Then the regional migrant education program got computers and needed help. I trained myself and took a few courses and my knowledge grew as the equipment list grew. The biggest single help to learning the computers was my willingness to forego a new car for the purchase of a nearly top of the line system to learn on at home. Deadlines are the killers. Applications for grants and contracts and user requests that don't allow for the time needed to get the information out.
New software can be tough.
User training can be a challenge. That can ease the pain at times. Communication seems to be the toughest part of any job. Knowing what people mean as opposed to what they say. Knowing why they say what they say and what they feel is really important is all very tough.