“A dash of daydreaming” – Pinterest’s Ashley Cook on her experience partnering with New York City’s Rising Ground

When I started to seriously think about what I wanted to do with my life, no one told me I could get a job using my imagination.

My parents worked as a nurse and boilermaker — the advertising world was as foreign to them as Mars. After seeing Free Willy one too many times, I thought I’d grow up to be a marine biologist, but when I realized that profession entails more than just playing with dolphins and whales, the dream was quickly nixed. The next logical choice was a morning radio show host because it was the aughts and I thought it would be a great way to meet famous people, but I really, really don’t like waking up early, so I once again went back to the drawing board. I didn’t know how to pick a path, but I knew I needed to do something that embraced my love of problem solving in a stimulating way and included a dash of daydreaming.

I eventually stumbled into my career by chasing emo bands, making memes, and learning as much as I could from everyone around me. When I first started out, I had no idea what a “Creative Director” was, I didn’t know what RFP stood for (spoiler alert, it’s not Really Funny People), and the closest thing to digital marketing was trying to find and re-watch a funny commercial on the internet. That’s why as I’ve grown in my career it’s become more and more important to give young people, especially women, the help and vocabulary I didn’t always have.

I joined Pinterest a little over two years ago. Towards the end of my first or second week, my manager asked if I wanted to fill in for him in a meeting with Rising Ground. He gave me no information whatsoever, but said “I really think you’ll love it.” And he was right. The first time I met the students I felt something I hadn’t felt in a very long time. Part of my long and winding resume includes teaching kids yoga, which was the most fun and fulfilling thing I did in my 20’s. So when I felt the same way after leaving my first Rising Ground session at Pinterest, I knew I had found something special.

Since its founding 190 years ago as the Leake and Watts Orphan House, Rising Ground has transformed from being one of New York City and Westchester County’s first orphanages and the first social service agency in the nation to support children with HIV/AIDS, to a leading nonprofit organization. They currently focus on providing children, adults, and families across the five boroughs with the skills, resources, and support they need to rise above adversity and live positive lives. Their philosophic cornerstone being that everyone can flourish when their life is full of opportunity and hope.

There is so much overlap between Rising Ground and Pinterest’s mission and values. At the core, we’re both committed to helping people create a life they love. So when the opportunity to partner came up as a Knitting opportunity, it was a no-brainer. “Knitting” is where cross functional teams and people who might not always get the chance to work together, join forces to create or do something memorable. It could be developing a new product, it could be a day of volunteering – it could even be learning how to make balloon animals and then teaching 40 coworkers you’ve never met how to do the same – which is something that’s actually happened, and I’ll let you imagine what a room full of popping balloon animals does to the nervous system.

When we started our program with Rising Ground, it consisted of six monthly meetings where Pinterest employees would welcome 20 high school students from Rising Ground’s Yonkers residential campus to our office. We’d talk about interviewing, working in media, personal finance and more. The students came back month after month, ready to learn and feast on pizza, while Pinployees offered advice and also feasted on pizza. We developed rapport and relationships. We got to see students come out of their shells and really blossom.

After a year of volunteering, I was presented with the opportunity to step up and lead the program. I was terrified, but I saw what positive changes were happening and couldn’t say no. I took over exactly a year from joining my first session. I rounded up volunteers, ordered the pizza, was able to greet a new set of students, and then the pandemic hit. As we were all trying to get our bearings and deal with the fear of unprecedented times, I couldn’t stop thinking about Rising Ground. I missed the students, and selfishly, thought that being with everyone might make life feel a little more normal. After a few months of check-ins I met with seasoned Rising Ground employees, and developed a plan. We would revamp the original program, but adapt it for problems we were dealing with at the moment.

So we started over, again. This time we would be meeting monthly via Zoom with students from different schools enrolled in Rising Ground’s Relationship Abuse Prevention Program. The students range in age from middle school to high school, live across the boroughs, and most have a passion for marketing. It wasn’t as easy to get volunteers involved during a global pandemic, so I relied on spreading the word and asking my Creative Strategy coworkers who are spread out across the country to join our sessions. Since they thankfully said yes, I was able to pair students who love advertising with seasoned creatives. This move gave us a chance to refocus our curriculum. Instead of giving general career advice, we decided to take a deep dive into what exactly it means to work in advertising from the perspective of a Pinterest Creative.

We were ready to kick off our new program and met with students virtually for the first time in October of 2020. There was no pizza this time, but there were ice breakers and first-time-meeting awkward laughs, an introduction to Pinterest, and a career panel featuring multiple creative women with eclectic résumés who are in unique stages of their flourishing careers. Over the course of our time together, students learned about different forms of advertising and were tasked with various projects, such as developing a campaign for a fake, waterproof headphone company. They were given a brief and had to create a name, tagline and big idea for their company based on a target audience. Small groups of students were placed in breakout rooms with several Pinterest Pals, where they brainstormed together and even mocked up potential video Pins before presenting back to the entire group. For a final project, students were given several weeks to create original Pins that would resonate with other teens during Mental Health Awareness Month. They focused on “slow living and calming rituals,” and brought these Pins to life using Pinterest’s best practices and formats they had learned in previous sessions. The Pins they delivered were so incredible, that they were recently featured on the Today tab.

In our final meeting, I asked everyone to reflect on the last six months. Was our time together helpful? Fun? Did they learn anything? One student said they felt like they learned more through our program than they had from some of their schoolwork. Another expressed apprehension about joining, but said from day one they felt welcomed into a space where they were supported for sharing their ideas and could truly put their imagination to use. And that’s when I tried to (unsuccessfully?) hide my tears, because that was the exact reason why this partnership is so important to me. Not only were the students successfully daydreaming together, and feeling heard, but they were exploring new possibilities for their futures.

Whenever anyone asks me what I love most about working with Rising Ground, I say “When I leave a room my heart feels full and my cheeks physically hurt from smiling so much.” How lucky am I that I get to feel that way at work?