was also holding these monthly “summits” at my apartment where creative folks and friends would talk about projects and share resources.

[Paper Doll Editor’s Note: My late, great high school history teacher, Mr. Fred Murphy, would have wanted me to draw the parallels between Kara and Madame de Staël, an 18th- and 19th-century Frenchwoman and writer, famous for connecting the greatest minds of her era in salons.]

I took notes during these meetings so that one editor’s name or that great productivity tool was recorded for anyone who needed it. I wrote up a summit recap and sent it out to the group.

After a year or two, my friends Alison and Daphna asked if I ever thought about starting a newsletter. So…I did! And it’s the smartest thing I’ve ever done for my career and also my sense of self as a writer. I always tell people to own something for themselves, even if that something is small.

The newsletter gave me a daily deadline that wasn’t attached to an editor or assignment. I didn’t have to answer to anyone, except my own nagging guilt if I skipped a day. And it gave me a place to collect all the inspirations, book quotes, and my own thoughts on creating. The newsletter collects them and allows me to let them go — basically, it’s my most important tool for organization! 

[Paper Doll Editor’s Note: Brass Ring Daily often has delightful cameos by baby animals.]

WORDS AND MUSIC: KARA’S NAME UP IN LIGHTS

You’re also a musical theater lyricist and librettist, and from your newsletter, I know you’ve worked on a wide variety of projects as part of the BMI Musical Theatre Advanced Workshop and the BMI Librettists Workshop. Can you tell readers about Letters from May and The Marvelous Mrs. Maisel Musical?

The Kara of 2008 would think it is completely wild that the Kara of 2023 writes musicals. I got into the BMI Workshop, which has been around since 1961; the workshop self-describes as “the setting where the writers of A Chorus Line, Little Shop of Horrors, Nine, Ragtime, Avenue Q, Next To Normal, and The Book of Mormon, among many others, learned their craft.”

For the first two years, lyricists and composers attend a two-hour weekly workshop and present songs they’ve written and get feedback from the room. I only cried like five times. Learning something new is hard. Being a beginner is hard. Thankfully, now I cry much less often.

Letters From May is a 10-minute musical written with composer Kristoffer Bjarke as our first-year project. It tracks the life of an artist, May Dalton, over 50 years as she wrestles with questions of fame and sacrifice. Last year, it was produced at a festival in New York, which was a joyful experience after the pandemic knocked the wind out of the sails of many musical theater writers (myself included).

During year two of the workshop, composer Ron Passaro and I adapted [the Amazon Prime TV show] The Marvelous Mrs. Maisel into a musical, which was another great joy. 

Musicalizing such strong and vivid characters was a fun challenge — and of course, Julie, you know I love Amy Sherman-Palladino’s writing more than anything. [Paper Doll Editor’s Note: Sherman-Palladino created Gilmore Girls, Maisel, and the under-appreciated Bunheads, which starred Broadway’s beloved Sutton Foster. It’s streaming on Hulu. Thank me later.]

Right now, Kristoffer and I are developing Marathon, which is an original one-act musical which takes place entirely during a race. It’s about patience, persistence, and finding the capacity within yourself to do hard things. 

THE TURNING POINT: MOTIVATION & GETTING PUBLISHED

I usually ask interviewees, “What would you say was the turning point that helped you identify your true calling and fine-tune what you do professionally?” But you seem to be what folks have been calling a multipotentialite. Have you HAD a turning point, or are you still discovering many different true callings, all around your love of words?

LOL. I usually feel like I have no idea what I’m doing and also like I’m just getting started. The last 15 years have felt like a prolonged learning process — a stage I named “percolation” in Do It Today. Culture editing informed my freelance writing; editing influenced my lyric writing; and on and on. I want to do a lot of things and am always worried about not finishing enough or over-thinking what I’m making. 

One kind of guiding light over the past 15 years was following random flickers of interest. What sounds interesting? Where do I want to go? What do I want to learn? I’ve never regretted going toward those new endeavors.

