Designer Ariana Gupta wants to redefine what an heirloom is. Image: Ariana Gupta.

“If I was paid for the hours I spend worrying,” said Damian Bradfield, We Transfer Chief Creative Officer, “I would be a trillionaire.” Truth.

There is a lot that can keep an ambitious creative person up at night: big ideas, tight project deadlines, client feedback, random thoughts, a little too much red wine, forgetting to respond to that text, the state of the world, early morning wake up calls for the airport, and much, much more.

So we’re here to take a collective breath and hear from creative leaders — including Skip Wilson, VP, Brand Marketing, Shutterstock; Dhiya Choudary, Creative Director, Magic Spoon; and Jaime Lopez, Chief Design and Marketing Officer, Flatiron Health — as they share what to-do list items keep them up at night. May it be a cathartic experience. As a wise person once said, “To worry is human, to fall back to sleep, divine.”

1. Damian Bradfield Thinks About the Meetings He Forgot to Cancel

I can worry about something I might have said to someone I just met and chew over my response to their simple innocuous question all night long. I can worry about who I might have offended, lunch appointments I haven't confirmed, meetings I forgot to cancel, parents evenings I avoided, whether I picked up my dog’s foot-long turd from the dog park yesterday or not. If I was paid for the hours I spend worrying, I would be a trillionaire.

–Damian Bradfield, Co-Founder and Chief Creative Officer, WeTransfer

2. Meena Yi Thinks About the To-Do Lists That Come with More To-Do Items

Checking the latest in news and emails. And the emails usually have additional to-do items in them.

–Meena Yi, Creative Director, The White House

3. Mauro Porcini Thinks About What Makes Him Happy

To make my daughter happy by inspiring and empowering her to be herself. Make my wife happy, by being there for her. Make my dogs happy, by being the parent that they never had. Make people around me happy, by simply being kind. Make my company happy, by creating meaningful solutions to people’s needs and wants. All of this is what finally makes me happy too.

–Mauro Porcini, Chief Design Officer, Pepsi

4. Jaime Lopez Thinks About All She Still Has to Learn

I’ve been fortunate in my career to take a lot of leaps forward, but the flipside of that is I’m often just out of my depth. It’s a good thing, but not always comfortable. If something’s keeping me up at night it’s usually that I’m trying to learn a big chunk of new skills. I often have a stack of books next to my bed that’s a reference library for whatever space I’m trying to figure out.

–Jaime Lopez, Chief Design and Marketing Officer, Flatiron Health

5. Chí-An Benjamin De Leo Thinks About Side Hustles

There’s so much opportunity here in Vietnam, as it’s one of the fastest growing economies in the world. I have a side gig (queue plug #2) which I started a couple of years ago with four other racing enthusiasts. It doesn’t exactly keep me up at night right now but add in a slew of other ventures I’m planning and it will start to keep me up. So much to do in so little time!

–Chí-An Benjamin De Leo, Founder & CEO, Rice Studios

6. Skip Wilson Thinks About Family and Life

I have always been career-focused, and I’ve moved around several times to accommodate that career. Obviously, the pandemic has changed many of our preferences, and what we prioritize in life. So, my thoughts are often dealing with aging parents and my family spread across the U.S. which has me thinking, “Am I spending enough time on the things that are really important?” And that’s family, people, relationships and experiences. Conversely, in a very demanding professional role, I ask myself, “Are we prioritizing the right thing? What’s the mood of the team? Am I being the best leader I can be to empower the team to move?” So, I spend a lot of time worrying about the health of the team professionally, but the same is true of whether I’m spending the time contributing to my friends and family in a meaningful way.

–Skip Wilson, VP, Brand Marketing, Shutterstock

7. Cathie Urushibata Thinks About Her Daughter’s Dance Class Sign Up

Being a working mom is tough, so I can either be worrying about deadlines for work or making sure I signed my daughter up for the right dance class. But knowing my alarm will go off at 5:30 a.m. for work is an incentive to make sure I get a good night’s rest.

–Cathie Urushibata, Creative Director of Shake Shack

8. Matt McCue Thinks About His Alarm Clock Going Off

I usually have no trouble falling asleep, but on those special nights I wake up for no reason in the early hours of the day, I start thinking about…my alarm going off. Most mornings it’s 5:41 a.m., so I can be up, out, and back from my morning run before my children wake up. On Wednesdays, I meet my business partner Tucker Margulies for a run so I definitely can’t oversleep that day. And it feels like I’m always headed to the airport. On those mornings, I’m lucky if I sleep at all, worrying about flight delays and cancellations and, of course, oversleeping, which is exactly the thing you don’t want to have to worry about when you can’t sleep.

–Matt McCue, Editor, Creative Factor

9. Dhiya Choudary Thinks About that Email She Meant to Send to You

That email I forgot to respond to months ago, but now it’s so awkward, I can never respond. Or can I?

–Dhiya Choudary, Creative Director, Magic Spoon

10. Ariana Gupta Thinks About Starting Her Own Magazine

There are so many, but the one that keeps me up all night is my dream of starting my magazine. And now I’m finally at a point where I can’t take it anymore, so I’m starting to take some action. I want the magazine to be about family heirlooms and redefine what an heirloom is. I’m still trying to connect with people in the research phase, but I’ve given myself a year, so you’ll probably see the magazine in the wild sooner than later. My second dream is to make another film. I made a short film in my junior year of college and fell in love with filmmaking, which I want to do more of. So script ideas often keep me up at night.

–Ariana Gupta, Designer and Filmmaker

11. Arianna Orland Thinks About “All That Will Ever Be Known”

There are just so many talented folks making incredible art and designing incredible things all over the world at any given moment. Most of the time I feel happy about that, occasionally I feel a pang deep inside my heart because I know no matter how hard I try to drink it all in, there will always be multitudes beyond my grasp.

–Arianna Orland, Director of Product Creative, Meta

12. Jocelyn Florence Thinks About Texting You Back

Texts I haven’t responded to. I’m pretty social and spend a lot of time texting with…everyone. Sometimes I’ll suddenly remember I didn’t respond to a text and I’ll have to get up and do it (because *obviously* I don’t sleep with my phone next to my bed, I got that digital hygiene routine down pat).

–Jocelyn Florence, Partner, Parallel

13. Sam Wilkes Thinks About Side Hustles

What doesn’t keep me up at night is the better question! I’m a restless person, and I always have a side hustle going on — from writing children’s books to running Dirtbag, my coffee brand, and helping my friends set up the next doggy daycare center in NYC. As my partner always says, “Do you ever stop working?”!

–Sam Wilkes, Creative Director, Vault49

14. Jeffrey Ibañez Thinks About Everything