Deep Dive: An In-Depth Look Into The Creative Mind Of Connecticut Folk Singer-Songwriter, Dancer, Ex-Circus Performer, & More Anna May

Every now and then you stumble upon an artist who seems to just ooze wisdom in every note that’s sung and every chord that’s strummed. Anna May is one of those artists. 

As a Connecticut-born singer-songwriter, impassioned dancer, innovative teacher, and ambitious traveler, Anna May has established herself as an eclectic artist whose sole intention is to cultivate an open, positive environment for those around her. And she’s had quite the life to show for it. 

May began studying piano at age six, later leaving high school early at fifteen in favor of gaining a creatively fulfilling education from independent mentors, finally becoming a mentor herself in 2013. She incorporated her love for music with the love for dance, joining the circus in 2015, where she found an enthusiasm for trapeze, aerial silks, and West african dance, to name a few. May ultimately returned her focus solely to music, releasing three albums that showcase an inside look into her life – authentic relationships, joyful affairs, spiritual enhancement, and self-reflected awareness all bundled up into one common entity: mere existence. 

Listening to her is an experience in itself. May’s voice lulls you in like a siren; smooth like butter as it creeps its way into your arteries, entwining your veins in silk and locking you in its embrace. With nothing but a lively ukulele or a haunting electric guitar to accompany her, May manages to capture the human experience in all its glory: freedom, growth, rebirth, unity, reflection, and peace. 

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Her new single “Come Down, Dreamer” is unsurprisingly as malleable as a dream could possibly be. You know that feeling you get when you’re driving in the middle of the night under the sheen of the city lights, and no one else is around? An atmosphere that was once bustling with people and noise now engulfed in serene silence? And the consciousness that you can be or do anything if just for that moment? That’s this song to a T. Wistful, comforting, peaceful. A state of divine tranquility that’s worth paying attention to. 

We got a chance to ask May about her new single and the impact music has had on her life.

Let’s start by going back to where it all began. What was it about the art of music and writing that made you want to create it yourself?

While I was growing up, I loved artists like Billie Holiday and Alison Krauss, and songwriters like Leonard Cohen, as I got older. Artists like these ones, and so many others impacted me incredibly, in creating such a wealth of profound, singular, and intentional music. I learned that there could be a space for all of the creativity that was inside of me. I was inspired to do that same life – searching & human – searching work that they were doing. These artists were isolating critical and sensitive moments of our often frenzied human experience, and that is exactly what I felt a desire to do, from a young age. I have always cared about people, and about what they do, and so, I enjoy writing about them.

I have always written, because it has made people around me feel better, or happier, when I sing or write. I feel that I’ve been a writer by nature. Writing has been my favorite form of therapy, and is what I have done whenever I did not know what to do. Writing has aided in connecting me to myself and to others, more significantly. 

Writing is a very natural way, I think, for us all to process the world. It is a quiet, sensitive, vulnerable act, and so is music. Writing or playing music have felt like familiar and instinctual processes. The world slows down when we do this stuff. When I recall being a child, I think about feeling immersed in melodies, dreams and in words. I spent hours listening to music, and singing, or making my own songs, all day long. I also did this during school, very much on my own.

I did quite a bit of listening, and eventually realized that i had my own phrases & story ideas. I began compiling these in notebooks. I still have so many of these notebooks, all containing songs, and poems.

When I was six years old, I began playing piano and loved it. I was able to decompress from school by practicing every night, and writing my own songs, as well.

I am an only child, and so my house could often seem overly quiet and peaceful. Writing and creating stories is something that I can always remember doing, in part, to keep myself company. I was brought to lots of live music when I was young, too. If someone were to describe me as a child, they might have said that I was lost in thought. Maybe I am still now.

I love the specificity and details associated with writing and with music. Writing music and lyrics provides us with the challenge of documenting our experiences with flavor, excitement, and awareness.

Both skills of making music and making lyrics seem to grant us opportunities to clearly express what we feel and perceive. These are such important & satisfying exercises for all of us to engage in. Doing these sorts of activities trains us to become excavators of both the immediate experience, and of the subconscious.

By the looks of things, you have lived a very adventurous life so far. What would you say has helped you shape your music for what it is today?

