Kicking Through the Glass Ceiling: What Miley Cyrus and Taylor Swift Can Teach Us About Reaching the Next Levels of Success in Online Business

Hitting a plateau in your online business can be frustrating, but it's often a signal that growth is within reach. Think of this moment as a challenge waiting to be conquered. To break through that glass ceiling, it can be helpful to seek inspiration from successful entrepreneurs, learning from their journeys, and tailoring their insights to your unique situation. In this article I aim to share two of the most successful women of our time and how their journey to success took a turn when they did the most unexpected thing ever! Maybe this is exactly what you need in this moment too. Persistence coupled with a willingness to adapt will help you shatter that glass ceiling and ascend to new heights in your online business like the rockstar that you are.

Take a Page out of Miley Cyrus’ Book

I’m a music junkie. In part, it’s where the name “The Sparkling Hippie” comes from; my love for 60’s and 70’s rock music. But Spotify tells me that in 2023 I listened to over 78 genres and that’s apparently, like, pretty unusual and wild for the majority of Spotify listeners, which is cool I guess. Anyway, I like to really study the careers of famous artists and musicians. Two that have been particularly interesting to me lately are Miley Cyrus and Taylor Swift. I’ve made an interesting parallel between their exponential success and online business.
(>>I also previously wrote an article about The Beatles and Online Business Success. If you want to read that one, you can check it out here.) 


Looking at Miley and Taylor, they both started out as “America’s Sweetheart” type personas. Taylor was only 17 when her debut hit, “Teardrops on My Guitar” took over country music stations nationally. Similarly, Miley Cyrus was only 13 when the first episode of “Hannah Montana” was aired. It’s totally understandable that both of these artists were seen as “sweethearts” for the first few years of their careers. What's interesting to me, though, is that childhood celebrities seem to have two options. They can either stay typecast as a sweetheart and go down in history as the way we originally viewed them collectively, and reside to a quiet life of collecting royalties and doing reunion shows periodically, maybe hosting a game show here or there, OR they can shatter their persona in a shocking and transformative way so that their public perception is inherently altered, the glass ceiling is broken and they are respected as experts in their industry. With the latter, society “allows” them to transform again and again and again for the entirety of their lifetimes.


I’d love to know the deep-depths of the public relations strategy that most definitely went into the persona-shattering strategy for both of these women, but I don’t have that information so I’m purely speculating here.


Miley Cyrus took the first step in shattering her childhood persona in her 2010 album, “Can’t Be Tamed” but I don’t think the album had the persona-shattering effect the artist (or her publicist) were looking for. Personally, all I remember about this album was that MTV thought it was very wild for her to be dressed as a bird in a cage for the “Can’t Be Tamed” music video.” Not that shocking now that we know the true power of Miley…

Moving forward, it was her 2013 album “Bangerz'' and the publicity around it that shooketh the world and transformed our public perspective of Miley forever. This album gifted us the songs ``We Can’t Stop” and “Wrecking Ball” which took the album all the way to #1 on the US charts. Miley’s style, sound and performances around this album were so surprising and different for her, that the world couldn't help but stop and stare. Remember her iconic 2013 performance at the MTV Video Music Awards? Yeah, the one where she humped a tongue? Call it ridiculous or what you will, but this act of boldness was nothing short of Miley busting through her own public glass ceiling so she would have freedom to transform herself and her art again and again eternally. Most of us didn't know it at the time, but this move was literally brilliant and set her up for unparalleled success as she moves forward creating awesome things.  She’s now dropped several different albums, all with wildly different sounds.  But - she wouldn’t be able to do this successfully without first shattering the people-pleasing, everyone-loves-me persona she started with.

Are your wheels turning yet?


How Taylor Shattered Her Ceiling

Meanwhile, Taylor Swift inched into her transformation slowly over a few years, moving from a country music breakout start toward the pop princes we know and love today. Her kick in the face to her sweetheart persona came with the release of her iconic record in 2017, “reputation”, and all of the branding and imagery that went with it.  If you do a quick Google image search you’ll see a stark contrast in her image from the “1989” album to the earth-shattering “reputation” album. In 1989 she’s wearing lots of pastel colors, soft flouncy skirts and the promo is met with sweet smiles. When emerging from her transformation with the release of “reputation” you’ll notice Taylor’s style reflects her glow up. This tour and promotional images were met with lots of black structured pieces such as hoods and blazers. She has a more serious look on her face and the tone of her lyrics is that she means business. 

