This mishnah, according to our numbering mishnah 6 in chapter 2 (and in other editions mishnah 5), contains several separate ideas that Hillel taught. We will go through them in order.
"Ein bor yerei cheit":
The word "bor" is used in other contexts to describe land that has not been worked, virgin soil. Once it has been plowed it is called "nir," but as long as it lies in its wildness and does its own thing it is called "bor." Here the mishnah is speaking about a person who is a bor - an uncultivated person, who is missing two dimensions:
According to the Bartenura: he has no Torah and no wisdom, he has not cultivated his mind; and he is also not engaged in derech eretz, meaning he is not occupied with earning a living and is not involved in human interactions and everyday commerce.
According to the Rambam: the two things he is missing are Torah and good character traits - that is, he has not developed his character at all.
As a result he has no manners and no social skills. Whether he is supported by others or lives in the bushes makes no difference: since he has developed neither his intellect nor even the basics of human relationships, he cannot be a person who fears sin. Had he worked in a grocery store, he would have understood what it means that your word is your word, to treat people pleasantly and not to cheat anyone. But he has none of this, and therefore he simply cannot be someone who fears sin.
"Yerei cheit" translates roughly as a good person, someone capable of doing the right thing. The bor is incapable of this, because he is entirely uncultivated: he does not understand what is right and what is not right, and he has no intuition in the matter, since he is not involved. If he were at least engaged in derech eretz and in honest work, he would understand the way of the world, and that alone would teach him enough not to be a bad person.
"V'lo am ha'aretz chassid":
This part deals with a level higher up. The am ha'aretz is also unrefined, but he is nothing like the bor: he has derech eretz, he has a job and he earns his living honestly, he is simply not learned (and likewise according to the Rambam - he has good character traits and a good character, but he is not learned). Such a person can certainly be a person who fears sin and a good person.
But a "chassid," a term that is hard to translate precisely, is one who goes above and beyond - a devoted person who is on an entirely different level. This is not an obligation and not a requirement, but a person is entitled to aspire to spiritual greatness. However, without a Torah understanding of the fine points of what the law is, what is right and what is not right and how things are supposed to work, it is impossible to be a chassid at all.
The basis for this is the principle that one who is commanded and does is greater than one who is not commanded and does. A person who does something not because he was commanded but because he wanted to, even though he did a good thing, receives less reward than one who is commanded and does - one who fulfills a command of the Holy One, Blessed be He, as an expression of being commanded. This seems counterintuitive: seemingly, someone who needs to be commanded is a "less good person" than one who does it of his own free will and out of his own intuition.
But there are people who were simply born nice fellows. Doing the right thing because you feel like doing it is simply you being you - there is nothing wrong with that, but there is also nothing particularly impressive about it. What is impressive, as far as the Torah is concerned, is using the power of choice to confront the urges not to do the right thing and to overcome them. There has to be an urge that says you would like to do this, and you answer it: do not do it, do something else - and you listen to that.
Therefore it is impossible to reach the level of a chassid without first understanding what the parameters of halachah are: what you are required to do, what is expected of you, what it means precisely to be honest in business, what it means precisely not to take interest, what it means precisely to keep Shabbos. Only then can you choose. You are not obligated to go beyond the letter of the law, but if you have decided that out of love of people you will fulfill "v'ahavta l're'acha kamocha," or that out of love of Hashem you will fulfill the mitzvah of loving Hashem, and therefore, even though it is not an obligation, you want to go beyond it and be especially careful or especially stringent in a particular area - you must know the parameters. Without them it is impossible to be stringent, and therefore it is impossible to be a chassid.
"V'lo habayshan lomeid": - and a bashful person does not learn.
The next pair Hillel focuses on relates to learning. The basic assumption of effective education in a Jewish context is not simply receiving information, but asking questions that expose what is unclear and receiving good answers. That is why the Mishnah says that a bashful person cannot learn properly.
Ordinarily we say that a sense of shame is a great virtue. The Jewish people are described as bashful, as modest people, and also as merciful and doers of kindness. A person should be bashful and possess a sense of shame - but not in the context of the classroom and of learning. There he must not be embarrassed or hesitant to ask questions, and he must admit that he does not understand something. Anyone who finds this difficult must push past himself, because if he does not ask the questions he needs to ask, he will remain stuck in uncertainty forever and will never learn.
One point worth highlighting: in the previous Mishnah we discussed Hillel's extreme humility, and shame must not be confused with humility. What is shame? Shame means disgrace, which is different from embarrassment. It means that in your own mind you expect yourself to be held in one place, while your actions are in a lower place, and that gap is what produces shame. Its source is in the opening narratives of Bereishis, with Adam and Chavah, who were ashamed after their sin.
Very often it is precisely the most socially inhibited person who is not humble at all, but the opposite:
The bashful person: he thinks of himself as a five out of ten, but the image he presents to the world is a nine out of ten. Hence the inhibition: he does not want people to realize that he is not everything he wants them to think he is.
The humble person: the humble person is one who knows what he is and what he is not. He says: these are my abilities, I am a five out of ten, and if you discover that, it is no revelation, since I admit it myself. I have nothing to hide.
The bashful person is afraid to reveal what he does not know, lest people think he is slow to grasp things, that he was not paying attention, or that he is disrespectful. This is not good, and he must overcome it: learn to be brave, ask when something is not clear, and not worry that the rabbi is too great and important to approach, or that people will laugh at him. None of that - you have to be brave and ask your questions.