I guess so! I would say that the elements of adventure that are so infused into my life have lent freedom to my songs. I would also say that, encountering difficult circumstances has pushed me to put more into my songs, and into the subtleties within them. Confronting doubt from others has led me more deeply into my own abilities, and has allowed me to find new musical territory. Becoming absolutely trusting of the quietness of creativity has been the most important lesson, for me.

This quietness seems to yield the most. I do not shy away from the quietness, or from moments in my day that feel to be pulling me towards something that is almost divine, or outside of myself, as I did at one time. Creativity is an interesting process because it is not so much, taught. It is more about the fact that we must learn how to listen. Music is almost, this necessary cry for something, whether it is love, acceptance, fear, etc. Music has often reflected what feels to be missing in my life.

I learned the creative importance of feeling things viscerally, early in my life, and learned to give myself to those feelings, completely, in terms of writing music. I listened to hear everything that those feelings were saying to me.

Taking the pauses, when pauses present themselves, has taught me so much about who I am, and about who I can be. This is how we come in touch with the feeling or desire that is essentially, running beneath our lives, unseen. That, I feel, is creativity. It can be easy to miss, if we are distracted by something else. There can be challenges with vulnerability. Vulnerability is an art, but, fighting through it, for the purpose of reaching something honest is worth an uncertain process that may hurt. Stumbling is part of making music.

Writing songs can often be an illustration of the most fragile and confused aspects of a self. I saw a huge benefit for me in not being overly “locked in” to what others were doing, at various points in my life. I did only what drew me. Being able to see the world firsthand; to explore all of the crevices for yourself, and understanding the huge possibilities that exist in it, can provide an artist’s music with that same identity of freedom and rebirth.

Remaining outside the lines, so to speak, saved me, creatively, again and again, because i felt as if I had adequate space to witness the undercurrents of every story that I cared about telling. Being out in the world in really substantial ways was uncomfortable for me.

I was away from my piano, and from all of my other comforts, in a great unknown that I did not at first recognize as relative desolation, but, the experiences caught me that wonderful things can come from discomfort, and served to convince me that, everything is a lot less limited than what i had previously thought. I also discovered that creativity moves more slowly and more intentionally than the world does, sometimes, and we may need to change, in order to tap in. Creativity is limitless in the number of shapes that it can take, too.

I learned that it was up to me, to find the right path. I had to recognize that the guideposts would be different, on that path. I was able to make a home for myself upon unsteady ground, when I traveled, and this convinced me that I could accomplish anything.

As artists, there is no other way but to concede to this unpredictable process, that requires patience and compassion for oneself and others. I know for certain that the music that I’ve made comes almost directly from the wellsprings of the mountains, the oceans, the trains, and from the hearts of people. It is experiential music, and I think, that is what can cause it to feel foreign to some. Trying out a variety of disciplines when I was younger, helped to inspire me, and helped me to see the unbelievable possibility that every day holds; a myriad of directions.

A creative way of being can come with isolation, detachment and uncertainty, in addition to inspiration. These days i am quite a bit less adventurous than I might have been, previously; I tend to stay in one place more often, and am not hanging off of any trapezes. This new mode of being lends itself to writing and reflection.

From my perspective, adventure is born from a fear of what might become possible should we rise to new challenges. Fear and doubt manage to take me beyond what were my previous limits. At a certain point, I was ready to throw myself at a whole bunch of different pursuits, without fear. Good music needs good nurturing.

Giving music the time that it needs has been an important lesson for me; if the pace feels out of sync, or too slow, then that usually means that it is the proper pace. The music is not me but rather, its own entity, on its own timeline, and that is always something to remember.

I remind myself of the patience and fortitude that it takes of someone who is embarking on a serious mountain hike, or the discipline that it takes to play a complicated piece of piano music.

Every experience shapes our identity. Much of what I experienced growing up, in some ways, in a shelter of suburbia, felt compressed. When I left that environment, more or less, I began to feel more expansive and more open to the possibility of creating, but, I carry so much from every circumstance.

The pain that I’ve experienced in breakups, loss of family members, and other hardships has added unexpected shades to my songs, undeniably so, and has brought them into a more spiritual dimension. I hope to reflect the complexities and nuances of life, with all that I make. I love writing about landscapes, because there is something so beautifully untouched about them. I like to reflect freedom, insecurity & pain. I definitely hear it on newer songs like careless and kites, but also on older music from my Hey Houdini album, and I’m Still Thinking of You.

