Chloe Charles could have made one of the most spirit-crushing albums in recent years, for which she would be totally forgiven. But she didn’t, and With Blindfolds On is a testament to her irrepressible musical spirit.

In the space of a year, the Toronto- and Berlin-based singer lost several family members, tragedies she touches upon in the song “Through Your Eyes.”

“Through Your Eyes” was written to “work through the strange and confusing feelings of loss, and also for my family,” says Charles. “Each verse is for a specific family member, written from the perspective that when you lose someone, you not only lose them but you lose a piece of yourself, as nobody will ever see you through those same eyes. Every time I sing this song, I’m thinking of my family members. I’m taken back to them, often hear their voice, their laughter. At times it’s very trying, but for the most part, I feel closer to them when I sing it.”

In addition to dealing with those losses, the bi-racial Charles seems to also be dealing with the subtle racism she sometimes finds in the music industry, and marketing types who don’t know what to do with her. These experiences manifest themselves in several of the album’s songs.

“People misjudge me based on the colour of my skin and attempt to box me into [only] jazz, or soul, or R&B, even before ever hearing a note,” she says. “However, I just make music which doesn’t have a race, and shouldn’t. As well, I’ve been urged many times to create music with a different sound, something more cohesive, something more ‘radio,’ something easier to market.”

“I want people to feel more than just entertained after my concert. I want them to remember those feelings and roll through them alongside me.”

Charles shared an excuse she hears often – “Your music is amazing, but we don’t know how to market it” – and calls it ridiculous, “because if you’re good at marketing you should be able to find a creative way to market anything that you deem good.”

Despite these trials, Charles has achieved considerable critical acclaim. She launched the self-produced With Blindfolds On, her sophomore album, with two sold-out shows at hip Toronto club The Burdock in late May of 2016. Publicity for the launch included a national-television performance on one of the last episodes of CTV’s Canada AM, and coverage in NOW magazine. Her critically acclaimed 2013 debut album Break the Balance received major accolades from Billboard magazine, the German edition of Rolling Stone, Mojo, The London Times and Elle magazine. Charles has toured Europe extensively, and has also won a 2014 Sirius/XM Indie Award and Harbourfront Centre’s Soundclash Award.

She feels artists are more stylistically promiscuous than ever before and says “music needs creative people around it who appreciate discovery, experimentation and risk-taking rather than approaching music and artists as a commodity.” She isn’t fazed by narrow-mindedness and lives by her philosophy that music should be “creative, fearless and push boundaries.” So it’s no surprise that With Blindfolds On sees Charles brilliantly straddling pop, folk, electronica, chamber pop and R&B, appealing to those whose tastes don’t fall into one specific music genre.

Her smoky, versatile and powerfully captivating voice and deeply felt, honest songwriting continue to be the stars of her records. Nowhere is this more evident than on the album’s lead track, “Black and White,” which won the 2014 John Lennon Songwriting Contest in the Pop Category. Co-written with her friend and fellow SOCAN member, singer-songwriter Steve Fernandez, “Black and White” was composed a year after her father passed away. Hearing her describe the creative process behind it is heartbreaking.

“I was still struggling with feelings of hurt, anger and abandonment,” says Charles. “We had a deep talk, and I explained the story of my relationship with my father to Steve. I ended up expressing things I hadn’t had the courage to say to my father while he was alive. Steve just began writing down pieces of what I was saying, and from those snippets we developed this song.”

Charles says she tries to write songs that “have some sort of emotional pull on me, that are based on true experience, so that I’m better able to share that sentiment with the audience,” she says. “I want people to feel more than just entertained after my concert. I want them to remember those feelings and roll through them alongside me.”