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.

The slow erosion of meaning from the brands we build and the work we create.

Marketing has been slowly losing its nerve for a while now. Not in some dramatic implosion … more like a house settling wrong. Quiet. Gradual. You don’t notice until the door won’t close anymore.

Somewhere along the way, creativity got flattened into “content.” Content got flattened into output. Output got flattened into deliverables. Brands started acting like software companies. Agencies started promising scale instead of ideas. And a lot of smart people quietly handed their instincts over to dashboards and algorithms, like those things were better listeners.

Somewhere along the way, we forgot that brands aren’t machines. They’re not funnels. They’re not logos waiting for feedback. When they work, when they really work, they feel alive. And anything alive needs a soul, not just a growth chart.

The next few years are going to make this painfully obvious. The brands that last won’t be the ones producing the most AI-generated noise before lunch. They’ll be the ones that actually stand for something. Meaning beats volume. Every time.

“Soul,” unfortunately, has become one of those words people like to embroider on pillows and then ignore. It’s not your tagline, your color palette, or your mission statement from that offsite no one remembers. It’s the conviction underneath all of it … the thing that makes people care, root for you, stick with you even when you’re imperfect. 

People don’t connect to perfection; they connect to humanity. They connect to tension, ambition, conviction, identity, vulnerability, aspiration. They connect to the feeling that a brand stands for something real. A sense that someone on the other side actually believes in what they’re doing.

What kills that soul is usually two things: speed and safety.

Speed is the obvious one. We’re addicted to immediacy: weekly reports, instant performance, constant optimization. When creativity is compressed into timelines that leave no room for insight, emotional intelligence, or the kind of deep listening that makes good work great, we lose the moments where breakthrough ideas are born. The unexpected connections. The uncomfortable conversations. The willingness to walk past the obvious answers in search of the right one. We end up with something that looks like creativity but feels like nothing.

Craft becomes an afterthought. Care becomes optional. Soul becomes collateral damage.

Speed isn’t the only threat. There’s another force quietly draining soul from the work, there’s safety, which is sneakier. Especially when it comes to partners. Safe agencies say the right things, avoid friction, and deliver work that offends no one … which is exactly why no one remembers it. Comfort feels good in the short term. It also quietly murders breakthrough ideas. The cost isn’t what you paid; it’s the risks you never took and the stories you never told.

The antidote isn’t revolutionary. It’s just unfashionable. Real Partnership.

Real partnership ... the kind built on honesty, curiosity, and a willingness to challenge each other. Not transactional politeness, actual collaboration. And a commitment to the long game. Because connection compounds. Trust compounds. Meaning compounds. That’s the moat no competitor can copy.

And, yes, it takes courage. To be different. To tell the truth. To resist the constant pressure to be faster, safer, louder.

The world doesn’t need more content. It needs more meaning. And the one thing that will always remain … the one thing no competitor can copy, no algorithm can manufacture, no shortcut can replace … is soul.

And the brands who honor it, articulate it, and express it with courage will own the future.

Trust Issues

 

Somewhere between the thud of the first Macintosh commercial and the day your fridge started asking for your Wi-Fi password, we developed a peculiar kink in our collective confidence.

Human instinct -- the kind forged in the furnace of 30 years pitching ideas, breaking ideas, rebuilding ideas out of caffeine and ego and last-minute panic -- suddenly became the red-haired stepchild of the decision room.

Gut feeling? Experience? Intuition?

Cute. Nostalgic. Like vinyl or hand-written thank you notes. Lovely to romanticize. Hard to expense.

Now the magic words are: “The model recommends.” And everyone nods like they’re at a wine tasting and know what “hints of gooseberry and attractive saddle leather notes” means.

We’ve gone from “show me the justifiation” to “well, the black box burped so I guess we pivot.” We treat the algorithm like some sleek digital oracle … cold, hard, algorithmic truth … while conveniently forgetting it’s trained on… us. Our thinking. Our patterns. Our triumphs. Our flops. Our messy, inconsistent, human sausage-making of ideas. Even though it's just our instincts, blended, baked, pressurized, and served back to us in a stainless-steel voice.

But here's the psychological plot twist nobody wants to admit: We don’t trust AI because it's smarter. We trust AI because it's not us.

There’s relief in outsourcing doubt. There’s comfort in handing the wheel to something that can’t blush, stammer, or have a Sunday-night existential crisis about whether Gretchen in finance secretly hates your brainstorming energy.

If the machine's wrong? Well, that’s engineering’s problem. If you’re wrong, that’s… you. Your reputation. Your gut. Your call.

And maybe that's the real fear.

AI didn’t take our jobs, insecurity did. We didn't hand power to the algorithm, we evacuated it from our own bellies.

So here's a rebellious thought to leave rattling around your decision-making cortex:

Ask the machine. Ask it, poke it, prod it, use it like the fantastically strange tool it is.

But don’t exile the organ that got humanity through sabertooths, stock markets, and the dark age of 56k dial-up modems.

Your intuition has a resume too. And unlike ChatGPT, it can smell fear. And fire. And a client about to say, “We’re going in another direction.”

AI is a co-pilot. Not the head honcho.

Trust the algorithm. But trust your gut more … it’s got emotional connection and better stories earned through triumph, trauma, and resiliency.

“I hope this message finds you well!”

 

Let’s talk about the outreach line that refuses to die: “I hope this message finds you well!”

Ugh! The limp handshake of opening lines. The verbal equivalent of flat soda served in a paper cup that smells vaguely like waiting room coffee.

Sure, the phrase is polite, but it’s overused, making emails feel generic and easy to ignore. It’s the beige throw pillow of business language, showing up and it whispering: “I have nothing to say, but protocol demands I say something.”

I get it. You’re being polite. You don’t want to come in hot like a used-car version of a sales guru yelling about synergy. But this line? It doesn’t “soften the ask,” it puts your reader in an emotional waiting room where nothing ever happens … it wastes the first few seconds of attention in a world where attention has the shelf life of mayonnaise at a summer picnic.

So what do you do instead?

You start like you mean it. Start with value. Start with a question. Start with something human. Start with something weird if you're brave and caffeinated enough. Understand that politeness alone doesn’t build connection. Presence does.

Try something along these lines instead:

• Quick question about [specific topic] on your site…
  
  
• “I’ll get to the point, because your time matters.”
  
  
• “I saw your recent work on _____________ and needed to reach out.”

• I saw [a specific trend] and thought of your site…"

• “Quick thought for you ... might be useful, might spark something wild.”

or even:

• “Look, I know you have 147 unread messages, so I’ll be brief.”

Now you have my attention. Now it feels like a human wrote this.

Ya gotta sound alive. Show intention. But, please, don’t lead with a sympathy card. “I hope this message finds you well!” can take its polite, neutral little suitcase and go retire in a quiet cul-de-sac of forgotten phrases next to “Per my last email” and “Sorry to bother you”

The world doesn't need more well-finding ... it needs well-doing.

Now go write like you showed up on purpose.

And if this post finds you well?

Great.

But more importantly, I hope it finds you awake.