Is it "Ok" to fail a student?

In the late 70's and early 80's, a movement in parenting and education started which was unofficially called the "Self-Esteem" movement. Basically, the philosophy of this was that in order to be successful at learning, we need to shelter kids from failure in order to boost their self-esteem and make them feel better about themselves, for if we told students they were "not good enough" they would, shut down, tune out, and turn into at-risk kids. Feeling good about oneself, it was argued, was the most important pre-existing condition as a learner, and if we didn't preserve that, we'd turn kids off of learning forever.

This wasn't validated by research. It was basically an opinion that got traction without any data or evidence, but notable figures in education were quick to spew support for this fad as it portrayed them as caring, loving educators. Some notables:

"Self-esteem is more important than test scores," said Mitchell, who became Loren Miller's principal this year. "If we're interested in raising lifelong learners, it's important that . . . we also address the emotional and social sides of children.“

-Principal Loren Miller

"When they don't excel, we say they have potential," Vail said. "You don't cast them out and say, 'You're not good or irresponsible or lazy.' You say, 'You didn't make it this time. Here is the mark we want you to hit and we're going to help you hit it.'

-Principal Michael Vail

Of course when some authority figure says this, people are told to listen. No one knows better about education than the principal, right? Why would we dare question their opinion?

Opinion is not fact. However, it's often claims to be the same. "The World is Flat." "Santa Clause is real." Both opinions that metasized as facts to the gullible, the uneducated and the desperate.
I'm reading a fantastic book right now called "The Self-Esteem Trap-Raising Confident and Compassionate Kids in an Age of Self-Importance" by Polly Young-Eisendrath. She has shown how years of tracking generation X and Y generation kids have produced kids that are lethargic, apathatic, and entitled. The backlash she says is that by shielding kids from failure, we don't teach them how to adapt to it when they finally confront it. By allowing kids to retake tests, make-up projects and raise their grade accordingly, we have created a system where kids don't have to try hard because they'll get a third, fourth and fifth chance. Is that what real life is like?

I think if we're going to raise generations of motivated, autonomous learners, we can't let them play the system. "Yes, Johnny bombed his last test and while I will make every effort to reteach him the material, I will not raise his test score, because at the time the assessment was given, that was the level of his understanding." I've said lines this verbatim to some parents this year and they were shocked that I wouldn't "give" him a better grade. Grades are earned, not given. To this I have answered back "He did very poorly, but let this lesson of failure help him prepare better in the future by taking better notes, reflecting on his learning, asking questions and coming in for help." This, I argued, is was truely raises self-esteem. Want kids to feel better about themselves? Teach them how to do something for themselves. Don't candy-coat their failures.

“Assessments need to be accurate and honest; not inflated”-Tom Schimmer. If that means failing a student to help them overcome adversity, so be it. I've known teachers in the past to arbitrarily change grades right before report cards because they'll say "Janie got an "F" but she seems to have improved, so I'll pull it up to a C-". Janie will then learn that that C- doesn't really mean anything because it's inflated and not indicative of her academic abilities. What will happen to her when she goes to high school and college where grades are cumulative? What happens when she tastes failure in the real-world?

Let them fail now. Let them know what rock bottom feels like, because the only place they can go its up. Especially in middle school where grade point averaging resets every semester. Last semester, I had 10 students get an "F" on their major assessment of the semester. Did they shut down? Of course not! I retaught them the material, but didn't allow them the retest as I wanted them to learn the importance of reviewing, asking for help, etc. By the end of the semester, the number of students who were failing dropped from 10 to 2, and the 2 failing students still did make notable progress with their student skills.

“Having high self-esteem certainly feels good, psychologists say. But, contrary to intuition, it doesn't necessarily pay off in greater academic achievement, less drug abuse, less crime or much of anything else. Or, if it does pay off, 10,000 or more research studies have yet to find proof. “

-Fathers for Life