THE ART OF FIGHTING OUR INNER ESAV
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THE ART OF FIGHTING OUR INNER ESAV
The story of Yaakov battling Esav is not just ancient history. Inside each of us are Yaakov and Esav voices. Every test in life is a struggle between the two: The Esav voice focuses only on short-term gain, with no concept of long-term consequences, justice, or truth. The Yaakov voice counters this by fighting for truth, justice, and long-term perspective, recognizing that every action has a reaction.
We can read the parasha as a story of the past, or we can view Yaakov’s dealings with Esav as a battle plan to fight the Yetzer Hara in our own lives. Here are twelve key lessons:
- Have a Plan. The Shaarei Teshuva teaches that regret without a concrete plan for change is incomplete. If one falls again but had a plan, the second failure does not combine with the first. Yaakov didn’t just face Esav; he made a plan. To overcome your yetzer hara, identify your vulnerabilities and plan practical steps to address them.
- Send Your Angels First. Yaakov sent angels ahead to prepare for Esav. How do we send “angels” to fight the yetzer hara? Judaism teaches that burning desires create angel—for good or bad. Build strong, positive desires for Torah learning, enjoying mitzvot, living modestly. These “angels” pave the way for victory.
- Sometimes, Give the Yetzer Hara a Gift. Yaakov gave Esav gifts to pacify him. At times, you need to negotiate with your yetzer hara to gain control: Internet Use: If filters are blocking necessary access, consult a rabbi for a controlled alternative. For safety, have someone watch alongside you. News Obsession: Make a deal: “I’ll check the news after I finish my Daf or Amud of learning.” Addictions: Under guidance (e.g., an addiction counselor), some cases require gradual steps. Controlled gambling or substance intake may be a “gift to the inner Esav” to prevent sliding into worse habits while preparing for full recovery. Even Yom Kippur reflects this idea: we send a “gift”—the Azazel goat—to pacify negative forces so we can focus on prayer.
- Pray for Success. Yaakov davened before meeting Esav, recognizing that he could not succeed alone. Fighting the yetzer hara requires Divine help. Pray for miracles, strength, and clarity to overcome temptations.
- Be Ready for War—and Know When to Run. Yaakov prepared for battle and split his camp, ready to cut losses if necessary. Sometimes, this is the only way to defeat the yetzer hara: firm boundaries, say “No” with conviction. Run Away: When controlled measures fail, it’s time to escape completely. If filters don’t work, leave the internet, until you have a filter you can’t get around. If controlled gambling isn’t helping, drop it entirely. Cut your losses, don’t chase them, if you want a chance to save your future. Sometimes, surrendering the failed past is necessary to build a successful future.
- Bowing to Your Inner Esav – Recognize Your Limits. Yaakov humbled himself before Esav, saying, “I am your servant.” This teaches us to recognize our limitations—a powerful tool against the yetzer hara. Sometimes, humility is the key to defeating the Inner Esav. Pride fuels the yetzer hara, but admitting weakness dismantles it. Say: “I’m not perfect, but I’ll keep trying.” A strong person knows when and where her is weak. Don’t deny it: If alcohol, chocolate, drugs, social media, gambling, or overeating are stronger than you, don’t pretend you can handle them. Instead, admit these things are dangerous for you and act accordingly. Only then can you take the proper steps to deal with them.
- Don’t Wake the Sleeping Dog- Yaakov sent angels to investigate Esav—a move our Rabbis criticize. By checking on Esav, Yaakov “woke up the sleeping dog.” Don’t test your limits. Don’t see how strong your filters are by trying to bypass them. Don’t experiment with things others have abused, thinking you’ll be immune. You may awaken an “inner Esav” you’re not prepared to fight. Hashem will give you the strength when the test comes—not before. There’s no need to “check the coast” for dangers that haven’t arrived yet.
- Alone and in the Dark – Prime Moments for the Yetzer Hara: Yaakov was injured by Esav’s angel during the night and when he was alone. The yetzer hara attacks strongest when we are alone, as isolation weakens us. Tiredness and exhaustion leave us vulnerable. If you know you will face a challenge, ensure you are well-rested and surrounded by people who support you. Don’t face inner Esav when you are alone in the dark.
