Kathryn Cloward and Kathryn the Grape - Through the Years

Growing My Wings to Sing

How I Transformed my Pain to my Purpose

When I was a little girl, I loved writing songs and singing them for my dolls in the sanctuary of my own room.  For as long as I can remember, I’ve heard lyrics and melodies in my head at the same time. My life’s dream was to write songs and share them with others.

As the youngest child in my family and the only girl, I always yearned to be understood and “seen,” and the songs I wrote shared those needs. I have always been deeply passionate and energy sensitive, and writing songs was a way for me to express myself and be understood.

I didn’t write about riding my bike down the street to my best friend’s house. I wrote about the injustice of being sent to my room on hamburger night because I wouldn’t eat my dinner. (I didn’t like hamburgers at all.) I remember standing at the top of the stairs crying and yelling, “You only love the boys!” While my brothers teased me about this tantrum story for many years, this was a deep hurt I carried with me for a while. I poured that hurt into the songs of a misunderstood little girl.

When I started writing the stories of my life for the Kathryn the Grape series, I synthesized that struggle and the lessons learned from my journey into stories. In fact, in my second book, I share the hamburger night story as the internal struggle of my character who then goes on a journey to learn how to use the tools of a magical charm bracelet to express herself differently.

A Little Girl Dreaming of Singing

But long before grown-up me was writing stories about little-girl me, I was a little girl with big dreams! I dreamed of singing! I loved singing so much that I used anything available to me as a microphone—toothbrush, hairbrush, handcrafted cardboard toilet paper roll with balled-up paper taped to the top—and I sang all of the time.

The day I got a Mr. Microphone was the most amazing day ever! With that magical device, I could hear my voice over the radio as I sang along with the Go-Go’s, Pat Benatar, and all of my female-led band favorites. The photo above on the left is the photo I gave to my Kathryn the Grape illustrator to create illustrated me in my favorite childhood outfit with my magical microphone in hand.

When I was discerning the right example to share with young readers about what it feels like to shine their orange charm (how I teach about passion/excitement sacral chakra in my Kathryn the Grape’s Colorful Journey book), I knew that sharing the excitement I felt while singing was how I could translate that soul-shining lesson with ease.

Yet singing and the creative arts were not in my parents’ scope of awareness when I was growing up. Instead, I was guided into sports and scouting. Additionally, I always wanted to be like my three older brothers. I felt that I could do anything my brothers could do and I was not restricted from anything just because I was a girl.

Although I was naturally good at sports, I did not feel overflowing passion about any of the sports I played. Yes, I absolutely enjoyed playing soccer and softball. I made many friends through sports, friends I am still close with today.  And scouting was fun for a while especially when I would organize dance numbers and lip syncing routines for talent shows or the summers I attended horse camp in Wyoming. But the overall scouting model didn’t hold my interest.

Girls With Guitars

With the desire to be creative and express myself always surging within me, I often pursued the arts on my own. I sang in the school choir, at church, and at karaoke clubs, and I even recorded a demo tape of popular country cover songs when I was 19 and sent it off to all of the Nashville labels. I chose to work for Club Med immediately after college because I was able to sing and dance in live stage shows every night. I was one of the featured solo singers at our Club, and I loved belting out my renditions of some of Martina McBride’s and Wynonna’s hits at the time.

I bought my first guitar when I was 18 years old. I bought it at Freedom Guitars, a shop that was next door to the tattoo shop I went to a year later to get my cowboy boot tattoo (as shared below). In guitar selection, I did not care about brand or tone. I only cared about getting a shiny black guitar like Wynonna’s guitar.  I taught myself a few chords by watching a how to play guitar video that I bought from an infomercial. I taught myself how to play “Take It Easy” and “Peaceful Easy Feeling” because those songs had just a few chords that I could actually play. I was not very good but I tried. I kept that guitar for many years even though I wasn’t really playing it often. I eventually sold it in a garage sale a few years after starting my career in entrepreneurial sales and marketing.

Even though singing cover songs were fun for me throughout the years, I had a deep desire to sing my own songs. The first time I sang a few of my original songs in a coffee shop was when I was 28 years old. All of my friends came to see me and it was quite special.

Pursuing the American Dream

But something inside me held huge doubt, and a sizable amount of fear. I realized just how far I had to go from being I’m almost 30 years old career-driven Kathryn to I’m recording my own album Kathryn. My dream of singing my own songs on my own album felt too big and too out of reach for me, and my confidence in my talent started to dip really low. Any time I received a nugget of negative feedback, I stopped singing. It would devastate me. And it took everything in me to work up the courage to sing again.

Then one day, the flame of my dream went out.

I stopped singing all together.

I didn’t just stop singing in front of other people; I stopped singing around the house and in my car.

