A Mastermind in Strategy
- Jennifer Crago
- Aug 14
- 4 min read
Updated: Nov 7
Yesterday, Taylor Swift’s soft launch of the Life of a Showgirl era stirred deep emotions in me (I admit it, I’m a Swiftie). But that feeling was short-lived. Within ten minutes, I felt something else: guilt.
What have I accomplished since December 2024, when her record-breaking Eras Tour ended?
Before long, the lyrics from Mastermind, the 13th track on her 2022 Midnights album, started playing in my mind:
“If you fail to plan, you plan to fail. Strategy sets the seed for detail...”
Taylor Swift has complete control of her narrative, both creatively and commercially. On May 30, she reached a significant milestone by securing full ownership of her music catalogue, from songwriting to production. This marked the end of a long and public battle for creative control. It also serves as a powerful lesson in accountability and vision.
Taylor doesn’t just work hard; she works strategically, with purpose, precision, and extraordinary clarity. Her career is a case study in innovation, risk management, and flawless execution.
Business leaders, especially those in small and medium-sized enterprises (SMEs), can learn valuable lessons from her journey.
A Masterclass in Brand Strategy and Cultural Agility
The colour orange is suddenly everywhere, from Dunkin’ to M&M’s to United Airlines. These brands are syncing their marketing with Swift’s latest era. Even the Empire State Building lit up in orange with the caption: “Onto the next era.” That was no accident; it was cultural agility in action.
Brands that moved quickly gained exposure worth millions, capitalising on a global wave of attention. Those who hesitated missed out. In the UK, it’s hard not to wonder where Sainsbury’s or EasyJet were in that moment. Which teams spotted the trend but couldn’t act? Which approvals took too long?
Strategic organisations empower teams to act decisively and with autonomy. They build cultures where creativity is encouraged, experimentation is welcomed, and calculated pivots are not only allowed but expected.
In business, as in music, those who wait too long to act miss the moment entirely. A study by Deloitte found that agile organisations grow revenue 37 per cent faster than those with rigid hierarchies. Swift’s team embodies this agility, and SMEs can too.
Trust, autonomy, and clarity of direction are key.
Vision: Staying the Course
Taylor Swift’s defining trait is her unwavering vision. Every decision, from artistic direction to contract negotiations, connects to her long-term goals. She recognises the power of consistency in achieving autonomy and maintaining reputation and engagement.
For SMEs, having a clear vision provides a crucial anchor.
According to the Federation of Small Businesses, SMEs with a solid strategic plan are twice as likely to achieve year-on-year growth compared to those that react to challenges.
Leaders should ask themselves:
• Does every team understand where we’re going?
• Can every employee explain how their work supports that vision?
When clarity becomes a shared understanding, strategy transforms from a mere document into a way of working.
Strategic Consistency: Messaging with Intention
Last summer, while touring across Europe, Taylor was already writing and recording her next album. She flew to Sweden between shows to collaborate with producers Max Martin and Shellback. Physically drained but creatively unstoppable.
At the same time, she began teasing her next “era” with colour cues, cryptic posts, and subtle Easter eggs. This slow-burn campaign was a masterclass in intentional storytelling. Fans are now decoding every lyric and every shade of fabric.
This consistent, multi-layered messaging builds emotional loyalty. For SMEs, the same principle applies. Brand consistency can increase revenue by up to 23 per cent (Lucidpress).
When your story is told clearly, repeatedly, and authentically, customers don't just buy your product; they buy into your mission.
Relentless Productivity: Passion Meets Precision
This October, Taylor will release her twelfth studio album, not forgetting the multiple "Taylor’s Version" re-recordings. She writes or co-writes every song, co-produces every album, and oversees tours across continents.
Her work ethic is outstanding, but it’s also well-organised. Each era is meticulously planned, with timelines, stakeholder coordination, and risk management that rival those of a global enterprise.
SMEs can learn from this: productivity thrives when passion merges with precision. Bain & Company reports that SMEs with strong operational discipline achieve 30–50 per cent higher profitability over five years than those without defined systems.
The lesson? Creative freedom flourishes when it has structure.
Strategy as a Way of Being
Taylor Swift’s entire career is founded on a mindset of strategic ownership; clarity, consistency, creative courage, and emotional authenticity. For SMEs, that mindset leads to sustainable growth, cost efficiency, and competitive strength.
Whether scaling internationally or stabilising operations, the principles remain: • Define your purpose. • Empower your people. • Execute with discipline.
As a Strategy Director, I’m constantly reminded that success isn’t only about setting direction. It’s about ensuring every decision and every person aligns with it.
Taylor’s discipline showcases that alignment, reminding us that strategy is not an event; it’s a way of being. Personally, I feel inspired to think bigger and act bolder.
Although I’ve spent years developing growth strategies across sectors, there’s always room to sharpen my focus and be a mastermind in my own practice. Thank you, Taylor.
How about you?
Do your teams need to recalibrate, working not just hard, but smart?
Do you need to revisit your vision and embed it across every function?
Are you ready to foster a culture defined by innovation, resilience, and purpose?
At Scarlet Kites Strategy, we help businesses unlock clarity, agility, and growth.
Find out more about how Scarlet Kites Strategy can collaborate to define your next era, strategically: Scarlet Kites Strategy | Corporate Strategy
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