SYSK's 2025 Shocktober Halloween Spooktacular

Published October 30, 2025
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About This Episode

Josh and Chuck present their annual ad-free Halloween Spooktacular by reading and lightly commenting on two public-domain horror stories. First they perform E.F. Benson's "Caterpillars," about a haunted Italian villa, grotesque luminous caterpillars, and a possible supernatural link to cancer. Then they read Allison B. Harding's science-fiction tale "The Deep Drowse," in which a writer and his wife survive a mysterious global sleep catastrophe thanks to an air-sealed room, only for animals to inherit the Earth.

Topics Covered

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Quick Takeaways

  • Josh and Chuck continue their Halloween tradition by reading two full-length public-domain spooky stories with occasional asides and reactions.
  • E.F. Benson's "Caterpillars" features a haunting in an Italian villa that manifests as foot-long, crab-footed caterpillars seemingly connected to a fatal case of cancer in an unused bedroom.
  • The narrator of "Caterpillars" struggles to decide whether his terrifying encounters were dreams or a deadly, practical haunting that later appears to doom his friend Arthur Inglis.
  • Allison B. Harding's "The Deep Drowse" follows a hay-fever-stricken writer whose hermetically sealed, air-conditioned study becomes a refuge during a mysterious wave of overwhelming sleepiness that appears to disable nearly everyone else.
  • In "The Deep Drowse," radio silence, unreachable phones, and failing authorities suggest a massive, unseen event that puts humanity into a lethal sleep.
  • A far-future epilogue to "The Deep Drowse" reveals that animals, not humans, now study the past and conclude that a change in the atmosphere put humans into a fatal suspension, clearing the way for animals to inherit the Earth.
  • Both stories play with the tension between rational explanation and supernatural or cosmic horror, leaving characters uncertain about what is real until it is too late.
  • Josh and Chuck briefly comment on stylistic quirks of early 20th-century horror and pulp writing, such as elaborate house descriptions and heavy use of parentheses.

Podcast Notes

Introduction and Halloween Spooktacular setup

Opening greetings and SpookFest framing

Josh welcomes listeners to Stuff You Should Know and introduces the Halloween SpookFest / Spooktacular tradition[0:01]
Josh notes that he and Chuck are "flying solo" for this special episode[0:05]
They explain this is their ad-free Halloween spooktacular where they each read one story: one chosen by Josh and one by Chuck[0:30]

Introducing Story One: 'Caterpillars' by E.F. Benson

Chuck confirms the first story is "Caterpillars" by Edward Frederick Benson, better known as E.F. Benson[0:42]
They identify that the story was first published in 1912 in an anthology titled "The Room in the Tower and Other Stories"[1:04]
Josh notes that the story is not "The Room in the Tower" itself but one of the "and other stories" in that volume[1:11]
Chuck remarks that many public-domain spooky stories end up being about creepy houses and internal dread rather than actual creatures[1:22]
Josh says "Caterpillars" has a real payoff with actual "creep stuff" rather than just atmospheric dread[1:34]

Credit to guest producer Ben

Josh and Chuck tip their hats to guest producer Ben for his strong editing work on the previous year's Halloween spooktacular and express confidence he'll do it again[1:49]

Transition into reading and tone setting

They emphasize they have not discussed the stories in advance, maintaining spontaneity in their reactions[2:52]
Josh does a playful cheek-flopping sound check and they advise listeners to get cozy with Halloween props and "bat juice" before the story[2:50]

Story One: 'Caterpillars' by E.F. Benson - reading and commentary

Narrator's introduction and rationale for telling the story

The narrator explains that an Italian newspaper reported the Villa Cascana, where he once stayed, has been demolished and replaced by a factory[3:14]
Because the villa no longer exists, he feels free to describe what he saw or imagined in a certain room and landing there, along with subsequent circumstances that may or may not be related[3:36]
Josh pauses to clarify they're pronouncing it "villa" (with an L sound), and they briefly joke about the pronunciation[4:43]

