By the time you’re reading this, you probably know who Chappell Roan is.
Her rise seemed so fast – Jimmy Fallon had to Google her before she performed on his show.
She went from 2 million downloads on Spotify to 200 million and has not one but three songs on Billboard’s Top 100.
Less than a year ago, she didn’t make enough money to pay her rent.
If you haven’t heard of “Good Luck, Babe!,” take a moment to listen here.
The path to success is a bitch and Chappell’s rise wasn’t instant.
Her path was full of staccatos – crazy challenges and tantalizing triumphs.
Her story offers amazing lessons in resilience and branding for entrepreneurs.
“Everybody said if you haven’t made it by now, maybe it’s time to give up.” – Chappell Roan, “Pink Pony Club”
Chappell Roan’s Story: Raw Resilience
Chappell Roan, born Kayleigh Rose Amstutz, grew up in a trailer park in Missouri. Despite a tough beginning, she started singing at age 13 and signed a record deal when in high school.
She left Missouri for Los Angeles and then got dropped by her label.
Out of money, she took on various jobs, from working at a donut shop, production assistant to nanny, and even worked at a drive-through when she had to eventually move back home to Missouri.
She stayed with it, reunited with her producer which eventually led her to share the stage with stars like Olivia Rodrigo.
“We’ll chase the stars, no matter how far.” – Chappell Roan, “Runaway”
The 10,000-Hour Rule
Chappell’s story shows you need to put in the work.
According to psychologist Anders Ericsson’s study, it takes around 10,000 hours of practice to achieve mastery in a field.
Chappell’s “overnight success” was actually a more than decade-long process, involving countless hours of honing her craft, performing, and pushing through setbacks.
In her song “California,” she captures the essence of this struggle:
“Cause I was never told that I wasn’t gonna get the things I want the most.
But people always say, ‘If it hasn’t happened yet, then maybe you should go.’
Come get me out of California.”
Branding and Success: Discover Who You Are
Building a strong brand, like achieving personal success, is a marathon, not a sprint. Here’s how Chappell’s journey can guide your branding:
1. Discovery is Key
Chappell discovered drag culture in a place called The Abbey in West Hollywood and once she discovered her true style – drag – she stayed true to it.
Her music also made an immediate left and the rest is history.
She wrote a song about it. Listen to “Pink Pony Club” here.
Discover who you are and make sure your brand consistently reflects who you are.
“I believe in the magic of what we can create.” – Chappell Roan, “Love Me Anyway”
2. Be Real.
Chappell connects with her audience on TikTok, where she shares her makeup, dances, and previews of her new music. Her direct and personal approach shines through, creating an authentic connection with her followers.
For instance, when she wrote “Pink Pony Club” in 2021, she immediately shared a video about it on TikTok. This raw and unfiltered style has not only built her brand but also created a genuine following that continues to support her.
“Hold on to your dreams, don’t let them fade away.” – Chappell Roan, “Fantasy”
2. Embrace Authenticity
Chappell’s persona comes out through in her music and story. Let your brand’s unique voice and story be heard. Share the human side of your brand to connect with your audience on a deeper level.
“I want to live in a world where we don’t have to hide.” – Chappell Roan, “Casual”
3. Flex and Be Flexible
Chappell adapted to her circumstances, trying on various musical styles before finding her breakthrough drag and dramatic persona. Be open to changing your brand in response to the market. Be open to criticism and feedback!
Try new things and when your audience responds positively – double down on your offerings.
“We’ll fight till the end, this is where we begin.” – Chappell Roan, “School Nights”
4. Put in the Time
Just as Chappell put in over 10,000 hours, you need time to perfect your brand’s products or services.
Stay committed to being your best! Be excellent. Be exceptional.
“Through the fire and the rain, we will rise again.” – Chappell Roan, “Phoenix”
Chappell Roan’s story is a reminder that success is rarely an overnight phenomenon. It’s a journey of persistence, learning, and growth.
Take a moment to listen to Chappell Roan’s latest album and draw inspiration from her music and journey.
Remember, every step you take brings you closer to your dreams.
Wishing you all the luck in the world!
Kalika Yap