I had given up so completely on my dream that I eventually covered up my first tattoo that I had imprinted onto my back at the age of 19. The cowboy boot with a music note symbolized my dream of being a country singer but I covered it up with a blazing heart of fire, which actually looks more like a big fire blob. How symbolic!  I replaced my dream with a heart of fire but my heart was most certainly not on fire for anything that truly mattered to me…hence a blob.

So instead of pursuing my dream of singing my own songs, I set my sights on living the “American Dream.” I chose to do what I felt I was supposed to do—career/marriage/family.  I enjoyed many aspects of those years of my life, most importantly I became a mom to my crimson haired little boy. (“My crimson heart” as the lyrics in my The Healing Road). I gained tremendous wisdom in business as I continuously made risk-taking choices in my entrepreneurial career to soar to incredible heights.

Yet, all the while I felt a lacking in my own being.

While I kept proving to myself that I could and would achieve every goal I set for myself in both personal and professional endeavors, I was not even trying to fulfill the greatest desire of my life to write and sing my own album of original songs.  As I was in pursuit of everything else there were moments when that little voice inside me would remind me of who I really was and what I always wanted to do. That little voice would remind me about the joy I felt as a little girl singing in my room and the joy I felt while singing on stage at Club Med.

That little voice inside me was trying to remind me that I had a voice to share.

Just Have Fun With It

Then one night at a birthday party at a karaoke club a friend whacked me over the head with an energetic two by four. While everyone was encouraging me to sing and I was deflecting with self-deprecation, my friend said to me, “Kathryn, this isn’t American Idol. It’s karaoke. Just have fun with it.”

Just have fun with it.


It was such an aha moment for me. “Just have fun with it” was exactly what I needed to hear! I needed to be reminded that singing was fun for me. Singing and songwriting had been joyful experiences for me for many years. I needed to get back to that.

And that is exactly what I did. I chose to take off the coat of self-doubt and the overinflated expectations I carried for myself, and I decided to step into the simplicity of feeling joy again.

From that intention, I started singing again.

Slowly, the joy of singing came back to me. Slowly, lyrics and melodies started streaming through me again.

One day the clarity of purpose came to me. My dream of singing wasn’t about being known in a famous way. It had never been about fame. My dream wasn’t about being a great singer or a perfect performer of other people’s songs. My dream had always been about writing songs that mattered to me and singing them for others.  My dream was to reveal myself—make myself known—through the lyrics of my life. As a lyrical storyteller, I desired to inspire and help others through my music the same way other songwriters had inspired and helped me throughout the years.

My first step back into singing and songwriting was with the first edition of the Kathryn the Grape music CD in 2011.  I enjoyed that entire process, from collaborative songwriting to recording in the studio.  But, I chickened out at the last minute with singing lead on any of the songs. Yes, that’s right. Someone else sang lead on the first album of original songs I co-wrote and executive produced.  I did sing backing vocals…but not lead vocals.

To be transparently clear, I chickened out because I knew I wasn’t ready. I lacked confidence. Big time.

But thankfully, swallowing that pill was like kindling to help light the fire of desire in my belly to finally do what I always wanted to do!  That process helped me learn important lessons about the music business. I also gained confidence in myself as a songwriter.  That experience helped me finally do what I always wanted to do — write, record, and release my own original “Kathryn Cloward” music.

The songs I knew I wanted to share with my “adult” music were much like the stories I have been sharing through Kathryn the Grape—stories that help others awaken, heal, transform, and shine. The work I’ve done through illustrated me, and continue to do, has provided a river of clarity to navigate myself back into the flow of my soul’s purpose of being an intentional storyteller and a messenger of love.

Once my true intention was in alignment with that energy of love, the songs started pouring out of me.

The Purposeful Path

The songs started pouring out of me so much that in June 2015, I fulfilled the dream of my life! I released two albums with 22 songs that reveal the woman that I am—the woman behind the illustrated children’s character in a purple sweat suit.

Through my Free to Fly and A Soft Place to Fall albums, I made myself known in extremely transparent and vulnerable ways. The songs on my Free to Fly album reveal my journey of empowerment, transformation, love, and pain. They are the songs I lived as I grew my wings to fly free. The songs on my A Soft Place to Fall album came through me the summer of 2014 after I released myself to live the life I really wanted to live, which included opening my heart to experiencing deeper levels of vulnerability through love, hope, and healing.

As I was releasing Free to Fly and A Soft Place to Fall, I was flooded with more songs channeling through. Intuitively knowing that my unique path was to get our more messages without hesitation, I took another risk taking leap and in 2017 released two more albums, Ripple Love and Secret Keeper. I am so proud of these songs and the process of personal growth I’ve gone through to bring these stories to life. Ripple Love shares 12 songs that ripple consciousness-focused, unconditional loving messages (self-love included). Secret Keeper shares 11 songs that dive into the most vulnerable parts of my life story by revealing some big truths about my journey, and how choosing to heal and be honest with myself and others transformed my life completely.