Taylor Swift images for Google search “1989”

Taylor Swift images for Google search “reputation”

Make no mistake, this transformation (like Miley’s) was met with tons of criticism from fans and critics alike. This wasn't the Taylor we’d always known and adored. This wasn’t the people-pleasing angel we’d grown to love. This was Taylor with a voice. She had an opinion and she was ready to share it, regardless of where the chips fall.

Despite the criticism, many would say this was her powermove that took her from a successful country artist to a global pop-culture icon. She’s now on the Forbes 400 List of Most Wealthy Women in 2023. I wrote all about that list here.


So what does all of this have to do with your spiritual online business? What does this have to do with creating a powerful online brand that resonates with people? What does this have to do with your EVOLUTION AS A SOUL??

I’m so glad you asked. 

You can’t market to everyone.

You aren't for everyone.

You as a person, can’t please everyone, can’t appeal to everyone, can’t be responsible for everyone - so why are you trying to do so in your business?


It’s literally a career-killing move to stay in people-pleasing mode.

In fact, it’s soul-sucking for you personally too.


So, who do you need to piss off? Who do you need to provactively offend in order to karate chop that glass ceiling and become who you are here to be? How can you profoundly and effectively release the *ducks* you are carrying around about what others think?

I’d be willing to bet that these *ducks* you’re carrying aren’t so much about what EVERYONE thinks. I bet they are much more about what a handful of people think. Maybe it’s your family you’re afraid to offend. Or your hometown community. Or your coworkers. Who is it for you? 


Ask Yourself:

1. How can you personally and energetically drop the emotional ties you have? I’m not saying be a bitch, but I am saying release your need to appease this person or persons. 

2. How can you create or put out something that is so vitally empowered with your TRUTH that it scares you? This something must be potentially offensive to the people you are most afraid of offending. It must be scary for you. Because the fear shows its potency and on the other side of fear is freedom.  Are you ready to claim your freedom? Are you ready to powerfully kick through that self-limiting persona you’ve been hiding behind? Why or why not???

3. How can I feel more like me? Do you love your work enough to accept the challenges that come with the path less traveled by?? How can you tune into your own rockstar energy around being boldly controversial and empowered in your work?


Pro Tip for Finding Next Level Success in Business

We often aren't taught this, but one of those big, major secrets of life is that the more unafraid you are to rock the boat and stand in your truth, the more magnetic you[‘ll be. I remember going through my 20’s in rural America, you know, the Mayberry’s of the world where everyone gets married before age 25 and those of us who don’t are well, a little weird. Like Miley and Taylor, I had always been a sort of “sweetheart” for my hometown, at least in my head I was. I held a very public position in my community from ages 22-24 and due to the nature of the job I had to schmooze every organization and business in town while also staying completely out of opinions and political campaigns. Talk about being a people pleaser! (I nailed it, by the way). As I grew older and wiser I started to realize how unhelpful it is to be liked by everyone.

All of the girls who were loud and hateful, dramatic and needy were on marriage 2 and 3. I was single. 

The people around town who demanded change and openly expressed their opinions were often scrutinized, yes, but they also got stuff done. 

Somewhere around 30, I began to realize that being true to yourself was way cooler than being everyone's hero.

This affected my business too.  If you try to serve everyone, you’ll effectively serve no one.

Your best strategy is to look to the peacock for inspiration. Flaunt your wild, weird, creative, bold and mystical self. Fan those feathers wide and strut yo ish! You are the one and only version of you, so wear it proud and loud and on display for all to see. In this way you’ll magnetize clients, customers, love and wealth and anything else you want far quicker than you will by fawning and pawning. 


How do you need to be more bold in speaking and standing in your truth?

Are there places where you are shying away or settling for less than what you truly want?

How can you set boundaries in place to bring more divine masculine structure to your dreams and desires?




Did you find this article helpful? This is one snippet from our full-length guide “How to Master The Energetics of Instagram and Online Marketing for Spiritual Business Owners: Journaling Prompts and Things to Consider for Next Level Success”


” download the PDF Journal here!

Haley HooverComment