Dylan and Swift: Musings of a Businesswoman

There is a connection between them that speaks to both heart and strategy—an artistry rooted in honesty, and a business built on bold reinvention.

Growing up in Minnesota, Bob Dylan was a key component of my childhood. My dad came from the same Iron Range as Dylan’s family, and the connection to his music in my life runs deep. Dylan’s words shaped the way I thought about stories, irony, and justice long before I could articulate it.

Fast-forward a few decades to raising tweens, and my daughter—without meaning to—introduced me to Taylor Swift. Through her, I fell in love with Swift’s music. What started as background noise in a carpool became a soundtrack I couldn’t ignore.

I am a passionate person by nature, and music has always moved me in ways I can’t quite explain. The frisson, the goosebumps, the hair standing on my arms—those sparks of recognition first came from Dylan’s Simple Twist of Fate. The irony in that ballad connected me to feelings bigger than myself. Then came Hurricane, its haunting portrait of injustice burning a hole in my teenage heart. Later, Forever Young would become the song I danced to with my father at both of my weddings—a sweet, eternal message of love Dylan first wrote for his own mother.

And then, there’s Taylor.

Her music captures the emotional complexities of being female in today’s world, friendships, breakups, growing up, and starting over. She gives voice to feelings that many women didn’t know how to name. At any given moment, half the women around you believe Taylor has written a song specifically about their life. That kind of connection is rare.

So what ties Dylan and Swift together beyond being prolific songwriters? For me, it’s not just their melodies and words—it’s their business.

Refusing to Be Boxed In

Neither has ever stuck to a single genre. Dylan shifted from folk to rock to gospel, while Swift traversed country, pop, and indie with unapologetic ease. Both resisted cultural expectations and criticism, staying true to their evolving artistry rather than conforming to public opinion.

Humanity Behind the Stardom

Both also managed to balance being human while living as superstars. Dylan took up painting, ironwork, and welding. Swift bakes and dotes on her cats. They remind us that even icons put their pants on one leg at a time.  

Unconventional Business Moves

Their business savvy also strikes me as incredibly similar. Swift recently extended her reach into the sports world, while Dylan once shocked audiences with his unexpected appearance in a Victoria’s Secret commercial. Both delight in surprising us, showing up where we least expect them, broadening their audience and legacy.

Changing the Industry

Most importantly, both have challenged the music industry itself. They’ve pushed against exploitation, fought for fairness, and capitalized on shifts in technology and distribution. Instead of resisting change, they adapted, ensuring their music stayed relevant, powerful, and alive for new generations.

At the end of the day, art is subjective. You may not resonate with Dylan or Swift. And that’s fine. But for me, these two artists have been the most meaningful companions in my life’s evolution—offering soundtracks for childhood, adulthood, motherhood, and business.

And so I wait for the next musical gem, the next surprise, the next lesson they’ll teach us—not just about music, but about resilience, reinvention, and humanity.

Now, back to figuring out who the Jack of Hearts really is. Any ideas, Taylor?

Mastermind. Masterpiece.