"V'lo hakapdan melameid": - and a strict, exacting person cannot teach.
A kapdan is someone who is strict, exacting and demanding, and he cannot be an effective teacher, because that very sharpness creates a pressure that stops people from asking questions. Interestingly, in Shabbos 31 it says that a person should be humble like Hillel and not exacting like Shammai - and here it is precisely Hillel who teaches that this trait prevents a person from being an effective teacher.
In a classroom setting I have seen this many times: there are clever, sharp-witted teachers who fire off cutting remarks, and the children love it and it keeps them engaged. It is quite an effective tool for many children; they laugh and admire the clever, quick rabbi who puts people in their place. I once had a rebbi who used to say: "There is no such thing as a stupid question, only a stupid person" - and a statement like that obviously does not encourage asking questions.
But that is only half the class. The other half is held back and afraid, and does not feel comfortable being on the receiving end of those cutting remarks. So they retreat to the back of the classroom, they are not engaged and they do not learn. It is important for a teacher to be aware not only of the children he is succeeding in reaching, but also of the children he is pushing away - and that is a serious failure.
That is why the Mishnah says that a teacher must not be a kapdan: he should have all the time in the world for a student, and be patient with what look to him like stupid questions, understanding that people find things hard. Perhaps it was not as clear as it seemed to him, or the matter is not as easy as he thinks. And as with everything, the answer to any question is obvious once you know the answer. A teacher must encourage questions and invite them rather than suppress them, and be kind, patient and accepting - not exacting, demanding or impatient.
"V'lo kol hamarbeh bischorah machkim": - and not everyone who engages excessively in business becomes wise.
Someone who throws himself into commerce and business without limit cannot become wise. The idea here is that a person who is heavily involved in business lacks two things that Torah study requires:
Time: the raw number of hours. It takes time to master Torah and the mesorah, and when the active businessman's time is divided, he is left with less time to learn and will not arrive where he needs to arrive.
Concentration: the active businessman's head is somewhere else. He is sitting in the beis midrash, but his mind is on the shipment, the supply, the taxes and the tax strategy.
This point should speak to us directly, whether or not a person is a big businessman. When you sit and learn, you have to be what the verse "adam ki yamus ba'ohel" - "a man who dies in a tent" - demands: to be like a dead man with respect to the world. You have to concentrate and say: I am now sitting to hear a shiur, it will take thirty minutes, I am shutting off my phone and putting it away, and I am not thinking about the weather, about sports, about emails or about what I have to do when I walk out. No and no - I am present, I am here.
This is true about everything. People love to multitask, two or three things at once, but it is a wasted effort: it is not more efficient, it is less efficient. When you are using your mind, do one thing at a time and do it as well as you can. While you are learning you cannot be distracted: shut off the phone, put it on airplane mode and put it away. And if you cannot get through the whole seder without checking it, check it once an hour on the hour - but between those times be engaged, focused and present, because understanding something as difficult as Torah demands an attention span and concentration.
"U'vamakom she'ein anashim hishtadel lihyos ish": - and in a place where there are no men, strive to be a man.
Hillel is speaking here about a very common phenomenon: the good, humble, modest fellows notice something lacking in the shul, in the community, in the school, in the classroom or at home, and they say, "Somebody really ought to do something about this," and immediately add, "But who am I to do it?" To this Hillel says: if nobody else is doing it - make the effort. Maybe you are up to the task and maybe you are not; you will never know until you try, and it will make you grow. Do the best you can and do not be afraid, and do not say "Who am I?" The answer is that you thought of the idea, you see that it is a problem, and so it is yours: you have to do what you are able to do and not hesitate.
Interestingly, the English word for taking on a leadership role that was not given to you, as if without permission, is "to arrogate," and it is etymologically related to the word "arrogant" - thinking you are better than you really are. The point of the Mishnah here is that one should not be afraid of what is called yuhara, of holding oneself with yuhara, that is, appearing haughty because you took something that you do not feel is really yours to take. Do not do that: you should not be worried about how you look and about what you are, but about the goal that matters. And as Rav Noach used to define an anav: humble means that what is significant is what is important to me. Therefore, if it is the right thing to do - do it, and do not worry about what people will say.
There is an important conclusion here, which is even brought as halachah in the Mishnah Berurah: if there are people already doing the job, and you simply think you could do it better - that is a shame, unless what they are doing is incorrect, or bad, or harmful. In such a case you should let the existing leadership do its thing, keep a low profile, develop yourself and focus on yourself. The time will come when you will be able to let all your light shine, but when somebody is already there, you have no right and no need to overshadow him and take his place.
In summary: in this Mishnah we learned that the bur, who has neither Torah nor derech eretz (or good middos), cannot be a yerei cheit; the am ha'aretz, who has integrity but no learning, cannot be a chassid, since chassidus requires knowing the parameters; the bashful person does not learn, and therefore one must distinguish between embarrassment and humility and overcome the fear of asking; the short-tempered person does not teach, and the teacher must patiently invite questions; the one immersed in business does not become wise, because of lack of time and lack of concentration, and from here comes the obligation to be present while learning; and in a place where there are no men - strive to be a man, provided that there is nobody there already doing the job.