I believe that everything we do contributes to who we are, creatively. Over time, I’ve grown to love running, yoga, art and other practices, so I feel that all of it contributes to & ends up in the creative output.

While you’ve traveled to many places, is there anywhere specific that you believe can be heard in the core of your sound?

Absolutely. I feel that my travels have all provided me with something unique that has translated to a musical idea somewhere, but, the western united states probably shines through the most in my music, lyrically and melodically, for its sense of breadth and wanderlust.

There are certain albums of mine that reflect the nature of the western landscape, so much, and also, so unwittingly. Quite a few of the songs on my Flimsy Diatribe album are examples of this reflection, very much including the title track, “Jai guru deva om, take me to the mountain .. jai guru deva om, take me home.” “Take me to the well, to the water, to the brand new day .. take me to the sunny earth where children still play.”

This phrase in particular always transports me to a single moment, while I was exploring a boutique in Nevada City, California, and envisioned the imagery that was very much assigned to that lyric. I may have written the song and visited this place spiritually, before I visited it in actuality. I cannot remember if this is where the song itself was born; sometimes this is a blend of many destinations and moments.

For me, there is so much resonance attached to that particular landscape, and vibe, of the west, and I never tire of revisiting it for melodic or lyrical inspiration. Most of the other songs on the Flimsy Diatribe album feel to be made from the same thread; it is a melancholic western album, with a few hints of New Orleans. The album made before that one, in 2014 was largely written on the road, and tells stories about the same places and people, but in a different tone, and by a younger self, though still really with that western lens, in terms of atmosphere.

Flimsy Diatribe ended up being mostly an album about recovery; it became the scorched Earth and scorched pieces of self, remaining after the fire. There are certain songs of mine where I can almost hear a particular mountain range, a particular travel, or a particular moment, in a musical phrase, whether or not that was my intention. There is a stirring, chilling, antediluvian, and almost foreign quality to spots that I’ve seen in the American west, one of those spots being, Death Valley. 

These startling but limitless landscapes translate beautifully to melodies that reflect their silent grandeur. There are specific destinations on Earth that have been distinctively and endlessly inspiring for me. We definitely take a little bit from everywhere that we land, and I’ve been fortunate to have lived in some beautiful, and decadent places, like New Orleans, and Buenos Aires, but, there are certainly those places that feel the most familiar, and nearest to our souls, appealing most to who we are, elementally, and for me, that is the mountains and oceans, and innocent, spiritual ways of being that can be found in the western aesthetic, and then sometimes it is the humbler snapshots of New England, where I grew up.

Capturing the grandiosity of landscape, as well as human subtleties, in lyrics, has been something that I’ve always cared about accomplishing, and blending together. I hope to capture time, space, travel, and freedom, if that is possible. I always want for my music to have an open ended quality about it.

As a dancer myself, I wonder if you strive to create music that you could see yourself dancing to? Or is it just a naturally instinctive element that happens to come across along the way?

I feel that humans are all instinctual dancers and movers, whether we realize that we are or not, just as much as I believe that we are all musical. I was dancing from a young age, mostly in lyrical or modern styles, and learning to develop my own vocabulary of movement in dance class. 

Later in my life, I studied other styles like jazz, tap, hip hop, gymnastics and ballet, that broadened my creativity in so many ways. When I think about music that I like to dance to, I certainly like for there to be space & movement in the piece, and phrases that are easy to cling to, and adapt to movement. This is a quality that I do think about when I am making music, in the form of a key change or melodic departure. I like to add spots of melody where I can take off, so to speak. This works well for dancers, I notice, because the music emphasizes a moment where variation with movement can happen, easily. I hope to create music that feels interesting for dancers, even if the song is of a slow or introspective nature.

Most of my melodies are designed to be pretty rhythmic, too, which is ideal for dance. Dancing is a huge and important way for people to connect emotionally to music, if they are not playing themselves. There are several songs of mine where these sorts of transitions happen- like “Flimsy Diatribe”, “Come Down Dreamer”, and some others. 

