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This isn't something I necessarily associate with design. Do you find that it's more common for a designer to express this kind of "defensive pessimism"?
Personality affects the ways we communicate, that's for sure, despite being a designer or not. In this article @AndyBudd recognizes a pattern across his experience. Designers ask questions to themselves and to others to solve problems. Sometimes they could be uncomfortable to answer because there's no data or evidence for it to happen, consequently opening doors that were not considered before.
Only thing I know is that answers come from research, tries and fails, the infinite feedback loop... A process that is commonly under evaluated.
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