Dive into our captivating conversation with the multi-talented Anna May, an artist whose unique journey is as diverse and enchanting as her music. As a Connecticut-born singer-songwriter, dancer, teacher, and ambitious traveler, Anna has painted a vivid canvas of life, underpinned by a steadfast intention to cultivate an open, positive environment for those around her. Her journey, both unconventional and inspiring, resonates in the music she crafts and the wisdom she imparts.
May’s artistic journey began with a piano at age six, blossoming into the world as a singer-songwriter. At fifteen, she boldly stepped away from traditional high school education, instead seeking wisdom from independent mentors. The world often feels tailored for those who are more boisterous, and for someone who is somewhat shy, the environment frequently imposed from the outside doesn’t always fit. It’s through art that she has found a way to navigate this world that predominantly accommodates the outspoken. “I find that telling the truth and being real can bring us to the best connections and to the greatest forms of love. This is a hard feat, in a society that embraces fakery and concealing as a mode of everyday existence, from social media to the makeup industry, and beyond.”
Throughout our interview, Anna May offers a deep and insightful perspective on life and music, and an intimate glimpse into her creative process. Her practice, rooted deeply in extemporaneous expressions of her experiences and emotions, is a testament to her desire for authenticity. She also delves into her past, sharing the challenges she overcame as a victim of bullying, and how the journey towards a self-directed path of education shaped her life. Her experiences, colored with elements of Zen, nature, literature, and music, weave a compelling narrative that echoes in her songs.
header photography by Chelsea Mandes
all other photos by Mallory Olenius
“The moment when creativity happens is the essence of it and feels most beautiful to me.”
Taking a minimalistic approach to recording has never been intentional for me. I love the concept of a fuller sound, but I have not yet encountered people with whom I’ve related musically in a sustainable way, and who care about my songs as much as I do.
My thought has always been to just do it myself until that comes along. Steve Rizzo records me in a way that places emphasis on my lyrics, and I am so appreciative of his ability to do that. There is a fuller sound for my songs, I know, but the timing hasn’t been right yet. Integrating with a band has always been my weakness as a musician, in fitting myself into other arrangements, and so I was eager to do things in my own way.
I have loved playing with a band, on the rare occasions that I have, as long as the band is exploratory and open-minded. I am also so in love with the quality that the recorded songs have, just as they are. I don’t think musicians need to carry the expectation that bigger is always better. Subtlety is precious.
“I am more of an intellectual and emotional person by nature and so the quiet times spent writing in my bedroom are the most gratifying for me.”
As musicians, so many of us have played in noisy environments where our lyrics couldn’t really cut through, so I especially enjoy having my recorded work done in this way, that can feel bare and haunting.
Taking a minimalistic approach to music affords space for a lot of lyrical complexity. Lyrics have become the centerpieces of my songs. I have quite a bit of freedom, too, in designing these solo arrangements, that I might not necessarily have if I were locked in with a band. It feels expansive…
Throughout my life as a younger person, I often felt that my voice had either been silenced by those around me or was not heard clearly. I was a very shy kid. On some level, knowing that my voice is heard clearly in my recorded work feels very special.
Your music has been described as alternative tragic Americana, with a focus on peace, judgment reshaping, and bleeding heart stream of consciousness poems. How do you find the balance between these heavy themes and the sense of hope and connection you aim to create in your music?
We are ultimately bonded and brought together by what breaks us. The heavier or deeper we get, the greater our ability to see each other and appreciate the complexity of our suffering becomes. I have always found wisdom in my suffering. After all of the muddiness and difficulty of what we experience, there is an opportunity for transformation towards joy, empathy, and healing.
I want, on some level, for oppressed or marginalized people, in any capacity or situation, to feel highlighted in my music. Many of my songs are about rejection, trauma, and betrayal. So much of what I have made has been a reaction to the persecution that I’ve experienced in my own life, and ultimately about coming to restoration and rebirth after a long and big battle.
Our awful experiences can bring us to enriched understanding, and to empathy that we did not have the capacity for before our traumatic experiences. Feeling helpless at moments in my life has ultimately made me feel stronger and able to witness my own power.
“Seeing firsthand that there are no guarantees or being totally blindsided empowers us, I think.”
