Meet Debbie Cunningham

We were lucky to catch up with Debbie Cunningham recently and have shared our conversation below.

Hi Debbie, thank you so much for opening up with us about some important, but sometimes personal topics. One that really matters to us is overcoming Imposter Syndrome because we’ve seen how so many people are held back in life because of this and so we’d really appreciate hearing about how you overcame Imposter Syndrome.

I was turning 40, when I decided I wanted to realize my dream to become a professional jazz singer. I had put my music aspirations on pause to be a stay at home mom and raise my kids. That year, my kids were 6 and 9 years of age, and I couldn’t shake the feeling that at the end of my life, I would regret not giving myself a chance to accomplish those dreams. I think imposter syndrome often seeks to stop us, even before we start. We have a big dream or goal we want to accomplish but self doubt jumps in to tell us all the reasons why we can’t do it. What if I’m not good enough? What if I fail? What if I’m too old now? The truth is, these swirled in my head before I took the risk. Even so, I made a decision to pursue it, I assessed what it was going to take, made a plan and executed the plan. I created a process to walk myself through the steps of achieving my initial goal and then I just took one step at a time until I realized the dream.

But it all started with giving myself permission. I gave myself permission to try and to possibly fail. My husband and I talked about my fears and fleshed out, what’s the worst that can happen if I fail? I lose some money set aside to be invested in the dream? I lose time invested in the dream? Not really. I reminded myself that even if I failed, it would be a part of the process of learning and moving me to the next step in the journey. Life is a process. So is accomplishing your dreams.
The interesting thing is, I didn’t fail. I actually became a jazz recording artist, recorded two albums (which are still available on streaming platforms), and even wrote and produced my second album. That album then led me to write and publish a book! So I became a jazz recording artist, an author, a speaker, and now a podcast host—all because I gave myself permission, and all after the age of 40.

That doesn’t mean imposter syndrome disappeared. It kept whispering that I didn’t belong because a record label didn’t choose me. But I chose me and made it happen. But here’s the thing, there are no “music police” coming to haul me away. Just like there are no “dream police” coming to stop you because you’ve overstepped some invisible boundary. Who told me I was too old or wasn’t allowed to pursue a dream? Society and our culture? And who told you? Those are whispers in the wind. They only have power over us if we listen to them. So, I stopped listening. I realized I was the only one telling myself I wasn’t permitted to try. That’s actually how I overcame imposter syndrome – by giving myself permission to try and possibly fail. If I failed, I’d at least have given it my best effort, learned something and moved forward, instead of living my life plagued by what ifs. Even if the results turn out differently than you expect, and they often do, isn’t it worth giving your dream a chance?

Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?

Since I was a child I knew I wanted to be a professional singer. Music was the thing that carried me through all those growing up years. I didn’t start with Jazz though. I grew up singing in church and school choirs then studied at Temple University in Philadelphia and received a BA Music in Classical Voice. I had a good friend who was a jazz pianist there who kept telling me I should be in the jazz program! I thought he was crazy. It was quite a moment, 20 years later, when I called him to produce my first Jazz album. That was a fun reunion!
As a professional singer, I love entertaining a crowd and giving them moments to be moved by the music—to laugh, to feel, to connect. Music isn’t just sound, it’s communication to the very soul of another human being. I think my favorite part has been that connection with the listener. When someone is moved to tears as I sing a song or the audience is so silent you can hear a pin drop, those are the moments we share. It’s amazing. My fans were also the catalyst that helped me have the courage to record my own music. I would occasionally sing a song I had written mixed in with my jazz standards and they started emailing me and asking me why I wasn’t recording those songs?

When I wrote and released A Million Kisses, I held my breath. It is a jazz inspired album about the journey of lasting love, the ups, downs and celebration of it all. I didn’t know how they would respond. It was astounding to me that not only did they love it but they resonated with the lyrics. So much so that many of them reached out and told me I should write a book on the same subject. I thought they were crazy! I had no idea how to write a book. But with their encouragement, the support of my husband and a few close friends, I gave myself permission to try, yet again, knowing full well, it could fail.

