Leadership is often very difficult. This may be attributed to a host of factors, including:

• Leadership decisions may involve a struggle with morality
• The easy/cheap/quick path (of least resistance) is often not the right one
• Many decisions reside in a gray area: there are no clear cut correct answers
• There will either not be enough ideas on how to proceed or there will be too many ideas. If the former, need to figure out how to stimulate more; if the latter, need to be able to sift through and find the diamonds in the rough
• Decisions must be made without all the facts
• It's necessary to be nice to people you may genuinely dislike
• It may be necessary to be careful when the first instinct is to be impulsive
• It may be necessary to be composed when the inclination is to scream
• It may be necessary to commit when it is easier to waffle, procrastinate, or "pass the buck"
• It may be necessary to say "no" to an unhappy audience
• Leadership requires an understanding of the difference between authority and responsibility. With authority comes responsibility. The former can be delegated, but the latter cannot.
• Leadership is not just a group act. In fact, the most fundamental version of leadership is a solitary act: leading self – making personal decisions. A person who is not sufficiently self aware to lead himself, will find it much harder to make decisions for others
• Leadership is a lonely act. It’s lonely at the top. This is the case even more so when leading others, because the burden of leadership is that much greater, and the number of unaffiliated people to whom one can vent or from whom one can seek advice is relatively smaller
• There may be a lack of appreciation for the leader's efforts and sacrifices
• There may be lack of support from the leader's superiors
• There may be prejudgment from a whole slew of observers, including the media
• Expectations may be too high to meet; a leader may be (unrealistically) expected to be perfect
• The situation may be doomed to failure for a number of factors, including lack of appropriate resources, lack of support infrastructure, lack of interest by stakeholders, lack of commitment by participants
• Regardless of the decision and its objective quality or necessity, it may make some people unhappy
• Risks may be unbounded, leaving a lot of potential downside
• A leader may not be allowed the time to learn from mistakes or introspect after setbacks
• A leader may be unsettling an entrenched bureaucracy, eager to defend its turf
• A leader must unite people with disparate ideas and agendas