Summary
After the morning's deadly battle, Jim finds himself trapped in the hot, blood-soaked stockade while Dr. Livesey ventures out alone to meet Ben Gunn. The contrast between the doctor's freedom and Jim's confinement breeds a dangerous restlessness. Despite knowing it's foolish, Jim decides to sneak out and find Ben Gunn's hidden boat—partly from boredom, partly from a desire to prove himself useful. He carefully prepares by packing biscuits and pistols, showing he's not completely reckless, just young and impulsive. Jim successfully escapes the fort and makes his way to the eastern shore, where he discovers Ben Gunn's makeshift coracle—a crude but functional boat made from wood and goatskin. Instead of returning safely, Jim hatches an even more dangerous plan: to sneak out under cover of darkness and cut the Hispaniola loose from her anchor, preventing the pirates from escaping. This chapter reveals how isolation and the desire to contribute can push even sensible people toward risky decisions. Jim's actions show the classic teenage pattern of knowing something is dangerous while doing it anyway. His careful preparation suggests he's not suicidal, just desperate to feel useful in a situation where adults have sidelined him. The discovery of the boat represents opportunity—but also temptation toward greater danger.
Coming Up in Chapter 23
With darkness falling and the fog rolling in, Jim prepares to launch Ben Gunn's tiny coracle into dangerous waters. His mission to cut the Hispaniola loose will put him directly in the path of Long John Silver and his remaining crew.
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An excerpt from the original text.(~500 words)
How I Began My Sea Adventure There was no return of the mutineers--not so much as another shot out of the woods. They had “got their rations for that day,” as the captain put it, and we had the place to ourselves and a quiet time to overhaul the wounded and get dinner. Squire and I cooked outside in spite of the danger, and even outside we could hardly tell what we were at, for horror of the loud groans that reached us from the doctor’s patients. Out of the eight men who had fallen in the action, only three still breathed--that one of the pirates who had been shot at the loophole, Hunter, and Captain Smollett; and of these, the first two were as good as dead; the mutineer indeed died under the doctor’s knife, and Hunter, do what we could, never recovered consciousness in this world. He lingered all day, breathing loudly like the old buccaneer at home in his apoplectic fit, but the bones of his chest had been crushed by the blow and his skull fractured in falling, and some time in the following night, without sign or sound, he went to his Maker. As for the captain, his wounds were grievous indeed, but not dangerous. No organ was fatally injured. Anderson’s ball--for it was Job that shot him first--had broken his shoulder-blade and touched the lung, not badly; the second had only torn and displaced some muscles in the calf. He was sure to recover, the doctor said, but in the meantime, and for weeks to come, he must not walk nor move his arm, nor so much as speak when he could help it. My own accidental cut across the knuckles was a flea-bite. Doctor Livesey patched it up with plaster and pulled my ears for me into the bargain. After dinner the squire and the doctor sat by the captain’s side awhile in consultation; and when they had talked to their hearts’ content, it being then a little past noon, the doctor took up his hat and pistols, girt on a cutlass, put the chart in his pocket, and with a musket over his shoulder crossed the palisade on the north side and set off briskly through the trees. Gray and I were sitting together at the far end of the block house, to be out of earshot of our officers consulting; and Gray took his pipe out of his mouth and fairly forgot to put it back again, so thunder-struck he was at this occurrence. “Why, in the name of Davy Jones,” said he, “is Dr. Livesey mad?” “Why no,” says I. “He’s about the last of this crew for that, I take it.” “Well, shipmate,” said Gray, “mad he may not be; but if HE’S not, you mark my words, I am.” “I take it,” replied I, “the doctor has his idea; and if I am right, he’s going now to see Ben Gunn.” I was right, as appeared later; but...
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Intelligence Amplifier™ Analysis
The Road of Useful Rebellion
The tendency to take increasingly risky actions to prove worth when feeling capable but sidelined.
Why This Matters
Connect literature to life
This chapter teaches how to distinguish between taking calculated risks to solve real problems versus taking risks to prove your worth when feeling sidelined.
Practice This Today
Next time you feel the urge to break rules or bypass authority, pause and ask: 'Am I doing this to solve a problem or to prove my value?' If it's the latter, find a safer way to demonstrate worth first.
Now let's explore the literary elements.
Terms to Know
Mutineer
A person who rebels against authority, especially sailors who turn against their ship's officers. In this story, it's Long John Silver's crew who've taken over the ship and are hunting for treasure.
Modern Usage:
We see this pattern in workplace rebellions, union strikes, or any time employees band together against management.
Stockade
A defensive barrier made of wooden posts, like a fort. Jim and the loyal crew have barricaded themselves inside this makeshift fortress to protect against the pirates.
Modern Usage:
Similar to how people 'circle the wagons' or create safe spaces when under attack - whether it's a gated community or just locking your doors.
Coracle
A small, round boat made from animal hide stretched over a wooden frame. Ben Gunn built one from goatskin and wood - crude but functional for short trips.
Modern Usage:
Like any DIY solution when you can't afford the real thing - using duct tape to fix your car, or making furniture from milk crates.
Restlessness
The anxious energy that builds up when you're stuck in one place while important things happen elsewhere. Jim feels trapped and useless while Dr. Livesey gets to go on adventures.
Modern Usage:
That feeling when you're stuck at home during a crisis, or when everyone else seems to be living their best life on social media.
Reckless courage
The dangerous combination of bravery and poor judgment, especially in young people who want to prove themselves. Jim knows his plan is risky but does it anyway.
