Skip to main content
The M Dash

Live with purpose.

Cindy Gallop on Ambition, Sex, and Doing Exactly What She Pleases

October 01, 2016 | Filed in: Woman of the Week

Cindy Gallop, an advertising industry giant turned global phenomenon, ran the U.S. branch of London-based ad firm BBH before she struck out on her own in 2005. In addition to advertising consulting, she now runs two companies—IfWeRanTheWorld, a web platform designed to turn good intentions into actions, and MakeLoveNotPorn, an organization that provides realistic information about human sexuality instead of what’s shown in pornography. We met Cindy at her New York apartment last month to discuss micro-actions, bullshitting, and when to quit your job. Her words, below.

I’M A BIG FAN OF RADICAL SIMPLICITY, and so I like to give simple advice. I’m regularly asked, “Cindy, what’s the one piece of advice you would give to a young person starting in advertising today?” And to that I say: “Don’t.” And what I mean is, don’t go into advertising to “go into advertising.” Go into advertising to make what you want to happen, happen. And that applies to every other industry as well. Go into your chosen industry to make what you want to happen, happen. Come in at the entry level, take a long hard look around you, and identify what you think is missing. What should be there that isn’t? What do you think the industry would benefit from? What would make you happier about working there? And then make that happen—whether you do it for the company that’s been lucky enough to employ you, or whether you then strike out and start a business on your own.

YOUNG WOMEN WHO ARE STARTING OFF TODAY—and this is true of young men as well—have the benefit of a completely fresh perspective, and a clear-sighted lens. You can see things that the people at the top of the industry, who have been stuck at the old world order for decades, cannot see. Use that to your advantage. That lens is the way you can be of enormous value to the company that’s just hired you, even if they don’t fully understand that yet themselves. Your perspective might also contain a business waiting to happen, that you can start and grow and make an awful lot of money from.

EVERYTHING IN BUSINESS AND LIFE starts with you and your values. So take a long, hard look at yourself, and ask, “What do I believe in? What do I value? What do I stand for? What am I all about? What is my stance, and what is my worldview?” And then decide what you want to do accordingly. Because you should only ever live and work what you believe in. And if you apply that attitude, then you are only ever doing things that are true to you. And that is where happiness lies.

I DON’T GIVE A DAMN about what anyone else thinks. That’s about it, really. It was a gradual realization, just like anything. Of course, you can’t just sit down and figure things out on command. When I say, “Figure out your values,” what I mean is that it’s important to have a dialogue with yourself. You go, “Oh, I’ve found myself doing this, and feeling that, and that means these things matter to me.”

YEARS AND YEARS AGO, I read about a study that had been done on stress in the workplace. What this study had identified was that the single biggest cause of stress in the office is not the number of hours you work, or the amount that you have to do. It is when, because of the environment, the culture, and the people above and around you, you are forced to do your job in a way that does not come naturally. The definition of stress is operating in a way that you would not normally choose. So if you find yourself working somewhere that does not welcome your skills and your talents, does not welcome what you uniquely bring to the business, and does not allow you to innovate in the ways you want to, get the fuck out. Don’t work there. There is no point.

I LITERALLY WANT TO WEEP when I think of the skills and talent of women and people of color that businesses are failing to tap into. Women write to me all the time—particularly in the past year, in light of ad industry kerfuffles—and tell me appalling stories of sexual harassment at work, and of retaliation, and of careers being thrown off track because of the gender bias they encounter. And the most depressing thing is their use of the single recurring phrase: “For a long time, I thought it was me.” I want to cry when I read it. For women working in male-dominated environments—and in my industry, advertising, there are often just one or two female creatives in an otherwise all-male creative department, and they report to a male creative director who’s probably out down the pub with his favorite male employee—they often do their best work, but it’s never “good enough,” and it’s never bought or made, and they think it’s them. And it’s so bloody not.

IT’S REALLY IMPORTANT TO OPERATE YOUR OWN FILTER. When you decide what you stand for, and then you put everything through that filter, it tells you very quickly whether something accords with your values or not. And if it doesn’t, get the hell out, because it’s never going to. You on your own are not going to be able to change it. That doesn’t mean it won’t change at some point. But you could spend a very long time getting nowhere. You could waste a lot of time being in an organization that does not recognize your value, is full of unconscious bias, and promotes the men and pays them more. And by the way, all of this is changing, thank goodness. But if you’re being pushed back at every turn, there comes a point where it’s absolutely not worth trying to continue in that workplace.

