Summary
A nighttime military operation reveals how even the best-laid plans can crumble when human nature takes over. Count Orlóv-Denísov's troops are supposed to coordinate a surprise attack, but most units get lost in the darkness. Only his small Cossack force reaches the right position. At dawn, a Polish deserter offers to lead them to capture the French commander Murat. Despite initial enthusiasm, Orlóv-Denísov's confidence wavers as he watches the enemy camp. The doubt eating at him makes the deserter's story seem like an obvious lie, so he recalls his men just as they're about to succeed. When the Cossacks finally attack on their own, they achieve stunning success—capturing 1,500 prisoners and 38 guns—but then get distracted dividing up loot instead of pressing their advantage. Meanwhile, the other Russian columns stumble around lost, arriving too late and in the wrong places. General Toll, furious at the chaos, takes out his frustration on General Bagovút, who responds by charging into battle with just one division. This rash decision, born of wounded pride and anger, gets Bagovút killed along with many of his men for no strategic gain. The chapter shows how second-guessing, poor communication, and letting emotions drive decisions can turn potential victory into costly failure.
Coming Up in Chapter 286
The aftermath of the botched attack ripples through the Russian command, as leaders struggle to make sense of what went wrong and what comes next.
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An excerpt from the original text.(~500 words)
Next day the troops assembled in their appointed places in the evening and advanced during the night. It was an autumn night with dark purple clouds, but no rain. The ground was damp but not muddy, and the troops advanced noiselessly, only occasionally a jingling of the artillery could be faintly heard. The men were forbidden to talk out loud, to smoke their pipes, or to strike a light, and they tried to prevent their horses neighing. The secrecy of the undertaking heightened its charm and they marched gaily. Some columns, supposing they had reached their destination, halted, piled arms, and settled down on the cold ground, but the majority marched all night and arrived at places where they evidently should not have been. Only Count Orlóv-Denísov with his Cossacks (the least important detachment of all) got to his appointed place at the right time. This detachment halted at the outskirts of a forest, on the path leading from the village of Stromílova to Dmítrovsk. Toward dawn, Count Orlóv-Denísov, who had dozed off, was awakened by a deserter from the French army being brought to him. This was a Polish sergeant of Poniatowski’s corps, who explained in Polish that he had come over because he had been slighted in the service: that he ought long ago to have been made an officer, that he was braver than any of them, and so he had left them and wished to pay them out. He said that Murat was spending the night less than a mile from where they were, and that if they would let him have a convoy of a hundred men he would capture him alive. Count Orlóv-Denísov consulted his fellow officers. The offer was too tempting to be refused. Everyone volunteered to go and everybody advised making the attempt. After much disputing and arguing, Major-General Grékov with two Cossack regiments decided to go with the Polish sergeant. “Now, remember,” said Count Orlóv-Denísov to the sergeant at parting, “if you have been lying I’ll have you hanged like a dog; but if it’s true you shall have a hundred gold pieces!” Without replying, the sergeant, with a resolute air, mounted and rode away with Grékov whose men had quickly assembled. They disappeared into the forest, and Count Orlóv-Denísov, having seen Grékov off, returned, shivering from the freshness of the early dawn and excited by what he had undertaken on his own responsibility, and began looking at the enemy camp, now just visible in the deceptive light of dawn and the dying campfires. Our columns ought to have begun to appear on an open declivity to his right. He looked in that direction, but though the columns would have been visible quite far off, they were not to be seen. It seemed to the count that things were beginning to stir in the French camp, and his keen-sighted adjutant confirmed this. “Oh, it is really too late,” said Count Orlóv, looking at the camp. As often happens when someone we...
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Intelligence Amplifier™ Analysis
The Road of Second-Guessing - When Doubt Destroys Success
The tendency to destroy our own success through excessive doubt and second-guessing at crucial moments.
Why This Matters
Connect literature to life
This chapter teaches how to identify when our own doubts are creating the very problems we fear.
Practice This Today
This week, notice when you have a good idea but start finding reasons it won't work—that's the pattern beginning.
Now let's explore the literary elements.
Terms to Know
Deserter
A soldier who abandons their army, usually switching sides or fleeing entirely. In this chapter, a Polish sergeant leaves the French army claiming he was passed over for promotion. Deserters often brought valuable intelligence but couldn't always be trusted.
Modern Usage:
We see this when employees quit and go to competitors, sometimes sharing inside information.
Cossacks
Elite Russian cavalry known for their fierce independence and unconventional fighting style. They were excellent scouts and raiders but difficult to control in formal military operations. Tolstoy shows them as brave but easily distracted by loot.
Modern Usage:
Like special forces units today who excel at specific missions but don't always follow standard procedures.
Corps
A large military unit containing multiple divisions, typically 20,000-45,000 soldiers. Poniatowski's corps refers to Polish forces fighting alongside Napoleon. Understanding military hierarchy helps readers follow the scale of these battles.
Modern Usage:
Similar to how large corporations are divided into divisions and departments with clear chains of command.
Coordinated attack
A military strategy where multiple units strike simultaneously from different directions to overwhelm the enemy. Success depends on precise timing and communication. This chapter shows how easily such plans fall apart in practice.
Modern Usage:
Like planning a surprise party where everyone needs to arrive at the exact same time - one person being late ruins everything.
Second-guessing
Doubting your initial decision and changing course at the critical moment. Count Orlóv-Denísov does this when he recalls his troops just as they're about to capture Murat, turning potential victory into missed opportunity.
Modern Usage:
When you're about to ask for a raise but chicken out at the last second because you start doubting yourself.
Fog of war
The confusion and uncertainty that happens during military operations when information is incomplete or wrong. Units get lost, orders are misunderstood, and commanders make decisions based on incomplete information.
