Practice Insights

Shake It Off: What Taylor Swift Can Teach Women in Family Enterprise

Weekly Edition • October 15, 2025

When Taylor Swift was interviewed as TIME Magazine’s 2023 Person of the Year, she said: “My dad, my mom, and my brother come up with some of the best ideas in my career. I always joke we are a small family business.”¹

Although she may have been quasi-joking, the reality is that she has thrived on support and encouragement from her family, their insights and assistance, and their connectedness to her, her business, her success—matters.

After reading There’s Nothing Like this: The Strategic Genius of Taylor Swift,² it occurred to me that Taylor Swift offers several powerful lessons that can be directly applied to women in family businesses, especially when it comes to balancing traditional values with modern leadership and personal empowerment.

Here’s how her journey can inspire and guide women navigating the complexities of a family enterprise:

1. Own Your Voice and Your Narrative

A private equity firm sold (legally) the rights to her song collection. Swift mobilized and decided to re-record her albums and regain control over her intellectual property—a bold statement on the importance of owning the narrative. For women in family businesses, this is a crucial lesson. It’s about the client asserting her leadership, ensuring her voice is heard and actively shaping the story of her role within the business—not letting others define it for her.

2. Adaptability and Innovation

Swift has reinvented herself countless times—shifting musical genres, exploring new technologies, and adjusting to changing market dynamics. This adaptability is an important lesson for women in family businesses, especially in industries facing rapid change or disruption. Not only has Swift mastered music and the industry, but she has also mastered the use of social media.

3. Resilience in the Face of Setbacks

Taylor has faced countless public setbacks, criticism, personal attacks, and business challenges—but each time, she comes back stronger. For women in family businesses, resilience is crucial, especially when navigating family dynamics, societal expectations, or when facing external pressures that undermine their authority.

4. Building Authentic Relationships and Trust

One of Taylor’s greatest strengths is her authentic connection with her fans, which has helped her maintain an incredibly loyal following. In a family business, trust is a non-negotiable asset. Women in family businesses often can nurture these authentic relationships within the family and with stakeholders, setting a tone of transparency and mutual respect.

5. Turn Conflict into Opportunity

Taylor’s ability to turn public conflicts (such as the dispute over her music rights or Kanye West coming on stage to take the microphone out of her hands at the VMA Awards) into creative energy and further success is a perfect example of transforming adversity into advantage. Family businesses, by their nature, are prone to conflict—whether it’s generational differences, differing visions, or power struggles.

6. Negotiate Your Worth and Step into Power

Swift has consistently negotiated her worth in an industry that often undervalues women. She has repeatedly secured favorable deals and demonstrated that her success is directly tied to her ability to negotiate terms that align with her value.

7. Work Hard, but Prioritize Self-Care

While Taylor’s work ethic is legendary, she also understands the importance of balance, both in her personal life and career. Family businesses often demand immense time and effort, and women, especially, may feel pressure to prove themselves. Taylor shows that hard work is important but so is maintaining your mental and physical well-being.

8. Support Other Women and Foster Collaboration

Taylor has used her platform to support fellow artists, especially women, advocating for better treatment and opportunities. In family businesses, collaboration among women is key to fostering an inclusive environment that encourages diversity of thought and action.

9. Make Philanthropy a Core Value

Taylor is deeply involved in philanthropy, using her success as a platform to support causes she believes in. For women in family business, this focus on giving back can serve as a powerful means of connecting the family’s wealth with larger societal contributions.

In the epilogue to Kevin Evers’s book, he quotes scholar and risk analyst Nassim Taleb and describes Swift as “antifragile.”³ The concept refers to things that not only withstand stress and shocks but thrive and improve because of them. In describing what it means to be anti-fragile Taleb uses the metaphor of wind and fire: the same strong wind that can extinguish a candle will make a large fire burn more intensely. According to Taleb, in business and in life, “You want to be the fire and wish for the wind.”⁴

Taylor Swift’s story is not just about a pop star who conquered the music industry—it’s about a woman who took control of her narrative, overcame setbacks, and built a powerful, multifaceted career on her own terms. The principles she embodies—resilience, authenticity, innovation, power, and anti-fragility—are all critical lessons for women in family businesses who aim to lead, evolve, and leave a lasting legacy.

References

¹ Sam Lansky, “2023 TIME Person of the Year,” TIME, December 6, 2023, https://time.com/6342806/person-of-the-year-2023-taylor-swift/.

² Kevin Evers, There’s Nothing Like this: The Strategic Genius of Taylor Swift (Harvard Business Review Press, 2025).

³ Evers, There’s Nothing Like This, 239.

⁴ Nassim Nicholas Taleb, Antifragile: Things That Gain from Disorder (Random House, 2012), 3.