Modern Usage:
Teenagers taking dangerous selfies, or anyone doing something stupid to impress others or feel important.
Cabin fever
The psychological stress of being confined in a small space for too long, leading to irritability and poor decisions. Jim's isolation in the stockade drives his need to escape.
Modern Usage:
What people experienced during COVID lockdowns, or anyone stuck in a dead-end job or toxic relationship.
Characters in This Chapter
Jim Hawkins
Protagonist
Jim struggles with feeling useless and confined in the stockade. His restlessness leads him to make the dangerous decision to sneak out and find Ben Gunn's boat, then attempt to cut the ship loose.
Modern Equivalent:
The teenager who feels sidelined by adults and makes risky choices to prove they matter
Dr. Livesey
Mentor figure
The doctor gets to leave the stockade safely to meet with Ben Gunn, highlighting Jim's confinement. His freedom contrasts sharply with Jim's trapped feeling.
Modern Equivalent:
The trusted adult who gets special privileges while everyone else has to follow the rules
Captain Smollett
Authority figure
Though wounded, the captain represents the legitimate authority that Jim respects but also feels constrained by. His injury adds to Jim's sense that he needs to step up.
Modern Equivalent:
The boss who's out sick, leaving younger employees feeling they need to take charge
Ben Gunn
Wild card ally
Though not physically present, Ben Gunn's hidden coracle becomes the tool for Jim's escape plan. His resourcefulness in building the boat inspires Jim's own risky scheme.
Modern Equivalent:
The eccentric friend who leaves useful but dangerous tools lying around
Key Quotes & Analysis
"The more I thought of this, the more certain I became that I was neglecting my business and the lives of others for the sake of my own comfort."
Context: Jim justifies his decision to leave the safety of the stockade
This shows how young people often rationalize risky behavior by framing it as heroic duty. Jim convinces himself that his dangerous plan is actually selfless service to others.
In Today's Words:
I felt guilty for sitting around while everyone else was in danger, so I had to do something.
"I was dead tired, as you may fancy; and when I got to sleep, which was not till after a great deal of tossing, I slept like a log of wood."
Context: After discovering Ben Gunn's boat and making his plans
The physical exhaustion masks Jim's mental turmoil about his upcoming dangerous mission. His deep sleep suggests either peace with his decision or complete mental fatigue.
In Today's Words:
I was so wiped out that I crashed hard, but my mind was still racing about what I was planning to do.
"It was quite dark when I awoke, and I judged it to be somewhere between nine and ten o'clock, the moon was not yet up, and it was the very time for my enterprise."
Context: Jim wakes up ready to execute his plan to cut the ship loose
The darkness both conceals and symbolizes the moral ambiguity of Jim's actions. He's chosen the perfect time for stealth, but also the most dangerous moment for a solo mission.
In Today's Words:
It was pitch black when I woke up - perfect timing for what I had to do.
Thematic Threads
Identity
In This Chapter
Jim struggles between being seen as a child to protect versus a capable contributor
Development
Evolved from earlier acceptance of adult guidance to active resistance against being sidelined
In Your Life:
You might feel this when your experience is dismissed due to your age, position, or background.
Class
In This Chapter
Jim's working-class practicality shows in his careful preparation despite the risky decision
Development
Continues showing how working-class characters prove worth through action rather than words
In Your Life:
You might recognize the pressure to prove yourself through doing rather than talking.
Personal Growth
In This Chapter
Jim's decision-making shows growing independence but also dangerous overconfidence
Development
Building from earlier chapters where Jim followed orders to now making autonomous choices
In Your Life:
You might see this in moments when you're ready for more responsibility but others aren't ready to give it.
Social Expectations
In This Chapter
The conflict between what adults expect Jim to do (stay safe) versus what he believes he should do (contribute)
Development
Intensified from earlier tension between Jim's capabilities and others' protective instincts
In Your Life:
You might feel this when family or supervisors' protective intentions feel like limitations on your potential.
You now have the context. Time to form your own thoughts.
Discussion Questions
- 1
What specific preparations does Jim make before sneaking out, and what does this tell us about his mindset?
analysis • surface - 2
Why does Jim feel compelled to leave the safety of the stockade when he knows it's dangerous?
analysis • medium - 3
When have you seen someone take unnecessary risks because they felt sidelined or undervalued?
application • medium - 4
How could Jim have addressed his restlessness and desire to contribute without endangering himself?
application • deep - 5
What does Jim's behavior reveal about the human need to feel useful, especially when others are making important decisions without us?
reflection • deep
Critical Thinking Exercise
Map Your Own Useful Rebellion
Think of a time when you took a risk or broke rules because you felt your skills weren't being recognized or used. Write down what drove you to act, what you were trying to prove, and what the actual outcome was. Then identify what you really needed in that moment - was it recognition, autonomy, or something else?
Consider:
- •Consider whether you were solving a real problem or proving your worth
- •Think about what safer alternatives might have achieved the same goal
- •Reflect on whether the adults or authorities in your situation had valid reasons for their restrictions
Journaling Prompt
Write about a current situation where you feel sidelined or undervalued. What would useful rebellion look like versus destructive rebellion? How could you demonstrate your capabilities while minimizing risk?
Coming Up Next...
Chapter 23: When Plans Meet Reality
What lies ahead teaches us to adapt when your tools don't work as expected, and shows us timing and patience matter more than force. These patterns appear in literature and life alike.