Description of Villa Cascana and its layout

The narrator calls Villa Cascana delightful in all ways but one and says nothing would induce him to return, because he believes it is haunted in a very terrible and practical manner[4:34]
He contrasts most ghosts, which he claims usually just terrify and then are gotten over, with what he experienced at the villa, which he regards as truly dangerous[4:43]
Josh and Chuck interject that it's presumptuous to assume people easily get over ghost encounters, joking about hair turning white from fright
The villa stands on a holly (ilex)-covered hill near Sestri di Levante on the Italian Riviera, overlooking the sea and backed by chestnut woods and pines[5:43]
The garden is lush and fragrant with magnolia and rose, and sea winds carry scents through cool vaulted rooms; Josh remarks that Benson "can write" and the house sounds lovely[6:13]
A broad pillared loggia runs around three sides of the ground floor, forming a balcony above; Josh explains a loggia is a corridor with arches and jokes about Robert Loggia's surname meaning "Robert Corridor"[6:23]
The main gray marble staircase leads to a first-floor landing with two big sitting rooms and an unoccupied bedroom en suite; further stairs lead to more bedrooms upstairs, including the narrator's room, and to another set of rooms used by artist Arthur Inglis[7:00]
Jim Stanley and his wife, the narrator's hosts, stay in another wing with the servants; Chuck remarks the house layout feels overly detailed, and Josh agrees this is common in old stories and not very helpful as a mental map[7:41]

Narrator's uneasy arrival and first night

The narrator arrives on a bright mid-May noon, enjoys the coolness of the house after a hot walk, but instantly feels something is wrong[9:23]
He expects bad news in letters waiting in the hall, but the letters instead "reek of prosperity"; nevertheless, the vague but strong uneasiness does not dissipate[9:02]
He notes he is normally an excellent sleeper but sleeps very badly the first night; he is careful to catalog anything that might have influenced a vivid and original dream he later has[10:01]
After lunch, Mrs. Stanley shows him around and gives a somewhat over-explanatory reason why the first-floor bedroom is left unoccupied, referencing his stated preference for staying higher up in a house[10:52]
Chuck and Josh observe that her explanation feels like too much detail and the narrator suspects there is more to explain about the unoccupied room
At dinner, the conversation briefly turns to ghosts; Arthur Inglis declares that anyone who believes in supernatural phenomena is unworthy of the name of an ass, and the subject drops immediately[12:51]

The first nocturnal encounter with the caterpillars

That night, the narrator goes to bed in a rather hot room, opens the windows to moonlight and nightingales, and initially feels wide awake but happy to lie listening[13:39]
He thinks the nightingales cease and the moon sets; deciding to read, he remembers a book left in the first-floor dining room and goes down with a candle[14:28]
In the dining room, he sees the door to the unoccupied bedroom open with a strange gray light not of dawn or moonshine emanating from it; he looks in and sees a large four-poster bed opposite the door[15:10]
The bed is covered with huge caterpillars, about a foot long, faintly luminous; Josh and Chuck note this is where the story turns into real monster horror rather than just dread[16:26]
These caterpillars have crab-like pincers instead of sucker feet and move by grasping the surface and sliding forward; they are yellowish-gray with irregular lumps and swellings and form a writhing pyramid on the bed
Occasionally one falls to the floor with a soft fleshy thud, and its pincers leave impressions in the hard concrete as if it were putty before it crawls back up to the bed
They appear to have no faces but possess sideways-opening mouths that move in respiration; Chuck praises Benson's creepy imagination[16:52]
The narrator senses they become aware of him, all mouth-ends turning his way, and they start dropping off the bed and wriggling toward him[18:01]
Paralyzed for a moment, he then runs upstairs barefoot, feeling the cold marble steps, and slams his bedroom door, sweating with terror and expecting the caterpillars to break through any barrier[18:15]
He sits or stands all night, too afraid to lie down, until dawn's light and wind gradually dispel the horror[20:09]