I CAN’T POINT TO ANY ONE THING THAT GAVE ME CONFIDENCE. Most of it comes from the vast benefit of 56 years of hindsight, but a lot of it particularly has come from the past 11 years of my life, because I left the corporate world in 2005. I am a huge proponent of working for yourself. I absolutely believe that gaining experience from working at companies can be great, but at some point, I really encourage women to think about how they can start their own business and do their own thing.

I HAD MY OWN PERSONAL MIDLIFE CRISIS in 2005, when I turned 45. I’ve always thought of 45 as the mid-life point. Hopefully I’ll live to 90, fingers crossed. So on February 1, 2005, I decided to take stock of my life and what I wanted to do for the second half of it, and I realized, “Oh my god, I’ve worked for 16 years at the same advertising agency.” Wonderful agency, BBH. Adore them to death. But it was time to do something different, and I had to decide what that would be. A vast amount of thought ensued, and I decided that if I wanted to review every possible option open to me, maybe the best thing to do would be to put myself on the market. Very publicly, like, “Here I am! What have you got?” So I did that. I took a massive leap into the unknown, and I resigned as chairman of BBH in New York in the summer of 2005 without a job to go to, and it’s the best thing I ever did. I was very lucky—lots of things came to me, 90 percent of which I never would have thought of myself. I decided to be an employment slut. I took every meeting and every phone call, with no preconceived notions. It was a fascinating exploration, and it was as good at telling me what I didn’t want to do as what I did. I would come out of a meeting and go, “Well, now I know that I would never want to do that, in fifty million years.” Sometimes it’s good to have a bad experience, because then you can say, “Wow. That episode tells me, boy oh boy, I’m never going to put myself in the way of that again, so let’s find a way not to.”

Cindy Gallop

Cindy wears the Alexandra dress.

IF YOU’RE MISERABLE IN YOUR JOB, try to improve your scenario before you jump ship. The great thing about knowing you want to leave is that you have nothing to lose. Think to yourself, “What would persuade me to stay?” And it might not be anything that exists at the moment. It might be that you’d only want to stay if they created a role and then put you in it. Then, go to your boss—you have to lie a bit, obviously—and say, “I’m loving working here. However, there are these things I think I could contribute to the business, which I’m not at the moment.” The key is to frame it in terms of what’s good for business. You say, “I’ve put a lot of thought and research into this, and I feel that I could bring real value to the company and see real results if you created this role and put me in it. And here it is, all written out.” And if they say yes, fantastic. And if they don’t, you say, “Bye!”

WHEN I WAS A YOUNG, THRUSTING ACCOUNT DIRECTOR at BBH in London, ferociously ambitious, I did what a lot of young, thrusting account directors do: I pinned Nigel Bogle up against the wall—he’s one of the B’s in BBH—and I said, “Where am I going at this agency?” And he turned the question back around on me. He said, “Cindy, you tell us where you want to go, and we’ll make it happen. And by the way, don’t be bounded by the realms of the possible. If you want a job that doesn’t exist yet, tell us.” Which is a fantastic thing to say to someone. So I went off and thought about it, and then I came back and said, “My dream job is to run BBH North America.” And this was back when BBH only had one office, in London. And Nigel said, “Okay. We’ve been thinking about looking into the U.S., and when we do, you’re logged for it.” Then, the first office we opened outside of London happened to be in the Asia-Pacific region, and I went out there as the number two. And then, two years later, they gave me my dream job, and I got to come out here and open up BBH New York, in 1998. All credit to Nigel, for having said to me, “If you want a job that doesn’t exist yet, decide what it is, and tell us.”

I ALWAYS TELL WOMEN TO DO WHAT THE MEN DO—go in there and bullshit. And the reason I feel perfectly confident telling women to do that is because women have a very long way to go before they bullshit the way that men do. Women say, “Oh no, Cindy, I couldn’t possibly bullshit!” And I say, “I know, and that’s why I’m telling you to. You think you’re bullshitting, but you’re not. You already undervalue yourself so much that if you do what you think is bullshit, all you’re doing is actually representing yourself as you should be represented.” You know, Joe over there is bullshitting like mad, way beyond the bullshit state you’re capable of. So don’t worry about it!

