I've been enjoying the philosophy articles on Aish.com. The approach to life resonates with me much more than the Western style of consumerism and media hype. Regarding the obligatory nature of mitzvot, however, I think sometimes humans have to disregard the boundary and be disobedient against the command. It might be painful, but I believe you come away with a higher appreciation that God and His commands are ultimately correct. Do you agree with this thinking?

You have touched on a deep truth, but ultimately your principle is mistaken. The Talmud states: "In a place where a reformed sinner stands, even a righteous tzaddik does not stand." The idea is that after having erred, you can analyze your negative acts, learn from them, and use that knowledge as a foundation to motivate you further.

While all this seems to imply that it is better to make mistakes and then correct them, rather than never have made the mistake in the first place, that is not true.

Let's take the mundane example of the rule: "Always look both ways before crossing the street." There are two ways to learn this lesson: 1) Listen to the advice of teachers and parents to look both ways before crossing, or 2) cross recklessly, get hit by a car, and then while lying in the hospital acknowledge a lesson well-learned.

The problem in choosing the second path is that there is always a residual effect from our mistakes. A teenager who experiments with drugs may grow up to realize the dangers, but a lot of brain cells have been killed in the meantime.

There is one other danger: That the person will never correct their mistake. The child who recklessly crossed the street may be killed in the process, or the teenager who experiments with drugs may wind up in an advanced stage of addiction.

We human beings like to basically think of ourselves as independent. We have a built-in resistance to authority, and have a difficult time acknowledging that we need someone else's information.

The great kabbalist the Arizal explains that was the mistake of Adam and Eve - and look how much it cost us. In the Garden of Eden, the Snake argued that by eating from the forbidden fruit they would taste the flavor of evil, reject it, and then achieve a new level of holiness!

Nobody builds a skyscraper without expert advice and a plan. But "life" is much more complicated than constructing a building or performing surgery. You'd never dream of using trial and error in the operating room. So why do so with your personal life?

Many people would rather make their own mistakes, then learn from those who have already made them. We think we can learn everything by ourselves. We imagine we can get married, raise children, and live a meaningful life - "figuring it all out" as we go along!

Life is too short for this. We're bound to make mistakes; why add those we could otherwise prevent? Instead, Judaism teaches us to seek out people who truly possess wisdom. Hang around them, and bring a whole list of questions to ask them at every possible opportunity. On the wisdom scale, you can achieve in a few years what might otherwise take a lifetime.

The Talmud says that we are to give particular honor to two types of people: an elderly person, and a Torah scholar. What they both have in common is wisdom. The elderly person by virtue of life experience, and the Torah scholar by having absorbed the deep wisdom contained in Torah books. Note that they have both attained wisdom, but the Torah scholar can do so in a fraction of the time - and without suffering the many bumps and bruises along the way.