I am grateful to have a background in dance. It is a unique gift that one art form can feed another. The perspective of a dancer is incredibly different from the perspective of a musician; I hope to always be working with both perspectives.

Occasionally my inner dancer emerges, while I am playing music, and I seem to act more as a dancer than I act like a musician. This might manifest as, a breaking away from a particular pattern in favor of improvising in some way, as if I were dancing away, or charging what I am playing with new fluidity and rhythm. I am probably not the easiest musician to follow, for other musicians, because of this tendency to depart from what has been set or written, but often I will do what feels the most fitting, for a piece of music, at a particular time, or in a particular performance of a given song. Surrendering to fluidity and space is vital.

I know some musicians who are incredibly bound to rhythm or to notes, in a way that becomes a stifling adherence. I feel that improvisation opens us to so many new directions and potential, and has the power to reshape songs. I like to make music that feels dreamy, or that could inspire dancers to make movement. Instinctiveness and freedom give way to dance, and I certainly aim for that.

Correct me if I’m wrong, but your songs seem to be primarily lyric-driven. Would you say that your lyrics are the most important aspect to you when creating your songs?

Lyrics are pretty important to me. I was a writer before I played guitar, and for a long time felt that i would drift in the direction of writing books or poems. Adding that extra element of music satisfied the process, for me, and served to combine two of my favorite things.

Most of the time, my writing is done before the musical layer is added, because i usually have such a stream of lyrics to handle, right away. I studied piano from a young age and so, in my mind, classical music occupies a separate space from lyrics and writing, still. I look for the best ways to fuse the two forms, and that can take some careful thought. 

I care about both the musical complexity and the lyrics, although they seem to begin as two distinct pieces, before they come together. My songs are certainly intended for close listeners, and those who care about lyrics and stories. I feel that lyrics are really nothing until they live alongside a special melody.

I do put quite a bit of thought into cultivating something melodically that will perfectly compliment a particular story. For the future, I feel more interested in complex musical ideas, and the concept of layering my newer works.

I love that I am able to look back on my recorded music and see all of my experiences and impressions in what i have written. I like to blend real stories with spiritual elements. I love what happened with guitar for the Flimsy Diatribe album; it became this really brooding and bleeding feel that happened, and ended up complimenting the lyrics so perfectly, and was so much more sonically robust than what I felt it would be.

Can you tell us the message behind your new single “Come Down, Dreamer?”

I don’t know that “Come Down, Dreamer” has a clear message. I want it to be an exploration, primarily, that is not entirely finite. This is certainly one of my songs that is laden with metaphor.

This song feels so separate from other music of mine, and separate from myself, really. Some songs can be that way. The song began to form after an abrupt breakup with a person who held a very spiritual draw over me, and the magnitude of our separation affected me deeply. I wrote this alongside my song “Careless”, which is about the same person, but feels more literal and like more of a pleading cry. This is the dreamier counterpart.

“Come Down Dreamer” also has a pleading tone, but is meant to do something deeper; to trace our entries & descents from a more spiritual realm. This process happens often in our daily lives, whether or not we are wholly aware & well in tune with our spiritual natures, that are quite alive, and pulsing through us, always, I believe.

The song details two characters who are essentially the same in their intentions and desires- one who is having a more difficult time coming down from the wrath & splendor of their spiritual life. These two dreamers are a mere strand away from one another in actuality, yet are separated by insurmountable blockades, as if they were on two different planets. One has not landed yet. 

The two dreamers are unable to align. “Dreamer in the night .. don’t we always twist in fright” is a lyric that stands to detail a dissatisfaction with, what is; what is fear driven and complacent, along with an accompanying desire to transcend this way of being, that is often so flawed and riddled with miseries, and where we are sometimes dwelling in darkness.

I wanted to explore concepts like, Elevation & Humility, within the context of spirituality. Coming down, and going up, and our need for traversing both paths at different times in life. The imagery in this song summons something akin to an alien dropping down to our world from another realm. Don’t we all feel this way, once and awhile; foreign in our own home, and wishing for something different? Musically, I wanted this song to feel as if it were gliding. You’ve also been working on your fourth album, Kites.

What can your fans expect from it once it’s released?