Additionally, in December 2016 my all new Kathryn the Grape Affirmation Series of positive books and music released, with an all new Kathryn the Grape music CD with me singing lead vocals this time.

When I look at the photo of me as a young girl (above) holding my microphone, I realize that every choice I’ve ever made has led me back to me—back to the soul-shining little girl in my room who always knew that sharing my light and my heart through stories, both written and sung, was my source of joy—my dream.

But I wasn’t able to live my dream until I aligned with my purpose. And, I wasn’t aligned with my purpose until I felt the pain of my deepest wounds and healed them all. In fact, the song Secret Keeper is the story of my story. When people ask me what motivates me to keep going, it is wrapped up in the story of little girl me who was controlled and manipulated by a troubled soul. That secret I kept for decades, which was locked away in the unconscious parts of my brain, steered my life in many self-protective ways. It was through healing that I became whole and felt the freedom to shine my light and share my stories. I am motivated to help others to do the same.

Dream Living

It was in being brave enough to be transparent and exposed that I have transformed my pain into my purpose. My mission is to ripple love through stories and songs.

Now by living my purpose, I am living my dream and illuminating the most transparent expression of who I am. I am also learning and growing while in the public eye. I never felt like I had to have it all perfect before I stepped out in front of people to share my songs. I felt that I just needed to start trying—to start doing it.  And that is what I did.  That is what I am still doing!

I don’t know what the future holds, but I am wide open and receptive to continuing down my path on this joyful adventure I am on. I am going to keep writing songs and books as long as the messages continue to channel through me. I am going to keep moving forward with my intention to ripple love, compassion, and unity throughout the world.

I share all of this information not just so you can know more about who I am, but because I know there are many people with similar stories to mine. I encounter many people who are carrying around a dormant dream that they feel they can never, ever pursue.  Perhaps you, reading this at this moment, are one of those people.

I want to encourage you to try. Simply try. Step outside of what’s comfortable, harness a few nuggets of courage, and try.

Because guess what? There is no age limit in the manifestation of our greatest desires. The only limitations are the ones we set for ourselves. This is a truth that we often don’t want to admit to ourselves.

One of the greatest limitations I hear people say is that they can’t do this or that because they don’t have the money. That is just an excuse that blocks us and tethers us to fear-based thought patterns.  I can say this with integrity because I have walked the walk. I did not come from money. I was fortunate to have been raised by parents who taught me that I was basically entitled to nothing and if I wanted something, I had to work to earn it. Period.

I paid my own way through college by waiting tables. I have only had a salary — guaranteed income — for one year of my 17+ year career. I started my first company with some money I had earned and saved, and I cold-called my way to building a business one day at a time. (And when that company folded as a result of the recession of 2007-2009, I had to start all over again from ground zero!)

Choosing this entrepreneurial path for myself also meant that I didn’t have maternity leave when my son was born. I delivered my son on a Thursday night, on Thanksgiving, and was sitting at my desk in my home office on Monday morning working. I did whatever I had to do. I independently produce and publish my Kathryn the Grape series and all of my music Kathryn Cloward CDs. I don’t have a magic money tree…although that would be helpful. I simply make conscious choices and calculated risks to do what matters most to me every single day and I’ve released the grip of soceity’s definition of “success” and chose to live my version of personal success.

And yes, there have been some real pivotal moments when I was unclear about how I would come up with the money to do a major project but I trusted Spirit and the guidance of my Angels and I was led to solutions.  Trust is always key for me.

Manifest Destiny

I am now ready to elevate myself to the next level of awareness and manifestation. I trust the vision I was gifted with almost a decade ago will fully manifest. I trust my music will open hearts and heal souls. I trust Kathryn the Grape become a household name internationally to help people of all ages shine their unique colorful light. I trust the process. Manifest destiny!

As you may gather, nothing has happened for me easily or overnight. I’ve persevered through decades of diligent work. I have fallen more times that you can possibly imagine. I have come to countless forks in the road and had to make courageous decisions. I have encountered people on my path who have tried to shroud my light. I have had to stand up for myself and what is rightfully and legally mine many times. I have been betrayed multiple times. I have been misunderstood. I have been the target of toxicity.

But I keep going.

I keep going because I know there are way more people rooting for me, loving me, believing in me, and most importantly, needing me to continue to be a clear conduit for receiving and sharing Universal messages of love, hope, and healing on this planet.

I keep going because the feeling of joyful fulfillment that I now live each and every day is something no one can ever take away from me…and that joy ripples to others who are seeking to live more fulfilling lives.

It has not been an easy path, and I am thankful for that.

If I can do, so can you! You are capable. I encourage you to have the courage to try. I encourage you to awaken to your true path and allow your passion to create ripples of love and encouragement to others, too. Believe in yourself. Trust the process. Simply try.


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