Writing is obviously a passion for you. Your first book was Do It For Yourself: A Motivational Journal, beloved by readers and reviewers for the combined uplifting wisdom and snazzy design. For people struggling, procrastinating on doing the big things that would make their hearts sing, you offer exercises to change mindset, overcome obstacles, and pursue follow-through.

How did you come to publish it? Can you tell us about that writing experience? What did writing that book change in your life?

Do It For Yourself actually came from writing my newsletter! Madeline, an editor at Abrams, read my newsletter and reached out — the publisher wanted to release a motivational journal and she said she liked my writing style and point-of-view. At the time, I was working as a consultant at Money Magazine covering personal finance and careers, and I had also just gotten into the BMI Workshop.

But I’m a big believer that you can do almost anything if there’s a clear goal and end date. Your life organizes itself around these important pillars. So I wrote the journal in a few months, then it was published, oh, 18 months later! (Book publishing exists on its own timeline.)

pov you find out the motivational journal that TikTok & Pinterest keep selling out is by none other than @karacut !! pic.twitter.com/NFA54npegZ

— delia (@delia_cai) June 23, 2021

Seeing people connect with the journal and hearing how it improved their own practices and projects has been incredibly rewarding. It was also nice to create something tangible and concrete, and beautiful enough that people want to display it on their nightstands (or their TikToks).

This past fall, you published Do It Today: An Encouragement Journal, the second in your “Start Before You’re Ready series. I reviewed and profiled it in-depth last month in Paper Doll Presents 4 Stellar Organizing & Productivity Resources. It is freakin’ superb!

Can you tell us how this book came together? With its accent on motivation and productivity, I have to ask, did you write this for yourself? Do you follow the advice and follow the journal prompts yourself?

Do It For Yourself kind of took off — it’s currently in its ninth printing! — and my editor and I started talking about a possible follow-up. I asked myself, what might people need right now? And the answer was obvious: encouragement. Encouragement to try new things, pick up old projects, bounce back from rejection, and expand their web of connections.

So this journal features short essays and prompts along those lines — and yes, I wrote this entirely for myself because I needed all this encouragement, too. If you don’t connect with the work you’re putting out there, it’s unlikely it will resonate with other people. You have to believe it! I need constant reminders about all of these things and often turn back to the journal, hoping a prompt will thaw some frozen part of my brain or create a new idea. And it does.

You’re not a coach, but your books play a cheerleading, guiding role in helping your readers create and achieve. Aside from what you write in your newsletter, do you test your advice out on your friends and fellow creators? 

I’m lucky enough to have many brilliant friends and collaborators and we bounce ideas around all the time. From “can you read this email and let me know if it sounds OK” to “could you edit this draft” or “do you want to set a mutual deadline by Friday to accomplish that nagging task?” So all of this “advice” is actually a distillation of what I’ve witnessed and experienced around other people.

The writing experience is different for every author. In the lingo of NaNoWriMo, there are “plotters” (writers who outline) and “pantsers” (those who write by the seat of their pants). What are you? What’s your writing routine like? 

I do not like outlines. Let me rephrase that: I HATE OUTLINES. But I have convinced myself to try to outline – or reframe what an outline is in order to make it less painful. For my last two journals, I wrote a loose structure, basically a paragraph of what I wanted to cover in each chapter. I’m working on a new screenplay right now, and forced myself to write a bullet point list of scenes I wanted to include. Technically that’s an outline, but my brain still resists that word. Figuring out what I want to say usually comes from the writing itself. 

My routine is all over the place. Some days I’ll write nothing, other days I’ll write 10 pages! If a deadline is involved, I’ll get it done — it’s the old journalism training, knowing that the story had to be finished by a certain time or the page in the magazine would be left blank. You gotta get it done.

