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Jorge -
There are scores of factors to consider and these are determined by the context and nature of the project itself. You've certainly identified a common one which is underestimated, but others include: - availability of funding and people when the project needs them - impact of other projects and operations activities on the project - external influences and events Kiron
Jorge,
if we look at main reasons why projects fail, we may have a hint what we lacked in planning for it. For example, if missing executive support is a frequent reason for failure, it is certainly that the project setup missed to analyse the support and define actions to improve it. Stakeholder management often is done downstream or horizontal but less upstream, though this is very important. Or if scope creep is another root cause for failure, there is a gap in planning for scope management, scope change handling, maybe requirements identification, scope control. Thomas 
Network:775
Two I encounter regularly are the difference between stretch-goals and unrealistic expectations, and managing the transition between preliminary design and detail design.
Stretch goals challenge the team and even if you don't quite reach them, you are likely to achieve more than a plan with zero risk. If you set the goals too high however, people can feel they are set up to fail. That can demoralize the team, and people let it fail because they have no personal investment in the outcome. It's already doomed. The transition issue is also a common source of disruption. Early in the project we can experiment with many things, and it can be a fun time without being constrained by formal processes and due dates. As we approach delivery, we become more concerned with repeatable processes, requirements verification, release schedules, and the processes become more formal. Transitioning from less to more formal project management without stifling creativity can be very challenging as we have to manage changing expectations within the team.
Planning how to run faster than your stakeholders when things go wrong...Happy new year!
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