The Wandering Trail: Episode Seven

Hello wanderers, and welcome back! As part of our episode notes, we've created this "Wandering Trail." In our seventh episode of Beyond the Brandywine, we turned our attention to the unsung, the overworked, and the downright doomed — the worst jobs in Middle-earth. Not everyone gets to be a king or an Elf-lord; somebody has to clean the stables, deliver the mail, and yes, build ships for a king who thinks he can challenge the gods.

Tolkien's world is famous for its grand quests and noble heroes, but beneath the surface runs a vast network of ordinary (and extraordinarily dangerous) labor that keeps Middle-earth functioning. From the thankless tasks that won't kill you (probably) to the assignments that come with cosmic consequences, we explored what it might actually be like to clock in for work in the Third Age — or worse, the First.

This is our tour of Middle-earth's employment nightmares, ranked from "unpleasant but survivable" to "your job description includes being set in the sky forever."

Tier 1: Thankless But Not Deadly

The Michel Delving Postal Service

The Shire's postal workers represent perhaps the most deceptively difficult job in Hobbiton. At first glance, it sounds pastoral — walking the rolling hills, delivering letters, getting some sunshine. But consider the logistics: the Shire spans at least 40 miles east to west, all traversed on foot (hobbits are too small for horses, and only the tallest Tooks can ride ponies). There are no standardized addresses in many areas, requiring intimate local knowledge. And the volume of mail is staggering.

Tolkien specifically mentions in the Prologue to The Lord of the Rings that the Shire has a messenger service, and that the Mayor of Michel Delving also serves as Postmaster-General. This detail, easily overlooked, reveals how essential the postal system is to hobbit society. Without internet, phones, or rapid transit, hobbits rely entirely on physical mail for communication, gossip, business, and social coordination.

The real nightmare comes during major events. Bilbo's birthday party — which invited "half the Shire" while the other half "showed up anyway" — would have created a postal crisis. Hundreds of invitations delivered to loosely-defined addresses across multiple Farthings, all on a deadline, with the added pressure of knowing that failure to deliver on time means facing the wrath of proud hobbit families. The Sackville-Bagginses alone would have complaints.

Then there's the question of pay. The Shire's economy seems to run partly on barter, partly on some form of currency (Bilbo does pay people to help set up his party). Either way, it's unlikely postal workers are compensated proportionally to the miles they walk or the complaints they field.

Where to find it:

• The Lord of the Rings, Prologue "Concerning Hobbits" establishes that "the Postmaster and the First Shirriff were the only real officials in the Shire-moot"

• The Fellowship of the Ring, Book I, Chapter 1 depicts the chaos of Bilbo's birthday party preparations

• The Return of the King, Book VI, Chapter 8 "The Scouring of the Shire" shows what happens when Shire infrastructure breaks down

Barliman Butterbur's Staff at The Prancing Pony

Working for Barliman Butterbur of Bree would test anyone's patience. He's scatterbrained, disorganized, and prone to forgetting crucial information (like, say, delivering a letter from Gandalf that could affect the fate of Middle-earth). His two hobbit employees — Nob and Bob (not official names, but close enough) — are expected to handle everything: stables, cooking, cleaning, serving guests, running errands, and dealing with whatever goes bump in the night during the declining years of the Third Age.

The workload is unreasonable. The Prancing Pony serves both human and hobbit guests, requiring rooms and accommodations of different sizes. There's no indication Butterbur employs enough staff for this, instead apparently relying on two hobbits to do the work of five people. And unlike hobbit-sized work in the Shire, this involves managing full-sized horses, human-scaled rooms, and occasionally dealing with Rangers, wizards, and Black Riders.

The verbal abuse is a bonus. Butterbur's favorite insult — "you wooly-footed slowcoach" and similar — suggests a management style heavy on criticism and light on appreciation. When the hobbits return to Bree at the end of The Return of the King, we learn that Nob has started going home at night rather than staying at the inn, suggesting he seized the first opportunity for work-life balance when Bree became dangerous enough to justify it.