My music will always be a, perhaps idealistic, pursuit to eradicate judgment, and a quest to voice perspectives in authenticity. Writing my albums has been a way to heal myself, and a way to reach out into the abyss for understanding. In doing this, we can find our way up from the ashes, to meet others who have done the same. Hardship can lead to rebirth… not necessarily to defeat and failure, as I have seen for myself.
I find that telling the truth and being real can bring us to the best connections and to the greatest forms of love. This is a hard feat, in a society that embraces fakery and concealing as a mode of everyday existence, from social media to the makeup industry, and beyond.
Many of my songs were born from deep wounds and visceral traumas in my personal life. What I craved in those difficult moments, and did not have, were: ultimate peace, non-judgment, honesty, and art. I did not find those elements that I needed in my immediate environment at that time of distress, and so, I created them in my songs. The songs were the way through, and I hope that they can be the way through for others who are also needing a channel to hope, while in a space that might feel vacuous or oppressive.
I feel as if we cannot recover hope without moving through the drudgery first. We bleed together and we heal together.
With your music honoring the nomadic spirit and offering fresh interpretations of folk music, what are some of your key influences and inspirations that have shaped your sound and your approach to songwriting?
My history of travel has definitely shaped my songs, and having come from a pretty unconventional foundation has, as well. I was exposed to music when I was young, and have incorporated so much of that influence into my music – Billie Holiday, Shawn Colvin, Bob Dylan, Leonard Cohen, Chris Isaak, etc.
I developed my love for songwriting as a teenager, starting with 1960s folk and beyond, in seeing a need and desire for getting to the heart of things.
In cultivating a sound, it has been about doing what was natural and moving away from affectation. I came to realize that meditation is something that all people need and might not even realize that they need it, or know how to go about integrating it into their lives. A meditative approach to music is not so readily accessible everywhere in America, at least. Music can provide deep solace and meditation but isn’t available in the mainstream. I am aware that what I do is niche in some parts of the world. There are wonderful oases of music and meditation out there, but this is not something that everyone has come to recognize as a need. We are so heavily influenced and programmed by trends, it can be difficult to tell what we might truly be needing. My path and my experiences were non-linear and afforded me many important explorations into doubt, danger, joy, sadness, trauma, etc., and all of it seems to come through in my songs.
“Art is really a natural instinct if we turn ourselves on to it.”
It is cool sometimes that I can look back and think, “You’ve had an interesting life so far,” not without its share of weirdness and things that you could have done without, but that nonetheless shaped you.
I was bullied pretty badly in school. I took my time to do tasks. I was often singing and writing, and never felt like I was in the right environment to thrive.
I became extremely unhappy as the bullying worsened, and I started learning more about unschooling and the option to follow a self-directed path. This was wonderful for me and started me early on a path geared towards my love of Zen, nature, literature, and music. In seventh grade, I took my self-designed curriculum outdoors and studied outside. I wrote poetry and short stories, and really began to find what my interests were. Creatives need some extra space to do their thing, and to even find out what that thing is.
The world often moves at a different pace than the creative process does; our approach is just so different, and I found myself coming up against this sort of discrepancy while I was trying to find my voice. There was frustration and outright depression at not being able to have the time to write and to process my experiences. Out of a school setting, my mindset began shifting towards peace, focus, and security.
I knew that the only way out of bullying was out of school. I designed my own curriculum with help from my parents, and finally, I found myself in a nurturing environment, to really dive into my interests. I fell in love with writers like Thoreau, Lao Tzu, John Muir, Oscar Wilde, and so many more, who seemed to endorse this new path of mine.
Everyone needs access to artistic, emotional, and intellectual therapy like this. I am grateful that it was part of my life. My experiences at this time in life show up so much in the music that I make even now, coloring it with a wistful and nomadic texture.
“Out of a school setting, my mindset began shifting towards peace, focus, and security.”
After this time spent in one place, I began to explore the world in an outward sense, taking trips through the South, the West, and elsewhere, with an intentional view as a writer. I explored Colorado and Argentina with fellow unschoolers. I wrote a novel and then started writing albums.
I’ve wanted to cultivate a languid sound while dealing with heavy topics and to offer a sense of meditation while processing difficult emotions.
I try to cover a lot of the resentment, backlash, and hostility that I’ve received from family members and from others. I love to write about the nuances of past relationships. Writing helps me to navigate through trauma and frustration. I try to examine subconscious elements to the best of my ability in the work that I do, and hope to employ something that is metaphysical and mysterious in nature.
In your journey as a singer-songwriter, what has been the most rewarding or unforgettable moment for you so far?
