William Hamilton

Pioneers

Today, I want to talk about self-doubt. Some people walk around without the slightest whiff of it. Their certainty is odious. Then there are some who struggle mightily with it. Tugging at the bottom of their pant leg, not far from their achilles, a question worries: Am I good enough? 

Still others visit self-doubt from time to time. I’m recalling the remarkable leadership of female IDF Battalion Commander, Or Ben Yehuda. “I go back and forth, asking myself if I’m good enough, if I am fit for the job.” Over time she came to realize something profound, “Confronting self-doubt pushes me forward.” 

How so? She sees the positive side of this kind of deliberation. She tries to always inch its end-point a bit forward. That is, when the inner conversation gets to where it did last time, she pushes it one step further. “Here I go again” I tell myself with frustration. But then it occurs to me, “It’s been longer since my last go-around. Maybe that counts for some progress.” 

In this week’s portion of Torah, Moses sums up the thought-infection that raced through the minds of those unfit for entry into the Land: “You sulked, because God hates us, God took us out of Egypt to deliver us into the hands of our enemies” (Deut. 1:27). Can you imagine? Ascribing such ill-will to God? 

Moses’s words here land like darts for a reason. To teach us how treacherous it can be to get mired in motives. I once heard sound advice – hard to follow – but very sound: try to stay away from motives. The impact of reckless words may be unrelated to their intent. I’m not talking about people known to be violent, deceitful, or hypocritical. Rather, with others, you can often afford to stay open to the prospect of more charitable motives. 

Ours are very trying times. Small-minded leaders hold too much sway. Wise insights, now so familiar, feel more like worn-out maxims. Whether your primary sensation is fear or fatigue, disgust or despair, it’s likely that your low point fits neatly with this Sunday’s annual low point, the anniversary of Jerusalem’s Destruction. 

Yearning to drag ourselves from quicksand onto firmer ground, consider how the portion includes Deuteronomy’s only mention of the word for pioneers: chalutzim (Deut. 3:18). A pioneering spirit founded Israel. And a pioneering spirit will refound it. By taking our needed inner-confrontation with self-doubt, another step forward.

About the Author
Rabbi William Hamilton has served as rabbi (mara d'atra) of Kehillath Israel in Brookline, MA since 1995.
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