Keep Asking: Taylor Swift Edition
What. A. Night.
Leah, her sister, and I all went to Taylor Swift—along with 60,000+ other folks from around the world for her final night in Singapore.
In honor of the conclusion of the first leg of the Eras Tour, we’re going to make this week our Taylor Swift Edition. We’ve done this before with some other folks as well (Kenny Smith, Jimmer Fredette, Donovan Mitchell). It’s a way for us to look at how questions impact everyone’s life and how we can use their answers as one potential way for finding our own answers.
Are you ready for it?
What era are you in?
In case you don’t know about the single most successful music tour in history—the entire tour is based on the different eras of music she’s created throughout her career. It’s basically a journey through the many different versions of Taylor Swift.
You and I are no different.
By this stage of your life, you’ve likely already experienced several eras.
Here’s a few of mine:
Classical musician era.
Breakdance era.
Toy and Candy era.
Singapore era.
Why does it matter? Why should you care about what era you’re in?
Well, have you even given it any thought at all?
So many of us never stop to examine our lives—to really look at what we’re doing and why we’re doing it. Asking this question is actually a really fun and low stakes way of just examining the current state of your life. What are some of the defining elements of the life you’re living right now? Maybe it’s a job, maybe it’s a place, maybe it’s a group or team you’re on, maybe it’s a particular skill or hobby you’re into.
Maybe you’re in your travel era, fitness era, self development era, fantasy fiction era, or maybe you’re some combination of eras right now.
If you don’t like the era you’re in, the great thing is, you can move on to a new era. Like Taylor, you might need to move into the villain/Reputation era, or a lighter more 1989 type era, or a folksy Folklore era.
The point is, you get to decide.
What are you willing to do?
Every day I would run on the treadmill, singing the entire set list out loud. “Fast for fast songs, and a jog or a fast walk for slow songs. Then I had three months of dance training, because I wanted to get it in my bones,” she says. “I wanted to be so over-rehearsed that I could be silly with the fans, and not lose my train of thought.”
(Taylor Swift, TIME Magazine 2023)
I was talking with a friend at work whose whole family went to see Taylor Swift last week when she kicked off her Singapore shows. They loved it so much they were talking about grabbing more tickets and going again. And then her husband said, “I don’t know if I have recovered enough from the first show to do it again.”
Honestly, she’s a freaking athlete. No timeouts. No half-time or intermission. No bench players.
Just tens of thousands of people hanging on every word and move she made made for over three hours.
Everybody has things they want but how many people have a plan for getting those things and even more importantly, how many people follow through with their plans?
If you want something you’ve never had before, you’ve got to be willing to do things you’ve never done before.
Are you willing to spend months on the proverbial treadmill to get what you want?
What’s in your control?
Whether she knows it or not - one of Taylor’s boldest career moves was also her most Stoic.
“After I was denied the chance to purchase my music outright, my entire catalog was sold to Scooter Braun’s Ithaca Holdings in a deal that I’m told was funded by the Soros Family, 23 Capital, and the Carlyle Group. Yet to this day none of these investors have ever bothered to contact me or my team directly. To perform their due diligence on their investment. On their investment in me. To ask how I might feel about the new owner of my art. The music I wrote. The videos I created. Photos of me, my handwriting, my album designs. And of course, Scooter never contacted me or my team to discuss it prior to the sale or even when it was announced.”
(Taylor Swift, Billboard Music Awards 2019)
What do you do when your entire life’s work is sold off like a piece of real estate where you can no longer live?
You do the only thing left in your control.
Do ALL of the work again…. but even better.
Over the last few years, she has methodically begun to re-release every song she’s ever recorded along with a number of additional bonus songs.
The result? She’s now taken back the one thing she thought lost—control.
You can’t control anyone else, the economy, the nature of your genetics, and countless other things. But you always have control over your response to what life throws your way. It’s not easy - but you always have another move you can make.
What’s your story?
Taylor is a master storyteller.
She’s taken so many elements of her life, synthesized them, made meaning of them, and then packaged them in a way that allows people around the world to connect with her.
Have you thought about your life as a story?
Have you looked back on certain events and reflected on their meaning and how they might connect to other pieces of your life?
You don’t have to turn the stories of your life into a series of songs. But imagine having a series of meaningful stories you can draw on to guide future decisions, use to bring you the joy of nostalgia, or laugh about with friends.
Instead of always living in a state of perpetual anticipation, make time for reflection, make time connecting the dots and making meaning of what’s happened.
Whether you’re a Swiftie or a metal head, you can always learn something from the questions used by others to tackle the challenges we share as we make our way through life.
Dont forget—I’m doing a daily question Reel over on Instagram and over here on YouTube as well, so join me on one or both of these if that’s your type of thing.
Keep Asking,
Kyle
P.S. Congrats to @whereismare who won the book giveaway from last week!