Patterns of Enterprise Application Architecture by Martin Fowler helped me make the jump from small systems built for myself to large, sophisticated systems built for others.
The Mythical Man Month by Fred Brooks really helped me learn to think about large projects from a personnel and planning perspective. There are some ideas there that have become part of the CS canon; "no silver bullet" and the slightly sexist but accurate metaphor for throwing more people at an overdue project, "nine women can't make a baby in one month." The Mythical Man Month was written in 1975, but it holds up remarkably well.
The Mythical Man Month by Fred Brooks really helped me learn to think about large projects from a personnel and planning perspective. There are some ideas there that have become part of the CS canon; "no silver bullet" and the slightly sexist but accurate metaphor for throwing more people at an overdue project, "nine women can't make a baby in one month." The Mythical Man Month was written in 1975, but it holds up remarkably well.