When Every Choice Costs You Something: The Ed Sheeran Leadership Lesson

Summary: What do you do when no choice feels comfortable? Ed Sheeran found out very publicly. Read on for my thoughts on what to do when you’re caught between a rock and a hard place.

Dear Dr. Sylvia,

There is so much polarization in our world right now; we can’t even go to a concert and just have fun grooving to the tunes. I would love to hear your suggestions for what to do beyond siding “with or against.” It is getting old!

Signed,

Loves Music

When One Voice Creates a Ripple Effect

Dear Loves Music,

During Ed Sheeran’s Loop Tour, rapper Macklemore, one of his opening acts, used his time onstage to express support for Palestinians and declare “free Palestine” to the audience. The reaction was immediate and intense.

Several upcoming venues objected to Macklemore remaining on the tour, and the tour promoter ultimately removed him altogether. Sheeran said publicly that the decision was not his and that he had spent days talking with venues, trying to find a way forward.

Then things got even more complicated.

Other supporting artists withdrew from the tour in solidarity with Macklemore. Suddenly, Sheeran wasn’t simply dealing with one controversial performance. He was facing angry fans, departing musicians, venue owners, promoters, employees whose livelihoods depended on the tour, and a political conflict where almost any statement, or silence, would be interpreted as taking a side.

Welcome to Leadership in 2026

Not the leadership we put into PowerPoint presentations. The real kind, when there is no “right” way forward.

We love leadership stories after they’re over. For example, someone makes the courageous decision. The organization survives. The case study gets written. But that’s not what leadership feels like when you’re living through it. Sometimes you stand in front of several doors, and each one comes with a price. So what would you do in Ed Sheeran’s position?

Protect freedom of expression? Honor contractual obligations? Protect the livelihood of hundreds of people working on the tour? Respect the rights of venues? Protect your relationship with the artists? Stay true to your own values and protect your audience? Which comes first?

That is where leadership gets difficult, because the hardest leadership decisions aren’t always between right and wrong. Sometimes they’re between right and right, two values you believe in that suddenly collide.

Then Sheeran Did Something Interesting

At first, Sheeran tried to stay outside the political debate. He has said that he wants his concerts to be places where people from different backgrounds and viewpoints can come together. But the controversy kept growing. At his Philadelphia concert, Sheeran walked onto the stage alone and addressed it.

He condemned the October 7th attacks in Israel as horrific and described what is happening in Gaza as catastrophic and unjustifiable. He also expressed concern about those who control what artists can say onstage. And then he said something leaders rarely enjoy saying publicly: He acknowledged that he was making mistakes.

Think about that.

One of the world’s most successful performers, standing in front of thousands of people, essentially saying, I don’t have this perfectly figured out. That may be the most important part of this story.

The Unrealistic Expectations We Place on Leaders

We’ve created a strange mythology around leadership and expect leaders to be decisive, confident, certain, fast, and have all the answers. But what happens when certainty is impossible?(opens in new tab)

The temptation that follows is what I call JUBLA: to judge, blame, or attack as a method of self-preservation. Those are patterns. And under enough pressure, the patterns become louder.

This is precisely where I believe the GLIMMERS Effect™ becomes important.

Trigger → Pattern → Pause → Ugly Middle → Choice

The trigger arrives. Your familiar pattern wants to take over. Then comes the pause. And after the pause comes what I call the Ugly Middle: that uncomfortable territory where your old response no longer feels right, but you don’t yet know exactly what the new response should be.

Most of us want to rush through that part. Don’t. There is valuable information there.

The GLIMMER Isn’t Always a Perfect Answer

Sometimes the GLIMMER is simply the realization: Maybe I need to look at this differently. Perhaps you need to listen again, or admit that you made a mistake. Often, there are two people who profoundly disagree with each other, yet both are saying something equally important.

What if changing your response isn’t weakness, but growth? This doesn’t mean Ed Sheeran handled every part of this situation correctly. That’s not for me to decide. It means he found himself where leaders everywhere eventually find themselves: in a situation where every choice costs something.

Your version probably won’t involve stadiums, famous musicians, protesters, and millions of people watching. It might be firing a longtime employee, standing up to your board, or changing a strategy you once championed. Or it can be telling your business partner the truth. Admitting to your team that the decision you made six months ago isn’t working. Or listening when someone challenges something you deeply believe.

Here’s the $1M Question

The next time you’re caught between competing values, don’t immediately ask: “How do I make this problem go away?” Instead, ask: “What is this situation asking me to see that I couldn’t see before?”

That’s a very different leadership question. Pay particular attention when you feel defensive, angry, embarrassed, frightened, or desperate to prove you’re right. There may be a pattern talking. Pause. Stay in the Ugly Middle a little longer. Listen. Then choose.

Because sometimes the most important GLIMMER doesn’t appear when we know exactly what to do. It appears when we finally admit that we don’t.

To your success,

Sylvia Lafair

P.S. If you haven’t already signed up for a free copy of the introduction to my new book, GLIMMERS at Work: The Self-Aware Leader’s Advantage, do so here. (opens in new tab)

Sylvia Lafair

Creative Energy Options

Categories

Subscribe!