Remember what Amalek did to you on your way leaving Egypt. When they encountered you on the way, and you were tired and exhausted, they attacked those of you who were weak, at the rear, and they did not fear G-d. Therefore, when G-d gives you peace from all the enemies around you in the land that G-d is giving you to occupy as a heritage, you must obliterate the memory of Amalek from under the heavens. You must not forget – this weeks’ special Torah reading; Parshat Zachor (Deuteronomy 25:17-19)

G-d shall be at war with Amalek for all generations (Exodus 17:16)

What is it about Amalek that is so important to remember and never forget? Why the adamant need to “obliterate the memory of Amalek from under the heavens,” to the extent that G-d fights this war in “all generations”?!

There are various practical and legal (halachik) reasons given for the significance of the war against Amalek. This column has also addressed the basic question, how the compassionate Torah can possibly call for mass genocide of an entire nation.

But the full implications of the war against Amalek can be appreciated only by understanding its psychological and spiritual dimensions. The Torah, above all, is a blueprint for life. Every character, episode and event in the Torah is actually another piece of a comprehensive spiritual map that lays out the inner nature of our lives and all our challenges.

Amalek embodies the most potent enemy we face. That enemy is not an external force, nor a prowler or weapon on the attack. It is not an enemy from without, but one from within. The enemy is: Doubt.

In the words of the Rebbe Yosef Yitzchak: “The numerical value (gematria) of the Hebrew letters that spell Amalek (240) is equivalent to that of the letters that spell safek, “doubt.” All things holy are certain and absolute. Torah is absolute, the mitzvot are absolute, divine providence is absolute. Amalek is doubt; baseless, irrational doubt that cools the fervor of holiness with nothing more than a cynical shrug.”

Ahhh doubt.

Of all our enemies, of all the forces that impede our ability to grow, to love and to build, one root cause stands out among them all: Insecurity. Doubt has many names and many faces: Fear. Distrust. Uncertainty. Skepticism. Cynicism. Indecisiveness. Avoidance. Ambiguity. Complacency. The list goes on.

Is there someone, even the most confident of people, who has not at some point been plagued by self-doubt? And then, how many of us are actually self-confident? Insecurity is arguably today’s norm. Indeed, many people suffer from incessant fear and uncertainty – self doubts that affect your every move and choice.

What exactly is this thing called doubt? Doubt is basically the feeling – or rather the non-feeling – that you don’t have the tools or the strength to make a decision. Over an extended period such doubt becomes a debilitating poison that paralyzes us from making commitments.

Perhaps the most insidious element of doubt is its invisibility. Doubt does not have a shape or form of expression.

To have doubt for a short period of time is natural. But when doubt persists, and takes on persistent indecision, and time passes, a deep paralysis begins to fester and grow inside. On the surface level it, we can often appear completely functional. Lack of commitment can be explained away and be even justified as healthy caution, necessary introspection, sober skepticism, wise caution, when in truth it really is nothing more than a mask for fear and doubt. Our deepest insecurities often hide behind sophisticated justifications and a million rational reasons why one cannot commit – smokescreens to protect a frightened psyche terrified of commitment.

Often people replace the need for certainty in their emotional lives with aggressive confidence in business and the market place. But let that not be mistaken for true confidence.

Facing doubt – a force that is with us at all times – is the never-ending battle with Amalek, the battle with all forms of lurking doubts, that do not allow us the clarity and confidence to take risks, to make choices, to take on challenges and to forge ahead with our lives.

Amalekite doubt can attack at any given time. But it particularly likes to prey on us when we are “leaving Egypt:” As we are being freed from constraints (Mitzrayim – Egypt in Hebrew – means constraints), as we get inspired and motivated – there is always a counter voice casting doubt and throwing “cold water” on our enthusiasm.

How often do you find that just as you feel inspired to make a move, just as you become upbeat, another voice creeps in telling you how it can’t be done, how you don’t have the strength or the will, how you are bound to fail in your attempts to excel – doubts and more doubts feeding into all your insecurities and weakening your resolve.

This is Amalek attacking you just as you have found freedom and begin to feel confident. And it attacks your point of weakness – when you are “tired and exhausted.”

How do we protect and fend off the enemy of self-doubt? How do we build self-confidence in a world plagued with profound insecurity? How do we learn to trust in a life that can so often disappoint?

