My engineering career didn't provide any formal insight into the history and timeline of events that led to were software, and software companies are today. I never had a history of software subject, but I remember enjoying when some teacher would go out topic into historical anecdotes about when a technology appeared.
That's why I bought From Airline Reservations to Sonic the Hedgedog: A history of the software industry. Yeah a history book with a long title about the IT Industry, but it turned out to be really good reading.
It follows a business perspective, that might be a bit dense at times, but it's worth it. It starts with military software projects in the fifties, sage, sabre, fortran, cobol, and goes on until middle of the nineties. It covers software contractors, corporate business software, as well as retail mass market products, including a chapter dedicated to the video game industry.
It's good to learn how software companies and products were born and died, what were the strategies, revenues and historical contexts for the companies that shaped today's software industry landscape.