Breakfast discovery: the real caterpillar

At the late breakfast, the narrator finds a small cardboard pillbox between his knife and fork; Inglis says he found a caterpillar crawling on his "couch of pain" the previous night and wants help identifying it[21:19]
Inside is a small grayish-yellow caterpillar with bumps and crab-like pincer feet, extremely active and starting to spin a cocoon; it is a miniature version of what the narrator saw on the bed[22:04]
Inglis jokes about naming it "Cancer Inglisensis" after himself, using the Latin word for crab, and the narrator suddenly connects this with his night's vision[23:28]
Overcome, the narrator impulsively throws the pillbox, caterpillar and all, out the window into a fountain outside, surprising the others at the table[24:08]
He later explains he "lost his head" because the box's inhabitant matched the horrific creatures he had seen, and this did not lessen his horror but made the vision more real

The caterpillar returns and is killed

Later, as Josh reads, the narrator and Stanley head out to bathe and pass the fountain; the cardboard box has disintegrated, but the caterpillar is crawling up a marble cupid figure, still spinning its cocoon[26:30]
The caterpillar seems to notice the narrator again, breaks out of its web, crawls down, and amazingly swims like a snake across the water toward him with great speed[27:16]
Inglis appears, recognizes it as "old Cancer Inglisensis," watches it crawl onto his shoe, then shakes it off onto the gravel and crushes it with his foot[27:57]

Second night: mass invasion and horror on the staircase

That afternoon, a Sirocco wind builds; that night the narrator again feels a sense of danger before falling asleep and later either wakes or dreams he wakes with an urgent feeling he must get up or be too late[28:29]
He fights the impulse, blaming nerves and the Sirocco, but eventually gets up and opens his door, only to see the landing below completely covered in swarming caterpillars[29:33]
They squeeze through cracks and the keyhole of the folding doors to the sitting room, elongating to pass through and swelling again on the other side; others move toward the steps that lead to Inglis's room[30:07]
The narrator is frozen with horror, unable to shout and afraid that making a sound would cause them to turn toward his own staircase instead of going to Inglis[30:40]
He watches them reach Inglis's door and force their way inside, then notes the passage is empty and becomes conscious of the cold marble under his bare feet as dawn breaks[31:07]

Six months later: cancer revelation

Six months later in England, the narrator meets Mrs. Stanley at a country house; she mentions "dreadful news" about Arthur Inglis from a month earlier[32:09]
She says Inglis has cancer so advanced that doctors will not operate and say he is riddled with it[33:54]
The narrator notes he has thought about the Villa Cascana dreams almost daily for six months; Mrs. Stanley says she feels he may have "caught it" at the villa[33:00]
When he asks how she knew, she is surprised and reveals that a year earlier there had been a fatal case of cancer in the unoccupied bedroom, and doctors had only cautioned her not to let anyone sleep there[34:07]
The story ends abruptly with that revelation and the implication of a malign connection between the room, the caterpillars, and cancer[34:28]

Josh and Chuck's brief reaction to 'Caterpillars'

They interpret the lumps on the caterpillars' bodies as tumorous and link the creatures to the room's "cancer" history and Inglis's fate[35:21]
Josh suggests it may function as a kind of morality or "vanity" tale, and both agree they prefer to read the events as real rather than just dreams, to preserve the horror impact[34:20]

Transition to Story Two and background on Allison B. Harding

Introducing 'The Deep Drowse' and Weird Tales context

Chuck introduces his pick: "The Deep Drowse" from the pulp magazine Weird Tales, September 1949 issue[34:48]
He notes the story is credited to Allison B. Harding, a mysterious pen name associated with 10-15 stories in the 1940s and 50s, mostly in Weird Tales, after which the writer disappeared from publishing[34:41]
Josh says some people suspect Allison B. Harding might be Jean Milligan, though that is unproven, and other theories include Lamont Buchanan or a husband-wife team[35:14]
Chuck suggests the pseudonym might have been used to avoid professional conflicts or because the author had another career where pulp writing might be frowned upon[35:30]
They agree the writer, whoever it was, produced some overlooked but great horror fiction[35:56]

