Anna May Creates a State of Tranquility With “Careless”



From Waterford, Connecticut, Anna May is an artist with an alternative tragic Americana style who has just released a single called “Careless.” Her goal is to create music about memory and meditation. She draws aspects from jazz and folk music to give her songs a refreshing sound. As an artist, Anna May uses her connection with audiences to spread positivity by enhancing joy and humility. She has performed at many famous venues including Boston Arts Festival and Broadway Comedy Club in Manhattan.


Anna May’s “Careless” is stripped down to the simplicity of a guitar and a voice; it is a gentle, acoustic track that spotlights her soft vocals. Anna May creates an energy of peace and serenity with “Careless.” She plays a relaxed guitar melody to accompany her voice. Anna May showcases her natural musical talent and diversity as she plucks acoustic guitar at a slow pace. Her vocals are high pitched and soft, comparable to the slower-paced Dixie Chicks songs. She shows off her vocal range with drawn-out “oohs” throughout “Careless.” Lyrically, Anna May asks a love interest not to be “too careless” with her heart. The song is relatable for many people who have struggled with trusting again after heartbreak.


Listen to “Careless” here

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Welcome to BuzzMusic Anna May! Your new release "Careless" has tranquil energy that spotlights your vocals. Can you elaborate on the message behind your lyrics?

Thanks so much:) Careless has felt special to me. I was fortunate to get to the studio to record careless and some other new songs in the weeks before the pandemic hit the east coast in a big way. It was very much a precursor to quarantine to spend a few days in those sessions & to emerge, into the markets and shops of Newport, Rhode Island to find an already palpably changing world. I intended for careless to be a plea for kindness and accountability, rather than something that might fall into a category of shame or blame. Songs of this nature can be attempts to recover love and can be potent illustrations of fear and trauma. As painful experiences become further internalized, we undergo an often, prolonged physiological response.

For me, a challenge of translating emotions into song, is, achieving a perfect balance of melodic satisfaction, and insight, while acknowledging one’s own perspective, and someone else’s, as well. I actually don’t remember the experience of writing it, but I remember that it was a quick process, with very few edits. Those are the luckiest moments for songwriters. This song came to me in a way that had little to do with chiseling and crafting. Some songs are crafted, and others are written from a purely emotional perspective, because, the emotions that you wrote about were so widespread and encompassing. Careless was written with hope for the outcome of a situation that sits with me as unresolved & not having the beginning that it deserved. The song reflects on the aftermath of being told, starkly, that a relationship is over, before it has had an opportunity to flourish and evolve. For whatever reason, the other person had backpedaled from that point of unison joy and connection, in favor of something else. Sentiments like these have always been a common thread throughout my music, in efforts to lend a voice to the unspoken yet definitive relationships that never saw the light of day, and for all of the many people who were not well protected or treated with sensitivity. Writing songs can provide me with closure that I did not fully receive, and songs help me to grapple with the frustrations of loss. Writing is a powerful therapy into and past all that haunts each one of us. Lyrically, this song asks a basic question: “why weren’t you careful with me?” The word careless helped to define the sense of desolation that I experienced, and examine what it was that caused me to feel it for so long afterward, as I was forced to sift through a very mixed bag of good memories and contradictions. In songs, unlike in reality, writers have absolute freedom to divulge and fully explore the emotional impact, as a way to work through the numbness. There is no getting around anything in the context of a song, and no sugar coating, in some cases. 

The emotional impact is not quite black and white, and that makes it tricky and interesting to dissect, diagnose, understand, and interpret.  We might all benefit from encouraging a more empathetic and nurturing way of being, for the sake of collective survival.  Right now, this song and other ones are very much resting in a vat of uncertainty from a pre-pandemic world, and I see this one specifically as a call for someone, that is hanging in space. The song itself asks for a response that it may not receive. So much of songwriting is examining a past that is no longer existing but only in the minds and hearts of the artists who choose to make these passionate dedications for who and what found a way into their lives and left gifts with them. Songs are ways to wonder if these sweet souls who are absent, might come back. Songs can be spaces for us to step back and reflect on the importance of each interaction, that holds sacred integrity. Careless is about the people who we see with lucidity and love, but who did not quite see us; who hurt us in ways that felt or feel unimaginable, but who we forgive.

We are vulnerable to change and heartbreak, but are also, characteristically resilient. If there is a really clear lesson that I’ve learned throughout my twenties, it is that interaction is tremendously important. In a society that moves quickly, I am valuing these current times that urge us to practice care and respect in all that we do, and that urge us to uncover lost layers of ourselves.

You have performed at a variety of famous venues and even opened for the award-winning songwriter, Jann Klose. Can you tell us how these experiences have inspired you as an artist?

Totally.. all of those experiences mostly inspired humility, a sense of elevation, and a sense of validation, too  .. having one’s work noticed or respected by reputable venues, and opening for gifted artists is one of the unmatched joys of performing. These kinds of experiences also inspire a striving to do more, or a desire to expand in new creative directions, based on what you’ve absorbed in the context of a new setting. I’ve been fortunate to get to play at some stellar and unique venues. These are all stepping stones along the way to cultivating a clearer artistic vision, and towards knowing what my next step might be. Learning from other artists is crucial, and can make us feel like we have permission to try something new.  

