The Working it Out Podcast
Desi Oakley

The Power of Staying Ready with Desi Oakley

Desi Oakley is a singer and actress known for her work in musical theatre. She has traveled the world performing in shows like Waitress, Chicago, and Wicked, but her talent and opportunities were not developed overnight. Rather than being a child prodigy, Desi brought with her a passion, fire, and drive to work and expand her skills. It was that early passion that landed her pivotal roles in musical theatre and that has driven her to mentor young performers that are just making their way.

Listen as she shares more about her life and career and why her positive experiences have made it possible to reach back and help pull others up. After you listen, will you message me on social and let me know your thoughts? Use the hashtag #workingitoutwithJV so I know you’re part of my podcast community!

[00:38] How We Met Desi

After Jessy went to school at Marymount Manhattan College she signed up for a workshop that was Pop Rock Broadway and met Desi. Since then our relationship and friendship has simply grown and become deeper. 

[03:31] Her Early Life and Career

Desi grew up in Kansas and fell into theatre very early in life. She’s played roles like Gabriella in High School Musical and Dorothy in The Wizard of Oz, and she credits those roles for shaping her future career and her desire to mentor the next generation as well.


[07:57] Piano and Her Entrance Into Musical Theatre

Her grandmother purchased one year of piano lessons and it was something that drove her curiosity and passion for musical composition. She says she was never a child prodigy, but she wanted to work and her drive, passion, and personality made others want to work with her. 

[13:43] How Her Career Changed at 16

She had started writing her own music after 13 years of playing piano, but knew that she couldn’t do it all. She sat her family down and let them know that if she was offered the role of Dorothy, then she’d pursue musical theatre. If not, then she was going to pursue music. 

[16:23] Musical Theatre Must-Knows 

After making the pivotal decision to continue to pursue her career in musical theatre, Desi was accepted to the University of Michigan, one of the top schools for the industry. Listen as she shares how those experiences helped develop her talent and generate opportunities post-graduation.

[26:09] Just Get in the Room

Stop telling yourself that you don’t have a place in the community or room that you’re looking to join. Get in the room, learn from the people doing the work, and then implement. 

[27:54] Her Role in Wicked and Beyond

She was the swing and understudied every female role in the production which led to her continually being called back for various iterations of the show. She stayed ready and open to the opportunities she was provided. Her story about being called into Annie and was further affirmed by Jane Lynch. 

[40:47] How One Phone Call Changed Her Life

In between shows she would nanny and teach kids about musical theatre and one day she got a call asking her to do Waitress in London. Within 9hrs of that phone call she was in London and making her West End debut a day later. It had been 7 months since she had physically played the role. 

[47:57] The Power of Staying Ready

At this point in her career she knew exactly what she needed to be able to step back into this role. Reading through the script was like reading another language. Instead she needed to step into the room with the cast and to make connections. 

[55:46] Her Covid Experience and Pivot

Covid has allowed her to expand on her teaching endeavors and to pursue some of the things she’s always wanted to do. Being able to connect with and walk with young people, wherever they are, has been extremely rewarding. She’s looking forward to seeing their careers evolve and grow.

[01:00:50] Desi Wants You to Know…

Stay open and stay positive. Know that having bad days is fine and being open and honest is beautiful, but lean on the positive and practice gratitude. 

[01:01:51] Get to Know Desi

Listen as she shares her favorite books, movies, and where she plans to travel when the world opens up again. 

Links and Resources: 

Untamed by Glennon Doyle
Becoming by Michelle Obama
Reese’s Book Club

Connect with Desi: 

Desi’s Website
Pop Rock Broadway
Desi on Instagram

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