Thinking back to childhood, there were those who lined up their crayons, organized them by color, and sharpened them in that crayon sharpener in the back of the crayon box before ever touching crayon to paper. And then there were those who had crayons flung everywhere, mixed old and new crayons together, and basically worked in total anarchy.
The former grew up to be designers who start a project with a focused plan of attack and a perfectly structured workspace from the moment they open Photoshop. All their palettes, toolboxes, and grids are in perfect position before they put a single pixel on their PSD. They've already thought through the design and know what they'll do. They are generals, armed with strategy and schematics, to face down and conquer a design. There is a benefit to working this way. As this article from Do Your Best Work states:
Organization is in part about being prepared for the moment when insight strikes. It's about creating the conditions for creativity to flourish, so that when you enter into creation mode, your physical world is set up to support you. Being organized also creates the mental order that many people need to be able to put aside mundane things and enter a creative head-space.
The latter became designers who open Photoshop and face the blank canvas head on. Perhaps with some wireframes in hand and general directions from a client, but otherwise not knowing exactly what they're going to do. Those people are hitchhikers, knowing they have a destination, but not knowing how they'll get there, or what they'll come across along the way. Mike Kus's blog post "Web Design Is A Journey" about his redesign of Carsonified illustrates this beautifully. The designs at each stage of his redesign are drastically different, with ideas going in all kinds of directions.
Malcolm Gladwell says here about working in this kind of chaos:
Anyone who is in a creative space...you have to reverse the normal human tendency, which is to edit. Creative people...their brains are messy. Their imaginations are messy. Why, because they don't want to throw anything out...they believe on some level that there is always something of interest or value in whatever they encounter. They know enough about how mysterious and serendipitous and unpredictable the creative process is that they realize that it's dangerous to kind of make too hasty a judgment about the value of anything that they come across...
Embracing of messiness and understanding its contribution to the creative process is something that writers and creative types, artists, whatever have got to cultivate, have to learn to be comfortable with. Because it goes against a lot of our kind of instincts and training as kind of educated people.
So where do you fall on the spectrum?
And here's my double dog dare. It's the same challenge an art professor once gave to my class: for your next project, work in the completely opposite way you normally would. Get outside your comfort zone and see what new and different design solutions you come up with when you approach the work from a different perspective.
And then come back and tell us how it went! :)