Ashley Orlando | Vocalist, Ukulele Artist & Joyologist

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Real-World & Messy - Living, Learning & Loving Life

A Dash of Courage

8/8/2025

 
Two-ish years ago, I bought a beautiful red tulle dress for a "big gig" (as a soloist with the symphony)!

The dress was a tad too large in places, but it was also unlike anything I had ever worn before and made me feel bolder just looking at myself in the dressing room mirror.

"Woah!" I remember thinking when I first tried it on.

"Maybe it can be easily altered."

I felt enchanted enough by the uniqueness of the dress to at least take a chance and paid $40 to bring it home.

In the days that followed, my mom and I tried to "fix" the dress with our minimal sewing skills, but it wasn't working out quite like I hoped. In that state, I did not feel comfortable wearing the dress to sing in front of a symphony and 1,800 spectators.

Disheartened, I hung the dress up in my closet, and there it stayed...HAUNTING ME.


Until last Saturday night.

Two+ years later...

When I could finally zip up the dress again (FUN SIDENOTE: I learned a couple days before that aforementioned symphony concert that I was pregnant with my son, so technically, it was his "onstage debut" :P).

And I dared to TRY AGAIN.

This time I was fully committed to the dress and called in the professionals at a bridal shop around the corner from my house. The lovely ladies there didn't know me from Adam, but they immediately took me under their wing like my fairy grandmothers and worked their magic so that that night I could FINALLY (AND COMFORTABLY) muster up my courage to wear "the dress" for a "big gig"--this time with a "big band!"

And I'm so glad I did :D

As my 1-year-old's books remind me every night before bed: "When things don't work out like you hoped the first time around, don't give up too easily. Trust your gut and try again!"

With gratitude,

Ashley
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    Ashley Orlando is a jazz vocalist/ukulele artist and joyologist on a mission to help 1 million women find their voice through music, inspiring stories, and communication skills.

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