The answer lies in a previous verse: Just before Amalek attacks the Jewish people, the Torah tells us that the people doubted and questioned: “Is G-d with us or not?” (Exodus 17:7). Once they allowed doubt to seep into their psyches Amalek was empowered to launch a full fledged assault. To explain the sequence, Rashi cites a Midrashic analogy (Tanchuma Yitro 3; Exodus Rabbah 26:2): [G-d says:] “I am always among you, and always prepared for all your necessities, but you say, ‘Is G-d with us or not?’ By your life, the dog will come and bite you, and you will cry out to Me, and [then] you will know where I am.” This can be compared to a man who mounted his son on his shoulder and set out on the road. Whenever his son saw something, he would say, “Father, take that thing and give it to me,” and the father would give it to him. They met a man, and the son said to him, “Have you seen my father?” So his father said to him, “You don’t know where I am?” He threw his son down off him, and a dog came and bit the son.

All doubts begin with the first cosmic doubt: “Have you seen my father?” “Is G-d with us or not?”

In Kabbalistic terms, Amalek is Kesser of klippah, the crown of all impurities. Doubt is the root of all maladies. And that doubt originates from the primordial Tzimtzum, which concealed the Divine conscious presence, thereby setting the stage for all forms of uncertainty. In the pre-tzitmzum state, the Divine presence is the all pervasive, all-consuming reality. In such a state of seamlessness – above the heavens – there are no doubts; all is clear. But “under the heavens” – once that unifying presence is concealed and we feel alone, doubt is its inevitable product: “Is G-d with us or not?”

Self doubt is driven by insecurity. But why should we be insecure? Because we live in an independent universe whose existence is possible only by virtue of concealed light.

Certainty is the converse of doubt. How is it possible to find certainty in an uncertain world? Everything in this universe – its very nature – is forever changing, in unpredictable ways. We can make the greatest plans, everything can seem right, but then… things happen and all our plans are upset. We all age, everything erodes, everyone dies – how can we ever expect to find certainty in such an unstable environment?

The one and only answer is that we have within us an inherent connection to the eternal, to the absolute – to the pre-tzimtzum unity – that gives us a sense of utter certainty. Some call this faith – not the blind faith of the fool, but the sophisticated belief in something greater than arbitrary logic or ever-changing circumstances.

This connection is the power of the soul. The body and everything material, by its very nature, is in a state of flux, and thus always shrouded in doubt: What will come next? The soul is a consistent flame, always sure of itself, always connected. It is the sense within that we are not alone. And when we really feel that we are not alone and G-d is with us, all doubt melts away.

As children, when our parents and support systems nurture and validate us, they cultivate our soul’s natural connection to its source and build our self-confidence – inbuing us with a profound sense of certainty and belonging. But when our love and nurturing is compromised, doubts begin to fill up our psyches, only reinforced by the narcissism we begin to witness in others.

The vicious cycle is now in relentless motion. Doubt breeds doubt.

Thus we are commanded to “go forth and fight against Amalek.” And do so with absolute vigilance – “obliterate the memory of Amalek from under the heavens.” Because doubt is our greatest enemy; one that brings on all our other problems. With confidence we can take on any challenge. But when we doubt ourselves, and have no self-confidence, every difficulty becomes a monster. “Obliterate Amalek” – obliterate every doubt, even the memory of doubt, “from under the heavens.” Because above the heavens there is no doubt; doubt is only possible in a post-tzitmzum, material world where truth and reality are concealed.

And we don’t fight this battle against Amalekite doubt alone. Led by Moses and his trusted disciple, Joshua, we have the power to overcome any doubt. Moses is the ultimate spiritual mentor – the selfless leader that helps us connect to the Divine. His prayers help us overcome the Amalekite doubts. As the Torah relates: While they fought Amalek, Moshe held up his hands in prayer, entreating G-d to strengthen His people. When his arms weakened, Moshe sat on a stone while his brother, Aaron, and his nephew Chur supported him on each side. A night passed this way, and by the time the sun rose, the Amalekites were defeated.

The same happens in the story of Purim: Everyone bows to Haman the Amalekite, except Mordechai. Mordechai refuses to bow to any man or man-made idols, and the inevitable insecurity and doubts that these human forms bring. Only through connecting to the Divine does one reach clarity and certainty.

Just as all doubt stems from the cosmic concealment, all certainty originates from the clarity that “G-d is with us” and the concealment is just that: Concealment with the purpose that we reveal the Reality within.

And just as doubt breeds doubt, certainty breeds certainty. Once you open the doors of certainty in your life, that you are connected to the Divine, it begins to spill over into other areas of your life.

[Some of you may argue that there are many confident and secure people who don’t have any connection to the Divine. I submit that if they indeed are that secure, they are connected to the Divine, even if may be called by another name].

The battle against Amalekite doubt is in every generation and in every situation; perhaps the single most important battle of our lives – because when we overcome our doubts and conquer our fears everything else becomes possible.