Story Two: 'The Deep Drowse' by Allison B. Harding - reading and commentary

Opening: Arthur and Fran Hodges' life and Arthur's hay fever

The story opens by stating that Arthur Hodges has very bad hay fever and lives with his wife Frances (Fran) in a cheerful white wooden country house with a big stone chimney and a stone terrace[36:28]
The narrator notes that their living in a country house is one factor securing the Hodges' place in the history of the world, because many elements had to "dovetail" perfectly[36:39]
An analogy is drawn to accidents like a man hit by a falling brick, where his entire lifetime of seconds must synchronize with the brick's fall; similarly, multiple conditions align in the Hodges' case[36:54]
Arthur is a writer, and not only a writer but a successful one whose work appears in major magazines, giving him enough money for comforts like two cars and modern conveniences[37:33]
Crucially, his success funds a hermetically sealed, air-conditioned study/bedroom for the summer months so his severe hay fever will not torment him in the country[38:12]
Arthur jokes to neighbors about this special refuge and calls it their "cave"; Fran is methodical and manages the household budget, but both take the setup for granted like other appliances[38:21]
From July through September Arthur does errands in town, and Fran can predict how red his eyes and nose will be depending on how long he has been exposed, which they treat as a running joke[38:20]
He often returns claiming he feels fine and joking they could shut off the air conditioner, only to immediately dissolve into sneezing and be pushed back into the sealed rooms[39:34]

Movie deal letter and decision to celebrate

On the late afternoon of August 14, Fran returns from the village and finds Arthur putting on the lawn when a registered letter arrives from a movie company offering to buy his latest serial for a high price[40:13]
Arthur downplays it but is clearly pleased; Fran is openly excited and calls him wonderful, and he remarks it will at least pay for the air-conditioner for another summer[41:22]
Fran suggests they celebrate by inviting old friends-Jack and Cynthia Fisk, and Tim and Mary Barnes-for a weekend party with bridge and golf[42:05]
Fran notes it is very warm and humid outside, with fog pockets in low-lying land, and finds the cave's cool air nicer than the oppressive outdoors[42:25]

Phone calls to friends: signs of unusual lethargy

Around 8 p.m., Fran calls Cynthia Fisk to invite them; Cynthia squeals with delight, but Jack is already asleep on the living room sofa after a long day, which Josh and Chuck note as odd given his usual busy persona[43:20]
Arthur chats with Jack, who mentions a big case and says depending on how it goes he might have trouble making the weekend but generally agrees to come[45:26]
Fran and Cynthia joke about the heat and the "cave" setup; Cynthia says the city is unbearable and tells Fran to call back later once Jack hears from his client[45:57]
After hanging up, Fran comments that Jack seemed to be sleeping very early and that she and Arthur, supposedly the country idlers, seem more energetic than their city and suburban friends[47:08]
Fran then calls Mary Barnes; Tim is not yet home from the city and Mary sounds as if she might have been awakened by the call[47:29]
Fran invites them to the country and tells Mary they will call back after Tim returns; Arthur jokingly contrasts their "bucolic" life with overworked city commuters[49:19]

Arthur's nighttime walk and first hint of the "deep drowse"

Arthur insists on going out to close the electric garage doors "on principle" despite Fran saying it's unnecessary and might aggravate his hay fever[50:05]
Outside, the night is starless and very dark; Arthur uses a flashlight, plays with the up-and-down door switches, and wanders a bit into the yard, noticing how the trees and shrubs look lifeless, like stage props[51:06]
He briefly signals a distant airplane with his flashlight and feels a sudden loneliness as the plane disappears into the northern night, then hurries back to the lighted house[52:53]
Returning to the cave, Arthur is surprised he has not sneezed once despite being outside in prime allergy conditions[54:03]

