Alright – so today we’ve got the honor of introducing you to Caroline Milby. We think you’ll enjoy our conversation, we’ve shared it below.
Caroline, thanks so much for taking the time to share your insights and lessons with us today. We’re particularly interested in hearing about how you became such a resilient person. Where do you get your resilience from?
As a singer-songwriter and performer, I’ve been told no a lot, and I’ve been ignored a lot, and that’s part of the game. It’s an occupational hazard. My resilience is hard-won by choosing to still believe in myself every time that happens.
Anyone that goes into the fine arts will have to learn this lesson at some point. The first time you choose to believe in yourself after being rejected is the hardest, but then it gets easier after that. I still get disappointed when it happens but it doesn’t shake my trust in myself like it used to. Plus there are a couple of adages I always remind myself of that help; “rejection is protection” and “what’s meant for you won’t miss you.”
In addition, my resilience came from moving around a lot as a child and being the new kid. I went to a different school every year between kindergarten and 7th grade, and sometimes more than one school a year. It’s made me much more adaptable and comfortable in many different environments and among many different types of people.
Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?
Caroline in the Garden is the imaginative pop project of singer-songwriter/producer Caroline Milby. Known for warm minor chord energy, off-kilter piano hooks and lush orchestrations, Caroline explores what it means to unhinge yourself from societies’ expectations after spending decades on the capitalist conveyor belt.
Heavily influenced by Kate Bush and 90s Lilith Fair icons, Caroline got her start in the Philadelphia art rock scene opening for acts such as Electric Six, Here Come the Mummies and Low Cut Connie.
Her debut album, Act Two, (coming April 10, 2026) was inspired by her wayward career jump from full-time attorney to full-time musician. Try explaining that to your parents. The album blends intimate storytelling and clever lyricism to explore the depths of an inner world that refuses to cooperate with societies’ expectations. It has been heralded as “intensively forward thinking” and “uniquely resonant.”
If you had to pick three qualities that are most important to develop, which three would you say matter most?
1. Persistance
Most people don’t fail they give up!
2. Self trust and self worth
If you don’t believe in yourself no one else will either.
3. Flexibility
Music is a highly dynamic and fluctuating business right now, don’t get too attached to having concrete plans or steps towards success, because nothing is predictable.
I’d also like to add that in this business, it’s important to have a few trusted friends and mentors. There are a lot of contracts that get passed around. Very early on, I almost signed something that basically would have stripped me of the rights to my music and I am very thankful for the knowledgeable folks I have around to help me.
Additionally–and this is not just for music–any entrepreneur is going to have to learn skills that have nothing to do with their primary business. For instance, I’ve had to learn video editing and graphic design to properly promote myself and my music. To be fair, they’re both creative fields and I enjoy them, but there are plenty of administrative tasks that have nothing to do with writing, performing or producing songs that I spend a lot of time doing.
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?
Indeed! I come from a background of playing in bands, and I’d like to get back to having a few musicians around to support and fill out the songs live I’m a piano player primarily, with occasional guitar, and I’d love to have a regular bass player and drummer to round out my concerts. If you’re interested, get in touch at my website–carolineinthegarden.com!
Contact Info:
- Website: https://carolineinthegarden.com
- Instagram: https://www.instagram.com/carolineinthegarden_/
- Linkedin: https://www.linkedin.com/in/carolineinthegarden/
- Youtube: https://www.youtube.com/@Carolineinthegarden
- Other: Bandcamp: https://carolineinthegarden.bandcamp.com/track/mine-2
Image Credits
Photo Credit: Ben Rollins
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