A challenging yet surefire way this works is when you read something in Chazal that doesn't quite line up with your personal experience. Yet because it was a tzaddik who said it, you know that he's right and you are wrong.
The question is -- how?
You've got this paradoxical contradiction of him being right, yet you honestly just don't see it, and he seems wrong.
(Note: I'm not talking about era-specific statements in Chazal, which assume a primitive world without electricity or without a modern indoor plumbing system, etc.)
That's when you have to stretch your mind to encompass what the Sage is saying. (You can also hash this out with God or a like-minded friend or write it out or engage in further reading to see if someone else already fleshed it out.)
I know that for decades now, the fashionable attitude is to say "nishtaneh hateva (nature changed)" about anything that doesn't fit perfectly into one's current world view or to insist that's how it was pa'am (back then), but it doesn't apply to us now. Or to swoon about the great level of the Sage and how we cannot possible understand anything he said if it's a bit challenging to understand.
Convenient, but not helpful. It's just not true that so much of what they say is simply inapplicable to the modern Jew.
Due to the great darkness and muck of our generation, we just have to dig a bit more to get to the gems hidden within Chazal.
Let a Contradiction Simmer until Fully Cooked
Just by mentally identifying that person's good point, without ever saying a word to that person, can propel that person to self-transformation.
The thing is, that didn't match up with my personal experience...which made me uncomfortable because if you need to chose between listening to him or listening to me, then the only choice is him. Rav Bender wins every time!
So I was caught in this uncomfortable contradiction because I couldn't dismiss his wisdom, yet I also could not deny my own experience.
Just as an example: I kept running into people who had serious problems in life and sought help for them. I assumed that they just needed a hand up, some chizuk, maybe even some practical help, and so on. I assumed that they wanted to do the right thing and were willing to work on themselves. Indeed, they were already going to enormous lengths to deal with their problems: expensive treatments, a wide variety of consultations, traveling great distances (even flights to other countries), medications (in some cases), and following very difficult-to-implement techniques, and so on.
Yet over time, I couldn't remain blind to the fact that they weren't really willing to work on themselves in order to achieve whatever it was they sought (shalom bayit, good children, etc.). Underneath the surface, most were investing a lot in pursuit of that non-existent magic wand that would fix their problems with the flick of a wrist.
Because they were running around so much and throwing around so much money, it looked like they were making herculean efforts. But really, it was all a distraction to avoid the raw yet beneficial cheshbon hanefesh necessary for real transformation.
And some of them really didn't care about or like their own children, which I did not believe at first because such a thing simply did not compute in my mind.
Yes, I know there are parents who don't really care or don't really love, but it just didn't seem like these people were of that ilk. And they said stuff or behaved in certain ways that I initially dismissed as "she's just kidding" or "she's just stressed out" or "she doesn't mean it" or "I'm missing something; I'm sure I'm not seeing the whole picture" or "she's just struggling now; it's normal for people to behave/speak like that at a low point."
(Note: Often, these favorable judgements are true. The person really is just reacting from stress or a low point, etc., and shouldn't be judged negatively.)
The problem was that these people weren't just kidding, they did mean it, and weren't going through temporary stress or the normal low point we all hit sometimes. The dysfunctional attitudes and behaviors really did reflect their true level (albeit not their true potential).
Yet I kept treating them and relating to them as if they truly did care about and like their children, as if they really did want to get better and make their lives better. Meaning, I gave them the benefit of the doubt. I judged them favorably! In my heart, I really was seeing them as better than they actually are.
And on the soul level, they could and did want to be more. But practically speaking, they didn't. They were blocked off from their soul and wanted a magic wand without doing the work.
So why did they never improve? In fact, they sometimes got even worse. And a lot of times, they either turned on me, took advantage of me, or started testing the friendship so aggressively that I had to shout "Stop!" in self-defense (both figuratively and non-figuratively).
Furthermore, things would happen or be said that forced me to face the facts:
They weren't interested in real self-improvement.
They weren't interested in truly helping their children (beyond maternal instinct).
My experience repeatedly seemed to contradict Rav Bender's philosophy. Yet that couldn't be. He had to be right. But how could I deny the facts? Not only were all my positive assumptions about these people being kicked back in my face and not only did giving them the benefit of the doubt end up hurting me, it also didn't seem to help them one whit.
So what was I missing?
I was missing the same thing they were: honesty.
Truth: It's the Real Thing
When we find a merit or a good point in a person, it needs to be a quality that the person actually possesses.
Unfortunately, the material I encountered on judging favorably and giving the benefit of the doubt tended to maintain a narrow focus. (Your experience may be and hopefully has been different. But this is the material I repeatedly encountered.)
As I continuously heard and read: People always meant well (or simply weren't aware of what they were doing), no matter how bad their actions were (except for obviously evil people, like child-attackers and violent psychos). If someone's bad behavior did seem intentional or genuinely problematic, then that was simply because you were seeing them incorrectly. You simply could not trust your perceptions.
When the above was true, viewing people through rose-colored glasses worked out really well.
But this didn't leave much room for dealing with people who enjoy hurting others, whether through mocking or sabotaging/gaslighting or sniping or slander campaigns or anything else. This also didn't leave much room for dealing with people who had serious blindspots that hurt them and others or for dealing with people who really didn't care.
Finally, I found out the hard way that pretending they're better than they are only encourages their dysfunctional qualities.
So ASIDE from their dysfunctional stuff, they possess good points. Meaning, maybe she can't see anything good in her children, but she always volunteers to make a scrumptious chicken soup for a sick neighbor and genuinely enjoys doing so. That's a really good quality!
Both qualities exist within her. Both are true:
- She cannot see anything good in her children. (This is true and very problematic.)
- She loves helping sick people get better and make a great chicken soup. (This is true and very laudable.)
The good and the bad exist together side by side.
The goal is to expand the good until there is no more room for the bad.
Judaism is very strict about Truth. Whitewashing isn't the goal of Torah.
Yes, you must see the positive side of people and situations.
Yes, you must judge favorably.
But it needs to be real.
And that's what Rav Bender meant.
BTW, that's also why these people kept turning on me. Deep down, they sensed I was dealing with them dishonestly (even though I'd thought at the time that my view of them was correct). Psychology would say they were responding from low self-esteem, and that was partly true. But it's also true that I wasn't seeing them honestly.
Thinking positive about people really isn't enough. It has to be real. And even the worst person has a good point, whether it's a well-intended (albeit distorted) motivation or an actual personality trait or a meritorious deed.
Saved by Hashem Yet Again
What if, instead allowing the seeming contradiction between my experiences and Rav Bender's words of wisdom to simmer until the mind-expanding "Ah-ha!" moment, Hashem had allowed me to drift down the more comfortable path of cognitive dissonance? "Oh, he meant that back then, but it's not for our times" or "Nishtaneh hateva!" or "He was on such a high level, there is no way to fathom such wisdom or what he really meant" (even though he was clearly speaking to an audience that included non-Torah scholars).
If I'd just dismissed the seeming (and extremely discomfiting) contradiction, I never would have learned the lesson I needed to learn. Hashem saved me from further bashing my head against the wall of my own blind spot.
Baruch Hashem for that.
The Most Effective Way to Fix Your Flaws
How to Avoid being a Pathological Pollyanna
The Secret to Judging Favorably