Second round of calls and growing worry

Later, Fran decides to call the Fisks again around 10:30; when Cynthia answers, her voice sounds odd and tired, and both Arthur and Fran initially suspect drinking or illness[56:22]
Cynthia describes intense city heat and a hissing sound in the background like a radiator or steam; she and Jack both sound worn out, and Fran becomes worried they might be sick, possibly with food poisoning[57:17]
They then call the Barneses; Mary says Tim came home from the station and "just sort of collapsed," and Mary herself sounds weak and sleepy[59:36]
Arthur jokes about both couples being exhausted as if from the same bad oysters; Fran has a moment of fear that this could be some kind of enemy attack like poison gas described in an article they read[59:37]
Arthur laughs off the attack theory, reminding her he is the one who normally uses his imagination professionally, and they turn on the radio, which initially plays typical late-night jazz records[1:00:40]

Radio silence and failure of telephones

They notice the disc jockey's usual between-record comments are missing, then the music stops after a noisy orchestral piece by Andrei Postolenets and is followed by ominous silence[1:01:59]
Expecting an interruption announcing war or some national emergency, they instead hear nothing; Arthur experiments with the phone, dialling operators and numbers without responses[1:03:51]
He calls their old doctor acquaintance, Dr. McCollum, who answers slowly and sleepily, acknowledges something is "funny" about what's happening, then trails off mid-conversation and cannot be roused again[1:05:57]
Arthur calls Tim Barnes, who can barely speak and sounds lethargic, and urges him to contact a doctor or police immediately, but Tim's responses are mostly unintelligible[1:06:39]
Arthur contacts the town operator and asks for the police; the operator and then the policeman both sound drowsy and fade out mid-call, leaving Arthur increasingly alarmed[1:08:54]
The radio continues to emit only hum when they scan the dial; there are no commercials, news bulletins, or live voices, and all attempts to reach an operator eventually fail[1:10:29]

Contacting the movie theater caretaker and confirming the danger

Arthur reasons that some people might be protected if they are in air-conditioned spaces and calls Mr. Hoskins, an elderly hay-fever-stricken caretaker who lives in the town's air-conditioned movie house[1:12:14]
Hoskins answers quaveringly and says he can see people lying in the street outside and feels compelled to go out to check; Arthur urgently warns him not to go, but Hoskins hangs up and leaves anyway[1:13:15]
Arthur concludes that a widespread event is making people collapse into sleep and that those who do not realize the danger are likely to succumb if they leave protected spaces[1:14:05]

First test outside the cave and confirmation of the "deep drowse" effect

Arthur tells Fran he must go outside briefly to understand what is happening; she is terrified and suggests it might be some sort of war-related poison gas[1:14:18]
He steps into the unconditioned part of the house and then onto the terrace, immediately feeling lightheaded, nauseated, sweaty-palmed, and overwhelmingly sleepy, as if under a sedative[1:14:34]
He forces himself back into the house and then into the cave, where the pure oxygen quickly restores him; his watch shows he was outside only eight minutes[1:17:04]
Over the course of the night and following day, he makes several short trips into the rest of the house and finds his tolerance for the outside air shrinking, with the drowsiness setting in faster each time[1:18:31]
Meanwhile, he brings all food and supplies into the cave, along with Sterno and other items they might need, and he and Fran resolve to avoid leaving unless absolutely necessary[1:19:37]

Calculating survival: oxygen and food in the cave

At 5 a.m., Arthur and Fran hold a "council of war" and estimate how long their canned food and oxygen cylinders will last; oxygen is identified as the limiting factor[1:21:57]
Arthur tallies their oxygen cylinders and calculates that with continuous use they would have about seven or eight days, but by running the machine only as needed they can stretch the supply further[1:22:36]
He reasons that within that span some explanation or resolution should emerge, even if it means an occupying enemy; they take some comfort in at least being protected for that time[1:24:10]
Fran later admits she impulsively went out once while Arthur was asleep, experienced the same near-anaesthetic feeling, and barely got back into the cave before collapsing, which angers Arthur because he could not have rescued her[1:26:48]

