We are a group of creative people who help organizations make their ideas beautiful.
Caroline May says this as though she really believes it. And it’s probably true, right? It sounds true. It’s definitely true for me.
But there’s something in the way she says it—quickly, fiercely, her eyes like tractor beams pulling you inexorably toward her perspective—that brings you to a different conclusion:
Caroline’s parents were both busy lawyers, and Caroline ended up basically raising her two younger sisters. How’d that work out? Annie got a degree in creative writing from Johns Hopkins. Grace is headed to Oxford to get her Master’s in philosophy.
In college, Caroline’s sorority sister took a shine to a handsome guy named Mitch who lived across the street. That guy is now Caroline’s husband. The sorority sister is still, miraculously, a close friend (and godmother to Caroline and Mitch’s son).
When she was starting in advertising, Caroline asked a well-connected friend to get her a contact at a St. Louis agency. She was given the email address of some guy named Bill Hughes at some place called HLK. It never occurred to Caroline that Bill might be the “H” in HLK. So she sent him a pretty casual email: “Hi! Here are all the things I want from a job with you. But I’m leaving for Peru for a month, so I can’t start right now.” Far from being offended, Mr. Hughes was charmed by Caroline’s bluntness and chutzpah. She got the job.
Caroline is the first writer I’ve ever known who likes to be on time. For our interview, we agree to meet at a coffee shop in Demun. I arrive 5 minutes early; she’s already there. She waves and, as I walk toward her table, she takes a fleeting, furtive glance at her watch. Caroline has things to say, and I am holding her up.
She enters a conversation like a muscle car enters a freeway. You can almost smell the burning rubber.
You know how most people kind of meander into a conversation, making small talk and slowly warming up before becoming extremely animated and forceful in their declarations? Caroline is not one of those people.
She enters a conversation like a muscle car enters a freeway. You can almost smell the burning rubber.
“OK, so how do we do this?,” she asks. “Do you just want anecdotes, or what?”
We start at the beginning: Houston, Texas. Late 1980s. Caroline is born to two lawyers, Jim and Liz. Life is pretty good. Her parents work a lot and, after her sisters land on the scene, Caroline is pressed into service as “Lieutenant Mom.”
By the time she’s 11 or 12, she learns to cook dinner for the brood. It’s a lot of hot dogs and mac n’ cheese. Nothing fancy. But Caroline is starting to become a surrogate adult. Her parents’ marriage is coming to an end, and she’s forced to ask questions and develop perspectives that most people get to postpone until, you know, actual adulthood.
When she’s not taking care of her sisters, Caroline roams downtown Houston, sneaking into shows, hanging out in coffee shops, smoking clove cigarettes. Her neighborhood, the Houston Heights, was a little rough. Not dangerous, mind you. Just a little more…interesting.
Maybe it was the competitiveness of her classmates, or maybe it was the precocious intellects of her younger siblings, but during high school Caroline started to suspect that she wasn’t very smart.
Caroline’s parents had means, and they sent her to the elite St. John’s School for middle and high school. Maybe you don’t realize it, but you’ve seen St. John’s. Wes Anderson is an alum, and he used the school as the backdrop for his 1999 film “Rushmore.” It’s a pretty fancy place, with a rigorous curriculum. Maybe it was the competitiveness of her classmates, or maybe it was the precocious intellects of her younger siblings, but during high school Caroline started to suspect that she wasn’t very smart.
“I was sure of it,” she says today. “But eventually, after I went away to college at Mizzou, I realized I was fine. I just set a very high bar for myself.”
Let’s cut to the chase: Caroline May is wicked smart. It’s a little bit frustrating how smart she is. But her intellect is not her superpower. Her superpower is that she knows what she wants.
In both her personal and professional lives, she moves forward without fear or confusion. She tackles creative briefs with relish. She presents her ideas with the same kind of bootstrapper’s confidence that led her to email Bill Hughes. And she is not wishy-washy in her advice to more junior creatives; she dips into a deep reservoir of empirical evidence about what works, and why.
In short, it’s Caroline’s world. You and I are just living in it. And, because of that, it’s probably a good idea to hear directly from her about some of the facts, rules and insights which govern that world:
On what constitutes totally appropriate advice for young children
“When I was young, my parents used to tell us: ‘Do no harm, but take no shit.’ And that kind of sums up my childhood. My grandfather on my mom’s side was pretty wise. He used to say: ‘Think for yourself, but learn from everyone you meet.’ He also liked to say he believed in free speech, because it lets you know who the assholes are.”
On her early advocacy for wealth redistribution
“When I was about 10, our babysitter was this woman who worked as a court reporter. My dad knew her through his job as a lawyer. I liked her, and I thought she was just hanging out with me and my sisters because she liked us. When I found out my parents were paying her, I took it pretty hard. I told my parents I deserved a cut of her earnings because I was still helping to take care of my sisters while she was babysitting. Basically, the way I saw it, she was subcontracting a lot of her work to me, and thought I should get my piece of the pie.”
