Congrats to LW for doing what he has to date. Some thoughts:

That old-school Catholic school mindset takes that concept of Original Sin and translates it to a concept of Original Incompetence. I know of no one who emerges from Catholic schooling without deep psychic scars, unless they remain a "true believer" and buy into the whole schtick. IF LW can udnerstand the inherent and fundamental flaw of that presumption of "original incompetence" (which may take some time with a therapist to sort out, at some point) he can move on to place his Catholic history firmly in the past.

Professional curricula are not designed to be inherently pleasant, and the bloodbath of professional graduate programs post-liberal arts education is frequently a cold shower. Professional schooling is a bit Darwinian, and as such, is frequently rude, crude and not always accurate. That said, LW got through. that, frankly, is a success.

Passing licensure exams is another Darwinian technique, and the issue is to not take it personally. In fact, my own approach towards my own licensure exam was to plan to take it for the first time "for fun" to understand what it was and how it worked. As it happened, that relaxed me enough to allow me to pass. Providentially. The licensure process in my profession (architecture) is as Draconian as law, involving, now, seven tests. IF you fail any one section more than three times, ya get to start alllllll over... and some folks do.

Once you have your bar, and you will, if not the first time, the second, your credentials in the marketplace will include your degree, your bar success and - your drive to succeed and your willingness to pursue a course of action with drive and persistence. In one of my old roles, I used to review resumes and conduct interviews; your "story" would tell me of your persistence, your focus, and your work ethic. That, to me, would be far, far more important than your grade average. In fact, in ten years of interviewing folks, I NEVER asked for a GPA. What was relevent to me was the personality, values and goals of the individual sitting in front of me. Is he/she focused? Willing to learn? clear about what they already do/don't know? Those are far, far more important than having a 3.8 GPA from a prestigeous school (I note that I DID graduate with the highest GPA from my school in my major, from a small southern school known for its academic rigor. No one has ever asked me about that whilst searching for a job, and frankly, mentioning it would be pretentious.)

Once LW has his bar exam well in hand, first time or second, then the issue will be to define what "success" is.. and that can be a moving target. Is it finding a nice niche in corporate America as part of a corporate law group? Busting your ass at 90 hours a week to achieve partner at an elite law firm that is willing to take you on/ (because of your drive)? Working for a socially conscious group activating change?

I would suggest to LW that, if he chooses to operate within the confines of that old Catholic mindset of "original incompetence", he will never define success in terms that he can reach. As an alternative, I would suggest that he define success as achieving passing the bar in three shots or less, and that he then also focus on what would be the most meaningful venue for his professional involvement. Whatever that choice is, I can guarantee that it will not satisfy the nuns......