Caroline Pay On Mental Health And Leaving Your Vagina At The Door.

Photo by Samantha Hunter

Photo by Samantha Hunter

Caroline Pay is the Chief Creative Officer at Headspace. She is a veteran of the ad world, having worked her way through some of the best creative shops London has to offer. Before moving client side, she made a name for herself at agencies like Mother, BBH, and Grey. She has earned the respect of creatives and non-creatives alike for her tenacity and unmistakable leadership abilities. These days her life is just as full in Santa Monica, but now she enjoys more time focusing on her mental well-being.

You recently made the transition to the client side. What is the biggest difference in your day to day life?

During my whole career in advertising (which was 20 years), I was always striving to find opportunities for new and different work. But it was always an uphill struggle because there were all kinds of proven, traditional approaches that were easier to buy and easier to make. Now, because Headspace is a much loved brand, there are so many incredible opportunities, and my job is flipped. I have to be a kind of an amazing prioritizer, and I have to turn down so many opportunities to do new and different work. That’s been a complete flip in terms of my day-to-day life.

You recently were a guest on the podcast “This Way Up!” where you spoke very highly of your creative partner Vicki Maguire at Grey. What do you look for in a good creative partner?

Trust and respect are the most important things. You spend more time with this person than anyone else in your life, and you really depend on each other in order to be as successful as possible. I think, practically, I look for a partner who has skills that I don’t have. Vicki, my last creative partner, is an incredible writer. We had a very different way of thinking about things, which led to such a beautiful relationship. I always loved hearing her point of view, and I was always surprised with the angle that she came in at. But most importantly, we could accept each other’s point of view and work through it. I just loved her surprising approach to certain things. I also think as you get older, you have to have respect for the other person’s real life as well. When you’re a 23-year-old creative, it’s all about working around the clock to get on in your career, but when you’re leading an agency, you have a responsibility to lead by example and have a really good work/life balance. At our age, we have massive responsibilities outside of the business, so we really supported each other in those.

How do you know when it's time for a career change?

I’ve done that quite a few times. The first time I left Mother, I felt very fortunate. I learned the agency inside and out in the eight years that I had grown up there. I was really privileged to work on the projects I wanted with the people I wanted. There was a real danger of me getting spoiled and getting too comfortable. I felt the need to get scared again and challenge myself, so I took myself out of my comfortable home at Mother and plopped myself into an equally exceptional agency that was run very differently. I could have just sat there very happy forever, but then I wouldn’t have grown or stretched myself as much as I have. Later, when I left BBH, I felt like I was pushing too hard in the opposite direction for them, and it just wasn’t the right match at the right time. The second time I left Mother, I was way too greedy and too ambitious, and I just wanted more all the time. I was feeling ready to lead a department, and obviously they have brilliant leaders at Mother, so there wasn’t room for me there. So again I went over to BBH and helped run the department over there. But once again, my ambition got the better of me, so I was always looking to move up. Instead of just running a department, I wanted to help run an agency, and that opportunity came up at Grey, which is why I then moved there. There had been a few moments in my career that I had interviewed and looked into going client-side, but they didn’t work out. So, it’s not that I hadn’t thought about it before, but after a year into Grey, I thought that was it. Vicki and I had both kind of committed the rest of our careers to Grey. We were so happy together. We saw that we could make a big difference. We were a powerful pair in terms of championing female creativity and female leadership. So, the Headspace opportunity was not in my plan at all. I didn’t plan to change my career this time. It just happened, but I’m very glad it did.

How do you get inspired when you run out of creative ideas?

Kim Gehrig and I got to our best ideas by just arguing until we came up with something. Kim and I, again, were very different creatures. Our approach to stuff, our point of view on things, our life experience, our characters were so different that when we hit on something that we both thought was brilliant, we knew it was going to be good. Besides arguing, I find walking and conversation to help. Real people and real life experiences are where I find most of my inspiration.

Headspace was co-founded by Rich Pierson, a man with a heavy advertising background. How did you keep your mental wellness in check when working in the advertising industry?

To be honest, I didn’t. I started having panic attacks at university and they carried through my early twenties, and then I suffered from depression in my late twenties. So I didn’t really begin to keep my mental wellness in check until it kind of went all horribly wrong for me. I started seeing a therapist, doing yoga, and meditating. I tried to keep an eye on myself and the signals, and I learned a lot of tools and techniques to try to regain my mental wellbeing. In the advertising industry, there is a lot of temptation to go out and get drunk and party a lot. There is also a lot of temptation to work around the clock. It is a very adrenaline-fueled, exciting industry, and often I would find myself not really thinking about my health and happiness at all for long periods of time. On the surface I was happy, thriving, and full of adrenaline. I was bouncing from pitch to pitch and shoot to shoot. I mean it was wonderful, but you definitely forget to look after your health and wellbeing while traveling around the world.

What is one thing young women must do when entering the advertising industry?

Leave their vaginas at the door. I think it’s the same thing young men must do, which is work as hard as you possibly can to become invaluable in the place where you would kill to work. Your gender is irrelevant.

Freelancing between jobs can be a bit intimidating. What is your advice to those caught in the in-between?

My experience with freelancing and observing those who have, is that it’s really slow to start and you kind of get a confidence knock. But once you get in, you feel good. I think you need to know your worth and act like your worth. Be really stubborn in how much you charge, where you work, and what you work on. Don’t be afraid to say, “No,” to opportunities. About a decade ago, I started seeing exceptional people turn freelance who could charge a lot of money and add a lot of value through winning business or running big accounts. So, I think the value of freelance has changed. And just know that if you put the energy in, you’ll get the payback in a big way. You have to throw yourself into the work.

What is your favorite Headspace guided meditation?

Every time a certain amount of people join Headspace, we go on a New Joiners Retreat where we spend a day with the co-founders, Rich and Andy. We hear the whole story of Headspace, and we hear about Andy’s history as a Buddhist monk. We do all sorts of activities, but I think the one that really took me up to a whole new level was a walking meditation. Andy taught us how to practice a walking meditation, and then we were given an hour to do an unguided walking meditation. I think that was a real turning point for me. In terms of graduating from an eyes-closed, seated guided meditation, into being able to at any point, wherever I am, to really really experience the benefits of doing a walking meditation. I know we just released a pack of walking meditations in the product, but that would be my pick. It’s really incredible.


Bailey Sward is a fourth year advertising student at the University of Texas at Austin. As a copywriter with one and a half thumbs, she has adapted the ability to type with nine fingers. Challenge her to a thumb wrestling contest or check out her work at