[Originally posted at brendamichelson.com in May 2017. Moved here 12.23.2020.]
I think best with a marker in my hand. Always have. My workspace, and all paths to and from it, are littered with box and line diagrams, doodles, code snippets, and my (at that moment) best idea ever, on any scrap of paper, notebook or whiteboard within reach.
Quirky, my friends think. But, I’m far from alone. Especially in the software field.
In the wonderful Software Design Decoded, 66 Ways Experts Think, an early section is Experts Sketch.
Experts Externalize Their Thoughts 
Experts sketch when they think. They sketch when alone. They sketch in meetings with colleagues or clients. They sketch when they have no apparent need to sketch. They sketch on paper, on whiteboards, on napkins, in the air. Experts know that sketching is a way to interact with their own thoughts, an opportunity to externalize, to examine, and advance what they have in their minds.
How do experts sketch? Messily, formally and in between. Pressing notation to their advantage, as a tool rather than constraint. Ever been in a room where the model’s notational correctness overtakes the problem (or solution) correctness? Consider these practices:
Experts Use Notations as Lenses, Rather Than Straightjackets 
Experts understand the true value of notations: they serve as lenses to examine a design solution from a particular perspective. Experts are not married to any notation and will use whichever notation best suits the task at hand…
Experts Invent Notations 
Experts choose a notation that suits the problem, even if the notation does not exist. New notations arise when, in the heat of design, shorthand symbols are used that take on a meaning of their own…
An insight that, frankly, was a relief to me: re-drawing is a good thing. Not all repetition falls under that insanity definition adage. Results can differ, for the better:
Experts Repeat Activities 
…Experts draw a diagram, then draw it again, and perhaps again and again. Experts repeat these activities because they know that, each time they do so, they must re-engage with a fresh mindset and re-explain to themselves or to others. Variations in how they engage, think, draw, and communicate, as well as variations in what they choose to focus on, uncover new issues and opportunities.
Experts Change Notation Deliberately 
Experts ask themselves what would happen if they remodeled what they have in a different notation, using somewhat different modeling concepts or somewhat different semantics. Differences in expression can prompt them to consider additional issues.
Beyond sketching, Software Design Decoded covers simplification, non-linearity, collaboration, uncertainty, fear and more.
If you are curious how your practices match with, or can be expanded to, expert levels, pick up this book.
And if you work with a manager that doesn’t get your seemingly random, casual, exploratory approach, drop a copy on their desk.