Q&A: Kara Cutruzzula on creativity, motivation, and why failure is good for you
Q&A: Kara Cutruzzula on creativity, motivation, and why failure is good for you
"Here's the secret: Failures make you create work."
Occasionally in this newsletter I do Q&As with people I find interesting and inspiring. This week’s Q&A is with Kara Cutruzzula. I’ve been a longtime reader of Kara’s excellent Brass Ring Daily newsletter on creativity and productivity, and she’s always inspired me with the way she juggles so many creative projects. This week, she’s releasing a new book called Do It For Yourself: A Motivational Journal, which channels all of Kara’s wisdom into a journal anyone can use to help reach their goals. Can you believe she wrote a book while juggling a million other gigs! So I asked Kara a few questions about her book, what she’s been up to these days, and how she’s staying sane and creative during the pandemic. I especially loved her philosophy on rejection. Enjoy!
NC: What are you currently working on? Are you fulltime somewhere or freelance? What kind of side projects and hustles do you have going on?
KC: I purposely haven’t had a "full-time job" since 2012 when I worked for The Daily Beast! Instead, my career is a kind of wild series of collaborations with new and old friends who I can learn from; usually it’s a mix of writing, editing, and creative projects. Right now I'm a consulting editor at NextAdvisor, a shiny new personal finance site partnered with TIME. It's a very interesting moment to talk about money! I'm also helping out at Reasons to be Cheerful, David Byrne's site full of solutions and optimism. As a freelance writer, I cover creativity, productivity, and careers for Forge, TED Ideas, and NYT's Smarter Living. I also write a weekday newsletter, Brass Ring Daily, which is typically encouraging notes grounded in my own experiences. Sometimes there are lemurs. As for projects, oh boy! I write plays and musicals, most recently adapting The Marvelous Mrs. Maisel into a musical with composer Ron Passaro. Finally, I wrote the motivational journal Do It For Yourself, designed by Tessa Forrest of @Subliming.jpg, which is debuting, well, right now!
How do you manage to find the time to juggle so many different side projects outside of work? How do you stay motivated to tackle so much?
My friend Nina just called this the "juggle struggle," which is so perfect. I've found every project needs its own structure. The newsletter is daily, so there's never a question of when am I going to write it. It's always due. The BMI Musical Theatre Workshop has weekly classes. Journalism comes with deadlines. There are plenty of projects I haven't done because they exist in a squishy "eventually I'll get to that" place.
And staying motivated, for me, is about remembering what each project is giving you. Maybe it’s creative fulfillment, maybe it’s learning from smart people, maybe it’s a nice paycheck. You do need at least one of those, though. Oh, and saying no to things you can’t or don’t want to do—you have to or the juggle becomes impossible.
In your newsletter you’ve written about countless productivity and motivational strategies. What are the strategies and tips that have stuck with you most and been most useful or illuminating?
You need different strategies based on how you feel about the work. Let’s say I'm procrastinating writing an article because I don't like the topic or going through a transcript is painful. In that case, I just need to crank it out—there's no other way—so I might use my favorite timer cube to start a 15-minute work sprint or text my brother Eric and say "hey, I really need to write this article today—I just wanted to tell you, and I’m going to finish it by 3pm." Also giving yourself concrete deadlines helps. If I tell Ron I'll send him a new lyric on Tuesday, he might get it at 11pm or 2am. But if I say "I'll get you the song by 3pm," my day automatically has more structure and doesn't balloon into madness.
For bigger-picture motivation, one of my favorite strategies is writing your own future Wikipedia entry. Go wild. What do you want to be known for? Once you figure that out, it’s easier to work backwards. If I want to be known as a sculptor, I can look at, "Hey, am I taking classes? Do I need supplies? Who can help me? How often am I actually working with clay?"
And I know a lot of people are in the middle of major career changes right now. If you don't know what you want to do next, my first question is always, "Who do you envy?" That answer is your arrow. That's where you should go.
I loved a piece you wrote a couple years back about tracking your rejections/failures. What did that experiment teach you about failure, success, and putting yourself out there?
