Cher Shedd, Head of Operations at The Grand
One afternoon, my sister, Regan, and I were out ordering lunch at Panera Bread. Regan wanted to pay for herself. When the cashier asked “What’s your name?”, she responded: “It’s Ray, R-A-Y,” in a way that I’d never heard before.
I asked her later if that was what she wanted to go by. She said she just liked the sound of it more. She'd changed it on her Facebook too!
All of this might seem like a normal every day occurrence to many people, but it was an identity-shaping moment for her. One that made me really proud and led me to reflect on both of our stories.
My sister was born with a rare genetic condition called velocardiofacial syndrome, or VCFS. It's often associated with being born with a cleft palate, but includes other conditions, like heart abnormalities, learning disabilities, and immunity issues to name a few. Growing up, Regan was sick often and experienced the unkindness of kids at school that didn’t understand her or show compassion. Unfortunately, the school system didn’t have many resources to support her learning needs. She developed an early preference to be alone and not be seen.
After spending most of her early twenties by herself, Ray got her first job at a department store. She walked into her first interview and proudly declared: “I come from a mall family, and I’m ready for this job!” Nearly everyone in our family has had stints working at the mall, including me, and it landed her the job.
She’s had more jobs since then, and built up her sense of self and identity in new ways. I noticed her personality and confidence shift as she grew out of isolation, connected with people, learned new skills, and earned money for herself. She’s Ray now!
My sister’s “Ray” moment at Panera struck me in more ways than one. It reminded me of the change that people can experience through different iterations of ourselves, opportunities that shape us, and how powerful connection versus solitude can be. And her story got me thinking of my own movement through different versions of me — and my preference to isolate early on too.
The first time I landed a "big" job in 2016, I hopped on a flight to New York in a floppy hat. It was a Gossip Girl moment in my mind - this hat was symbolic! I felt like Serena, walking around Manhattan, strong and empowered with this hat. I was thinking about building my independence for the first time through people with this new job, and less about how to preserve safety and comfort away from people. And it was the first time I started introducing myself as Cher versus Cherie.
I remember walking into the office and somebody said something like, ”Oh wow, okay, nice hat. You can definitely tell… you're from Texas, right?”
The hat might have found itself in a trash bin in a New York minute later that day…
I was so embarrassed. I was still navigating who I was supposed to be, and I just thought, “Oh, this hat didn’t work out.”
Still, that hat is so representative to me of the moment I became “grown up Cher,” “independent Cher,” “strong, ambitious Cher.”
Since then, I’ve experienced so many more iterations of myself through work, life, and human connection. Collections of moments like the floppy hat and the compounded effect of life’s twists and turns have all shaped me into who I am now.
I’m always trying to dig more into what independence means to me, and how that might be connected with loneliness. I’ve felt the isolation muscle a lot and it’s shown up as a pattern in all parts of my family. Ray’s Panera moment helped me to think about how important it is to me to keep it in check.
Growing up, I’d learned that I have always felt safest when I was isolated and independent. At home, I often assumed a caretaker role, and outside of home I really did not know how to connect or be social. In college, I didn't live on campus and I never really felt a part of anything at school. I was a very independent student.
My first big New York job forced me to get out of my comfort zone in every way possible, similar to Ray, with getting her job and getting out of her comfort zone and having to socialize.
Even today, working at The Grand, it can still be challenging for me to connect authentically or deeply with people. The act of trusting is difficult for me. Over the years, I've built up a real sense of security and safety in my space. When I’m outside of that space, my brain gets worried about safety: “I have to be careful. I have to tread carefully.”
I'm learning to let go of the fear. I am always trying to be in control of all the things in my head and how people perceive me, so there’s always a resistance to opening up and being authentic. I have to practice being okay with the fact that I might stutter over my words a few times, or feel anxious.
That’s where the hard work and discipline come in. After being in my Council for over a year, I felt like I could talk to my group about anything. I realize for me to feel what I did in my Council, it took over a year of meeting bi-weekly. I’ve had to invest the time to show up and to open up and to really hear what my group mates were saying so that I could support them, and vice versa.
When I’m feeling the resistance, I try to get oriented into the group or the experience. I tell myself: “I just need to care about these people right now. I just need to hear them, and I can do that.” I try to take the pressure off of me.
Usually, if I step into that (which I organically want to do, because I care so much about people and their stories and who they are), I can calm down and be more present with myself. It’s not a hundred percent success rate, but it helps.
Looking back on Floppy Hat Cher—first of all, I’ve never been a Serena, I’ve always been more of a Lily, so I had it all wrong—but, I do wish I would've kept my hat on. I think today’s Cher wouldn’t throw away the hat. I was feeling myself with that hat.
Floppy Hat Cher was very much in discovery mode. Everything was new. These days, everything feels more open. There are so many more opportunities and areas of life and work that I am excited about. I want to do more, in ways that I don’t think I could have approached before, as Floppy Hat Cher.
I’m excited to watch the world open up for Regan, as she embarks on her journey as Ray, and whoever else she might become.