Waiting, documenting, and the passage of twelve days

Arthur begins typing a chronological record of events, partly to keep busy and partly to document what has happened, while Fran fusses with supplies; she jokes initially that he may no longer have any audience[1:28:07]
Time inside the cave passes slowly; they intermittently check the dead radio and phones and stare out the windows at the unnaturally still, hazy August landscape[1:30:35]
They watch for the regular 6 p.m. four-motored passenger plane that usually roars overhead but on this day it never appears, reinforcing the sense of a total societal stop[1:31:11]
They anthropomorphize their oxygen cylinders as "people" because their lives now depend entirely on the dwindling supply; the labels warning "Oxygen. Dangerous. Inflammable" take on new meaning[1:33:10]
As days go by, Fran occasionally cries in private; both become paler and weaker, and talk less as oxygen runs low[1:35:15]
Arthur carefully rations the oxygen and manages to stretch it out five days longer than his initial estimate, giving them twelve days in total from the event[1:35:24]

Decision point: stay in the cave or risk the outside

On what Arthur calculates as the twelfth day, their last oxygen cylinder hisses nearly empty; they debate whether to stay in the sealed room and slowly suffocate or go out into the drowsiness-inducing air[1:37:03]
Fran independently has the same thought and raises it; together they decide the Known (the outside air's sleep effect) is better than the Unknown (slow asphyxiation inside), and plan to leave when the oxygen is gone[1:38:39]
They spend their last hours in the cave sitting together at the window, noticing the room's rising temperature and feeling increasing weakness as fresh oxygen stops[1:40:03]
Arthur reflects that it seems an ill-suited, warm day to die and thinks of each day marked for death as someone feeling the same; they kiss through tears and prepare to leave together[1:41:18]

The rabbit and collapse on the lawn

Fran suddenly gasps at something outside: a plump brown rabbit hopping casually across the green lawn, pausing briefly as if noticing them and then continuing toward the terrace and fields[1:42:02]
The sight of the unaffected rabbit galvanizes them; they open the cave door, move through the house, and step onto the terrace together, feeling immediate relief compared to the oxygen-starved cave[1:43:04]
However, after only a short walk on the lawn, the same overpowering drowsiness descends; the distance back to the door suddenly feels impossibly long and uphill[1:44:19]
They collapse together on the grass, overcome by sleep, and Arthur's last sensation is of the green grass enveloping him, as the rabbit continues unconcerned into the field beyond[1:45:29]

Far-future epilogue: animal civilization and 'The Suspension'

Institute of Hieroglyphics and analysis of the catastrophe

The narrative jumps far into the future to an "Institute of Hieroglyphics" that has studied ancient records to understand a great change in the solar system known as "The Suspension"[1:47:32]
One of the clearest records they find is by a biped called A. Hodges, whose hieroglyphic manuscript describes the first twelve days of the suspension[1:48:58]
Scholars of the present eon, now members of an enlightened animal civilization, conclude from Hodges's account that humans misinterpreted the event as war, focusing on concepts like "atom bomb" and "poison gas"[1:50:11]
These animal historians reconstruct that a cosmic shift altered Earth's atmosphere and its oxygen belt in a way that uniquely affected bipeds (humans), stupefying them by removing an ingredient necessary for consciousness retention[1:51:51]
Humans entered a state of suspended sleep and ultimately died of starvation, while later atmospheric changes allowed other species to adapt and continue[1:53:31]