I think that people can expect something familiar, and something different from Kites. The quarantine period has changed the trajectory of this album, already. This slowed down time has helped me in allowing me to dive into some new creative spaces, and to achieve a refined vision, in terms of my direction, my fears, my desires for the future, & has given me an opportunity to look at the world, critically and spiritually, in ways that I was not doing before, largely due to the fact that I felt so immersed & entangled in our Western ways of being. 

The pandemic has altered what were our customary ways. This album may end up being less ultra personal than the last one was, and most likely will be more global, in nature. Already, this collection of music seems to possess a distinct flavor, and many blended notes of folk, jazz, and beyond, giving a sense of new sonic diversity. This also feels like perhaps, the first pop album that I have ever made.

A period of such change, desolation & alienation has inspired me to write something that feels affirming.

What has been your greatest takeaway from being the teacher of music compared to being the student?

The opportunity to be a student is a gift, and so is the opportunity to be a teacher. Teaching music is one of the most inspiring things that i do. 

As teachers, we are in charge of smoothing the pavement, so to speak, for our students to travel on & excel. Teaching is such a sensitive act. Learning itself is sensitive and vulnerable, and is a unique process for each person. Teaching causes us to grow in our abilities to understand others in complex ways, so that we may best tailor a learning experience to a particular individual.

I love to witness students of mine progressing, and becoming excited about the same things that i am excited about. Teaching is different from being a student, in that as teachers, we have a real responsibility to sustain a positive and stable experience & environment for every student, that will have the power to fill them up for a lifetime, and provide them with desire to create music of their own. 

I want to be present with my students, at every step of their way. It is a new perspective of the musical process to be a teacher, and keeps us close to all of what we need to be close to, and refining ourselves, in order to assure high quality performances and lessons.

Teaching requires a different bunch of skills from what we do when we are writing or composing. While teaching, we are relating to another person with patience and with insight, and are more or less taking our personal concerns out of the equation, which can be a relief. It is truly an empowering gift, to be vulnerable with yourself and with your student. It melts me when students express that they feel uniquely touched or changed by the work that we’ve done together, because i know that my work with them, changes me for the better.

How have you attempted to remain creatively driven during this difficult time we’re all living in?

Times like these seem to be the most creative times for me. Difficult times always are.

It is often when we can see matters starkly, and when distractions are stripped away that our internal voice grows, because it needs to grow in order to meet the gravity of the moment. There is so much that we can respond to, in this time, internally or externally, despite the world feeling completely still. We are sitting with an identical set of problems and brokenness really, over the course of months, without a definitive answer coming our way, and this is a unique problem for us all to be enduring.

We are essentially and unfortunately, living in a hopeless reality, for the time being. The various regulatory systems that were in place have broken, and so, we are living in the context of extreme and unavoidable brokenness. I am learning that it is perfectly okay to sit with this all, too, and to remain somewhat inactive with it, for a bit. We are learning how to exist in a completely new way, after all.

The beginning of this period was incredibly productive for me. I immediately chose to view all that was happening, in positive ways. This new ability that we were granted, to have personal space that was outside of society’s often rigid paradigm, was something that I stuck to, for purposes of survival. This space even felt somewhat necessary and rewarding.

I felt more caught up on all that i had wanted to do, with so much more time, outside of a rather regimented context that can be difficult and demanding for people. I wish that this societal shift towards simplicity could have occurred more naturally, and did not have to come about as a result of a situation that proved so dire and deadly. We do not turn away from the awfulness, but we must find comfortable ways in which to cope. I learned from the outset of this collective crisis that my personal success and resilience would be determined by how I viewed the situation, and by what I would do with it. What I had a privilege to do with it. If I could transform stress & isolation into freedom and unity with my whole being.

It seemed that all of us were quickly & radically confined to a reality that felt immovable, so heavy, and close to the bone, in every possible way; all encompassing and insurmountable, driven only by a very real and inescapable fear. I did not wish to mask the horrible realities, but sought to find as much freedom and light as was possible. I remembered that creativity is at our disposal, always. 

Miraculously, while navigating & perceiving a world that contained so much new threat, and required so much modification to my behavior, i noticed that there was enough beauty available to me that could make each day survivable and even, enjoyable. There is much to grapple with, and much to grow with here, in this time, as we are processing all of these huge changes to life, and trying to put steps forward, and yet, while everything is changing, there are still so many lovely consistencies that remain in tact; little things that i am grateful for, like family, lattes, beautiful natural settings, my ability to examine the world & to write about it, food, children, etc. 

