Why Work Needs More Taylor Swifts – Kevin Evers

Work's Not Working... Let's Fix It!

In this episode of Work’s Not Working… Let’s Fix It! Siân Harrington sits down with Harvard Business Review editor Kevin Evers, author of There’s Nothing Like This: The Strategic Genius of Taylor Swift, to explore what Taylor Swift can teach us about leadership, reinvention and making work actually work.

At first glance it might seem unlikely but Kevin argues that Swift is one of the most strategic thinkers in modern business. She’s mastered brand control, long-term trust and antifragile thinking in a way most organisations only talk about.

In an era where people feel disempowered, stuck in rigid systems and burnt out by constant change Swift’s playbook offers something rare: clarity, conviction and control.

From re-recording her music catalogue to turning setbacks into strategy, Swift’s approach holds powerful lessons for leaders navigating transformation, employee experience and brand loyalty.

Whether you’re a CEO, a people leader or someone questioning how to take back agency in your own career, this conversation will shift how you think about power, trust and the long game in work.

Key Takeaways:

• Reinvention only works if you protect the trust. Swift has changed her genre, aesthetic and tone – without losing her audience. Leaders should take note.
• Owning your story is the new power move. Swift didn’t fight for control – she built her own. That mindset shift applies far beyond the music industry.
• Employee experience needs obsession, not just intention. Swift’s fan loyalty is built through care, consistency and surprise. Most organisations are still stuck at comms plans and pulse surveys.
• Data can’t replace instinct. Swift’s biggest decisions weren’t based on algorithms – they were grounded in clear values and audience understanding.
• Resilience is overrated. Try antifragility. Swift doesn’t just survive hits – she grows stronger from them. That’s a model more leaders need to adopt.
• You can’t build long-term loyalty if you panic every quarter. Swift plays the long game. Business should too.

This episode is about more than Taylor Swift. It’s about taking bold, strategic ownership in a world of broken work models – and reminding ourselves that reinvention is a skill, not a risk.

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Chapters

1. Obsession, joy and what work can learn from Taylor Swift (00:00:00)

2. Intro: Welcome to Work’s Not Working (00:01:21)

3. Meet Kevin Evers and the case for Swift as a business strategist (00:01:37)

4. Longevity in a brutal industry: how Taylor stayed on top (00:04:00)

5. Reclaiming ownership: the boldest move in music history? (00:05:43)

6. Strategic curiosity and reinventing with care (00:08:50)

7. Trust, identity and reinvention without losing yourself (00:12:12)

8. Handling backlash: antifragility and using criticism as fuel (00:14:40)

9. Fan obsession: what it really looks like to exceed expectations (00:20:45)

10. Resilience vs antifragility: the next step in leadership maturity (00:23:58)

11. Long-term thinking, instinct and bold decision-making (00:28:27)

12. Kevin’s top leadership lessons from Taylor Swift (00:43:58)