my wife accuses me of being far too analytical in the planning (mostly for spreadsheets listing airline/car options into and out of various airports at or near the destination), and far too schedule-driven during the actual trip (mostly in terms of being compulsively early)
however ... we always talk thru the travel options objectively before settling on at least the basics of the itinerary, and we always wind up scaling back my ambitious theoretical "well we could do X, Y, Z, W, and Q" to "X, Q, Z, and maybe we can think about Y"; while I freely admit that I do push for early starts, the often-unforeseen good consequence of an early start is extra time before the plane or train departs (or en route when driving)
and after the fact (we're in our 34th year of traveling together), there have been few if any complaints, and many good memories of "oh-by-the-way" serendipities