In the second in our October series of articles and podcasts related to the FFI annual conference, we feature an article by 2025 Conference Program Committee member, Patricia Annino. The point of departure is Taylor Swift—with ideas on teaching moments and conversation starters for advisors and clients.

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.

• Actionable takeaway for clients: Take charge of your career trajectory and business decisions. Don’t let others assume or dictate your path just because of your gender or family role. Whether it’s negotiating a key contract or stepping into a leadership position, owning your narrative is key to sustaining long-term power and influence.

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.

• Actionable takeaway for clients: Understand that the world is not static. In fact, it is changing at warp speed, and to be successful you must too. Embrace change and look for ways to innovate, even if that means disrupting the traditional way of doing things in the family business. You don’t have to follow the same path as previous generations; chart your own course while staying rooted in the family’s values.

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.

• Actionable takeaway for clients: Don’t let setbacks define you. Use them as opportunities to gain experience and grow. In family businesses, disagreements, changes in leadership, and challenges are inevitable. How you respond to them can set the tone for the future.

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.

• Actionable takeaway for clients: Build relationships based on trust, integrity, and open communication. As a woman, you may face challenges in being taken seriously or being viewed as less authoritative, but authenticity will give you credibility and long-term respect within the business.

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.

• Actionable takeaway for clients: Rather than avoiding conflict, embrace it as an opportunity for growth and clarity. Use disputes to strengthen governance, create new structures, or re-align family members around a common purpose. It’s not about avoiding tension but using it as a catalyst for better decision-making and forward momentum.

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.

• Actionable takeaway for clients: As a woman in a family business, it’s essential to understand your value and negotiate your worth—whether that’s in the boardroom, during succession planning, or when asserting your role in the business. Don’t accept being sidelined; instead, ask for and attain the recognition and compensation you have earned and deserve.

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.

• Actionable takeaway for clients: While it’s important to be committed to the business, remember that sustainable success also requires taking care of your personal health and boundaries. In family businesses, it’s easy to get caught up in the work and the drama, but self-care and balance are just as critical to long-term success.

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.

• Actionable takeaway for clients: Support other women in the family and within the business. Create spaces where women can thrive together, share ideas, and collaborate to drive the business forward. The collective success of women can amplify the entire family’s legacy and ensure its sustainability.

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.

• Actionable takeaway for clients: Use your influence and success to create a positive impact through philanthropy. In the context of a family business, consider establishing charitable initiatives that align with the family’s values and mission, helping to build a legacy beyond financial wealth.

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.

About the Contributor

Patricia M. Annino, FFI Fellow, is an attorney with Rimôn, P.C., in Boston. The host of the pre-conference session “How Sweet It is: Iconic New England Family Businesses” at the 2025 Global Conference, she is also the 2022 recipient of the Richard Beckhard Practice Award, a former member of the FFI Board of Directors, a founding member of the 2086 Society, and a frequent contributor to FFI Practitioner. She can be reached at patricia.annino@rimonlaw.com.