- Hitbodedut (Meditation) and Preparation Before the Fight. Before wrestling Esav’s angel, Yaakov spent time alone. This solitude was not isolation alone—it was preparation. To overcome the yetzer hara, take time for Hitbodedut, or quiet reflection and meditation. Time alone means time for Mussar self-improvement through Torah teachings. Winning life’s battles requires introspection and preparation before the fight begins.
- Reject Labels: Esav called Yaakov a trickster: “ויעקבני זה פעמיים—This tricked me twice.” Esav referenced the pot of lentils Yaakov used to acquire the firstborn rights, the same pot Yaakov later used to bring food to Yitzchak receive Yitzchak’s blessings. This “label” stuck to Yaakov. Even Yaakov suggested to Rachel that he can overcome Lavan’s trickery with his own. Even Leah justified tricking Yaakov on their wedding night, saying, that you Yaakov taught me to trick, since you told your father, “I am Esav, your firstborn.”
When Yaakov defeated Esav’s angel, he refused to let the angel go until he received a blessing. The angel didn’t bless Yaakov directly—he renamed him Yisrael. How is changing Yaakov’s name considered a blessing?
ישר means “straight” or “upright”, and not עקב, which means a trickster or cheat. Esav’s angel gave Yaakov the greatest blessing, an identity free from negative labels of the past! The inner Esav labels us—faker, loser, disgrace, and we suffer from Inner Esav labels for years!!! But when we pass life’s tests, each victory over the inner Esavs, our weaknesses and past struggles become our strengths. The labels fade, and we are crowned with victory.
- Torah Study – The Ultimate Weapon: Yaakov told Esav, “עם לבן גרתי”—I lived with Lavan. Our Rabbis explain that “גרתי” has the same letters as “תרי”ג” (613), symbolizing Yaakov’s commitment to all 613 mitzvot throughout his stay by Uncle Lavan’s house.
How could Yaakov claim to have kept 613 mitzvot while in Lavan’s house? After all, he wasn’t living in Eretz Yisrael and he married two sisters, which is prohibited by Torah law?!
The answer is profound: Torah study itself counts as fulfilling the mitzvot. When you learn about a mitzvah, Hashem considers it as if you performed it. Torah study is the ultimate defense against the yetzer hara. בראתי יצר הרע בראתי לו תורה תבלין But there’s a condition—modesty. Yaakov didn’t boast, saying “I kept the 613 mitzvot.” Instead, he hinted at his dedication to Torah study, subtly. גרתי, which only hints to תריג. If you want Torah to fight your inner Esav, learn consistently, and don’t flaunt it.
- Trust Hashem, Not Over-Defense: Yaakov hid Dinah in a box so Esav wouldn’t see her, fearing he might want her as a wife. The Rabbis teach that Yaakov was punished for this; Dinah later fell into Shechem’s hands. Why was Yaakov punished? Aren’t we taught to protect our children from bad influences? The answer is subtle: Yaakov wasn’t punished for hiding Dinah but for over-defending. On his lofty level, he was expected to trust Hashem more and rely less on physical defenses. As we know, Yaakov himself criticized Shimon and Levi for their self-defense in Shechem, calling it “the tools of Esav—כלי חמס מכרתיהם.” When dealing with the yetzer hara, excessive self-defense can backfire. The best defense is prayer, and trust in Hashem. Torah Study fills your life with spiritual strength. Sometimes, taking a passive approach—rather than over-fortifying—is the most powerful strategy. When you try too hard to protect yourself, your spiritual energy levels drop.
These 12 lessons teach us how to face our inner Esav, the yetzer hara. Yaakov’s struggles remind us that we are stronger than we think, and with Hashem’s help, we can win every battle. Confront the yetzer hara strategically—through planning, humility, introspection, Torah study, and prayer—and transform your challenges into opportunities for growth. Whether it’s planning, sending “angels,” negotiating, praying, or running away, we can learn how to fight our Inner Esav from this week’s Parasha!
