Don’t change the principle for the sake of details.
Rav Bender says:
There are those who want to diminish the importance of certain matters, reasoning that we have not the ability to do them.
Although it is not possible to do everything all the time—but Heaven forbid to say that it is not necessary to do so!
Yes, we cannot always do the right thing—we may have an emotional or physical weakness that stops us from fulfilling our potential at any given moment.
But at the very least, we should not pretend “It’s okay.”
We see that as any Jew increases observance, it is impossible to swallow it all in one gulp or to maintain the same high level from day to day (or even hour to hour, depending).
Yet we need to be careful not to deny the ultimate truth.
For example, if a fresh baal teshuvah says he can only handle davening just once a day or without a minyan, we understand. If a fresh baalat teshuvah says that she just can’t switch to a skirts-only style or isn’t ready to start covering her hair as a married woman, we understand.
Both they and we understand that spiritual progress is a process and while you have to start somewhere, you just can’t do it all at once.
But what if they would say, “Really, Judaism says it’s okay to do whatever I’m doing right now. I don’t need to do more. Ever. We just can't nowadays. Our generation isn't up to it. It's too hard.”
That’s wrong. And if we'd reassure them that it’s okay to just stop there, we’d be very wrong, too.
Without the spiritual goal in mind, no spiritual progress would happen.
Rav Bender gives the example of one of the students of Rebbe Nachman, Rav Ber of Techerin. Due to serious headaches, Rav Ber could not get up to daven Tikkun Chatzot at the exact halachic midnight (chatzot). So Rebbe Nachman told Rav Ber that Rav Ber's “midnight” was 3 o’clock in the morning.
That was a good alternative. But no one pretended that it wasn’t better to daven Tikkun Chatzot at exactly chatzot.
If we find ourselves unable to behave according to the Torah ideal, then Rav Bender encourages us to make special deliberations about what to do. We can find temporary alternatives for our personal level and capabilities, as Rebbe Nachman did for Rav Ber.
At the end of an American tsniut* class, a woman in a waist-length custom shaitel (wig) approached the rebbetzin with the declaration that she wanted to focus on covering her hair more tsniusly.
But how should she go about starting?
The rebbetzin said, “Have two inches cut off your shaitel, then come back to me in a month and we'll discuss it.”
A scarf-wearing woman from Eretz Yisrael witnessed the exchange. Later, she politely said to the rebbetzin, “I'm curious as to why could you suggested such a tiny change. To me, that seems like no change at all. I mean, why not tell her to shorten it to the middle of her back? Even though that would still be too long, it would be a great way to start. After all, she was so open to guidance on this issue.”
“You don’t understand,” said the rebbetzin. “She’s obviously very attached to her shaitel and it's clearly important to her to have it at that specific length or else she wouldn't have invested the thousands of dollars necessary to acquire such a shaitel. You can’t just tell people to make such a radical change or they may not complete the process—they could just give up halfway through.”
And she’s right.
But no one was pretending that a va-va-voom waist-length shaitel that looks exactly like real hair is in the spirit of tsniut.
Now back to Rav Bender.
Although he himself became a great tzaddik through unimaginable self-sacrifice, Rav Bender did not judge others who could not push themselves beyond their current level.
As just one example, he explains:
Let one choose for himself.
Concerning complications you are dealing with:
Know that your difficulty is a specific problem.
It does not relate to the general public or to another.
It is impossible to change the public for the sake of an individual!
Individual weaknesses are being catered to and plastered with stamps of approval.
And while doing so imbues one with a shallow feeling of goodness, ultimately that is exactly what stunts a person’s spiritual growth.
*Tsniut/tsnius describes a personal & spiritual dignity that includes physical & behavioral modesty.