Taylor Swift has sold out stadiums, topped charts, and redefined the music industry. But her boldest move this year wasn’t a new album or a global tour. It was a podcast. Just last week.
Two hours, unscripted, in front of a live audience of 1.3 million. Her first time sitting down in that format.
She laughed, she teared up, she shared pieces of herself in a way fans had never seen. For someone who has carefully controlled her image for two decades, this was a leap into the unknown.
But here’s what makes it even more interesting: the host was her boyfriend. That choice mattered. It softened the downside risk—she knew she was stepping into a safe environment, not a perhaps hostile press. She picked a space where vulnerability was possible without being reckless.
But the podcast was live-streamed—no second takes. And The Heights podcast is no slouch, the top rated sports podcast on both Apple and Spotify and one of the top podcasts overall.
While there was risk, 400 streams later suggest it was a risk worth taking.
400 million potential customers for the new album she announced halfway through.
That’s the essence of Pick Now.
Taylor Swift didn’t wait until she had the “perfect” setting or a guarantee of how it would land. She chose a move that stretched her, but with enough guardrails to make the leap survivable. She picked—knowing full well it could expose her in ways that felt risky.
And the truth is, waiting would have only compounded the fear. Action is what dissolved it.
By Picking Now, she gained what hesitation never brings: clarity, momentum, and yes, relief.
The payoff? Her fans are more connected to her than ever. And she got exposure to a sports audience who is not her core fanbase. Not because she controlled the narrative, but because she let go of control. Because she chose courage over caution.
That’s leadership.
Most of us don’t face the glare of a global spotlight, but we do face decisions that weigh just as heavily in our world. We stall, thinking more time will reduce the pressure. In reality, it only increases it.
The fastest way out of a stuck place isn’t more information—it’s more motion.
One step forward.
One move that unlocks the next.
Taylor Swift reminded us: even the most polished, successful people still feel fear before a leap. What sets them apart is that they choose anyway—often by finding the version of the risk they can actually take.
What’s the “podcast” in your life—the move you’ve been avoiding because you can’t know how it will turn out?
And what’s the version of it that’s bold, but survivable?
Pick it. Now.
#PickNow #Founder
Want a short video explaining how you, too, can make your next bold move? Comment “Pick Now” below and I will DM you the link.
And keep an eye out for the Pick Now podcast, coming soon.