Some thoughts on being a teacher:
1) Know what you are teaching really well for yourself, not only the territory, but how you got into the territory, and how to tell other people how to get into that territory, and have enough exposure to how other people got into the territory so that you can deal with variations in tendencies, proclivities, approaches, paradigms, abilities, personalities, etc.
2) Know enough of the standard dogmas to deal with people who are coming from that place so that you can address them from where they are. This usually requires a few thousand pages of reading at least. I am not saying you have to be a scholar, but the amount of textual and traditional stuff that people will come at you with is very large, and if you know the basics of where they are coming from and the context for those texts, it is a lot easier.
3) Have had a broad enough set of experiences of the territory you teach so that you can deal with the wide range of how this stuff can present. For instance, how the stages of insight can present given a range of levels of concentration and tendencies, as well as the samatha jhanas, some smattering of the powers at least, as well as a good, solid grounding in basic morality, relationships, work issues, and dharma in daily life topics.
4) Teach only what you know: this is harder than it sounds. In that same vein: acknowledge your strengths and limitations.
5) Learn everything you can about the psychological concepts of transference and counter-transference, as well as the basics of the personality disorders and enough psych 101 and 201 and perhaps 301 to deal with all the surrounding junk that adds complexity and sometimes danger to personal relationships, as teaching the dharma is very personal and is thick with this stuff. Beware at all times the amazing tendency of people (that means you and me and all other dharma teachers and students) to get caught in the transference: this is harder than it sounds also and requires constant work.
6) Keep the company of other friends who are good practitioners and teachers and talk with them regularly and honestly about your thoughts on the dharma, your own practice, teaching, your relationships with students, and the rest: external reference points help a lot to keep us real and down-to-earth. Dharma should be a team sport, and teaching even more so.
7) On that front, keep it real and down-to-earth.
8) Avoid the perennial temptations surrounding exploiting people regarding money, power, sex, drugs and the like: these bring down meditation teachers with great regularity, even those who think they are being careful. Attempting to make a living as a dharma teacher is a very complex topic, as trying to figure out how to make enough money from people either puts a large burden on a few people, which would seem artificial given how much good, free dharma there is out there, or a smaller burden on a lot of people, which nearly always results in watered-down dharma to make it palatable for mass appeal so that you have enough students to pay your rent: this is such a perennial trap as to be nearly universal, and the amount of fluff dharma out there so that people teaching it don't have to have day jobs is a tragedy. Making a living as a dharma teacher gets much harder if you want to support a family, send kids to college, pay for the health care of aging parents, etc., so realize that this is much, much, much more complex that it initially sounds, particularly as our expenses go up, which they tend to in our middle years. There are a few people who are doing this well, so make sure you have some long conversations with them about all the pros and cons before thinking seriously about this.
9) Consider limiting teaching until you are at least an anagami with 8 jhanas at least, but way better to be an arahat. The confusions, subtle complexities, fascinations, and the like that surround even anagamis can cause some substantial problems. That said, for getting people to stream entry, a stream enterer will often do, though second path is better, as it gives a wider range of experiences of the stages and related complexities. In that same vein: beware of overestimating your own practice: this is harder than it sounds. Even arahats continue to develop on many fronts, as is only natural.
10) Consider carefully the benefits and downsides of formal lineage or transmission in some order: the clout you gain from formal lineage is often balanced by rules and limitations on presentation, message, context of presentation, and other cultural limitations. Teaching outside a lineage has the opposite set of problems, lack of cultural context, lack of formality, lack of rigor, lack of expectations and norms, lack of logistical and hierarchical support, and so unless you have the vision and energy to create those, you may find that something seems missing or too loose.
11) Do not be afraid to refer people elsewhere to teachers who have more experience than you do if you run into students whose practice, experience or needs are beyond your ability to understand them or meet those needs, which can be a territory issue if you are trying to make a living doing this, particularly if you live in an expensive place. In that same vein, don't be afraid to send people to psychological referrals if they need it also, as there is much psychological baggage and pathology that interacts with dharma teachings.
This is the short list. There is obviously much more to be said on each of these.
Helpful?
Daniel