I find that the creative process itself is the most rewarding aspect of making music. I love the interior, internal, quiet moments of art the best. I can always remember where I was when I had ideas for certain songs. I am lucky that I feel inspired often, and experience creative phases where I can be writing almost all of the time. I identify primarily as a writer.
I love performing and all of the gifts that it can bring to us as people and as artists. I began performing at an early age, and I am grateful for the many lessons that it has taught me about myself, about human interaction, about my limits and comfort, etc.
Being an introvert and a performer is a challenge, as performing can take so much energy from me, but I continue to do it because live performance is a great teacher of humility and grace. It is an energy that some people never experience themselves, and for those that do it frequently, it is something unique.
I’ve never needed performance to feel satisfied as an artist, nor have I thrived on performing alone, as some artists do. I am more of an intellectual and emotional person by nature and so the quiet times spent writing in my bedroom are the most gratifying for me.
I’ve had some awesome performance moments during which I felt truly connected and received. The first time that I sang songs that I had written in public, when I was seventeen, was something that I always remember.
“My view is always evolving. Seeing so much go wrong globally and in our own lives makes us either perpetually anxious or perpetually open to new possibilities.”
Any video shoot that I’ve done has had a kind of magic about it, and, I’ve definitely had some career highlights when I felt… wow, this is actually working, like playing the same festival as the Jackson Five, and at times when I was complimented by artists that I admire.
The most rewarding piece, though, is always the creative process itself, and this subtle, accessible ability to come in contact again and again with these rare instances of truth, clarity, or spirituality. This feels hopeful and reassuring to me, and helps me make sense of the world, in distilling experiences and emotions for the purpose of greater connection and understanding.
Being able to feel that proximity to something so beyond us is incredible. If a song that I wrote were never performed, I would almost be okay with it. The moment when creativity happens is the essence of it and feels most beautiful to me. I have a lot of songs that haven’t seen the light of day since they were written.
Can you imagine composing film music?
Yes, absolutely. It has been a longtime dream of mine to work on a project with music for film, and to design something specifically for a film. I was very into film in high school and loved my time in Los Angeles, witnessing the synergy of music and film. This is a love of mine that has been on the backburner for some time. I am a huge movie lover, but that is untapped territory for me. I would like to focus on it in the future. I love the concept of working with an already existing storyline and trying to find music that might suit it well. It is a different channel of the creative process.
In one of your Instagram captions, you mention that you’ve experienced a dwindling sense of certitude as you’ve grown older. How does this evolving perspective on life and self-awareness impact your songwriting process and the themes you choose to explore in your music?
I have. I used to feel very sure of myself, and I find that I know less and less as I grow older. I think this article will come out on my 30th birthday… it feels that, when we come into our wisdom, we also realize that our time is limited. That is a strange realization to have; that time is gone in many ways.
This realization came sort of late for me and has been accompanied by an anxiety about what I want to accomplish. My writing has become more and more minutely self-aware over time. When I was writing music as a younger person, I was more broad and less specific. Now, I feel that there are crucial things that I have to write about.
I can perceive more possibilities as I age, and with more possibilities, there is a magnified uncertainty. There are more critical decisions to be made, and all the while, greater uncertainty. From an American perspective, especially true for women, I found myself socially conditioned in terms of a very linear view of life and a female’s customary trajectory, and when I look at my life, I truly see that nothing has been linear. I am grateful for that, and for the diversity of my experience, which I might not have thought possible at one point in my life. I find that my setbacks and heartbreaks have contributed deeply to my identity and my own power.
I ultimately find that luck plays such a big role in so much. I don’t think that anyone working in the world of art is ever standing on something concrete. That is part of the joy and mystery of art.
“I felt a lot more free once I could embrace that everything around me was flowing, maybe out of control, … but ultimately, who knows?”
Nothing is certain, and I feel more than ever aware of that ephemerality. It feels as if the need to make music is more important than ever when I find myself in this fleeting state of being. Climate change and political unrest have exacerbated this new collective perspective.
I find that delving more deeply into the creative process enforces this lack of certitude, as well.
Creativity can be so wispy, unsteady and difficult to tame and quantify, and when we are working with these fragile elements of elusivity and emotions, I think, it is inevitable for life to be colored by that perspective. There are countless rhymes, millions of ways to design a song, countless chords, countless words to express something, etc.
