I Miss the Pirates

 

I miss the pirates in advertising.

Not the jerks. Not the loud egos or the gratuitous rudeness. I don’t miss the chest-thumping or the performative bad behavior. I miss the people who would look at a perfectly reasonable idea and say, “This is safe. Let’s wreck it and see what’s underneath.”

Those people used to be everywhere. They were the ones who pushed back in meetings, who argued for the weird option, who weren’t afraid of the wrong joke or the uncomfortable reference. They didn’t ask for permission so much as forgiveness … and sometimes not even that. They made the room a little dangerous, which made the work better.

Somewhere along the way, that energy got quietly escorted out of the building.

What replaced it is competent safety. Process. Caution. Everyone’s very well prepared now. Legal shows up early. Strategy arrives with data. Nobody wants to be the reason a Slack thread goes nuclear. The work gets smoother, cleaner, more defensible. It also gets duller. Like furniture designed to survive a dentist's lobby … technically impressive, emotionally forgettable.

This isn’t about nostalgia for chaos. It’s about risk tolerance. When the cost of being wrong gets high enough, people stop trying to be interesting. They optimize instead. They aim for “won’t offend,” “tested well,” “aligned with brand values.” Which is how you end up with ads that feel like they were written by a committee that’s afraid of being quoted.

I notice it in the language. Everything is “intentional” now. Everything is “thoughtful.” No one ever just takes a swing. It’s like watching a band tune their instruments forever and never play the song.

The pirates didn’t win every time. Half their ideas were bad. Some were indefensible. But they understood something basic: surprise requires discomfort. You don’t get memorable work by sanding off every sharp edge. You get beige. You get work that looks fine on a slide in a pitch deck and disappears the moment it hits the world.

Most of those people didn’t vanish. They adapted. They learned when to stay quiet, when to nod, and when to save the real thought for the walk to the elevator. That might be the saddest part. The rebellion didn’t die, it got managed.

Advertising still has talent. It just has fewer people willing to look foolish in public. Fewer people willing to say, “This sucks, let’s try something else,” without a spreadsheet to back it up.

I miss the pirates because they reminded us that this was supposed to be fun. Dangerous fun, occasionally irresponsible fun … but alive. They inspired “thinking different” and sometimes, their swashbuckling translated into genius.