St. Paul, in a famous passage, talks about all of the things he would do in order to save people -- he would do one thing to save one, and another to save another.
The Orthodox standard is that of a pious ascetic monastic saint, living "the angelic life." Next to that, all of us fall short and miss the mark, so the question is how we pursue our life-long attempt to get there. There is a combination of strictness and mercy that is the hallmark of good Orthodox father-confessors -- strictness in teaching (as strict as the hearer can bear without going into despair), and mercy in forgiving and allowing for shortcomings (in a way that will encourage and give tools to the faithful to do better in the future.)
The starting point that a father-confessor will take is not with do's and don'ts, but rather with laying the groundwork of a life of prayer, from which ever higher levels of ascetical struggle can be built. Trying to do it in the reverse fashion is like starting a building by constructing the roof first.