We were lucky to catch up with Allie Chipkin recently and have shared our conversation below.
Allie, appreciate you joining us today. Have you been able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen? Was it like that from day one? If not, what were some of the major steps and milestones and do you think you could have sped up the process somehow knowing what you know now?
For the first half of my college career, I studied Musical Theater at The Boston Conservatory. I remember the most supportive teachers at ‘BoCo’ telling me: “Don’t wait for someone else to cast you in a role. You don’t need their approval to be good enough. Make your own work.” As a struggling BFA student who (spoiler) wasn’t getting cast in any musicals, that was the best advice I could have ever received.
So, I picked up the guitar and started writing my own songs. I had always secretly dreamed of being a singer-songwriter, and, certainly, no one could tell me I wasn’t the right person to sing my own music. My songwriting drive intensified when I transferred to Skidmore College to study poetry. I wrote my first record as my capstone project and played my first live show right before graduating.
After college, I moved to Boulder, CO, where I gigged and worked in coffeeshops for 4 years. During that same time, I started Give Love Originals (GLO)—a company that writes and records custom wedding songs. When GLO took off (thanks to a feature on the Betches Brides podcast), I could finally sustain myself making music. I honed my recording skills and grew the business when I moved back to NY.
I am still running GLO here in Brooklyn, and gigging often with my own music. In October of last year, I appeared as a featured songwriter on The Tonight Show with Jimmy Fallon, and I am currently recording on singles set to release in 2024. Since my income is steady with GLO, I am able to focus on making the kind of music I want to make for myself and only take gigs that advance my career or bring me joy, connection, and community.
GLO is not what I pictured “making it” in the music industry would look like for me… in fact, I originally started the business because, as a gigging musician, I wasn’t making enough to buy wedding gifts for my friends… so I actually considered myself a “failing musician” at that point. I am also technically making most of my money from the wedding industry rather than the music industry these days. However, I think this idea of “making your own work” and thinking creatively about the ways we can share our gifts with the world is worthwhile for any creative trying to “make it” out there!

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.
I have always loved to sing. My mom says I started singing around the time I learned how to talk. I remember singing to my unused glove out in right field and convincing my friends to perform or write stories with me during our playdates. I just loved stories – musicals, movies, songs, TV shows, and especially stories me and my friends made up ourselves. I was a spunky, creative little kid, and I always had this thought that if other people could do incredible things, why couldn’t I?
“Why can’t I?” became a mantra for little Allie, which it makes sense—my favorite song was Somewhere Over the Rainbow, in which Judy Garland sings: “If happy little bluebirds fly beyond the rainbow, why, oh, why can’t I?” I always knew I would accomplish my wildest dreams; I just had to keep dreaming and believing.
Fast forward to an adulthood of rejection and disappointment (BFA Musical Theater programs are not the easiest place to succeed). However, through the pain of rejection, I retained a quiet belief that my voice mattered. With encouragement from wise mentors, magical friends, and mindful therapists, I kept making things and believing in my own worth, even when others did not. I started writing songs and just kept trusting that if I liked them, others would too. I learned to embrace rejection, because I knew I would always be accepted and celebrated by myself. One of my highest values has always been authenticity; I could love and accept my work as long as it felt true to me.
Even now when I write songs, I ask myself: “Does this feel true?” The lines don’t have to be factual, but they have to FEEL honest to me. My songs celebrate the ordinary beauty of everyday life. They’re observational, humorous, modern, relatable, clever, and heartfelt. They’re a chance for me to speak not only my heart, but also my guts.
I feel so proud of all the places music has taken me: The Tonight Show with Jimmy Fallon, to Fenway Park to sing the National Anthem for the Red Socks, and national recognition in songwriting competitions. However, I feel most proud when a person hears my song, grabs their heart, laughing through tears, and says “Omg, that’s so true.”
In regard to my business, Give Love Originals (GLO), I help couples enhance the magic and memorability of their wedding day through custom love songs. In an age where weddings can feel so cookie-cutter, GLO helps couples celebrate their bond with a work of art as unique as their love story.
As far as me and my bigger picture, I’m continuing to write, building my audience here in NY, running Give Love Originals, and working part-time for Ari’s Take. It’s a rigorous balancing act, but I wouldn’t trade it!

Are there any resources you wish you knew about earlier in your creative journey?
Yes! The Small Business Association (SBA), the Small Business Development Center (SBDC), and Ari’s Take Academy (ATA). These organizations have incredible resources and mentors for artists managing their own careers or businesses (and ATA has resources specific to independent musicians). Check out their webinars, courses, and mentorship programs.
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Is there a particular goal or mission driving your creative journey?
Yes. Resonance. I want the words I say to resonate with people, I want my voice and my guitar to resonate the cells and the eardrums of the people listening to me, I want to feel understood and help others feel understood when they hear my music. The pursuit of resonance underscores my entire journey as a musician and as a person.
Contact Info:
- Website: www.alliechipkin.com | www.giveloveoriginals.com
- Instagram: instagram.com/alliechip | instagram.com/giveloveoriginals
- Facebook: facebook.com/alliechipkinmusic | facebook.com/giveloveoriginals
- Linkedin: https://www.linkedin.com/in/alliechipkin/
- Youtube: https://www.youtube.com/@alliechipkin
- Other: Google Reviews (GLO): https://rb.gy/hbmz9
Image Credits
Danielle Coulter, Daniel Herman, Paul Moody, Walnut Street Photography

