Add age about 38, I morphed my career from being a builder into being a software engineer.
For 16 or 17 years I was a full time IT contractor and therefore moved fairly regularly from company to company. From the client's point of view, taking on computer contractors is a phenomenally expensive exercise, and it is therefore only the largest and most well-heeled companies who can afford to do that!
In my time as a contractor, I worked for some of the biggest names in British, Belgian, Dutch and Luxembourgish industry and commerce. Based on that experience, I think I can safely say that most companies are pretty appallingly badly managed however some stand out as examples of just how excruciatingly poor management decisions can be.
I'm not going to mention any names except to say that the company I'm talking about are a household name in the United Kingdom. They employed a director responsible for IT who was an enormous enthusiast for Unix; preferring it to windows even as a desktop client. At the time the company in question was using a mainframe for data crunching operations and this IT director thought that an outmoded platform. He decided pretty much unilaterally the the way forward was to port all the code that currently ran on the mainframe to Unix server boxes and to replace all the PC's that currently sat on the hundreds of desks throughout the company's offices with some workstations running Unix.
At a cost of £ millions, he ordered the purchase of the necessary hardware and recruited a team of analysts and programmers to port the mainframe codebase to a programming language that would run on Unix servers. The job was estimated to take a couple of years after which the mainframe could be finally shut down. Three years later, the work was nowhere near finished and after five years serious questions were being asked! At around this time, The IT director responsible decided that it was time for a career move and left the company for a similar position in another company. This debacle had already cost the company £ millions and the board of directors together with the new IT director decided that it was a lost cause and cancelled the entire project. The Sun workstations that had been purchased to replace the windows PC's on every single desk in the company were sold off at a massive loss to the staff themselves.