Modern Usage:
Like trying to coordinate a group project when half the team isn't responding to texts and nobody knows who's doing what.
Characters in This Chapter
Count Orlóv-Denísov
Military commander
The only Russian commander who reaches his assigned position on time, but then loses his nerve at the crucial moment. His self-doubt causes him to recall his troops just as they're about to capture the French general Murat, showing how confidence affects leadership.
Modern Equivalent:
The manager who gets cold feet and cancels the big presentation at the last minute
Polish sergeant (deserter)
Informant
A Polish soldier who claims to have inside information about French positions and offers to guide the Russians to capture Murat. His story may be true, but Orlóv-Denísov's growing paranoia makes him seem untrustworthy.
Modern Equivalent:
The whistleblower whose motives everyone questions
General Toll
Frustrated superior
A Russian general who arrives to find the coordinated attack has devolved into chaos. His anger and need to blame someone leads him to unfairly criticize General Bagovút, triggering a chain reaction of poor decisions.
Modern Equivalent:
The district manager who shows up to a disaster and immediately starts pointing fingers
General Bagovút
Tragic victim of pride
Gets publicly dressed down by Toll despite the failure not being his fault. His wounded pride drives him to launch a reckless attack with insufficient forces, resulting in his death and the unnecessary loss of his men.
Modern Equivalent:
The employee who quits dramatically after being unfairly criticized in front of everyone
Murat
French target
The French marshal the Russians are trying to capture. He remains oblivious to how close he came to being taken prisoner, representing how success and failure often depend on split-second decisions and luck.
Modern Equivalent:
The CEO who never realizes how close the company came to a major crisis
Key Quotes & Analysis
"The secrecy of the undertaking heightened its charm and they marched gaily."
Context: Describing the troops' mood as they begin their nighttime advance
This shows how anticipation and mystery can boost morale even when the actual plan is falling apart. The soldiers feel excited because they don't yet know how badly things are going wrong.
In Today's Words:
Everyone was pumped up because they thought they were part of something big and secret.
"Only Count Orlóv-Denísov with his Cossacks got to his appointed place at the right time."
Context: Revealing that most of the coordinated attack has already failed before it began
This ironic statement highlights how rare competence is in large organizations. The one unit that does its job correctly becomes the exception rather than the rule, setting up the tragedy that follows.
In Today's Words:
Out of all the teams, only one actually showed up where they were supposed to.
"He ought long ago to have been made an officer, that he was braver than any of them."
Context: Explaining why he switched sides to the Russians
This reveals the universal human need for recognition and advancement. The deserter's motivation isn't ideology but wounded pride over being passed over for promotion, making his reliability questionable.
In Today's Words:
I should have been promoted ages ago - I'm better than all of them.
Thematic Threads
Self-Doubt
In This Chapter
Orlóv-Denísov abandons a perfect plan because his confidence wavers at the crucial moment
Development
Introduced here as a major factor in military and personal failure
In Your Life:
You might recognize this when you talk yourself out of asking for a raise or applying for a better job.
Pride
In This Chapter
Bagovút charges into battle rashly after being criticized, getting himself and his men killed for no strategic gain
Development
Continues the theme of pride leading to destructive decisions
In Your Life:
You see this when someone makes a bad choice just to prove they're not wrong or weak.
Communication
In This Chapter
Multiple military units get lost and arrive late because of poor coordination and unclear orders
Development
Builds on earlier themes about the chaos that results from failed communication
In Your Life:
This happens in your workplace when important information doesn't reach the right people at the right time.
Opportunity
In This Chapter
The Cossacks achieve great success but then waste it by focusing on dividing loot instead of pressing their advantage
Development
Shows how success can be squandered through distraction and short-term thinking
In Your Life:
You might do this when you get a good opportunity but get sidetracked by immediate rewards instead of long-term gains.
Leadership
In This Chapter
Leaders at every level make emotional rather than strategic decisions, leading their followers into unnecessary danger
Development
Continues examining how personal emotions compromise leadership effectiveness
In Your Life:
You see this when supervisors make decisions based on their mood rather than what's best for the team.
You now have the context. Time to form your own thoughts.
Discussion Questions
- 1
What specific actions did Orlóv-Denísov take when his confidence started to waver, and how did those actions affect the outcome?
analysis • surface - 2
Why do you think Orlóv-Denísov's doubt grew stronger just as success seemed most likely? What was happening in his mind?
analysis • medium - 3
Where have you seen this pattern of self-sabotage in your workplace, family, or community—someone abandoning a good plan because of last-minute doubts?
application • medium - 4
If you were coaching someone who tends to second-guess themselves at crucial moments, what practical strategies would you give them?
application • deep - 5
What does this chapter reveal about the relationship between confidence and timing? When is doubt helpful versus harmful?
reflection • deep
Critical Thinking Exercise
Map Your Doubt Triggers
Think of a recent situation where you had a good plan or instinct but talked yourself out of it. Write down what specific thoughts or fears made you hesitate. Then trace what actually happened versus what you feared would happen. Finally, identify the exact moment when productive caution turned into paralyzing doubt.
Consider:
- •Notice if your doubts focused on worst-case scenarios rather than likely outcomes
- •Consider whether you had enough information to act or were seeking impossible certainty
- •Pay attention to whether the stakes were actually as high as they felt in the moment
Journaling Prompt
Write about a time when you pushed through doubt and acted anyway. What did you learn about your own judgment? How can you recognize the difference between wise caution and self-sabotaging fear?
Coming Up Next...
Chapter 286: When Plans Meet Reality
As the story unfolds, you'll explore experienced leaders sometimes resist pressure to act, while uncovering unplanned outcomes can achieve better results than perfect plans. These lessons connect the classic to contemporary challenges we all face.