Music can open our minds to the infinite amount of possibility, and to the awareness that we would never possibly have time to get it all down. As artists, we are confronted with this reality, constantly in our quests to capture snapshots of existence.
I leave myself more open than I used to, and attach myself a little less.
It is a more liberal view of life. I think more now about luck than I once did. There is so much that we cannot control, and most of what we deal with in our lives is not permanent. This has become clearer to me as my time here has gone on. There’s a lot of beauty in that palette of unpredictability though, and in how we choose to live from that unsteady basis… in terms of how we might seize an opportunity, or care about something, or give our energy to something meaningful, because of uncertainty. I felt a lot more free once I could embrace that everything around me was flowing, maybe out of control, maybe towards something measurable, but ultimately, who knows? I could never possibly hold it all in my hands, but I could capture small pieces. I could not have predicted what has transpired in my own life. That’s uncertainty.
Someone at a show recently told me that my music was “beauty in a shaky place” and I really appreciated that. I think that is what all musicians are trying to find, and wanting to build something resonant, still, and meaningful out of the anxiety and unfinished sentences, so to speak, around them. Art is really a natural instinct if we turn ourselves on to it.
How can we possibly make meaningful things though, in the midst of a lot of change and a lot of movement? Artists are trying to, I think.
I think too, the uncertainty of touring, which can come with so many unforeseen circumstances and really is this thing that is so dependent on the chance that everything will possibly happen as planned, and usually doesn’t… really brings me further away from the concrete and fixed view of the world that I used to have. My view is always evolving. Seeing so much go wrong globally and in our own lives makes us either perpetually anxious or perpetually open to new possibilities.
By having relationships that I thought were so special not work out, or career opportunities not work out, I needed to forge an entirely new, revitalized perspective out of a tunnel of self-doubt. The manifestation of that is probably my music, and ultimately, an embrace of uncertainty.
It is magical really, and a blessing in disguise when we realize, things that we thought were one way, were in fact, not at all that way. It keeps everything interesting and keeps us questioning. What do we do with that and how do we move forward? Seeing firsthand that there are no guarantees or being totally blindsided empowers us, I think.
In a 2020 interview, you emphasized the importance of improvisation in your music and how it opens up new directions and potential for your songs. How do you decide when to break away from your initial pattern and allow your inner dancer to take over during a performance?
That’s a cool question. I do have an inner dancer, definitely. We all do. I’ve always listened to lots of jazz, of all varieties, and had a time in my life when I loved jam bands, which helped to solidify my love for improvisation and served to broaden my way of interpreting music. Improvisation is so important in life and in music.
I am mostly drawn to a folk-oriented style but have this desire to multiply what can be done in folk music. I want to make the genre feel more multidimensional, similar to a lot of the different styles of music that I’ve absorbed over the years. I really appreciate songs that have a great deal of space within them, and are not limited by a typical song structure. This makes for a freer creative approach. I’ve hit several walls in my career in terms of being exploratory, as this is not the typical choice for many folk artists. The folk world is very much conditioned to a three-minute song format, but I feel that folk can be more genre fluid.
“Being an introvert and a performer is a challenge, as performing can take so much energy from me, but I continue to do it because live performance is a great teacher of humility and grace.”
I studied piano from a young age and over time, improvisation became integrated into how I thought about music. This was all enforced by what I was listening to… There is a great version of a Neil Young song, Change Your Mind, that begins in a very typical folk format and opens up into something so beyond where it started. There are obviously so many beautiful works like that, evoking more of a Miles Davis aesthetic, but these explorations are more rare in the context of “folk”.
My parents put me in creative dance when I was two… it wasn’t ballet or tap, but were weekly classes designed to encourage us to create our own dances. This made improvisation a deeply rooted aspect of my nature, to the point where I cannot really avoid it in anything that I do.
I don’t think it is ever a conscious decision to improvise, but it happens, as an extension of being human, the more that we play and live and do… totally dependent on the environment and our state of being as an individual.
My songs are constantly evolving. I often change a lot of my songs while I am performing them. There are recordings of my songs that are entirely different from how those songs are played now. Luckily as a solo performer, I can take these sorts of liberties. It can be both frustrating and interesting to catalogue songs that are always changing. I think, it’s important to never become too locked into any paradigm, and to always be open to the possibility of playing or singing something in a different way. I’ve re-recorded some of my songs from earlier albums on later albums to incorporate some of the sonic changes that I’ve made, over time, and even after that, they have changed a few more times!
