Debbie Millman has an ongoing project at PRINT titled “What Matters.” This is an effort to understand the interior life of artists, designers, and creative thinkers. This facet of the project is a request of each invited respondent to answer ten identical questions and submit a nonprofessional photograph.
Douglas is the founder of Kingsland, a Brand Studio. He is a born-and-raised New Yorker, a writer, and a creative marketer. He lives in Greenpoint, Brooklyn with his dog, Gelato.
What is the thing you like doing most in the world?
Reading, especially books that have absolutely nothing to do with what I do for a living, and glossy magazines you’d buy in the airport. If I could sit in the sun and read for the rest of my life, I think I’d be very happy, and extremely red.
What is the first memory you have of being creative?
My parents are exceptionally smart and creative, but neither made a career as an “artist,” per se (although both probably could have). I was immersed in their passion for the arts from day one, and I couldn’t be more thankful for that. I grew up in the theater, and immediately identified it as a fit for me. From my first role as Raven #2 in a lower school play, I was hooked. (I also should’ve been Raven #1, but that’s another story.)
I acted in, wrote, and directed plays (and occasionally musicals, but you don’t want to hear me sing) for most of the first 22 years of my life, even receiving an acting scholarship to college, and that experience shaped my creative process in myriad ways.
The theater teaches you to handle rejection from a young age, that life isn’t fair, that stories are the simplest way to encourage behavior change, that aesthetics matter a lot, that improvisation is a tool you’ll hate learning but love applying, and that to put yourself out there in front of a bunch of strangers is always going to be step one in getting anything you want in life. In advertising, and the larger world of entrepreneurship in general, these are invaluable lessons.
What is your biggest regret?
Working for other people, and caring about what they think, for far too long.
Also, taking everything a bit too seriously. Fuck ‘em if they can’t take a joke.
How have you gotten over heartbreak?
I think anyone who says they have is lying to themselves.
What makes you cry?
I am very easily manipulated by a good story, especially if a main character is struggling against an unsurmountable absurdity of life or the human condition. Basically, the Sisyphus trope is what gets the waterworks going for me. Don Quixote does it. Death of a Salesman too. Please, don’t ever say “attention must be paid” to me.
How long does the pride and joy of accomplishing something last for you?
I never feel much pride or joy immediately after finishing a project. I see it as my job to create beautiful, effective marketing. So if everyone’s happy and the output is a huge success, I look at it as “job well done,” but I don’t necessarily feel that that warrants a celebration.
Not to compare myself to Carl Icahn, but I will. In his HBO documentary, Icahn spoke about how he doesn’t celebrate wins, but rather feels stagnant and anxious when he’s not winning. I feel similar. I am far more inspired by failure than success. Failing gets me going. Winning is essentially my vocation, it’s what I expect from myself and my staff. If we’re winning, we’re simply doing our jobs.
That being said, I will often feel joy months if not years after something has been accomplished for the most random reasons. Sometimes I see a brand I worked on in the wild or a person I know will share my creative without any idea that I was behind it. Those moments make me smile, and for a moment I feel a real sense of pride and accomplishment. Then I get back to work.
Do you believe in an afterlife, and if so, what does that look like to you?
To quote Agent Mulder, I want to believe. But no.
I think the afterlife is a bit of a cop-out. Life becomes a lot more interesting when you feel that this is your only chance at it. This is part of why I try to practice Momento Mori, and even incorporated it into the branding of my company, Kingsland. Through this lens, every day you don’t die is a good day. For young people with healthy families, this may sound macabre, but for those who have experienced real loss or sickness, you’ll understand the logic. Things can always be better, sure. But they could also be far, far worse. By embracing the inevitability of death, and the likely abyss of nothingness that comes after, you can remind yourself that every breath you take is, in some small way, a miracle.
This doesn’t mean I’m not spiritual. In fact, I find a great deal of spiritual relief in math and science, which prove out heaps of fascinating things that we don’t remotely understand on an annual basis. The Many Worlds Theory, for example, is becoming more and more accepted as probable in the realm of quantum physics. Some even claim the Big Bang may have simply been the beginning of our “multiverse,” so to speak, born out of an infinite number of previous iterations. So no, I do not think there’s a heaven or hell. But there may be boundless realities and our lives may be exactly the same or wildly different in each one. Thinking about that, to me at least, is a lot more interesting.
What do you hate most about yourself?
Hate is a strong word. But there’s always things I’m actively working on. I think self-work can be a lifelong challenge, but in many ways is one of the most rewarding elements of being a sentient human being on planet Earth. We have this wonderful evolutionary gift of introspection— shouldn’t we all be using it daily?
Right now I’m practicing both active listening and active rest. As an only child, I have had to train myself to shut up sometimes and deeply engage with what others are saying. In terms of rest, I tend to be a bit tense at all times. I realized last year, when I took my first vacation in three years since starting Kingsland, how important CHOOSING to chill out is, and that as a small business owner, you need to kind of schedule time into your calendar for rest. I’ve been doing a better job at it this year, whether it’s a steaming hot bath at night, a ten-minute walk with my extremely lazy dog in the morning sunshine, or a new dinner excursion with my partner.
What do you love most about yourself?
I’m at a point in my life where I feel authentically like myself and have extreme confidence in my decisions. I’m a lot nicer than I used to be. At the top of my career, I thought making it in corporate America was all about bravado and backstabbing. I realize now that it is, for most people at least. But those folks never make it very far. You can, indeed, kill them with kindness.
What is your absolute favorite meal?
An everything bagel (UNTOASTED!) with scallion cream cheese, red onions, capers, and lox or sable from Murray’s, ideally eaten on a Sunday morning with my parents. No kissing anyone after that for a good 24 hours but it’s worth it. This should always be accompanied by a small bottle of Martinelli’s apple juice. You know the one.
A perfect Vesper Martini with a twist and an olive, made with Dorothy Parker Gin. Usually not at the same time.