My boss handed me an assignment: find or build a band that could carry the company’s message through music.

In the late nineties I was a young brand manager at Pepsi in Mexico. It was the era of the Spice Girls, NSYNC, the Backstreet Boys, so the brief made sense, on paper.

I spent weeks meeting music people, trying to find the right partner. I landed on someone well connected, tied to a major producer, and briefed him on exactly what I needed.

A few weeks later he came back with exactly what I'd asked for. A fun, photogenic teenage group, dressed in Pepsi colors, ready to dance and smile on cue.

Then he said he wanted to recommend something else instead.

He represented a young Colombian songwriter, barely known outside Colombia. He thought Pepsi should back her instead of building a manufactured group.

A Colombian songwriter, I thought. That’s not the brief. What is this guy talking about.

I let him pitch it out of courtesy anyway.

Forty minutes on someone nobody at Pepsi had heard of.

At the end I said, "Nah, I'll stick with the teenage band."

The band ended up costing a fortune and went nowhere. No connection with the audience we were trying to reach.

On the other hand, the Colombian singer & songwriter was killing it.

Her name?

Shakira.

For years I told that story as a bad luck joke, the one that got away. It took a long time to see the real mistake, and it wasn't failing to spot a star.

The mistake was that I'd stopped asking the actual needed question.

My job was to find a way for Pepsi to connect with young people through music.

Somewhere along the way, "connect through music" quietly turned into "build a teenage band," and once that happened, I stopped weighing ideas against the real goal. I weighed them against the plan I'd already committed to.

We do this same work for a client every day.

A couple asks for a quiet honeymoon, and we don't just book a quiet island.

We ask what quiet actually means to them. Rest. Privacy. No group excursions. We keep asking until the real question shows up.

But we rarely do that same work on our own travel business.

Bookings slow, and the answer becomes post more.

Referrals dry up, and the answer becomes send another email.

The tactic feels like progress, so it starts standing in for the goal itself.

Once that happens, we stop checking whether it's still solving the right problem. We just keep doing it.

I did the same thing with a teenage band that never had a chance.

Next time something in your travel business slows down and you reach for the obvious move, stop for one question first.

What am I actually trying to fix here?

The answer might still be the tactic you already picked. You won't know until you ask.

If that question doesn't have an easy answer right now, reply and tell me what you're working on. I read every reply myself.

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