Where to find it:

• The Fellowship of the Ring, Book I, Chapter 9 "At the Sign of the Prancing Pony" introduces Butterbur and his harried staff

• The Fellowship of the Ring, Book I, Chapter 10 "Strider" — Gandalf's undelivered letter reveals Butterbur's forgetfulness could have doomed the quest

• The Return of the King, Book VI, Chapter 7 "Homeward Bound" shows the Prancing Pony staff dealing with new dangers

Denethor's Household Staff

The Steward of Gondor presents a different kind of terrible boss. Unlike Butterbur's chaotic incompetence, Denethor's leadership style combines depression, paranoia, and dramatic food waste. His staff must serve a man who sits alone staring at nothing, leaving elaborate meals untouched, while Gondor faces existential crisis.

Denethor's mental state has been deteriorating since his wife's death years earlier. In the books, it's explicitly stated that he was never the same after she died giving birth to Faramir — which partly explains his cruelty toward his younger son. By the time of the War of the Ring, he's secretly been using one of the palantíri to spy on Sauron's movements, an act that has poisoned his mind and filled him with despair.

For his servants, this means working for someone utterly unpredictable. You prepare elaborate meals that go uneaten. You stand attendance while he ignores you completely. You watch him treat his own son with shocking coldness (the line where Faramir asks if Denethor wishes their places had been switched, and Denethor essentially says yes, is one of the cruelest moments in the books). And ultimately, you're present when he attempts to burn himself and Faramir alive in the tombs.

The character Beregond, one of the Tower Guard who helps Pippin save Faramir, technically forfeits his life by abandoning his post — highlighting how rigid and dangerous the command structure is under Denethor's failing leadership.

Where to find it:

• The Return of the King, Book V, Chapter 4 "The Siege of Gondor" — Denethor's decline accelerates

• The Return of the King, Book V, Chapter 7 "The Pyre of Denethor" — his staff witnesses his final madness

• Unfinished Tales, "The Line of Isildur" provides background on Denethor's use of the palantír

Tier 2: Isolated and Exposed

The Gondor Beacon System

Maintaining the warning beacons between Minas Tirith and Rohan sounds romantic — a crucial link in the defense of the West, entrusted to dedicated keepers who hold civilization together. In practice, it's probably lonely, boring, and occasionally terrifying.

The beacon chain stretches approximately 150 miles from Minas Tirith to the borders of Rohan, a network of signal fires positioned on mountain peaks for maximum visibility. Each beacon must be kept ready to light at a moment's notice, which requires maintaining dry wood, storing oil or other accelerants, and keeping watch for the signal from the previous beacon in the chain.

The logistical challenges are considerable. These are mountain stations, some in snow-capped terrain, all requiring supplies, firewood, and fresh horses for couriers. The keepers must be rotated (we hope), provisions must be delivered regularly, and the whole system must remain operational year-round. In winter, this means enduring brutal conditions.

During peacetime — which Gondor enjoyed less and less as the Third Age waned — it means endless, vigilant boredom.

The real nightmare scenario: you're on watch, you see the beacon light in the distance, you light yours... and then you watch the next beacon in the chain fail to ignite. Do you wait? How long? Do you abandon your post to ride there and investigate? What if you're wrong and it's just obscured by clouds? The system has no redundancy, no way to communicate except through the beacons themselves. One failure could mean Rohan never learns Gondor needs aid.

Where to find it:

• The Return of the King, Book V, Chapter 1 "Minas Tirith" describes the beacon system

• The Return of the King, Book V, Chapter 3 "The Muster of Rohan" — the beacons are lit

For a deeper dive:

• Karen Wynn Fonstad's The Atlas of Middle-earth maps the beacon locations and discusses the distances involved

Barad-dûr Tower Maintenance Crew

If you've watched the opening sequences of The Fellowship of the Ring film, you've seen them: tiny figures on scaffolding around Sauron's tower, hammering away in the shadow of Mount Doom. These workers — whether orcs, enslaved Men, or some mixture — have

perhaps the most dangerous construction job in history.

The tower stands in Mordor, where the air is ash-filled and poisonous. The heat from the nearby volcano is oppressive. There are no safety regulations (Mordor's OSHA compliance is notably poor). Fall from the scaffolding and you're dead. Anger your orc overseer and you're dead. Fail to meet your quota and you're probably fed to Shelob or the fel beasts. The job combines extreme physical danger with zero workers' rights in an actively hostile environment.

