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Tip Jar: Staying True To Yourself While Navigating Non-Stop Career Twists And Turns

By DeeAnn

My journey as a singer/songwriter and recording artist is a bit unconventional because changing life circumstances led me to perform in various genres at different times over the years before I found my current creatively fulfilling niche, which incorporates the jazz sensibilities of my family’s roots into a soulful R&B/pop sound. 

I found singing in the choir growing up in the Catholic church boring, but the experience taught me a lot about working with vocal harmonies that would come in handy later in my career. My dad Frank DiMeo, a popular jazz singer in the Buffalo area, was my first musical mentor, while my mom turned me on to Barbra Streisand. Music was an essential foundational part of growing up in my family. I was always in the school choir and took as many music classes as I could. Helping form a 16-piece swing group in high school, in which we sang everything from ‘60s to Broadway music, got me even more hooked and allowed me to sing my first solo song. I learned more about blending harmonies through a quartet I created as an offshoot. I had been writing music from the time I was 15 or 16 and when I started recording music in my 20s, I arranged a lot of my own harmonies. 

Dreaming of becoming a professional singer came naturally to me in my teens and I was hoping to apply to several music colleges, hoping even that I would be accepted at Julliard, but my parents’ separation and then divorce at that time made attending college out of the question. My dad was this 100 percent jazz guy, but when I started looking for opportunities to make a living in music, the greatest opportunities were in Top 40 cover bands. I was good at it and I could adapt to multiple styles in what was considered pop music - but doing it for a long time stripped me away from how I envisioned myself as an artist. 

One of the musicians I worked with suggested I try singing country music, and I absolutely didn’t want to—until I realized just how great female artists like Trisha Yearwood, Shania Twain, and Martina McBride were. I started out only wanting to sing a few country songs per set, then got better at it and I envisioned a potential road for me in the genre. I started singing the National Anthem at county fairs throughout New York state, and the Erie County Fair hired me to open for country legend George Jones. I took it seriously enough to record some music (I didn’t write) in Nashville, and to this day some of the country I recorded plays in other countries throughout the world. Despite the diversity, every step took me one step closer to figuring out my musical identity.  

I’ve always admired women who can balance busy musical careers with family life, but when my husband and I decided to have children, raising them became my focus and I stepped away for a while. When the bug hit me again, as my son and daughter got a little older, I started teaching music at a Catholic school and even became a popular funeral singer. I seriously missed the stage, the lights, communicating with audiences and the passion I put into performing. 

For my soul to survive, I knew I had to make some changes. Here’s where the so-called “branding of DeeAnn” gets even tricker. I felt these deeper life experiences gave me a desire to sing something deeper and more soulful—and that led me to sing the blues! But I quickly realized that I couldn’t sing the blues all night long, so I fell into jazz, which of course made my dad very happy! I incorporate those jazz experiences, including my ability to scat into some of the R&B/pop music I make today.   

One of the biggest problems in not being true to myself was that I didn’t believe I could be a songwriter, even though my musical journey started out that way as a teenager. Meeting my first producer RiShon Odel, who has worked a lot with renowned smooth jazz artists Najee and Brian Culbertson, made a huge difference in getting me back in touch with this side of my artistry. Just as my confidence was at a low ebb, I sent RiShon the melody and lyrics of a song I had just written, and he created an incredible arrangement that developed into “Stay Here with Me,” which is to this day my all-time favorite original song I have released. He put so much soul into it. It was originally released on my 2019 live EP Stay Here and I released it as a single in 2024. I titled my debut album Desperately Seeking DeeAnn, first as a nod to the Madonna movie Desperately Seeking Susan but mostly because it captured the struggle of trying to find myself as an artist—and finally reconnecting with the vision I had for my life and career when I was younger before I joined all those cover bands. RiShon also produced my second album, It’s My Time

RiShon helped me believe in myself as a songwriter again and he brought my songs to life with some really dope musicians from his band Fifth Element who gave everything an R&B/gospel feel. The painful loss of my son William to a motorcycle accident has been a driving force for my artistry both spiritually and creatively because I sing much deeper and more soulfully and authentically, with so much emotion emerging from a place of pain. The albums I recorded with RiShon helped me lock in on who I am as an artist and taught me the value of not playing it safe. I bring the same blend of visceral emotion and freewheeling adventure to the three recent singles I recorded with my current producer Ted Perlman that re-imagine three of my favorite songs, Al Green’s “Simply Beautiful,” Sade’s “Kiss of Life,” and Brenda Russell’s “Piano on the Dark.” I feel like those songs, and the originals Ted and I are working on for my upcoming full length album, are authentically me. It’s been a long process, but I finally got here—and so can you! 

TIP No. 1: Always stay true to yourself, be honest and follow your gut because you might have different people trying to pull you in various directions based on what they think they know about you. No matter what you may be doing to make a living in the music industry, if you have solid ideas in your head about who you are as an artist, be consistent and stay real as you develop your authentic style. Trust in who you are because audiences relate to you best when you’re authentic and honest. They can tell when you’re faking it or just going through the motions.

TIP No. 2: Use social media to share what drives and inspires you as an artist to connect in a deeper way with fans. Take them behind the scenes into your process and things that have happened in your life that give you stories to tell in your songs. Your fans may not want to be saddened by your pain all the time, but they do want to know what makes you create your music. It’s also an opportunity to share other meaningful endeavors in your life. For me, that would include sharing the $84,000 I have raised for a scholarship at my son William’s alma mater, Canisius High in Buffalo, to fund national and international mission trips for male students.   

TIP No. 3: Finding the right producers and collaborators to work with is essential in helping you discover who you are. RiShon Odel and Ted Perlman have believed in me and my talent even when I haven’t. They bring their own experiences working with great artists into their work with me and I benefit not only from their musical brilliance but their life wisdom, which has helped take my own artistry to the next level.  

Building off the success of her sultry breakthrough track “Stay Here With Me,” DeeAnn’s 2025 got off to an inspiring start with numerous accolades in the 10th Annual JazzBuffalo Poll honoring musical greats in her beloved hometown. She was awarded Jazz Female Vocalist of the Year, received the most votes for the still very popular It’s My Time and was chosen runner up for the Most Memorable Performance and the John Hunt Jazz Artist of the Year Award. This extends a run of honors that began in her early days as a pop/rock singer, when she won Best Female Vocalist at the Buffalo Music Awards two years in a row.