This is what I'm referring to...
Example 1: Having a particular career in mind for your future, and doing everything you need to do to get there. Sometimes the outcome is happy, and sometimes not. But in an educational system like the one I grew up in (sure, let's pick on it, why not?), you're encouraged to pick a career and do everything you need to get there. This is all before you even know what having that career really entails. Again, sometimes the outcome is happy: someone chose a career, drew out the path, went for it, and they enjoy their career. Other times people are displeased with their premature decisions and either start over or remain miserable out of inertia. I'm calling the end point of getting the career "making it", and the journey "faking it". We have an end in sight, and we just do what we're told we're supposed to do to get there. We presumably don't know better. We may even question why we have to do some of the things we're told to do (eg. the necessity of electives in university), but we are told to just do it... to "fake it till we make it".
Example 2: A romantic relationship where one person has decided that he or she /wants/ to be with a specific other person (or kind of person), and concedes at every turn so as to avoid dealing with all of the problems in the relationship. So, "making it" refers to having a long and happy relationship with this person, and the "faking it" refers to how he/she just goes through the motions to keep the relationship from falling apart. The truth is, in a relationship (romantic or otherwise), to be genuinely happy, you need to be honest, and you can't "fake it". So, "faking it till you make it" fails in relationships.
Now with respect to math and physics in high school,"faking it" was doing all of the homework (lots of practice) without fully understanding the bigger picture. It can be useful for homework: "faking it" (doing all of the calculations without the understanding the theory behind it) enough times actually did help students eventually understand the concepts behind what they were doing.
So clearly, the blind guiding principle of "faking it till making it" is not always bad. There is a lot of good that may come from it. In the case of homework, it helped students develop their skills to grasp deeper concepts. In the case of getting a career, it gets you to your career. And in the case of the relationship, it helps you keep it. But! the problem in the latter 2 cases was that the end point was reached, but happiness wasn't guaranteed. If you made it to the end and wound up not being happy, then you'd have to either start anew or remain unhappy. It's in times like this (where I've reached a goal and realized that it wasn't what I wanted) that I regretted ever aiming for it. I begin to regret having done all of the things (making all of the sacrifices) that got me to that end. I begin to ask myself if I'm happy that I even did these things and question if the memories of these things make the goal worthwhile in spite of the fact that the end-point turned out to mean nothing to me. Or would I have been happier if I had not even tried? ...if I had been skeptical of what I was told I was supposed to do, questioned what I was doing BEFORE I reached the end... what if?
There were also many times when I did hesitate. I didn't do what I was told; I didn't act on blind faith. I didn't trust the advice of whoever it was that was "guiding me". And in retrospect I saw that if I had just shut up and done what I was told, I would have been able to reap the rewards of my obedience. I would have come to see the wisdom in their advice. ... And then there were other times when my insolence was vindicated.
So when I said "but not even he made it. I don't think some things ever become clearer.", I was saying... =D
[Note: the above two examples were provided for illustrative purposes only. Any number of examples could have been used.]