Better to Reign in Hell Than Serve in Heaven

Better to reign in hell than serve in heaven cover image: Lucifer falls from Heaven

‘Better to Reign in Hell Than Serve in Heaven’ is Part IV of the Constraints That Liberate series (there’s no need to read the previous posts first).

In my misspent youth, I slogged through John Milton’s epic Paradise Lost with the vague hope that reading 10,000 lines of 17th century blank verse would make me seem smart and interesting. It didn’t work.

I tried again recently—this time with purer intentions—but still ended up agreeing with Samuel Johnson: no-one ever wished it longer than it was.1

As far as I’m concerned, Paradise Lost has two redeeming features:

  • When you get bored, you can look at the lovely pictures by Gustave Doré or William Blake.
  • Lucifer/Satan is an example to us all.

Lucifer steals the show and gets all the best parts of the poem. He’s a surprisingly sympathetic character, while God is kind of a dick. This will not be news to anyone who has read the Old Testament.2

God would be the worst boss ever: petty, vengeful, micro-managing everything, always transforming Karen from HR into a pillar of salt. I bet He reheats tuna casseroles in the office microwave. This is enough to turn anyone into a being of pure evil.

And so, Lucifer rebels against God’s tyranny, is cast out into the darkness as the fallen angel Satan, and utters the famous line: “Better to reign in hell, than serve in heaven.”

Now, I know that Satan is meant to be the bad guy. He’s literally the Bad Guy!

But honestly… I’m kind of with the devil on this one.

Reigning in Hell

Lucifer slash Satan reigning up a storm in Hell
Free, and to none accountable, preferring
Hard liberty before the easy yoke
Of servile pomp

‘Better to rule in hell than serve in heaven’ is the fervently-held belief of many freelancers, entrepreneurs and digital nomads I’ve met over the last few years. They’ve all walked away from overbearing bosses, steady paychecks, and nine-to-five office hours to build their own dominions—with all the risk and reward that comes with it.

Being cast out into the darkness is liberating. There are no rules in hell! You can set your own hours and fire annoying clients and be your own boss and blow off work to go drinking at 11 in the morning.

But there’s a price. You’re no longer part of a heavenly choir singing in harmony. You’re one lone voice out in the wilderness. Your fate is in your own hands. You don’t have the comfort of a monthly salary to draw upon. Or sick leave. Or holiday pay. Or health insurance. And there’s no guarantee that your new boss (you) is any less of an asshole.

In my opinion, it’s still worth it.

I’m a relentless booster for personal freedom, but until recently, even I didn’t realise just how important it is to have autonomy over your day-to-day existence.

Like… life-and-death important.

Give Me Liberty, or Give Me Death

Satan arousing the fallen angels - William Blake watercolour
Will ye submit your necks, and choose to bend
The supple knee? ye will not, if I trust
To know ye right, or if ye know your selves

Newborns have no autonomy. They are at the mercy of the big people who pick them up, pinch their cheeks, and feed them. About all they can do is flail their limbs around and turn their heads to look at interesting stuff.

But even at three months, babies love to exercise whatever tiny scraps of control they can. In a landmark study, a group of infants were placed face-up in a crib. When they turned their heads on the pillow, it illuminated a mobile of dancing animals. This was hugely thrilling to the babies, who soon learned how to make the animals appear at will, and never tired of the spectacle.

A second group of babies were passive observers. When their cribmates turned on the mobile, they initially enjoyed the show just as much. But without the ability to turn it on and off themselves, they quickly lost interest.

The importance of being in control starts in the cradle—and it follows us all the way to the grave.

Another study: the residents of a nursing home were each given a houseplant to look after. Half of the old folks were told that they were in charge of watering it and taking care of it, while the other half were told that a staff member would be do everything. Six months later, 30 per cent of the residents in the do-nothing group had diedtwice as many as those who were given control.

Nursing homes are usually called ‘Paradise Lodge’ or ‘Eden Care’ or whatever, barely bothering to conceal that you’ve been dropped off in God’s waiting room. I’m sure some of these facilities really are heaven-like: the nurses take care of everything and give you sponge baths and listen patiently to your stories about catching the ferry to Shelbyville with an onion tied to your belt (which was the style at the time).

