Meet Cailin Simpson

We recently connected with Cailin Simpson and have shared our conversation below.

Cailin, so great to be with you and I think a lot of folks are going to benefit from hearing your story and lessons and wisdom. Imposter Syndrome is something that we know how words to describe, but it’s something that has held people back forever and so we’re really interested to hear about your story and how you overcame imposter syndrome.

I would say I haven’t fully overcome imposter syndrome, but then again, who has? In every walk of life, there are spaces where we find ourselves uncomfortable because of the actual and perceived skills of others around us that differ from our own. It’s natural, I’d say, to feel out of place, but it becomes a problem when we shrink ourselves to take up less space, blend into the walls, or try to escape our own skin.
I’ve always struggled with taking up space—as a woman, as a friend, as a daughter, as a person. The phrase “This isn’t about me” has plagued my mind in every sense when I find myself in uncomfortable settings. There’s the positive sense where a situation is bigger than me, and other people’s behaviors have nothing to do with me, so I shouldn’t take anything they do or say personally. Or, there’s the other sense where a situation has nothing to do with me, and I feel completely out of place and alone. Then there’s the combination, where I teeter between both. Do I stand out and act as if I belong because the majority of what I’m feeling isn’t real and is in my head, or do I shrink as small as humanly possible, or run? All these questions and all I feel is pathetic.
That was a complete anxiety/imposter syndrome spiral—a little glimpse of my thoughts.
Although, like many others, I have found tools to overcome those moments of endless spiraling. Stating boundaries for myself, even simple ones, helps. For example, if I know that I’m entering a space where things are different and daunting, I set a time when I allow myself an out. I also remind myself that the people in this space are human too; they probably have a whole different part of them that has nothing to do with the current environment.
I understand that creative spaces are often where people feel the most like imposters. As an artist, I have found that these spaces can be challenging at times, but they have also provided me with unimaginable experiences and relationships. Creative spaces—a very broad term—invite curiosity, storytelling, and empathy. The vagueness and profound difficulty of defining art have helped create an open community where exploration and vulnerability are encouraged and sought after. So, in short, we’d love to meet you and learn about you and your stories.
In a way, I believe we’re all imposters—whether in our own stories or those of others.

Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?

Hi! My name is Cailin Simpson, but Cailin Hope is my stage name and what people know me as online. I’m a singer-songwriter and videographer based in New York City. I was born and raised in Beijing, China, and moved to the city three years ago. My family is originally from Seattle, so I’ve traveled back and forth between Beijing and Seattle for as long as I can remember. To this day, I’m so grateful to have been able to travel as much as I have, and from such a young age. I must admit that even with how much I’ve gone back and forth, there’s still a culture shock every time I land. Landing in New York for the first time, I thought, would be the biggest culture shock I’d ever face. It wasn’t, surprisingly. It felt like coming home.
You can probably tell that I’m a sentimental person from that sentence, but it’s true. I’ve always felt big feelings, and landing in New York felt right. I still remember the warmth of the early morning sun while I waited for my first-ever yellow cab. Yes, I am a sap, especially in my writing.
I started writing at a very young age, like many other artists. I’m an only child, and growing up, I found communication to be very difficult—I still struggle with it today. All this is to say, writing was a safe space. I have a lot of material and songs stored in the pages and books under my desk. Although, I only just released my debut single this past March. The song is called Daughter, an ode and dedication to my mother and all mothers. I released it on my mom’s birthday.
My parents are my inspiration and greatest support system. They’ve encouraged me to dream, explore, fail, and everything in between. My dad is a cameraman for a large news broadcast company and a storyteller at heart. Every morning, he would say, “Words are your friends, ask a lot of questions!” before I headed to school. My dad’s side of the family is full of artists. My grandparents were illustrators, painters, and designers. My aunts are sketch artists and chefs, and I truly believe their laughter is an art form in itself. My mother—my best friend—is a woman entrepreneur, life coach, advocate for women’s rights in the workplace, singer, aerobics, and tennis coach, and she loves like no other. I come from a long line of strong women. I am the best and the worst of both of them. They are complicated and weird, but they are the greatest teachers and caretakers I could have ever asked for.
It was cathartic to finally have a song out in the world. I bit the bullet, and now I have great plans for the months and years to come. I am currently recording two new songs and plan to release them by the end of the year. I am also in the planning stages of my concept album, which I hope to release on Halloween 2025.
What I find special about songwriting, music, and music videos is the connections you make, the stories you find, and the people I get to work with. Stories and storytelling are a huge part of my life and how I’ve grown up. Art and music are exactly that and allow you to learn a lot about yourself and it’s deeply healing. I hope that this experience of creating my concept album will help me heal and I’m looking forward to telling my story.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

Looking back, I think honest communication, finding ways to multitask, and simply going for a walk outside have been the most impactful in my creative and personal journey. I’ve always struggled with communicating my needs or feelings. I’m a serial people pleaser, and it wasn’t until someone close to me called me out for not speaking my mind that I realized how much I was holding back. It felt like I had been holding my breath for the longest time, waiting for toxic fumes to come, thinking I’d already be safe and ready. But those toxic fumes never came, and instead, I was slowly suffocating myself. I was my own worst enemy.

I know that’s a weird analogy, but honest communication—about boundaries, needs, wants, and feelings—has completely changed my life for the better.

Second, finding ways to multitask. By this, I mean strategizing how to kill two birds with one stone. How can you get the most out of a new opportunity or even an old situation? Can you gain experience while also improving a specific skill? These are crucial questions to ask when you’re trying to maximize your time. Time is weird and messed up, but you are in control of how you think about it. Of course, it’s easier said than done, but this practice has helped me in more ways than one.

Lastly, just going outside for a walk or opening a window—it does a lot. A lot.

This might be old news, but I hate to say it: go outside and feel some grass.

One of our goals is to help like-minded folks with similar goals connect and so before we go we want to ask if you are looking to partner or collab with others – and if so, what would make the ideal collaborator or partner?

I would love to collaborate with anyone willing to share their story!!! I understand that this is very vague and can be anyone reading this but I value hearing and sharing stories. I believe that all art and creation comes from story and storytelling, if you agree or want to discuss this vast idea please reach out!

You can reach me via my email or Instagram:

cailin.hopes@gmail.com

cailin.hope
https://www.instagram.com/cailin.hope/?hl=en

Contact Info:

• Website: https://www.cailinhope.com/
• Instagram: https://www.instagram.com/cailin.hope/?hl=en
• Youtube: https://www.youtube.com/@cailinhope9649

Image Credits

Gigi Schweitzer

neighborsupply photography