On what it’s like to live a double life
“St. John’s was a great school but it wasn’t very diverse, socioeconomically. I kind of split my free time between my classmates, who had really wealthy parents, and the kids I knew from my neighborhood. I existed in a kind of strange purgatory between neighborhood friends who thought I'd become a snob and classmates who thought I wasn't well-bred enough to be at St. John’s.”
On the right way to be a bad influence
“I was definitely known as a bad influence. I wasn’t trying to get anyone arrested. I just introduced people to some sketchy places they probably wouldn’t have found on their own.”
On why she asks so many damned questions
“People usually think I’m interrogating them. Or I’m being too assertive. But I’m really just trying to understand something, and I’m not the kind of person who’s too shy to get the information I need. I can’t help it.”
On how certain people feel about engaging Caroline in a fist-fight
“People can find me scary at first. Or intimidating. I’ve had people say they wouldn’t want to fight me. I think I have strong and obvious opinions, and I wear my feelings on my face. Some people find that abrasive.”
On why Houston is awesome
“Houston is incredibly diverse. We lived downtown my entire childhood. There a lot of different races, a lot of different cultural influences, all piled right on top of each other. You can go far without going far, you know? The zoning laws in Houston are basically non-existent. Your next-door neighbor could decide to turn his house into an auto body shop, and there’s nothing you can do about it. It’s kind of messy, but in the best way. People are brought together in public spaces in ways they don’t in other cities. I love it.”
On how she ended up in Missouri (the first time)
“I loved English. I loved to read and write. But my dad, who had been an English major before law school, felt that English was a stupid subject to pursue. I saw journalism as a legitimate or acceptable version of getting an English degree. So I knew I was going to study journalism, and I knew I wanted to go to a big state school after going to a very small and insular private school. Mizzou was the perfect escape.”
On why the Midwest is weird
“Before I left for Mizzou, I had never seen snow. I had never seen brown leaves. When we toured Columbia, I thought all the trees were dead, but it was just Fall. People are also much more segregated and much more reserved. In Texas, it’s totally normal to just walk up and pat a stranger’s kid on the head. Not in Missouri. And there’s a very clear separation between races and cultures here. White, black, hispanic, Bosnian--everyone lives in their own little pocket of the city. It’s not that way in Houston. It’s much more integrated.”
On what keeps her interested in advertising
“I love working on new business. You aren’t constrained by a brief or a budget. Whether you win or lose, it’s really rewarding. And the longer I’ve done this, the more I see that if you’re smart or talented it’s not hard to look good. It’s much more rewarding to help other people push their ideas to be what they can be.”
On why her husband Mitch is perfect
“Mitch is kind of an introvert, and I’m definitely not. But Mitch has a kind of quiet confidence that’s incredibly attractive to me. He’s a mechanical engineer and he communicates his affection by teaching things. His intelligence is very assured. It’s not performative. He’s very charming, but you never get the sense that he’s trying to charm you or manufacture an opinion about him. He’s calm and unflappable. He just knows who he is.”
On forcing people to just get to the point, already
“After we had lived in Houston for a few years, Mitch and I started to talk about marriage. One night he made reservations at our favorite Mexican restaurant and when we got there he seemed a little nervous and suggested we take a walk. This restaurant is not in a scenic nor even particularly safe area, so I just flat out vetoed the walk idea. Mitch just stood there. Suddenly he took something out of his pocket and dropped to one knee. I cannot emphasize this enough...this was IN THE PARKING LOT. I didn’t know what he was doing and I felt weird being the only one standing, so I dropped to my knees, too. But of course he was trying to propose. I said yes and then we stood up, walked in and had dinner. The first person to congratulate was the security guard, who thought I must have lost an earring.”
On the importance of shared parenting values
“Mitch and I have a two-year-old son, Avett (named after the Avett Brothers). We have very different backgrounds, but similar parenting philosophies. Avett can be whatever he wants to be, as long as he tries hard. You know, like, go be a skateboarder, as long as you’re working at getting better every day. Mitch and I both agree that the goal is to raise people who are self-sufficient and contribute to society in some meaningful way.”
On how raising a boy is different
“As someone who helped raise her little sisters, I was unprepared for how different little boys are. I thought babies are babies, and gender is a social construct. Nope. With Avett, it’s just dismantle, climb, throw, destroy. I don’t know what I expected, but I didn’t expect him to take off his shirt and move furniture every day as soon as he gets home. And he has a pretty wicked smirk developing already. That comes from me.”
Talking about her son, Caroline’s voice cracks for the first time.
She knows what she wants for Avett, but she also knows the world out there isn’t a fair or easy place. It’s the kind of place where people form opinions about you based on where you grew up, or where you went to school. It’s a world in which you have to speak up if you want to be heard, and then get chastised for speaking too loudly. A world where babysitters basically don’t do shit but end up getting all the money.
But pretty soon Caroline’s eyes snap back into focus, and her spine stiffens. She picks up her coffee cup, takes a sip, and smiles. She knows what she’s doing, and she knows where all of this is headed—even if the world itself hasn’t quite caught up.
“What’s your next question?,” she asks.