But it might not be worth it. Not if everything is predetermined, the days bleed together, and fussing staff won’t let you do anything for yourself. No wonder so many ‘stubborn’ old people refuse to leave their own homes. Living independently is dangerous and difficult—but it’s better to rule in hell than serve in heaven.

As Daniel Gilbert put it, in Stumbling on Happiness:

The fact is that human beings come into the world with a passion for control, they go out of the world the same way, and research suggests that if they lose their ability to control things at any point between their entrance and their exit, they become unhappy, helpless, hopeless, and depressed. And occasionally dead.

The welcome flipside of hedonic adaptation is that we usually bounce back from misfortune, and return close to our baseline happiness. But we never adapt to losing control.

The likes of long commutes, loud noises, and tyrannical bosses are just as bad on the 1000th day as they were on the first. These things are endlessly frustrating, because they make us feel powerless.

This is why ‘autonomy’ is one of the strongest predictors of job satisfaction—alongside working with good people, feeling like you’re having an impact, and being good at what you do.

If you have a job that ticks all four of these boxes, you’ve won the lottery. Perhaps you’re better off serving in heaven?

Serving in Heaven

St Michael descending from heaven to kick some demonic ass
The Universal Maker we may praise;
Who justly hath driven out his Rebel Foes
To deepest Hell, and to repair that loss
Created this new happy Race of Men
To serve him better: wise are all his ways.

In Skin in the Game, Nassim Taleb riffs on the fable of the wolf and the dog.

The gaunt wolf lives in the woods, fighting hard for every bite he can find. On the fringes of town he meets a sleek and strong dog, who brags about his warm bed, loving family, and regular meals.

The wolf is enraptured by this apparent paradise, until he notices the worn fur around the dog’s neck. As he hears about the collar and chain, he is so horrified that he runs back into the woods, and is still running.

Personally, I might have considered taking the collar. Lone wolves hunt rats and scavenge rotting carcasses to survive, and often die of mange. It’s not nearly as glamorous as it sounds.

But the running theme of this series is that there is a third way.

You can deliberately impose constraints upon yourself—say, sign an employment contract—but only on your own terms. In other words, you can be a wolf among dogs.

A Wolf among Dogs

Satan kicking it in paradise
A mind not to be changed by place or time.
The mind is its own place, and in itself
Can make a heav’n of hell, a hell of heav’n

The necktie is the collar-equivalent of male office workers. It serves no function whatsoever, except to gently strangle you all day long and occasionally flop into your soup. It is the least-subtle symbol of subservience imaginable.

In December 1993, Nassim Taleb deposited his last business tie in the garbage can at the corner of 48th St and Park Avenue.

He could get away with this, because he had become so successful as a trader that he was too valuable to fire:

If you were profitable you could give managers all the crap you wanted and they ate it because they needed you and were afraid of losing their own jobs.

Taleb was a wolf amongst dogs.3

When I got my first proper job as a junior business reporter, I took out all my piercings and wore a suit every day and ironed my shirts and shaved regularly and made sure to turn up earlier than everyone. 

This was a big effort for me, because I am naturally a scruffy person. But I had to pay my dues. I was a nobody, with zero career capital, on a temporary contract, with no guarantee it would be renewed.

After a year or so, I proved myself, and got job offers from other companies. I slowly started to revert to my natural form: longer hair, earrings back in, jeans most days. My hours became more flexible, and no-one batted an eyelid when I took occasional long boozy lunches.

The unspoken rule: if you deliver the goods and aren’t an asshole, nothing else matters. I’m hardly claiming I was indispensable, but I was valuable enough to leverage some pay rises and get my own column and generally have a reasonable degree of autonomy over my work.

(Later on I was made to write an increasing volume of clickbait and listicles, so I walked away. I was probably going to quit for unrelated reasons anyway, but that was part of it).

In other words: if you accumulate enough career capital, you can get all the perks of being a dog, without having to wear the collar.

This is another valuable asset to add to the ‘fuck you’ independence stack:

1. Fuck-you money

Have enough savings to cover your expenses for a year or two, so you can walk away from a bad situation, find a better job, or retrain.

2. Fuck-you frugality

Follow Ben Franklin’s lead, and commit to living simply rather than sell out your principles.

