Winston Churchill called the 1930s his “wilderness years.” During this time Churchill, while far from inactive, held no official cabinet position and was out of the British government (though he was a member of Parliament). His views were judged to be out of sync with the mainstream and historians fault him for some poor decisions, including his support of King Edward VIII in the 1936 abdication crisis. Not one to waste opportunities, Churchill dedicated much of his time during these years to writing, painting, and lecturing.

What is most striking about Churchill is that while other people would have surrendered to circumstance and allowed such utter public rejection to end their careers, Churchill ultimately used this time to prepare for his most important job yet – leader of the British Empire during World War Two.


What finally catapulted Churchill to power were his prophetic warnings about Hitler (y”s) and the Nazi regime. In the years following the Stock Market crash of 1929, people were wary of spending money on the military. In addition, people still felt the pain of the massive losses of the Great War and did not want to believe that death and destruction would happen again so soon. Churchill thus was preaching a message nobody wanted to hear because they could not bear its weight. Despite his views being excoriated during the 1930s, history tragically proved him right. And when war broke out in 1939, Churchill was summoned to assume control of the Admiralty. In May 1940, when the Germans invaded Norway, Churchill became prime minister. The nation realized that he had been prescient regarding Hitler and that they needed his vision and determination (not to mention his oratory) to steer the helm of state.

What enabled Churchill to see the dangers the Nazis posed when most people dismissed such concerns? Unlike others, Churchill traveled throughout Europe in the early 1930s while researching and writing his books. Having the opportunity to witness up close what was transpiring in Germany, he came to the conclusion early on that Hitler and his movement were extremely dangerous and could not be trusted.

Leaders often find themselves with down time and time that they are down. They may be between jobs or projects or simply out of steam for the moment. The real challenge during this time is how they exploit their own “wilderness” period. Do they use it to reenergize themselves, to improve their skill set? To prepare for future challenges? Or do they waste the precious opportunity such a hiatus presents them with?

In this week’s parsha, Yehuda provides us with an instructive example of how to best use one’s wilderness period. Following the sale of Yosef into slavery the Torah records (38:1): “…and Yehuda went down…” Rashi explains that this episode is juxtaposed to the sale of Yosef to inform us that the brothers dismissed Yehuda from his leadership position due to his influencing them to sell Yosef. After the brothers saw their father’s anguish, they scolded Yehuda and claimed that he had told them to leave Yosef alone they would have surely listened to him. As a result, they no longer had confidence in him as their leader. The Torah proceeds to relate what occurred to Yehuda during what can be described as his own “wilderness years.”

It is at this time that Yehuda teaches us an important lesson. Far from leaving the scene, he ends up using this time to reinvent himself and develop into both the quintessential leader and founder of Bnei Yisrael’s leadership dynasty. Our rabbis offer many insightful comments as to this process. For example, Rav Chaim Shmuelevetz opines that it was during this time that Yehuda demonstrated and perfected his sense of responsibility – a trait that is indispensable for a leader.

Another approach is offered in the Sefer Chidushei Lev (a collection of mussar essays on the parsha, based on the teachings of Rav Henoch Leibowitz zt”l, which was compiled by Rabbi Binyamin Luban). Rav Leibowitz offers a very illuminating explanation as to how Yehuda transformed himself during his wilderness time into the mature leader we all look to emulate. Confronting his own tragedies and loss of children, Yehuda began to understand the pain he had caused his father. Accordingly, Yehuda developed a deep sense of empathy, which is another critical trait for leaders to possess. Following the events with Tamar, the Yehuda we learn about is always thinking of and fighting for others. He no longer sees things simply in light of narrow and immediate concerns. He is now able to take the long and broad view while simultaneously being alert to how everyone around him will be impacted by his decisions and actions.

Rav Leibowitz’s insight truly enables us to understand how Yehuda grew from the experiences of his wilderness years. Leaders who follow Yehuda’s example and extract the most from their own downtime will not only return to center stage but can be confident, like Churchill, that their “finest hour” has yet to come.


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Rabbi Dr. David Hertzberg is the principal of the Yeshivah of Flatbush Middle Division. He is also an adjunct assistant professor of History at Touro College. Comments can be emailed to him at