The Courage to be Disliked: Why Creative Leadership Still Matters

We talk a lot about collaboration in the creative industries. About openness, co-creation and flattening hierarchies. About listening harder, sharing power and creating space for more voices at the table.

These are good things. Necessary things. In many cases, long overdue corrections to an era when creative departments were driven by ego, hierarchy and the myth of the lone (white, straight, male) genius. But cultural corrections have a habit of swinging too far.

In pushing back against top-down authority, strong creative direction itself has started to feel unfashionable. Even uncomfortable. As if having a clear point of view – and standing doggedly behind it – is somehow at odds with being a good leader, or worse, a throwback to a thankfully bygone era where shouty Creative Directors were feared and ‘respected’, but actually behind their backs we all just thought they were dicks.

But what about the quieter, less discussed side of making good work: the courage to back an idea before it’s popular? Or proven? Or before it makes sense to everyone else in the room?

I was reminded of this recently by an article from Jason Bagley (former CCO of Wieden+Kennedy Portland who now advises Creative Directors), who wrote: ‘The most successful creative directors aren’t the most talented people in the room – they’re the ones willing to be hated for a while in order to make something great.’

That line landed because it articulated something many of us recognise but rarely say out loud. Borrowing a philosophy from the book The Courage to Be Disliked by Ichiro Kishimi and Fumitake Koga, there is a specific kind of ‘bravery’ required to separate your tasks from the tasks of others – and that includes the task of liking you.

The discomfort of big ideas

Big ideas are deeply uncomfortable. ‘They feel risky, expensive and often flat-out wrong’. As Bagley elaborates, ‘They are often counterintuitive – the exact opposite of what the “smart, responsible” people said you should do.’

Before they become the campaigns people celebrate or the brands people love, big ideas tend to create friction. With clients. With stakeholders. And, let’s be honest, within creative teams too. So it’s easier, isn’t it, to smooth the edges, keep everyone happy and avoid tension wherever possible? Sure, dilute the work, no biggie… but at least we keep the peace?

But comfort is a terrible design strategy.

“But comfort is a terrible design strategy.”

Andy Pearson, VP of Creative at Liquid Death, describes a similar realisation. Reflecting on his early years as a Creative Director, he recalls trying to placate his team by being nice, before having an epiphany: ‘I thought back to all my favourite Creative Directors who always asked me to do something that seemed too difficult or counterintuitive. In that moment I realised my job as Creative Director was simply “to be unreasonable”… I still have to remind myself of that at times. But it’s what makes all the difference.’

What’s important here is what ‘unreasonable’ actually means. Pearson isn’t advocating ego or tyranny. He’s talking about the willingness to ask for things that feel too weird, too prickly or too ‘unsafe’ at first. The kind of asks that stretch people beyond what feels comfortable, and ultimately raise the quality of the work. Because as George Bernard Shaw once wrote: ‘All progress depends on the unreasonable man.’

Bagley goes one step further: ‘When you hold the line… people stop calling you “inspiring” and start calling you “difficult,” “uncollaborative,” “too intense.” But if you’re serious about making something truly great, you have to be the unstoppable force that puts the work first – even when it means being unpopular for a while.’

The ‘dinosaur’ debate

This view has its detractors. David Shanks recently argued that this is an outdated position, writing: ‘The tough old unreasonable bastard of a Creative Director is dead. It’s a dinosaur approach.’ He suggests that in a world where the most effective content is made by teenagers on their phones, creativity no longer needs strong, top-down direction. ‘Doing things again and again to reach the standards of someone at the top is just not going to fly in a world of faster, better and cheaper.’ Instead, he points to collaboration and bottom-up leadership as the real engines of innovation.

He’s certainly right about where ideas come from. Creativity today is decentralised, participatory and community-driven. Shanks cites LEGO as an example of a brand that thrives by recruiting ‘highly skilled amateurs’ rather than relying solely on traditional creative hierarchies. That shift should absolutely be celebrated.

But I still believe there’s something we’re not talking enough about. While ideas can come from anywhere, clarity doesn’t. Taste doesn’t. And cohesion doesn’t simply emerge through collaboration alone. Someone still has to decide what makes the cut. Someone still has to connect the dots. Someone still has to say no, and be willing to take the fall if the shit hits the fan. That role isn’t about dominance. It’s about responsibility.

When leadership dissolves entirely into consensus, the work often ends up saying very little. It becomes depressingly polite. Beige. Averaged out. Optimised to offend no one and excite no one either. As Sir John Hegarty once put it: ‘Creativity isn’t a committee.’ He fervently maintains that original ideas rarely receive unanimous approval the first time, and trying to get a group to agree usually leads to the most timid, lowest-common-denominator idea being selected.

“While ideas can come from anywhere, clarity doesn’t. Taste doesn’t. And cohesion doesn’t simply emerge through collaboration alone.”

Bravery over bullying

Ironically, it’s the same quality that AI tends to produce when creative teams ask it to satisfy every stakeholder at once. A race to the bottom into an indistinguishable swamp of sameness. Even figures like Steve Jobs – often cited as the archetype of the ‘difficult’ creative leader – weren’t difficult for the sake of it. Jobs was obsessive about coherence and care. He was challenging because the work mattered more than being liked in the room. That’s the distinction worth reclaiming.

The courage to be disliked isn’t about bullying, ego or nostalgia for old power structures. It’s about holding tension without collapsing into people-pleasing. It’s about staying with an idea during its most vulnerable phase, when it’s messy, fragile and easy to kill through compromise.

Good creative leaders don’t crush collaboration. They channel it. They listen widely and then decide narrowly. They create space for ideas to come from anywhere, but they take responsibility for where those ideas land. As Bagley puts it: ‘You can make great work, or you can make everyone comfortable. But you can’t have both.’

“Good creative leaders don’t crush collaboration. They channel it. They listen widely and then decide narrowly.”

And yes, that sometimes means disappointing people. Saying no to your own team. Pushing back on clients. Defending something that doesn’t yet have the data, case study or precedent to prove it’s right. We’ve all been there and it’s a lonely place. But if we remove that role entirely, we don’t get freedom. We get dilution.

So perhaps the question isn’t whether the ‘unreasonable Creative Director’ is dead. Perhaps it’s whether we’ve confused kindness with avoidance. Collaboration with abdication, and perhaps even openness with a lack of judgement. Creative leadership today doesn’t need to be louder or more domineering. But it does need to be braver. Because collaboration makes work richer. But courage is what makes it matter.

—
Cat How is Founder & ECD at HOW+HOW

The Courage to be Disliked
This article first appeared in Design Week. Read the original.