I think that "boring" is being used here as shorthand for well known and predictable, which are attributes that I would rate highly when developing a platform or trying to work on a novel problem.<p>I believe a contributor to why choosing boring is hard is that often the problem we encounter in software is not new or unique, but may still the be first time a team/company is attempting it. Therefore, unless you know your company has the patience for unforeseen technical difficulties, and that your team has the skillset to overcome any fundamental challenges posed by the technology chosen, even if the technology is a better fit for a problem, it may not be a good match for the organisation.