I BELIEVE IN MICRO-ACTIONS, and my favorite one is enormously simple: Say what you think. Say what you really think. Nobody does! But it will have a dramatically positive effect on your life and your work. Because if you say what you think and it’s not well-received, then that’s important too. Be honest and straightforward and heartfelt and sincere. But it’s all about how you say it—and I tell you that as someone with 30 years of advertising behind her. You can construct anything to be positive, helpful, and constructive. It’s all about the phrasing, the tone of voice, the manner.

NICENESS IS ONE OF MY BIGGEST PRINCIPLES. Always be nice. The nicer you are, the more people like you. Incidentally, always meet evil with good. Whenever someone’s bitchy, just be enormously nice back. It’s also very satisfying, because it totally throws them.

I DATE YOUNGER MEN, and I have only one criteria: He has to be a very nice person. I only date utterly lovely younger men, in an atmosphere of mutual trust, respecting, and liking. Which means that my so-called casual relationships actually go on a lot longer than many people’s committed ones. I date younger men over periods of two, three, four, five, ten, or fifteen years. They might go on to meet girls their own age, and they’ll move to other parts of the country or other parts of the world, but we still like each other, so we stay friends. And we’ll meet for platonic drinks, or whatever. And sometimes their other relationships will end and they’ll come back.

MY APPROACH TO CASUAL RELATIONSHIPS would really benefit those who are looking for a committed one. A lot of people who are looking for a soul mate have tick box, but “very nice” tends not to be on it. And I think that’s more important than anything. I meet younger men on cougar dating websites, and then I put them through a stringent filter. I don’t arrange to meet in person until I’m absolutely sure. And that first meeting will be in a bar. They’re usually quite surprised by me. I’m a great deal more than they expected. And I think that’s why they like me.

FOR PEOPLE LOOKING FOR A COMMITTED RELATIONSHIP, when they go on that first date, they often say, “Oh, the only thing that matters is if he’s attractive to me.” Not true. When you’re looking for a committed relationship and you first set eyes on that person in that bar, you’re thinking, “What would my friends think if I walked into a party with this person on my arm?” You are looking for socially-endorsed attractiveness. And I’m not. I’m thinking, “If I like him, I’m going to take him home and fuck him.” So I don’t care! And the men I date absolutely do meet my friends, incidentally. But that is not my first criteria.

DATING YOUNGER MEN WAS AN ACCIDENT. 14 years ago, when I was still working at BBH in New York, we were asked to pitch a dating site. And in the ad industry, when you’re pitching an account, you have to experience the client’s product and the entire competitive landscape. So we all had to date online, and none of us ever had, because it wasn’t a thing yet. And everyone I worked with was in a committed relationship of some sort, so they all used fake personas. I was single, and so I decided to do it for real. So I posted on a bunch of websites, with my age included, and instantly got an avalanche of responses, which was very good for the ego. Much to my surprise, because I had not at all contemplated this as a dating strategy, but 75 percent of my responses were from younger men. And I suddenly realized that I was every younger guy’s fantasy: an attractive older woman with a high-flying career who never wanted to settle down, never wanted to marry or have kids, and just wanted to have some fun. And at that time, the fun was severely missing from my life. I was working 24/7 and traveling all the time. Fun was not happening. So I thought, gosh, I hadn’t thought about this, but hey! Works for me! So that’s how that happened, and it suits me down to the ground.

I KNOW I CAN TRUST SOMEONE because I follow my gut. A lot of us don’t trust our instincts, because there are so many other competing forces and socio-cultural dynamics that override them. And occasionally your gut is going to be wrong, but that’s just a fact of life. It doesn’t mean you should stop trusting it.

To learn more about Make Love Not Porn, check out their new documentary, “MLNP: The Social Sex Revolution.” To join MLNP’s crowdfunding campaign on iFundWomen, click here.

Share this post. We dare you.


Charlotte Cowles is a New York-based writer​ ​and editor.​ ​Her work has been published in New York Magazine,​ Harper's Bazaar,​ and Art in America. She'd always rather be at book club. Read more of Charlotte's posts.

Read on.

Back to Top