On my first day I literally walk across the city, to the extent it can be done…The next day I do another cross town walk, but in a different direction, filling in the blanks from the prior day’s walk.
Then, over the next week(s), I walk between 10 to 20 miles per day, picking and choosing from what I have seen before, highlighting what I like, what I want to know more about, refining the path, till by the end of my trip, I have a daily route that is roughly the same.
While that is certainly not the most efficient way to see a city, it is the most pleasant, insightful, and human. I don’t think you can know a place unless you walk it, because it isn’t about distance, but about content.
Learning to design is, first of all, learning to see. Designers see more, and more precisely. This is a blessing and a curse—once we have learned to see design, both good and bad, we cannot un-see. The downside is that the more you learn to see, the more you lose your “common” eye, the eye you design for. This can be frustrating for us designers when we work for a customer with a bad eye and strong opinions. But this is no justification for designer arrogance or eye-rolling. Part of our job is to make the invisible visible, to clearly express what we see, feel and do. You can’t expect to sell what you can’t explain.
This is why excellent designers do not just develop a sharper eye. They try to keep their ability to see things as a customer would. You need a design eye to design, and a non-designer eye to feel what you designed.