The books mention that Barad-dûr was still being rebuilt and expanded throughout the late Third Age, requiring constant labor. The conversation between the orcs Shagrat and Gorbag in The Return of the King gives us rare insight into orc workplace complaints — poor leadership, arbitrary punishments, dangerous assignments, and a general sense of being disposable cogs in Sauron's machine.

Where to find it:

• The Return of the King, Book IV, Chapter 10 "The Choices of Master Samwise" and Book VI, Chapter 1 "The Tower of Cirith Ungol" feature the conversation between Shagrat and Gorbag

• The Silmarillion, "Of the Rings of Power and the Third Age" mentions Sauron's fortification of Mordor

Tier 3: High Probability of Death

Bill the Pony's Journey

This entry requires a defense: Bill the Pony isn't technically employed, but his experience represents one of the most thankless roles in the Fellowship's journey. Rescued from the cruel Bill Ferney in Bree, nursed back to health by Sam, Bill thrives under good treatment and becomes an essential member of the company.

He carries most of their supplies through increasingly dangerous terrain. He survives the wolves at Hollin. He makes it all the way to the doors of Moria. And then — after narrowly escaping the Watcher in the Water — he's turned loose to fend for himself in the wilderness with the words "go back to Elrond" and hope for the best.

The Fellowship knew they were heading into extreme danger (originally planning to cross the Misty Mountains via Caradhras, later descending into Moria). Yet they brought Bill anyway, then abandoned him at the last moment when he couldn't follow. Sam barely has time to unload some of the gear before the Watcher attacks. Bill is left alone, in a dangerous region, with hostile wargs recently in the area.

Remarkably, Bill does make it back to Bree safely — Tolkien tells us this explicitly. The implication that Gandalf or possibly the elf Legolas put some protective magic on him is strong (Gandalf says "he will find his way" with confidence that suggests more than hope). Still, being set loose in hostile territory after months of faithful service represents a raw deal even with magical protection.

Where to find it:

• The Fellowship of the Ring, Book II, Chapter 3 "The Ring Goes South" — Bill joins the Fellowship

• The Fellowship of the Ring, Book II, Chapter 4 "A Journey in the Dark" — Bill is left at Moria's gates

• The Return of the King, Book VI, Chapter 7 "Homeward Bound" — Bill's survival is confirmed

Cirith Ungol Orc Patrols

We return to Shagrat and Gorbag, whose conversation provides the most humanizing (orc-izing?) portrayal of Tolkien's antagonist foot soldiers. These orcs are stationed at the tower of Cirith Ungol, which guards a pass into Mordor. Their job includes one notably terrible responsibility: patrolling the areas where Shelob hunts.

Shelob is an ancient evil, "the last child of Ungoliant to trouble the unhappy world." She's older than Sauron's control of Mordor, predating his fortifications. He tolerates her presence on his borders because she's an effective deterrent — few survive passage through her lair, and those few are usually already broken. The orcs are tasked with cleaning up after her, retrieving anything valuable from her victims, and occasionally becoming her victims themselves.

In their conversation, the orcs mention a companion who was caught in Shelob's web and left hanging there for over a week, still alive (Shelob paralyzes but doesn't kill immediately, preferring her food fresh). His fellow orcs saw him but made the pragmatic choice not to attempt rescue — angering Shelob wasn't worth saving one orc.

This workplace culture of casual betrayal, combined with the constant threat of being eaten by a giant spider, bureaucratic incompetence from above, and the general treachery between orc factions, makes Cirith Ungol one of Middle-earth's least desirable postings.

Where to find it:

• The Two Towers, Book IV, Chapter 9 "Shelob's Lair" describes Shelob herself

• The Return of the King, Book IV, Chapter 10 "The Choices of Master Samwise" and Book VI, Chapter 1 "The Tower of Cirith Ungol" — the orc conversations

Fatty Bolger's Mission

Fredegar "Fatty" Bolger represents an often-forgotten hero of the early chapters. He's one of Frodo's closest friends and co-conspirators in the plan to leave the Shire. Unlike Sam, who goes as Frodo's servant and companion, and unlike Merry and Pippin, who are family and co-heirs to hobbit nobility, Fatty is simply a good friend who helps.

His role: stay behind at Frodo's new house in Crickhollow and pretend to be Frodo for as long as possible, buying the real Frodo time to escape. This means staying alone in a house he knows the Nazgûl are searching for, with no backup plan except "run and raise the alarm if they show up."

