Hero’s Wisdom: The Trickster – Lessons from Taylor Swift

Hi there! Brittany here — welcome to this week's edition of Bold Insights & Practical Steps for Leaders on Their Own Hero’s Journey ⚔️

Each week, I share Hero’s Wisdom, a quick story or insight inspired by the challenges, wins, & lessons that leaders like you face. Together, we’ll explore new perspectives & discuss the bold steps you can take to confidently navigate your own work challenges. Let's dive in!

As a proud Swiftie (and someone who had the absolute best time scream-singing at her Eras tour last year in Detroit 🖤), I can’t resist drawing on Taylor’s story as inspiration. This week, as she wraps up her last U.S. tour dates in Indianapolis, she’s more relevant than ever—especially when it comes to the Trickster on our leadership journey.

In the Hero’s Journey, the Trickster is an essential figure that every hero encounters. Often unexpected, the Trickster brings challenges, shakes up the familiar, & encourages the hero to think differently.

In leadership terms, meeting a Trickster (or embodying that spirit) can spark the reinvention that every leader sometimes needs.

Taylor Swift is a prime example of a Trickster in action. Faced with a challenge — losing control over her own music — she didn’t let it defeat her. Instead, she rewrote her story by re-recording her albums & reclaiming her legacy. Her “trick” was bold, and it forever changed how artists view ownership + creativity.

Here’s what Taylor Swift teaches us about the Trickster’s impact on our leadership journey:

🧭 The Trickster Reveals New Paths: The Trickster archetype, often a wildcard figure, disrupts the status quo & shows us new ways forward. In Taylor’s case, her re-recordings didn’t just reclaim her music — they redefined her relationship with her fans AND the industry.

Leaders, where might you challenge “the way things have always been done”?

🫶 Standing Up for What Matters: Tricksters test the hero’s values, and the hero often emerges stronger by reaffirming what matters. Taylor’s stand to control her music ownership reshaped her career.

For leaders, this might mean setting boundaries, advocating for your team, or making decisions that align with your core values — even if it’s disruptive.

⚡️ Reinvention is a Superpower: Tricksters remind us that adapting is essential to growth. Taylor turned a heartbreak into a breakthrough, showing the world that reinvention can make you stronger than before.

Leaders, think about where reinvention could unlock growth for you + your team.

The Trickster doesn’t just disrupt - they inspire us to be bold.

As you prepare for next week, ask yourself: What new path could you create by challenging the norms?

With you on the path,

-Brittany

⚔️ Want deeper insights & actionable steps on your own Hero’s Journey? For a more in-depth dive into leadership strategies you can start applying immediately, subscribe to my Weekly 1:1 Tuesday newsletter — we go even deeper into practical tools & frameworks to help you grow as a leader, develop current + future leaders, and strengthen your teams.

And if you’re ready to bring this growth into your organization or explore leadership development with me, let’s connect! Reach out at brittany@whatyoudomattersmentality.com.

Remember, your actions as a leader matter. They create real change — for you, your organization, your team & your career.

Don’t forget to register for my free webinar November 12th on the Future of Work: The Untold Power of Working Managers.

I'll be covering:

→Why working managers are the superheroes of the future of leadership

→The hidden challenges leaders face every day

→Practical steps to move from overwhelmed to empowered

→What leadership will look like in 2025 & beyond

📅 Date: November 12th

⏰ Time: Noon EST (perfect for a lunch & learn!)

📍 Where: Virtual – Zoom link will be sent after registration

💸 Cost: FREE – registration required!

You can register HERE