I'm not sure which is worse - giving advice when you're not asked to or failing to ask advice when one could really benefit from it. In truth, each option leads to a perilous path.
I once asked my mother for the best piece of general advice she could give me. She responded, "Learn to listen to your instinct." I then asked my father the same question and he responded, "Learn to listen to your mother." I found both pieces of advice helpful, but difficult.
The thing about advice is that smart people don't need it and fools won't take it. Some people are born leaders and have managed to find the synthesis. They are neither afraid to ask for help and guidance, nor afraid to make uncomfortable decisions on their own, when necessary.
A story is told about President Lincoln who was conducting a cabinet meeting. I don't remember what the issue was, but "Honest Abe" polled each one of his cabinet members, all who voted nay. President Lincoln then said, "Well, I'm going to do it anyway, and it's unanimous." He sought advice, respecting the presence and positions of his cabinet members, but had the inner strength to trust his instinct to do what he felt best.
So when does a person get to the point when he can trust his instinct, go with his gut, and eschew advice? The answer once again is a hybrid. Trusting one's inner instinct does not preclude soliciting advice. In fact, I would argue that seeking counsel helps one develop his inner core and self trust. The self-confidence displayed to initially seek guidance is the same self-confidence that allows one to ultimately develop, and then trust, one's own instinct. But, there is a caveat.
One needs to know from whom to ask advice in particular situations. It's entirely possible and most probable that advice in one area from "person A" is not to be extrapolated to another area. Having different people at our disposal who have enjoyed success in different areas is the preferred path. How rare is it that we find one person who is a master at all trades. We must only seek advice from someone who has our best interest at heart, someone who knows us, so that we can build upon that advice, ingest it, and make it part of our conscience, so that future decisions we make on our own will reflect that advice. That is how we develop trust in ourselves.
Our goal is not to make us dependent on our "gurus," but to extrapolate and apply from their teachings. We, in turn, and in a similar fashion, give advice and guidance to our children, not to make them dependent on us forever, but to help them develop trust in themselves. The advice we give them, therefore, must be to make them feel better, and not necessarily to calm our own anxieties. A formidable task but one that is necessary if we ever want them to make responsible decisions on their own.
When we make decisions for our children that they should be making themselves (choice of a spouse), too often, disaster ensues. When we fail to advise them when we should be advising them (once again, choice of a spouse), disaster results. After all, the decision on whom would be a suitable spouse, a decision which should be guided by level-headedness and reason, is usually made at a time when the person is "madly in love," which is an emotion that bespeaks the height of irrationality. As a lawyer practicing matrimonial law, I have seen marriages fall apart because parents gave too much advice, and marriages ultimately fall apart because parents were absent while their 19-year-old was making the most important decision of his or her life.
We tend to live for the moment, often ignoring advice or warning signs about the future. Except for the "five-day forecast," we rarely alter our schedule or plans by what those forces (G-d) and those instructions (the Torah) warn us about. So let me share with you how two great Sages "reacted" to the advice given to us by our Torah as to how we are to conduct ourselves relative to our positions.
I had the privilege of knowing two great Torah scholars and find it so interesting that their actions, as revealed in the following vignette, reflect so aptly their distinct personalities.
Both Rav Shimon Schwab zt"l (Washington Heights) and Rabbi Yaakov Ruderman zt"l (Ner Israel, Baltimore) made a practice to have their hair cut far away from the Jewish communities where they respectively resided. When asked, Rav Schwab explained that were he to get his hair cut in the Jewish community where he lived, perhaps other Jews would walk in and see the Rav without a yarmulke on. This, Rav Schwab reasoned, would be a diminution of Kavod Harav, respect for the rabbinate. The Torah is very clear as to its instructions regarding Kavod Harav.
Rav Ruderman also received his haircuts far from the Jewish community of Baltimore, but for an entirely different reason. Rav Ruderman was concerned that if he received his haircuts in the Jewish side of town, perhaps a non-observant Jew would be sitting in the chair next to him, getting a haircut and having his sideburns cut in a manner which violated Halacha. Rav Ruderman, who was known for his sagely advice particularized to the individual, was worried that he, Rav Ruderman, would break down and cry witnessing a Jew who was violating, perhaps out of ignorance, one of G-d's commandments.
Giving instructions, taking instructions and just as important, dealing with others who don't necessarily follow instructions, is advice worth following.