I have not touched every subject that this crisis has opened up. There is plenty of time to do so. I do believe that an altering of our societal & structural norms is likely what we needed, collectively, in order to put racism and other pressing cultural matters into perspective, but, this was a drastic change for all to have to feel, at once.

It is unfortunate that positive lifestyle changes for some, have happened beneath a cloak of hardship & ugliness for others. This time has also shown me, again, the gifts of beauty and fortitude that the inner world can provide for us. It is there when we cannot feel safe in our outer world. While there is much less happening outside of ourselves now, as individuals, we are still equipped with insights, creativity and principles to sustain us. This has been the most profound discovery. My life feels simpler and easier to control.

It can be easy to become depressed these days, but, setting routines, going on drives, exercising, etc. has all helped to keep me focused and creative. 

There might be a part of everybody that feels a need to pretend that things are okay, while we are starved of happy and healthy connections, and of our normal ways of being. Validating the abnormality is important. This is a unique situation that challenges us daily.

And I have to ask: what was your experience like working in a circus?

The circus was an awesome time in my life. I wouldn’t have wanted to do it forever, but I think that there is tons of value in joining a circus for a bit! Everyone should do it, i think. The experience shifts the norms that most of us are accustomed to. Trapeze is grueling, but incredibly artistic in nature. I conquered tons of fears in a short amount of time while practicing circus arts, and what I accomplished on trapeze extended to every area of my life, enhancing my self confidence, mostly.

So many of us are out of touch with the art of playfulness, because the overwhelming structure of society is not necessarily founded on principles of playfulness .. yet, playfulness is essential to our being, if we are striving to be at our happiest, healthiest, and most balanced. We require that this element of ourselves, be in the mix.

The circus, hoop tricks, aerial silks, etc. was a life changer for me, and opened me up in new ways. The paradigm of life for adults is not always conducive to play. There is not enough space for it, unless it aligns with a very specific outlet. I felt freer and lighter during that period in my life, and have carried those lessons of athleticism and lyricism with me, applying them to my music.

I am forever grateful for that time of expansion and expression. The circus is interesting and challenging, because it is so linked to risk, and to defying the odds, in physical and mental ways. The practice takes us beyond our comfort zones. I think that the pursuit of music is similar in that it allows us to break with comfort zones in intellectual and spiritual ways. Both showed me incredibly positive new ways of being.

There is a deep history of circus that is steeped in darkness, but also in playfulness. I had always been fascinated by circus arts and by the mythic nature surrounding circus communities, but was never a gymnast, and so i did not feel capable of entering that world. It felt entirely foreign to me. I challenged myself and struggled greatly, but,

I surprised myself, and transformed in many ways, even if I did not become a stilt walker.

What might folks expect from Anna May to close out the year?

It is tough to believe that the year is almost over. I am still so much in a cocoon of writing, basically, though I am itching more and more to get back out. This does however, feel good to me right now. I do not have a set date in mind for when Kites will be finished, and things have been delayed due to the pandemic.

I do not think that the album will be done at least until 2021, but I am planning to either focus on releasing some new singles, or throwing myself into finally publishing my children’s book; one of the two. Most likely, people could expect more new music that may or may not be released right away, but I will definitely be in a process of making new music.

I am hoping for this release to be a longer album than past albums, to encompass more, and for it to feel more satisfying rather than open ended, as past projects have sounded. It has been fun to put together a mixture of songs that I’ve been playing for a long time, but have not yet recorded, along with some brand new songs, too, so, I plan for this album to cover quite a bit of ground and themes.

It will be a combination of different years and various times of life, as opposed to something that is centered strictly around one concept. Kites emphasizes that human beings are light, effervescent, and resilient, even when we are passing through windy skies. “Kites, suspended in the sky / we are just flying kites / do I ever cross into your part of the sky?”  

On Kites, listeners might be able to see pieces of my personal evolution or transformations, if they’ve listened to my music before. There has been quite some transformation over the past few years, and I am looking forward to sharing that, musically.

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