By Cheryl Gottlieb Boxer 
My 17-year-old daughter and I have spent every weekend for the past month shopping for a dress for her high school junior prom. She is, at heart, a sweatshirts and jeans sort of young woman. So, as you can imagine, these forays into every local store and nearby mall have not been the highlight of her week.
Every weekend she has doggedly tried on dresses in varying shades of blue or grey or beige, some with spaghetti straps, or no straps, or thin pieces of fabric barely covering one shoulder. Some of these dresses are form-fitting, some are billowing, and they all seem to have a million cutouts. None have been perfect.
Then last weekend she pulled one dress from the rack that was completely different from every garment she had considered thus far. A dazzling off-the-shoulder dress with a sheath silhouette, short sleeves, and a brightly colored floral print. The dress was hectic and full of color. She was uncertain. I loved it right away.
And even once she pulled that dress on it did not disappoint. It fit perfectly. The cut was flattering and complimentary to her body. The sunny blooms practically popped from their smoky background. She turned in front of the mirror, carefully considering the dress from every angle. I truly believed she was as enthralled as I was.
Then all at once I noticed her shoulders started to slouch a bit, her eyes darkened, she turned away from the mirror, and with a pensive look she said, “I just don’t think I’m bold enough for this dress.”
Those words floored me. That my free-thinking, outspoken, reptile-loving feminist of a daughter could be bested by a dress shocked me. I quickly formulated in my mind the words I would say to make her see what I saw:
You are a brilliant, beautiful, and BOLD young woman who should feel confident in anything and everything you wear.
It’s OK to step out of your comfort zone, to be different, to try new things.
Don’t worry about what others will think and don’t let anyone else dampen your spirit.
Embrace yourself, love yourself, and live this special moment to the fullest.
But then I just as quickly reconsidered my words.
When our children are young we pour our heart and soul into equipping them with enough confidence to not only survive, but thrive. Brick by loving brick we lay down a foundation of self-love, resilience, and pride that we hope will bolster them throughout their lives. We try to instill independence, a sense of adventure, and no small amount of grit in the hopes they will weather the storms they are sure to face.
And I realized in that moment these lessons were not lost on my daughter.
Her assertion that she was not bold enough for that dress was not self-criticism. In reality, my daughter was practicing self-compassion. She chose to be gentle with herself, to be mindful, to recognize instinctively, and without judgement, that this dress was not right for HER.
It is courageous to be this honest with oneself, this self-aware. It takes strength to acknowledge how you REALLY feel, rather than how you think you SHOULD feel, or look, or be. My daughter is boldly advocating for her own feelings, and defining her own values.
This was always the goal. This was always how I wanted her to experience life. It is the epitome of bold.
To me, she is the very definition of the word.
Originally published on the author’s blog
You may also like:
Dear Daughter, Do Not Be Perfect
Dear Daughter, Remember Who You Belong To
by Deanna Ryan 
by Cat Borg 
by Charissa Bates 
by Chelsea Drown 
by Kristin Johnson 
by Abby McDonald 
by Aimee C. Trafton 
by Jennifer White 
by Ashley Radzat 
by Melissa Steis 