3. Fuck-you career capital

Become such a useful and profitable employee—ideally, the only person who knows how to do some important thing—that you’re difficult to push around.

This doesn’t give you license to be a dick, or strut around radiating an aura of ‘fuck you’. Better to be mild and pleasant and treat people kindly. But it does give you license to push back against things you don’t want to do, gently brush aside arbitrary rules and norms, and maintain the option to go nuclear.

It’s better to rule in hell than to serve in heaven. I believe this right down to my core. But if you can find a way to get the best of both worlds—to rule in heaven, or be a wolf among dogs—perhaps that’s even better still.

Adam and Eve exploring their new home
The world was all before them, where to choose
Their place of rest, and Providence their guide;
They, hand in hand, with wandering steps and slow,
Through Eden took their solitary way.

Coming up next: Constraints that Liberate V: Exploring and Exploiting

Previously in the series: Constraints that Liberate III: Same Salad, Different Day

Introduction and overview: Constraints that Liberate

Further Reading

The public library will loan you these books for free. If you’d rather buy them, the Amazon referral links on this page send a few pennies to support this site, at no extra cost to you (read more here).

Skin in the GameSkin in the Game – Nassim Taleb

Taleb is the kind of guy who uses the independence that comes with fuck-you money to loudly say ‘fuck you’ to anyone who provokes his wrath. He’s a belligerent asshole, and makes no attempt to hide it.

In spite of this (perhaps because of it?) I am enormously fond of Taleb, and have learned more from him than just about anyone. The day he blocks me on Twitter will be the day I know I’ve finally made it.

His latest work, Skin in the Game, contains a bunch of useful heuristics for thinking about uncertainty, a section on fuck-you money, and an argument against cheap talk/the importance of taking risk for your opinions.

Paradise Lost – John MiltonParadise Lost - John Milton

I was mostly kidding about reading Paradise Lost for the pictures…mostly.4 Several of the books are boring filler in my opinion, and tough going. But this is one of the most influential pieces of writing ever, which gave us terrific words like ‘terrific’, ‘space’, ‘debauchery’ and ‘sensuous’ (Milton coined more neologisms than Shakespeare!). It inspired Philip Pullman’s His Dark Materials, and generally unlocks a treasure trove of references from the last 300 years of literature, film, music, and arts.

Stumbling on Happiness - Dan GilbertStumbling on Happiness – Dan Gilbert

One of the best books I read in 2018. Ignore the cute title: this is not a self-help book, so much as a guided tour through the problems with happiness research, the difficulty of trying to predict what our future selves will want, and a deep dive into hedonic adaptation. Gilbert is a terrific and funny writer, which is rare in popular books written by actual scientists.


  1. Someone has helpfully compiled a collection of Johnson’s sickest burns here.
  2. I quite like Jesus, but his dad is a bit much for me. I relate to Winston’s Churchill’s son Randolph, whose friends tried to shut him up by betting him he couldn’t read the whole Bible in a fortnight: ‘Unhappily it has not had the result we hoped. He has never read any of it before and is hideously excited; keeps reading quotations aloud: “I say, I bet you didn’t know this came in the Bible . . . ” or merely slapping his side and chortling, “God, isn’t God a shit!”
  3. And he still is: a recent thread on Twitter shows he has stuck to his no-tie rule at 10 Downing, the White House, etc, with the only exception being the US Senate: “They refused to let me testify without a tie, so I borrowed one.”
  4. Narrowing down the illustrations for this post was tough. In order: the first two engravings are by Gustave Doré (Lucifer falling, then reigning in hell), then William Blake’s watercolors (rallying the fallen angels), Doré again (St. Michael kicking demonic ass, Lucifer in the garden of Eden) and finally, John Martin (Adam and Eve starting their new life on Earth). I couldn’t find a way to shoehorn in Thomas Lawrence’s weirdly-buff Satan but will settle for including it in this footnote.