HOW WE ARE DOING IT TODAY

As I wrote in my review of Do It Today, my favorite part of the book was the section on “percolation,” or letting yourself have an idea on the back burner without having to constantly “produce,” non-stop, and noted that it reflected a lot of what I’d been writing about combating toxic productivity.

If you had to pick one journaling exercise/section from the book that you wish everyone would try, which would it be? 

Oooh, I love writing thank you notes to rejections! Failures and rejections are a part of life. But I try to remember that you get to choose how you respond. Rejection often stings, but I’ve found writing and sending off a thank you to whatever opportunity turned me down frees up a lot of mental space and allows me to move forward.

Writing and sending off a thank you to whatever opportunity turned me down frees up a lot of mental space and allows me to move forward. ~ @karacut Share on X

So if you didn’t get that residency/client/gig/opportunity, try not to simmer in the angst for too long. Consider why you were so drawn to it in the first place and use it as an arrow to move forward. Write a little thank you and get ready to start the next big thing.

What have readers been telling you is their favorite exercise/section?

Chapter two is called Start Before You’re Ready, and that idea seems to resonate with readers. Asking yourself, “What is the next smallest step I can take?” and then “How long will it actually take to complete?” changes your perspective. You’re getting honest!

So instead of saying “I need to reorganize my entire office,” I might ask myself, “Which area is giving me the most angst right now?” and “How long will it actually take to go through it?” The same idea holds true for our work and creative projects. Get honest with yourself about time estimates; it’s much less intimidating than a scary, open-ended task.

Last summer, as part of the launch of the Do It Today journal, you started the Do It Today podcast, where you interview people about how they are spending their days while they’re deep into creation mode or working on solving a problem. As you’re gearing up for season two, will you describe what this podcast experience meant to you? 

For most of last year, I felt like I was floundering. Truly. When you’re in charge of structuring your days, the freedom is nice but also overwhelming.

I wanted to know: How do other people do it? What does another person’s day look like? How do they overcome obstacles? How do they do their best work? So I impulsively started a podcast, mostly as an excuse to ask people I admire slightly invasive questions about their work and creative processes. Our conversations were incredibly encouraging, and I can happily say this year I’m in a much better daily groove, thanks in part to hearing about other people’s strategies. 

I’m gearing up to release next season, featuring a wonderful interview with you Julie, and also a Broadway producer, a personal finance expert, an author and keynote speaker, and an A-list screenwriter. There are so many common threads and themes between how people work — it’s extraordinary to see.

THE CURTAIN CALL

What else should Paper Doll readers know about you, your life, your take on motivation, creativity, and musical theater? What’s on the highlight reel of your life these days?

It’s never too late to try something new!!! That deserves three exclamation points.

I’m surrounded by people making big career pivots, adopting new skills, moving around the world, and also doing the less glamorous and equally hard work of showing up for their most meaningful work day after day. You can do it, too. I’m cheering you on! (That might be my most-used slogan.) 

My highlight reel right now consists of seeing lots of theater with my husband Colin (we just got married in December!) and taking winter naps with our rescue cat, Lula. And leaning into work and activities I actually enjoy. Everything else either gets paused or cleaned out. Life’s too short.

Before we wrap things up, tell us what’s next for Kara Cutruzzula, multipotentialite and musical maven?

My third book, Do It (or Don’t): A Boundary-Creating Journal is coming out September 12, 2023 and is now available for pre-order! Get ready to do a deep dive into setting boundaries for your projects, creativity, and relationships. (This is an area I wanted to work on myself, so figured we could all work on it together!)

This year I’m developing the musical and also turning back to screenwriting and playwriting, and have some big goals attached to those mediums. I’m also having fun connecting with people through my newsletter.

Most of all, I’m embracing empty space. It’s kind of like leaving one drawer in the closet completely free, and not believing you have to fill it up right now. I’m leaving a little space in my calendar for what is going to light me up in the future — whether that’s tomorrow or two months from now.

And that is music to a professional organizer’s ears.