Singer-songwriter Mike Maimone released ‘On My Way,’ the lead single from his upcoming album Guess What? I Love You, on March 7. The feel-good track holds deep personal meaning for Maimone, as it was originally written as a voicemail to his late husband, celebrated public relations expert Howard Bragman, during their long-distance relationship.
Maimone’s latest album ‘Guess What? I Love You.’
Maimone reflects on the creation of the song, recalling how he was eager to see Bragman during their courtship. “We were always hopping planes to see each other,” he says. “Just before one trip, I called him with guitar in hand and sang this little ditty that was running through my head about how excited I was to see him. He didn’t pick up, so I left it as a voicemail. He told me it was fun and catchy and encouraged me to turn it into a full song.”
The track is a key part of Maimone’s deeply personal album Guess What? I Love You, which documents his love story with Bragman and his subsequent journey through grief and healing. Tragically, Maimone held Bragman as he passed away the day after their wedding. Over the following two years, Maimone poured his emotions into the album, which tells the story of their relationship and Maimone’s path toward healing.
“Side A is about finding love, and Side B explores loss,” Maimone explains about the album’s structure.
As he worked on the album, Maimone revisited old voicemails exchanged between the couple, using them as inspiration to shape his story. The catchy hook in “On My Way” was born from one of these voice memos.
“It felt like Howard was nudging me to keep going,” Maimone says of revisiting those recordings during the creative process.
Photo: YouTube
Maimone, who grew up in Ohio, initially pursued a career in business and accounting before transitioning to music full-time. He had a brief but notable basketball career, even facing off against LeBron James. Since turning to music, his raw and emotional songwriting has garnered comparisons to renowned artists like Randy Newman, Leon Russell, Tom Waits, and Warren Zevon.
Now, as Maimone prepares to share Guess What? I Love You with the world, he sees “On My Way” as the perfect introduction to the album’s emotional journey.
“This song went from being a voicemail I had discarded to the lead single on my most emotional and profound album in two decades of music-making,” he says. “Howard saw something in it that I didn’t at the time, and now I get to share that with everyone.”
The release of “On My Way” marks the first step toward the full album’s debut, set to showcase Maimone’s deeply personal experiences of love, loss, and healing. With its mix of heart and emotion, Guess What? I Love You promises to be a heartfelt tribute to both Maimone’s late husband and his journey through grief.