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1 year ago

just did my English paper on this topic and I think we have the same brain. great work

michael black
michael black
3 years ago

dont tell me you guys are really believing this article heaven is way better than u can even imagine u get to be in a happy place with your family and with god sure he might do some things that make you angry and hate and wanna kill someone but he does it out of love everything that has happened to you is because of you god always gives us a choice and right now i see this and i refuse not to reply to this text god is a loving god he does things that are good for you they might not be good for you then but it will be after you see how one comment said he was a millionaire where will that get you in the afterlife u cant buy your way into heaven the only way u can get into heaven is through Jesus Christ and if you choose not to follow god u will be departed from him for all eternity because no one can say that god never gave them a chance to give god their life because he gives a chance or at least a minute everyday i am only 13 years yes i sin and yes i fall short from the glory of god but i ask for forgiveness continuously throughout the day. if you go to hell there will be no escape you will not rule there are thousands of people in hell and im pretty sure some of them were told exactly what was is this article if you go to hell you will not rule you will be controlled, tortured , and in pain fpr the rest of your life have u ever heard of the burning lake of fire if you go to hell that’s where you’ll be im not here to scare anyone into worshiping god that all up to you but if you choose that you want to be with god after this life u can repeat this prayer Dear Lord Jesus, I know that I am a sinner, and I ask for Your forgiveness. I believe You died for my sins and rose from the dead. I turn from my sins and invite You to come into my heart and life. I want to trust and follow You as my Lord and Savior.

Harrison Thornton
Harrison Thornton
3 years ago

I don’t know if you truly believe in God or Satan or angels and demons or Heaven and Hell, or if you’re just using this to paint a picture about earthly society. But I felt that I should warn you. If you do believe that God reigns in Heaven, you should consider the prophesied fate of Satan and all his fallen angels. They have power and “freedom” to do as they please as of right now. But when Jesus comes back, they will all be thrown into the lake of fire, along with Satan, where they will spend literal eternity in agony and suffering. There is no freedom, no joy, no life in that. No one has power over God; no one comes close to matching the power of the Almighty. Please, don’t entertain the temptation presented to you by the enemy – which is what Satan is. Your enemy. My enemy. Our enemy. He gives you a false offering of “freedom,” but in the end, if you choose to “reign in Hell,” you will be cast into the lake of fire where you will find only suffering for all eternity.

3 years ago

Hi this is a TRICK. No one will REIGNE in Hell.
And God, our Creator, how does it even make any
sense to accuse Him of “tyranny”, when He created
us inherently with a moral compass which shuns it?
Obviously He is of HIGHEST moral characteristics.
We cannot even begin to match. He could complain
about US, that WE fall short of HIS standards. Not
The other way around. You are believing The lies of
Lucifer. Hell is torture. No joy and NO control. U
will be CONTROLLED since you will be torturED
and can’t escape. There is no escape. Just like you’re
unable to escape earth, you can NEVER escape hell.
Save urself while u still can!

3 years ago


4 years ago

I have no idea how I originally found your blog, but every post is a 9 or a 10.

4 years ago

It’s true. How did you get an interview with de Botton?!

Also, I still feel a little bad that I promised web expertise and bailed.

4 years ago

Well, great coup there on the de Botton thing, seriously.

And I don’t mean to salt old wounds, it’s just half the time I can’t get your blog-site working on my iPhone at all. Have you ever noticed that, or is it just me?

4 years ago

I prefer the best of both worlds — Reign in Heaven: run an awesome company with a fantastic culture and great colleagues/friends. Requires hard work and/or a lot of luck, but it’s more than worth it.

4 years ago

Awesome! Hate to use the term but “millennial ” people like us do what we want. I’m a wolf among old dogs. It’s very hard to flout the rules and norms in amongst career punch clockers!

4 years ago

Nicely put Rich! But I think that even being a wolf among dogs still brings with it some limitations (giving away some freedom). From my point of view, I think seeking a complete autonomy has the biggest rewards. I have tried the complete servant, and moved a bit in the career ladder to enjoy some personal freedom in my work. But the ultimate goal would be to reach that wild wolf style! To have complete control over every aspect of life is the source of happiness.

4 years ago

After all it depends on one’s aspirations. Some prefer the “sense of safety” that comes with a job while others can’t bear an instruction from a boss. All comes with a cost 🙂

4 years ago
Reply to  Hussein

Like your first commenter, Liam, I chose to rule in heaven. And I loved it. I ran a billion dollar company and got to work with a great many friends. I still retired early, but only slightly early, because work was a favorite hobby. It is hard to pull off, but perhaps not as hard as many people think?