That book, Dancing in the Kitchen, shares its title with a lyric from the album’s title track:
“I want a Million Kisses Kind of Love,
the kind that dances in the Kitchen
when skies are turning gray,
The kind that holds you oh, so tight,
when the blues just won’t go away”

It was a risk but one that has proved well worth taking. You can find Dancing in the Kitchen anywhere books are sold online.

That album covers a relationship from falling in love, to dealing with and moving through trials in life, to celebrating all we’ve come through and how we are in it for the long haul. Even an Anniversary song for celebrations. It was very much a reflection of my own journey as my husband and I have been married over 37 years. There is nothing like being in the studio and hearing your ideas, lyrics and melodies come to life with a band. Definitely part of my journey that I will never forget. But for my fans to embrace it with applause, was mind blowing. And just think, none of it would have been possible if I had never given myself permission.

As a vocalist, I also love lending my voice to a variety of endeavors. I’ve sung background vocals on multiple music projects & albums, sung for ballets, with symphonies, recorded voiceover, an audio book and have continued writing new music as well. When my fans encouraged me to write that book, at first I thought, no way! But I’ve learned to keep stretching my goals and dreams, no matter my age.

After the pandemic, I did a little soul-searching about what I wanted to do in this next season of life. I’m still singing jazz when given the opportunity but I would love to do more symphony and voiceover work in the future. I’m writing a new book and I’ve launched a podcast for midlife women called Midlife Crescendo, to encourage women to be intentional in their aspirations even in midlife. Additionally, I’ve developed a course to help women pursue their dreams and overcome imposter syndrome—just as I did. That is an exciting addition to my life, allowing me to pour into others now that I’m approaching 60. As you can tell, I’m not someone who plans on retiring but just re-firing for this next season!

Our dreams don’t stop because we are aging, they just evolve. I even wrote a song called FLY, about believing in your dreams and the part failure plays in the journey. However, we must remain intentional or nothing will get accomplished. One of my favorite quotes is “untended fires soon die and become just a pile of ashes.” Dreams will do the same.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

First, I think pursuing excellence in whatever you do is important because excellence will be the foundation when opportunity comes. I pursued practicing my craft of music & voice even through my stay at home parent years. If you stay true to what you do best and stay true to your values, and keep pursuing what you love, success will come.

2nd, Give yourself Permission to try. As a perfectionist, fear of failure is really hard for me. I want to find the perfect way first, so I don’t fail. However, once you realize it’s okay to fail and that failing is actually a part of the process, it’s easier to succeed because fear of failure will keep you from starting. When I wrote my book, I had to go through 5 rewrites to get it right! I seldom get a song lyric right on the first try. It’s through the continued pursuit that excellence emerges. I know it sounds crazy but often failure has the ability to get you on the right path to success but you have to give yourself permission to try first.

Third, Have a supportive community around you. Being an entrepreneur or going after your dreams is a lonely pursuit. It takes tenacity and perseverance especially when things don’t work out exactly as you planned. You have to have people in your corner, cheering you on, that can encourage you when the gong gets rough! My husband, family and a few close friends, were definitely in my corner and it sustained me when the journey was hard. As a parent, I didn’t want to neglect managing family life while pursuing music. It ends up pursuing my dreams midlife inspired my husband and children for their own dreams. Their support when I started performing ticketed shows was invaluable, since as an independent artist I wore all the hats. They even performed with me at several of my shows and that was always a fan favorite.

Okay, so before we go we always love to ask if you are looking for folks to partner or collaborate with?

Professionally, I’d love to collaborate with musicians and composers in need of vocalists for their projects, symphonies seeking guest vocalists, and individuals looking for voiceover artists for their books or commercials.

Connecting with women looking for mentorship and a supportive community as they pursue and launch their own dreams is also a great joy for me.

To connect with me or to learn more about my music, book, podcast or course please go to my website- https://debbiecunningham.net
or soundcloud- https://soundcloud.com/debbie-cunningham-music/tracks

Contact Info:

Image Credits

Deanna Carter

album Cover, Kristy Belcher

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