I teach music and have come to know that improvisation is a weird thing. We are all wired so differently. For some, improvisation is a natural instinct, even unavoidable, and for others, it is entirely foreign and nearly impossible to do. Both of those energies come into play in music.
Whatever changes I make during performance are kind of unconscious, but I find that going to a different place can allow us to uncover something new from ourselves… it can be hard because I’ll make these changes in the middle of a show and have to take a quick break to make a note of it, or sometimes I just can’t remember. Usually, our muscle memory can bring us back to that space, but I can agonize over it sometimes, if I don’t remember.
If you could collaborate with any artist, past or present, who would it be and why?
It feels hard to choose just one artist that I’d like to collaborate with. I mentioned Neil Young before, and I think that a Neil Young collaboration would be extremely cool, for obvious reasons.
From the moment that I first ever heard his music, I was taken to a sacred and peaceful state of being… a space of energy that I seemed to know already, very deeply. His music brought out all of the special and poignant stuff of childhood for me. I feel a true sense of alignment with Neil in terms of song structure and lyrical intent. In Neil Young’s music, there is a unique proximity to things like elation, deep sorrow, death, enlightenment, etc., in such an unassuming context. His songs are so artfully and carefully put together, yet they also have an improvisational and extemporaneous quality. He has a way of being able to capture a conversation, or a time of night, or something belonging to the past, with a great degree of truth. He can capture stillness. There is something about his music that never strives to impress but that simply honors the intricacies and beauties of existence in a wise way. There is nothing contrived about his work. He is merely witnessing others and the world. He can honor imperfections in a way that is rare and gentle.
“I miss music that has a roughness about it.”
A big complaint of mine in modern music is that a lot of it seems very tidy and as if it might not be coming from a genuine place. I miss music that has a roughness about it. We have come to live in a world dominated by contrivance in art and nearly everywhere else, and that is very different even from the world that I grew up in. It felt that there was more space to breathe and to create and I really do miss that. I try to get to the most authentic place possible, whenever I am writing, and that might mean detaching from the internet or from people, in order to do that. Conveying something musically comes from listening deeply and I’m not sure that there is even a collective awareness about why we are singing and writing in the first place, in a culture that is obsessed with being noticed. The wells run deeper with music. It is a true connection to joy, and pain, and experience, and is more rare than it is common. Art has become very imitative and that’s something that I always want to be resisting. For those that have felt that connection to truth, then there is no other choice but to create. My hope is that everyone would get to that place, and engage in some profound, collective healing. The digital age can limit the quality of our experiences in many ways, I feel. We aren’t truly engaging in layered experiences.
It would also be very cool to sing a duet with k.d. lang. k.d. lang made serious headway for women in alternative music.
When you are not working on music, what are some of your hobbies or activities that you enjoy in your free time?
I love all kinds of writing.
I write down my dreams every morning, so I can make sure to incorporate a bit of creative writing into every day. I love poetry, too. Film has long been a passion of mine. I would love to make a movie someday. I also love photography, and made it a more serious focus when I was younger. I have been a longtime yogi and practice every day. I also love dance. I have studied West African dance, circus arts, hip hop, and modern dance. I love travel, too. During the pandemic, I took up running, which I have grown to love. I would love to make time to get better at visual arts. I have a whole lot of interests and I find it difficult to make time for doing all of what I like. My hobby away from songwriting is often other kinds of writing. I find it hard to allot the time that I need to work on my songs and also make time for my other creative writing projects. I have lots of unfinished work, but I do try to write in some capacity, every day.
Are there any particular themes or stories that you are eager to delve into in your future music projects?
There are certain subjects that I haven’t written about and want to write about, either of a personal or global nature, primarily about the female experience, as well as eating disorders and other subjects that are close to my heart, but deeply sensitive. I hope to become a more political writer, as time goes on.
Songs come frequently and naturally to me, so I don’t necessarily plan what I will write, but I’d like to explore some new territory. I write quite extemporaneously and based on what I am feeling.I am also open to stylistic changes, exploring my pop side, my soul side, my jazz side, etc.
I recently went to a Suzanne Vega concert; she is someone who has inspired me with her tender and subtle work and is known for writing music from the perspectives of other people. I would love to explore doing this. Putting ourselves in the shoes of others makes us more empathetic and opens up pathways for us.