They do show up. Fatty barely escapes, running through Buckland ringing bells and shouting "Fear! Fire! Foes! Awake!" to warn the community. He succeeds in his mission — he delays the Nazgûl and prevents them from catching up to Frodo immediately. His reward is spending the next year not knowing if his friends are alive or dead, enduring the Scouring of the Shire, and ultimately being left out of the great tales entirely.

The films cut Fatty Bolger completely, which in a way proves our point: his is the most thankless of jobs.

Where to find it:

• The Fellowship of the Ring, Book I, Chapter 5 "A Conspiracy Unmasked" — the hobbits' plan is revealed

• The Fellowship of the Ring, Book I, Chapter 11 "A Knife in the Dark" — Fatty's mission plays out

• The Return of the King, Book VI, Chapter 8 "The Scouring of the Shire" — Fatty's fate during the occupation

Tier 4: Cosmic Consequences

The Shipwright of Ar-Pharazôn's Fleet

In the Second Age, as Númenor descended into darkness under the corrupting influence of Sauron, the greatest king of that doomed island made the worst decision in the history of Men: he decided to wage war on the Valar themselves.

Ar-Pharazôn the Golden was, by all accounts, the mightiest king of Men who ever lived. His fleet that sailed to Middle-earth and captured Sauron was so impressive that Sauron's armies fled at the sight of it. But capturing Sauron was Pharazôn's undoing. The Dark Lord, brought back to Númenor as a prisoner, quickly became an advisor and then the power behind the throne, whispering poison into the king's ear.

Under Sauron's influence, Pharazôn established a temple to Morgoth. He instituted human sacrifice. He defied the Valar openly. And he ordered the construction of the greatest fleet ever built — a project that took nine years and required stripping Númenor of trees and raiding the coasts of Middle-earth for more timber.

Imagine being the master shipwright tasked with this project. For nearly a decade, you work on ships meant to sail against the gods themselves, watching your civilization crumble around you. Plagues strike. Storms destroy earlier work. The Valar send warning signs — an enormous eagle-shaped cloud, tempests, omens of doom. Your family members might be sacrificed in Morgoth's temple. The island is descending into nightmare.

But you keep building ships.

When the fleet finally sails, it's described as vast as "a forest of mountain trees upon the sea." Thousands of ships. Pharazôn lands on the shores of Valinor and sets foot on the Undying Lands, and in that moment, the Valar call upon Ilúvatar himself. The world is broken and remade. Númenor sinks beneath the waves. The fleet is destroyed. Every person involved in this project dies, and their island civilization is erased from the world.

Whether the shipwrights were willing participants in Pharazôn's madness or reluctant laborers forced to build the instruments of their own destruction, their fate was the same.

Where to find it:

• The Silmarillion, "Akallabêth" tells the complete story of Númenor's fall

• Unfinished Tales, "A Description of the Island of Númenor" provides geographical and cultural context

• The Lord of the Rings, Appendix A briefly summarizes the Downfall

For a deeper dive:

• The Lost Road and Other Writings (The History of Middle-earth Vol. 5) contains earlier versions of the Númenor story

• Sauron Defeated (The History of Middle-earth Vol. 9) includes Tolkien's late revisions and notes

Eärendil the Mariner: An Eternity in the Sky

Our final and perhaps most bittersweet entry is not traditionally considered a "bad job" at all. Eärendil is celebrated in Elvish song, referenced in The Lord of the Rings as "the most beloved of stars," and literally holds the Silmaril that Galadriel gives to Frodo as the Phial of Galadriel. But when you examine his fate closely, it raises uncomfortable questions about reward versus punishment.

Eärendil was half-elven, son of Tuor and Idril of Gondolin. He married Elwing, granddaughter of Beren and Lúthien, who possessed one of the Silmarils. When the sons of Fëanor attacked to reclaim the jewel, Elwing threw herself and the Silmaril into the sea rather than surrender it. Ulmo, the Vala of waters, saved her by transforming her into a great white bird.

Eärendil, faced with the utter devastation of the First Age wars and the desperation of Elves and Men, made a choice: he would sail to Valinor and beg the Valar for help. This was an act of incredible courage — mortals (and even Elves who had rebelled) were forbidden from the Undying Lands. He could have been turned away or destroyed for daring to approach.

