Deez Links: Meet freelance journalist / playwright / “Brass Ring Daily” writer Kara Cutruzzula, who’s got some extremely pure career advice for ya

Happy Friday, Deezers! This week’s interview is with Kara Cutruzzula, who you may know for her extremely excellent daily newsletter about productivity and creativity Brass Ring Daily (we called it “career soulcycle” a while back).

Tl;dr, Kara is an endless font of smart productivity hacks and super genuine inspiration, and it all makes sense considering her ability to juggle liiiiike everything: After making a name as one of the Daily Beast’s first rising stars, she’s has since turned into a freelance writer and editor extraordinaire, most recently working with the NYT, Money, and Bon Appetit — but um???? She’s also working on two plays??? So we asked her how she does ~it all~. Enjoy!


The interviewee: Kara Cutruzzula (follow her @karacut!)

The gig: Journalist, copywriter, podcast writer, newsletter writer, AND (gasps for air) playwright!!!

Obvious question: How do you manage to keep so many (so. many.) plates spinning all at once?

I’ve always liked a buffet. Bring on the plates! I wish I could reveal my secrets to time management, but the capital-H, capital-T Honest Truth is that I’m usually failing to do something at any given time. But since that’s not very helpful or aspirational, here is what I *have* learned from six years of being my own boss as a freelancer and becoming a playwright and lyricist at the same time.

  • Find real deadlines that scare you. We all know what a “real” deadline is. It’s one you’d be embarrassed not to hit. That’s the only way I ever finish anything.

  • Work with people you like. Even though every assignment (and therefore paycheck) is important, if I hear myself whining about an editor or outlet more than once, I won’t hesitate to pull the plug and find someone else to work with. As a free agent, choosing who you work with is a privilege. Even though it’s hard to remember, you do have a choice about who you engage with on a daily basis. Don’t work with jerks or people who don’t respect your time or your work or who are laggy with their payments.

  • Feel free to drop a plate or two. Depending on my workload, I’ve gone through spells where I’ve stopped writing plays, or stopped hanging out with friends, or stopped freelancing, all to focus on one larger goal. When you’re over a hurdle — or sped past a deadline — you can always pick the plate back up again and feast as much as you’d like.

How did your daily newsletter, Brass Ring Daily come about? Was it a natural extension of having to managing your own productivity?

My daily newsletter was a fluke! But I feel like there’s a good lesson in here. Three years ago, I started hosting a monthly gathering called the Brass Ring Summit at my apartment, where friends could discuss projects they’re working on. The goal was to feed off of each others’ insights and motivation. (Selfishly, I missed having coworkers and wanted to see my friends in one place.) I also wanted everyone to be fully present, so I took notes during each summit and sent these recaps out to the group the next day.

I really enjoyed writing them, so I kept doing it. (Lesson one: Follow what you enjoy.) One day during a breakfast meeting, my friends Alison and Daphna asked if I thought about turning my summit recaps into a newsletter. My brain said, “Hmm, that sounds fun” and now here we are, 430 newsletters later. (Lesson two: Follow what sounds fun.)

To get a bit more personal — how
do you organize your day?

I’m a repetitive list-maker. Writing deadlines and work commitments go into my Google Calendar. To scare myself.

I also have a paper planner; leaving it out on my desk makes it unavoidable. I also use the calendars to track how much money I’m making each week, and add it up every month (crucial for freelancers).

And when I have a really busy day, I’ll write out a to-do list on a single 5x7 notecard. Oh, and I use the Chrome plug-in Momentum, so every time I open a new tab, I see my daily to-do list in the right-hand column. Basically, I have to create a tsunami of to-dos so I actually do them.

Tell us a little about your theatrical work! How has your journalistic background informed your work writing (and directing!) plays/musicals?

When I was a culture editor, I always felt like I was on the wrong team. I wanted to be making plays and film and TV, not writing about them. So I wrote a short film. When I typed “THE END” I thought: Yes. This is what I’m supposed to be doing.

Now I’m grateful for my experience as an editor — I value collaboration and love chopping down sentences. Also, I love a news peg and so most of my playwriting projects have, in subtle ways, revolved around culturally relevant topics or things that are in the water.

You started out as the culture intern when the Daily Beast was originally founded, and Tina Brown has even referred to you as one of the site's first "new young stars." What is one of your favorite memories from your time there?

Ah, so many! Any major news event that happened from 2008 to 2012 is deeply lodged in my brain, from the Deepwater Horizon oil spill and Arab Spring to Michael Jackson’s sudden death and the (first) royal wedding.

Going to London for Prince William and Kate Middleton’s wedding and helping Tina, who was covering the event for CBS, and the team back in New York close Newsweek’s special royals issue and the weekly magazine was a sleep-deprived highlight. Those were simpler times.

Finally, what advice do you have for people starting out who are afraid that, both in terms of creativity and discipline, they don't have ~what it takes~ to actually **do** the big thing they're dreaming about?

Whose approval do you want or need? If you need an editor or mentor to help guide you, find one at work or through friends or on Twitter, or just send me an email and I’ll write you periodic emails encouraging you that, yes, you can do it. Whatever your “it” is.

If you need to believe in yourself, something I like to repeat to myself often — and which I think I got from Mindy Kaling — is that “someone’s gotta get it; why not me?” This applies to nabbing that big job you think is out of reach, writing a book, getting a fellowship, pitching a scary editor, developing an entirely new skill, quitting, starting. Why not you?

Most importantly, if the idea hasn’t left you yet — if it’s nagging you for weeks or months or years — that’s the biggest sign of all that you need to heed its call. Do it. Grab the brass ring. What’s the worst that could happen?


Yup yup go nab your dreams people!!!!! Kara’s got you and so do we. (Subscribe to Brass Ring Daily to get more of this kind of unadulterated motivation!)

Deez Links will be off for t-giving for a week. See you next Monday!