I spent fifteen years in advertising working on brands. Hundreds of them. Big ones, small ones, ones you've heard of, ones you have not. I sat in brand workshops and tone of voice sessions and positioning exercises. I helped write brand pyramids and brand keys and brand onions and whatever other vegetable-based framework was fashionable that year. I contributed to brand guidelines documents that were three hundred pages long, specifying the exact pantone of the secondary colour palette and the precise kerning of the logotype at 12 point.
And after all of that, here's what I know about brands: the ones that endure, the ones people actually love, are the ones that feel like people. Not polished corporate entities. Not carefully managed identities. People. With personality, opinions, quirks, and a way of seeing the world that you either connect with or you don't.
The best brands feel like someone you would want to have a drink with. Or at least someone you would want to sit next to at a dinner party. They have something to say. They have a way of saying it. And they don't try to appeal to everyone, because they know that trying to be everyone's friend means being nobody's friend.
The personality test
Here's a test I used to run in my head. If this brand were a person, who would they be? Not in the brand workshop sense, where someone writes "if our brand were a celebrity, it would be George Clooney" on a Post-it note and everyone nods sagely. I mean genuinely: what kind of person would this brand be?
Nike is the friend who pushes you. The one who texts you at 6am to go for a run when it is raining. The one who doesn't accept your excuses. The one who believes you're capable of more than you think you're. You might find that annoying sometimes, but you respect it. And deep down, you know they're right.
LEGO is the creative uncle. The one who gets down on the floor with the kid and builds something extraordinary out of nothing. The one who doesn't care about mess or rules or doing things the "right" way. The one who makes you feel like anything is possible if you just start putting pieces together.
Patagonia is the principled outdoorsman. The one who actually walks the talk. Who doesn't just say they care about the environment but structures their entire life around it. Sometimes preachy? Perhaps. But you never doubt their sincerity, and that sincerity is magnetic.
These brands aren't just identities. They're personalities. And the difference matters enormously. An identity is something you design. A personality is something you're. An identity can be constructed in a workshop and documented in a guidelines deck. A personality has to be lived, consistently, over time, in every interaction, every decision, every moment where the easy choice and the right choice diverge.
Why most brands have no personality
Here's an uncomfortable truth from the inside of the advertising industry: most brands have no personality at all. They have identities - logos, colours, fonts, photography styles, tone of voice guidelines. But personality? Something that you would recognise in a sentence even without the logo attached? Almost never.
This isn't an accident. It's the natural result of how most brands are managed. Personality requires conviction. Conviction requires risk. Risk requires someone senior enough to say "this is who we're, and I accept that some people won't like it." And in most organisations, that person doesn't exist, or is overruled by the committee that wants to appeal to the broadest possible audience.
So what you get instead is bland. Professional. Competent. Forgettable. The brand equivalent of a beige suit and a firm handshake. It won't offend anyone, but it won't excite anyone either. It won't make anyone feel anything. And brands that don't make people feel things are just logos on price tags.
I saw this pattern repeat itself dozens of times during my career. A brand would have a spark of personality - usually because of one brave individual who understood that distinctiveness beats blandness - and then the committees would get hold of it. The edges would be sanded off. The opinions would be softened. The personality would be replaced by a set of "brand values" that could apply to literally any company on earth: innovative, trustworthy, passionate, customer-focused. These aren't values. They're the absence of values. They're what you say when you have nothing to say.
Products have personality too
This is something I've learned from building my own projects: products can have personality in a way that brands often struggle to achieve. Because products are made by individuals, and individuals have personality by default. You don't need a workshop to discover it. You just need to let it come through in the work.
Modern Retro has personality. It's playful, nostalgic, slightly absurd. It takes modern brands and reimagines them in 1970s shop fronts, which is an inherently ridiculous concept, and it leans into that ridiculousness rather than trying to be serious about it. That personality wasn't designed in a brand workshop. It emerged from the work itself, from the choices I made about which brands to feature, how to present them, what the tone should be.
Taste OS has a different personality entirely. It's more cerebral, more analytical, more interested in systems and frameworks. It takes something subjective - taste - and tries to measure it, which is either brilliantly ambitious or gloriously misguided depending on your perspective. That tension is its personality.
The lesson is that personality doesn't come from guidelines. It comes from decisions. Every choice you make about your product - what to include, what to leave out, how to describe it, what it looks like, how it behaves - is a personality choice. The best products, like the best brands, make those choices with conviction rather than committee.
The personality paradox
Here's the paradox that I keep coming back to: personality is the thing that makes people love your brand, but it's also the thing that makes some people not love your brand. And that's exactly the point. A personality that everyone likes isn't a personality. It is wallpaper.
The brands I admire most are the ones brave enough to be divisive. Not offensive - that's a different thing entirely. Divisive in the sense that they have a clear point of view that some people will connect with and others won't. They've made a choice about who they're, and they accept the consequences of that choice.
This is terrifying for most brand managers. The entire apparatus of modern marketing is designed to maximise reach, to appeal to the broadest possible audience, to avoid anything that might alienate potential customers. But reach without resonance is meaningless. A million people who vaguely know your brand is worth less than a thousand people who love it. And love requires personality. Love requires someone to connect with. Love requires the risk of being disliked.
I think about this with my own projects. I could make them more generic, more broadly appealing, more safe. I could strip out the personality and replace it with professional competence. But then they would be forgettable. They would be just another app, another site, another thing in the infinite scroll of things. The personality - my personality, coming through in the work - is what makes them distinctive. It's what makes someone stop and say "this feels different." That feeling is everything.
The best brands feel like people because they're made by people who are brave enough to let themselves come through. Not the polished, committee-approved version of themselves. The real version. With opinions and quirks and a specific way of seeing the world. That's what people connect with. That's what people remember. That's what turns a brand from a logo into something that matters.
In an age where AI can generate infinite brand assets, infinite copy, infinite visual identities - the one thing it can't generate is genuine personality. Because personality requires a person. It requires someone who cares about something, has an opinion about something, and is brave enough to let that show. A brand without that's just another brand. A brand with that's a person you want to know.