Gosh, I'm a failure junkie. I've submitted a play to the Pulitzer Prize committee, I've pitched hundreds of stories, applied to dozens of fellowships and festivals. Right now I have an open tab with Submittable to see if The New Yorker has read the poetry I sent them yet. (They have not. I’ll wait.)
But here's the secret: Failures make you create work. Of course I'd like to hear "yes" at every turn, but even when I don't, each application or pitch forces me to move forward on a project. A Pulitzer would be nice (!), but actually finishing the play so I had something to submit was the real end goal. Writing the poetry so I had something in shape to submit was the goal.
I say "more is more" a lot. You need more attempts (and, yes, failure) to find where you wanna go.
Tell me about your new motivational journal. What led you to write it? What will readers find in it?
Three years ago I started writing my newsletter, Brass Ring Daily. It had 25 subscribers. But I kept writing it, whether from passion or madness or the simple joy this was something I could completely own. It found more subscribers until one day, an editor named Madeline from Abrams Books, who was a subscriber, reached out to me and said she wanted to create a journal that has similar themes to Brass Ring Daily — how to stay motivated and see through your projects. And that was it! Honestly, I come back to this often as an example of how important it is to write (and share) things you care about. I really believe that the right people eventually find you.
The journal is full of gorgeous designs by Tessa Forrest of @Subliming.jpg and prompts from me about working through projects. It's divided into sections, so if you're in a brainstorming phase you'd turn to "Getting Going" or if you're stuck, you can turn to "Overcoming Setbacks." We cover everything from finding easy wins and overcoming procrastination to saying no and starting creative rituals. It's a little place for you to put down your thoughts and commit to your creative goal every day.
What are the things that have been getting you through quarantine and helping you stay sane and motivated during the pandemic?
Right now, my boyfriend Colin and I are watching Northern Exposure. We're very hip, very modern. Bike rides are also a must. But as someone who's always thinking about the future, I've had to reorient a bit to stay motivated. If I asked myself, "What's the point of making musical theater when Broadway is shut down?" I would never write a lyric again. Instead, the only question that encourages me to keep going is: "What work makes me feel good when I'm doing it?"
Give me one thing you've consumed recently that you'd recommend to my newsletter readers (can be an article, book, podcast, movie, show, whatever) and why!
OK, the ads finally got me. I subscribed to MasterClass and it's the best money I've spent in the last six months. I've watched Joyce Carol Oates lecture about the short story and David Sedaris distill how to write humor pieces. Right now, my friend Ron (aka Ron Howard, I call all the instructors my "friends") is teaching me about directing. I watch a lesson or two during lunch and it always fills me with creative energy and a little something new I hadn't known before. And isn't that pretty much the whole ballgame? •
Check out Kara’s new motivational journal here and subscribe to her newsletter Brass Ring Daily here.
What I’m reading
For immediate release: lower middle class and loving it, Spike Art Magazine. On pandemic social media scolding, and more.
Going postal, Bookforum. A very good read on how social media has become an increasingly toxic place during the pandemic.
Generation work-from-home may never recover, The Atlantic. A lot of people say WFH will revolutionize work — and maybe it will! — but there are downsides, too, and this piece captures it all well.
The eco-yogi slumlords of Brooklyn, The Cut. Wow this story was a doozy! Worth your time.
Enter Planet Miranda July, Vulture.
You don’t know her, Vulture. An extremely good profile of Mariah Carey!!
My winter dread has never been worse, The Cut. Who’s ready for a pandemic winter? Not me!
On witness and respair: a personal tragedy followed by a pandemic, Vanity Fair. A beautiful, moving, gut-wrenching essay from author Jesamyn Ward about losing her husband.
A stranger helped my family at our darkest moment, The Atlantic. A beautiful piece on the connections we build with strangers — and how that’s been lost in the era of social distancing.
Now what? Predicting the future of restaurants, Eater. Thinking about the future of restaurants is stressful but this package does a good job of exploring it in a clear-eyed way.
Thanks for reading! If you like this newsletter, you can click the “heart” at the top of this post on Substack or share it on social media or forward to a friend — they can subscribe at nishachittal.substack.com. You can follow me on Twitter here and Instagram here. And if you have thoughts on this week’s newsletter or suggestions to include in the future, feel free to comment on this post and let me know.