Left behind while standing still
As Ray Croc said, "When you're green your growing. When you're ripe, you rot." This speaks directly to the first point of being married to a technology for too long. Too many folks without a strong business and finance background simply don't understand the concept of sunk costs. What you've already spent is a fraction of the costs of continuing to use a tool or technology that doesn't provide value. Experiment to find better solutions. Test those solutions regularly and ask the question, "Is there something out there that will do this better?" If you stop moving forward, the rest of the world will pass you by and you'll end up behind. IT has got to learn how to become the technology leader and trusted advisor within the enterprise.