‘The only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or say a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars and in the middle you see the blue centerlight pop and everybody goes “Awww!”’.

Contrast that quote by Jack Kerouac with the direction we are given in our everyday work lives to comply. Comply with process. Comply with systems. Comply with approach. Make decisions through committees. Don’t rock the boat.

The motivation for organizational compliance and conformity is obvious; it is hard to scale a business without rules, systems and processes. It makes for an uncomfortable and sometimes unpleasant workplace environment when there is constant disruption and chaos. Without organizational discipline, there can be no systematic output.

But ours is a creative industry. It is one that is constantly being disrupted by technology, by the need for innovation, by competition, and the need to cut through the sometimes deafening noise. And there can be no creation without destruction.

I don’t believe you can be a great digital strategist without being one of the mad ones, the ones that push the boundaries, that ask the difficult questions, that aren’t satisfied with the status quo, and that would rather die of thirst than drink from the cup of mediocrity.

So how do we square the need to be disruptive, to be difficult in order to constantly push the boundaries of creativity and performance with the need to work collaboratively within a broader team?

It all depends on how we define being difficult. Being difficult is not about being a prima donna. It’s not about refusing to comply for the sake of it. It is not about degrading and demeaning others. Being difficult in the context of the work of the digital strategist means never being satisfied with the solutions at hand. It means constantly asking questions about how the work can be done better. It means challenging the groupthink and pushing others to come up with new ideas. Being difficult means creating a platform or a space that allows others to innovate.

It is also necessary to be difficult in this way. Without this, we end up with solutions that look like everyone else’s. We end up with ideas that are safe, risk free, and mediocre. In short, we end up with commodity thinking and output, where the only way to differentiate is to race to the bottom on price. We need to be difficult in order to break this cycle, in order to shake ourselves and our colleagues up, in order to cut through the noise and stand out as an organization.

To do this means standing out as an individual and accepting the inevitable criticism. But as long as you have focused your efforts on challenging the thinking and the solutions rather than the individuals personally, it is criticism that can be handled. And it will reap rewards, for you, for your team, and for the company.

Don’t think this approach can scale? I think Apple would have something to say about that. As their iconic advertising put it:

“Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently. They’re not fond of rules. And they have no respect for the status quo. You can quote them, disagree with them, glorify or vilify them. About the only thing you can’t do is ignore them. Because they change things. They push the human race forward. And while some may see them as the crazy ones, we see genius. Because the people who are crazy enough to think they can change the world, are the ones who do.”

Being crazy. Being mad. Being difficult. We can’t be great without it.

Next week on octopus, we will continue to explore the role of the digital strategist. Please be sure to comment below. I’d love to hear from you. Please subscribe for alerts about new episodes and content. Thank you for listening to octopus. I’m Nasser Sahlool.

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