He succeeded. The Valar heard his plea, saw the Silmaril he bore, and agreed to intervene. The Host of Valinor marched to Middle-earth and overthrew Morgoth in the War of Wrath, ending the First Age.

Eärendil's reward for this service was to be set in the sky as a star, sailing the heavens forever with the Silmaril at his ship's prow.

But consider what this means: Eärendil had two sons, Elros and Elrond. He presumably wanted to return to Middle-earth and see his family. Instead, he was made immortal and placed in the sky, where he remains to this day — watching everything that befalls his descendants but unable to intervene or even communicate.

He watches as Númenor, the kingdom founded by his son Elros, falls into corruption and sinks beneath the sea. He watches his other son, Elrond, endure millennia of war, loss, and grief. He sees the whole sad history of the Second and Third Ages play out below him while he sails endlessly across the night sky, separated from everything he loved and fought to save.

Is this honor or exile? Reward or punishment? We call him blessed, but from his perspective — assuming he retained consciousness and memory — he's been separated from his family for over 6,000 years, watching them suffer while he can do nothing.

When Elrond looks up at the evening star, he's looking at his father. When Galadriel gives Frodo the Phial, she's giving him the light of Eärendil's Silmaril. The star gives hope to those who remain in Middle-earth. But for Eärendil himself, it's an eternity of witness without participation, service without end.

Where to find it:

• The Silmarillion, "Of the Voyage of Eärendil and the War of Wrath" tells his complete story

• The Fellowship of the Ring, Book II, Chapter 8 — Bilbo's song "Eärendil was a mariner"

• The Return of the King, Book VI, Chapter 1 — Galadriel's Phial holds "the light of Eärendil's star"

For a deeper dive:

• The Book of Lost Tales Part Two (The History of Middle-earth Vol. 2) contains the earliest versions of Eärendil's tale

• The Lays of Beleriand (The History of Middle-earth Vol. 3) includes extensive poetic treatments

Reflections on Labor in Middle-earth

What these jobs reveal is that Tolkien's world, for all its grandeur and heroism, runs on the same unglamorous labor that sustains any civilization. Postal workers ensure communication. Servants maintain households. Soldiers staff remote outposts. Workers build infrastructure. And some people, through no fault of their own or through tragic circumstance, end up in positions that define their existence in ways both profound and terrible.

The worst jobs in Middle-earth fall into distinct categories:

Thankless but necessary: The postal workers, the servants, the beacon-keepers — unglamorous work that keeps society functioning but earns little recognition.

Dangerous by association: Working for Sauron, whether willingly or under compulsion, whether you're building his tower or patrolling near Shelob's lair.

Heroically terrible: Fatty Bolger's decoy mission, Bill the Pony's abandonment.

Cosmically consequential: The shipwrights of Númenor who may have known their work served madness but built the fleet anyway and Eärendil's eternal vigil, a fate that blurs the line between blessing and curse

These stories remind us that not every hero carries a sword, and not every sacrifice is sung about in great halls. Some people simply do their jobs — delivering mail during a birthday party crisis, serving a mad steward with dignity, keeping a beacon ready for a signal that might never come — and their quiet competence holds the world together just as surely as the Fellowship's quest.

And sometimes, the worst job is the one that seems like an honor.

Further Reading

Primary Sources:

• The Lord of the Rings, Prologue and all six books

• The Silmarillion, particularly "Akallabêth" and "Of the Voyage of Eärendil"

• Unfinished Tales, various chapters on Númenor and the North-kingdom

Secondary Sources:

• The History of Middle-earth, Vols. 1-5, 9-12 (for development of these stories)

• The Letters of J.R.R. Tolkien, various letters discussing daily life in Middle-earth

• Karen Wynn Fonstad, The Atlas of Middle-earth (for geographical context)

Questions for the Reader

• What do you think is the worst job in Middle-earth? Would you rather have a thankless but safe position, or a dangerous job with the possibility of glory?

• How do you interpret Eärendil's fate — is it a reward or a punishment, or something more complex?

• What terrible jobs in Middle-earth did we miss? What roles would you absolutely refuse to take on?

• If you could reform one workplace in Middle-earth, which would it be and how would you improve conditions?

Share your thoughts at hello@beyondthebrandywine.com