The last human and animals' judgment

The animal civilization's greatest recent discovery was a living biped, the last human, found in a remote cave on a mountain ridge at the Lone River, where unique atmospheric conditions allowed a small human line to survive for generations[1:54:50]
This last human is brought before an administration council composed of animals (such as a lynx, giraffe, squirrels, and a bear) and given a tablet and writing instrument to record a message[1:57:05]
In his markings, the human angrily describes being captured by jackals and wolves and brought before an animal "jury," revealing that he still sees animals in derogatory, subordinate terms[1:59:00]
Despite being well cared for, fed, and attended to, the last human soon dies, raging at his caretakers, and his final tablet is studied by animal scholars as an expression of his species' mindset[2:00:50]
The Institute and other councils conclude that the humans' inability to adjust, their factional wars, and disregard for other species made their extinction inevitable and cleared the way for animals to inherit the Earth[2:02:30]

Closing reactions and Halloween sign-off

Josh and Chuck's reaction to 'The Deep Drowse' and episode wrap-up

Chuck comments that while "The Deep Drowse" is a good story, he feels its 15 pages could have been condensed to about nine because of repeated neighbor-calling scenes[2:04:50]
Josh notes the story includes a substantial "boondoggle" of phone calls to neighbors but still showcases why the author (whoever was behind the pseudonym) is regarded as one of the great overlooked horror writers[2:06:20]
Josh remarks that this is the "spooktacular 2025 style," situating the episode in that year's Halloween series[2:06:20]
They express satisfaction with the stories and look forward to what producer Ben will do with the edit, jokingly invoking "Ben and Jerry" in a playful mashup[2:07:00]
Josh wishes listeners a happy Halloween, encourages them to enjoy candy and beware classic urban-legend hazards like razor blades in apples, and promises a return to regular episodes after the holiday[2:08:30]

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

Our interpretations of strange experiences are heavily shaped by what we already believe, whether that's a supernatural haunting, a medical explanation, or an enemy attack.

Reflection Questions:

  • When I feel uneasy or sense that something is "wrong," what explanations do I instinctively reach for first, and what does that reveal about my worldview?
  • How could I expand the range of explanations I consider before locking in on one narrative about a confusing situation?
  • What is one current situation where I could deliberately pause and ask, "What are three alternative explanations for what I think is happening?"
2

Dependence on technology and infrastructure can create hidden vulnerabilities; when those systems fail, the gap between those with protection and those without can become life-or-death.

Reflection Questions:

  • Which comforts or tools in my life do I assume will always be available, and what would happen if they suddenly failed for a week?
  • How might I build a bit more resilience-personally or professionally-so I'm not completely disabled when one key system goes down?
  • What is one small contingency plan I could put in place this month for a resource I rely on (power, data, transport, a single supplier, etc.)?
3

Documentation in the moment can become invaluable later, turning isolated experiences into evidence and perspective for others who come after us.

Reflection Questions:

  • In what areas of my work or life would keeping a brief, factual record of decisions and events make future analysis or learning easier?
  • How could I make documentation a small, sustainable habit instead of an overwhelming chore?
  • What is one project, crisis, or learning process I'm in right now where writing down what happens each day would benefit my future self or someone else?
4

Species, cultures, or organizations that ignore their dependencies on their environment and on others can be blindsided when conditions change and are unable to adapt.

Reflection Questions:

  • Where am I or my organization assuming that current conditions (markets, regulations, climate, technology) will stay the same indefinitely?
  • How could I better map the external factors my success depends on and assess how sensitive I am to their shifts?
  • What is one scenario-a regulatory change, environmental shock, or social shift-I could proactively stress-test my plans against this quarter?
5

Facing the "known" difficulty can sometimes be wiser than clinging to a failing safety net, especially when that safety is clearly running out.

Reflection Questions:

  • Where in my life am I staying in a situation that is slowly deteriorating because it feels safer than taking a more direct risk?
  • How can I more clearly assess the tradeoff between staying put and stepping into discomfort when my current path is unsustainable?
  • What is one area this week where I could deliberately choose a controlled exposure to a known risk instead of passively waiting for circumstances to close in?

Episode Summary - Notes by Cameron

SYSK's 2025 Shocktober Halloween Spooktacular
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