A young man sits in the beis medrash trying to learn and learning is hard. Even once he discovers the geshmak it remains hard. It may seem strange but throughout one’s career of learning Torah enjoyment and difficulty continue to co-exist. Failure is an ongoing aspect of learning for everyone even for the greatest sages. Every time one doesn’t understand a gemara or a Tosafos or a Reb Akiva Eiger that’s a mini-failure of a kind — and who likes to fail?

But the very reality that failure is a built-in feature of limud haTorah can be a source of chizuk and a tool for achieving ultimate success. The fact that as Chazal (Gitin 43a) teach ein adam omeid al divrei Torah el ihm kein nichshal bahen a person will not comprehend words of Torah unless he first stumbles over them has two ramifications.

First it’s the nature of Torah that makes an initial failure of some sort inevitable. Part of the pain of failure stems from the message that people with less-than-perfect self-esteem — which is most of us — internalize as a result: “If I was better/smarter/more talented I’d have succeeded.” But knowing that the system is “rigged” for some degree of failure means our stumbles and falls don’t have to deter us from plowing ahead .

Moreover if the failure to understand and retain everything we learn is the inevitable prelude to the understanding and retention that will follow that means that all such failures are actually rungs on the ladder of success in learning. They’re not the problem but part of the solution.

W. Clement Stone a famed motivational expert would train a salesperson to overcome his fear of rejection by giving him 25 navy beans to be placed in his left pants pocket. After each sales call he was to remove one bean and place it in his right pocket and was not to quit for the day until he had transferred all 25 beans. Having to continue on until that point made him persevere despite numerous rejections until most often at some point each day he made a sale.

But even more I would suggest it transformed the inevitable rejections into stepping stones on the way to likely success. Rejection that much-feared experience of those who struggle with issues of self-worth had been turned into nothing more fearsome than a little bean sitting in one’s pocket waiting to be removed so he could move on to the success lying just ahead. And l’havdil difficulty in grasping what one is learning might also be seen as just the transfer of stones from one pocket to the other in anticipation of eventual success.

What is true of limud haTorah specifically can be said to hold true for life generally which inevitably contains its own share of failures. A fascinating article in Forbes describes how Jim Collins best-selling author and speaker on business success accepted an offer from theU.S. military academy atWest Point to deliver a series of seminars to officers and cadets.

While trying his hand at a grueling obstacle course that all cadets must master in order to graduate Collins observed that despite being highly competitive and extremely busy cadets regularly took time from their schedules to help their colleagues get through the course. In addition

they seemed to be happier — much happier — than students at civilian universities … [despite leading] extremely demanding lives [in which] nearly every minute of every day is programmed and every aspect of their lives is regimented down to the color of their socks and the way razors must be positioned in their medicine cabinets. Meanwhile they are constantly being tested both physically and mentally — and they often fall short….

How Collins wondered did such a burdensome environment produce such a happy lively and confident cohort of young men and women? … A cadet’s life is anything but fun. And yet these young people seem to get something out of their lives that is missing from the lives of many of their contemporaries.

Collins discovered that two elements pervasive atWest Pointhelped explain what he’d observed. One was “a commitment to service. Everything the cadets did grew out of their desire to serve.” The other was their attitude toward failure: “Repeated failure was built into West Point’s culture. Yet that didn’t seem to faze the cadets in the least. They came across as irrepressibly positive and devoid of the alienation that infected the other campuses Collins knew.”

He learned the same lesson from Tommy Caldwell a 35-year-old Coloradan who is regarded as one of the greatest rock climbers of all time whom he invited to share his experiences at one of the seminars. Traveling together to West Point they talked about Caldwell’s

… ongoing and so far futile attempt to scale the Dawn Wall ofEl Capitan… without any aid from climbing equipment or ropes. No one has ever done it.Caldwellwas preparing for his fourth attempt that fall … but the overwhelming odds were that he would once again fail to reach the top.

“Why do you keep throwing yourself at this?” Collins asked. “All it does is give you failure upon failure. Why go back?” “Because success is not the primary point”Caldwellsaid. “I go back because the climb is making me better. It is making me stronger. I am not failing; I am growing.”

In factCaldwellviewed failure as an essential part of his search for the outer reaches of his capabilities as a climber. “To find your limit and experience the most growth you have to go on a journey of cumulative failure”Caldwellsaid.

Collins’ description of certain aspects of the lives of West Point’s cadets sounds uncannily similar to that of the young men in l’havdil our own “academies.” So too does the happiness and confidence he found there. But not entirely. And it’s worth pondering to what extent an absence of the two elements he discussed — commitment to service and embrace of failure — might help explain the disparity.

BIG WORDS Last week I met a legend. I hadn’t seen him in a long while and the passage of time makes one reflect.

It was at a wedding of our close friends and Reb Nisson Wolpin the chassan’s grandfather had flown in from Eretz Yisrael. Reb Nisson Wolpin (he’s a rabbi too but nowadays when everyone seems to be a “rabbi ” “reb” seems like a more valuable honorific) is a bona fide literary legend. I and many other writers not to mention the broader community owe him a great deal.

He helmed the frum community’s then-preeminent English-language periodical the Jewish Observer throughout a long period in which it was more than just a journal; it was a concept. I have a recollection from 35-odd years ago of a sheva brachos in a Flatbush basement at which Rabbi Sender Goldberg spoke with his customary eloquence. The evening’s MC then rose to thank him for “reconfirming the thesis of the Jewish Observer that ‘you can be frum and still use big words.’$$separate quotes$$”

Funny line but serious point. The JO was a critical part of Orthodoxy’s coming-of-age as a confident contemporary faith community that not only had a coherent and well-considered worldview but also the ability to articulate it in a sophisticated manner. And Reb Nisson was that project’s supervising engineer: discovering and cultivating new talent and making wise use of that already known including his own; choosing the battles to fight mapping out the strategy and commissioning the warriors; charting new territory for intra-communal attention and discussion; putting those within and without who would defame us on notice that we were listening and would respond vigorously; opening up new vistas of thought biography and history to a broad readership.

There’s much more to say and he and his contributions really require a much fuller written appreciation. No one should think that these brief inadequate paragraphs are in any way that tribute.

But last week I said hello again to a legend and so these thoughts came cascading forth. Reb Nisson has gone back home to resume doing what retirement is made for: learning full-time in kollel. But although the JO closed in 2009 after 46 years in operation — Reb Nisson we’ll always remember.