Last year, singer-songwriter Jaymay returned to the Bayport street she grew up on and found herself walking down to the beach. Once there, she etched four “T”s into the sand and instantly found the cover of her second album, 2016’s To Tell the Truth. She references the sentiment, as well as the street and the beach, on “Cassie’s Song,” a stark, vulnerable elegy to her developmentally disabled sister who passed away in 2013 at the age of 26.
“It was very nostalgic and I really had to dig deep into myself for these songs,” said Jaymay, whose real name is Jamie Seerman. “I was revisiting a lot of things.”
She admits that her sister’s death didn’t come as a complete shock. Still, it couldn’t have come at a worse time. Only a few months earlier, Jaymay had been diagnosed with Crohn’s Disease, an extremely painful and debilitating bowel disease. “It was a very surreal experience,” she recalled. “It took me about a year of basically living at home while my mom fed me. Then my sister passed away and it was very dramatic. It was just hard times. It seemed like everything kept compounding.”
Luckily for fans, these hard times didn’t break Jaymay’s spirit. She began working on new songs and though quite a bit of time had passed since her 2007 major label debut Autumn Fallin’, she began rapidly releasing EPs of new music and launched a successful PledgeMusic crowdfunding campaign for the release of To Tell the Truth. Although it would have been understandable if Jaymay had quit music altogether she said, “I do this full time. I’ve never had another job—except for two months in Yonkers at a pizza restaurant. That was my first job and I was late the first day because I was at an open-mic the night before.” The thought of leaving her music behind never even crossed her mind.
Actually, Jaymay always gravitated toward music. As a kid, she spent time trying to play Billy Joel songs on the family piano. She took a few lessons and penned songs about the family dog, but didn’t take an immediate liking to the instrument. It was the violin, which she began playing in the third grade, where Jaymay started to truly find her voice.
“I learned by playing songs by ear. I would basically harmonize any song, but mostly The Beatles. I just taught myself to sing and that was my musical education.”
Once Jaymay finished high school, she bounced around to four different colleges before eventually landing in New York City. She remembers writing songs and learning guitar, but rarely performing them for people. She worked up enough courage to attend an open-mic and, at age 23, began playing regularly at the Sidewalk Cafe’s open-mic night before landing a residency at The Living Room, the legendary Lower East Side acoustic venue (now in Williamsburg). This helped Jaymay score a record deal with Blue Note Records and she released Autumn Fallin’ in 2007. She looks back at the major label experience with mixed feelings.
“I was never very eager to sign, but I really liked Blue Note,” Jaymay said. “I was not signed for very long. After a year, I was dropped and I didn’t even know it. It was very silly actually, but it was also an experience. I don’t regret it at all.”
Given all that she’s been through since the release of Autumn Fallin’, it’s a wonder To Tell the Truth doesn’t come across more jaded. Instead, it’s a beautiful and binary record of heartbreaking songs that also uplifts the listener: the closing of a chapter, but the beginning of a new one. Songs like “I Just Got Over You” and “I Was Only Lovin’ You” work as relatable break-up anthems, yet they’re rooted in reflective empowerment, not bitterness.
Above all, To Tell the Truth is about being honest with oneself and moving on. “I wrote these songs a while ago and I’m already writing new ones,” she said. Some of those new songs appeared on her Christmas album, Falling Like Snow, released in December. “I’m ready to let this go. This is kind of a goodbye to everything. The story on this album needs to be told and I don’t think people realized what I went through. I’d like to share that and then walk away from this experience and have a new one.” Jaymay has taken her past hardships and channeled them into a startlingly tender piece of art that will satisfy both old fans and new.