It took about six years of annual asset reviews with my financial planner, Joe Mackey, to confront a big question. After I spent my entire adult life trying to save enough to quit working by 65, Mr. Mackey wanted to know what my rush was.

“Do you even think you’ll want to retire?” I’m a 42-year-old writer with a job offering travel, intellectual grist and social connection. With few hobbies and an allergy for sitting still, it’s fair to assume my view of a comfortable retirement includes more work than quit. Maybe I’ll deliver...