I was given good advice from my aunt, that has remained with me. She encouraged me to seek collaborations with artists who might cause me to feel as if I were out of my comfort zone. Playing with people who are technically more experienced with music than you are, usually makes for a more well-rounded artist. There is naturally quite a bit of walking around on ledges involved in music-making, anyways, so, throwing yourself into a variety of situations doesn't hurt.  Traveling to play music has always enriched my perspective, and inspired songs, one of my favorite places being, the mystical town of Hoopa, in Northern California. The sense of movement that is inspired by travel feels spiritual and invigorating. Sinking into new places, realizing their depth and subtlety, feeling at home in them, and lending your energy to them is a unique privilege that musicians have. Storied music venues can have great vibes, and getting to play in particular spots can be surreal and special. I really enjoyed playing in Nashville .. there is just a huge sense of, having landed in the right place, and Petaluma, California was another favorite place. 


We could clearly see your musical talent with both guitar and vocals in "Careless". How does your talent with guitar benefit you as an artist? Why did you choose to make "Careless" a completely acoustic song?

Thanks for saying that! I am pretty critical of myself as a guitar player. I like to play rhythm guitar, with a few change-ups here and there. I feel humbled to have been surrounded by some really talented players, in my life. I consider myself first a piano player, but, learning guitar in my early twenties felt like the right thing for the type of music that I had been writing, giving my songs the rhythmic boost that they needed.

I am a lover of lyrical complexity more than anything, but at the same time, there is so much fun to be had with the guitar! I feel as if I am only at the tip of the iceberg, with such a limitless instrument.  On Careless, guitar helped me to create a pulsating dream-scape, where the lyrics could rest comfortably, while the guitar acted as a revving engine, accentuating, and allowing the energy of the song to dip and spike where it wanted. The guitar can be super inviting & familiar for listeners, and guided me in developing rhythmic and dynamic variety, along with syncopated stops that are subtle, but that adds tremendously to the mood & layers of emotion that I sought to illuminate. An instrument is an anchor. Careless ended up being, lyrically earnest, and even literal, with an ethereal and shaded musical backdrop. 

I wanted this song to begin from a typical structure, and then to meander into something that was sort of unhinged, and akin to an echo chamber of promises and questions; this is where song structure gets set free. That’s the magic part, where we part with our story and hand it over to pure emotion. I have an illustration that went along with the initial draft of careless, to highlight a movement into a new realm, metaphorically, and energetically, in the second part of the song. I am happy that the recorded version ended up dropping into some cool, rhythmic cadences, spontaneously, too. Guitar often is my security blanket, & what I can cling to if what I am singing about feels way too strikingly vulnerable. Guitar propels songs forward with a sense of movement, urgency, and fluidity, almost acting as a nucleus. The music in careless was envisioned as a driving pulse, to reflect hope, confusion, and insistence. I am actually playing an electric guitar, but it is quiet and sounds pretty acoustic! I chose for these new tracks to be mostly acoustic because Steve Rizzo at Stable Sound Studios did a particularly artful job of capturing exactly, the dream-like quality that I wished to infuse into the newer songs while keeping things stripped down. That formula keeps feeling right, and so, I’ve stuck with it. 


Your main goal as an artist is to spread peace and connectivity among your fans. Can you tell us why this is important to you, and how you send this message?

The world definitely needs a deeper sense of peace, right now. There is far too much that seeks to antagonize peace.  I believe that unity is very important in potentially solving some of the biggest issues that face us, personally and politically. We are without clarity if we live within a structure that feels distorted or unpleasant to us. The political atmosphere of the past few years has really, I believe, contributed to an upheaval of collective consciousness. We now somewhat unwittingly live in a social landscape that is often fed by fear and anxiety, perpetuated by such a variety of elements. This atmosphere has assisted in implanting a tone of bitterness and uncertainty in our emotional and interpersonal worlds.

 I’ve felt this from my own experiences. The next phase of being after this has to be an era of great peace and healing, and transcending of pain; an ongoing process for every human. Maybe, we must relearn what it actually means to extend genuine peace and healing to one other.


When the effects of global uncertainty are so overwhelming, they begin to trickle into our personal experiences, and I see so many examples of this happening, nearly everywhere. It wasn't until I began noticing and reflecting on exactly what I was really experiencing, that I started making music in the right way.  Music is a beautiful form of communication when it isn’t of an overly esoteric framework, as it often is. Music happens because people need to make it. Music reaches everyone .. anyone can create music, as long as there is something genuine to express. The most satisfied that I’ve felt artisticlly (though most artists would probably be lying if they said that they were completely satisfied) was whenever I was the most honest, and the clearest.  For me, the satisfying moments of music come when you can communicate something musical to someone who has never played music, or who thought that they couldn’t. What I hope to address in making music is .. the lack of connection; the disparities; the spaces between people that needlessly divide them;  I try to explore, how to possibly erase the arrays of notions and judgments that can cloud our ability to connect. How do we explore confronting and moving outside of these paradigms, to see one another? I hope to make music that acknowledges the obvious divisions, and the absences of peace. I hope that more vulnerability can bring about more global awareness and personal awareness and that eventually, something much less fractured might exist. I hope that listeners will feel urged to close gaps, that have been placed by society, race, sexual orientation etc. in listening to music that brings us deeply close to people and their stories.  Songs help us to connect with people that we miss; those that we feel separated from. We all have stories to fill up the song space, dream space, or inner world, constructed with hope, regret, or memory. Songs are pure connection, and the more that we share them, the more we all can heal, I believe. 


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