10 Existential Riddles Life Asks Each Of Us

Fundamental Life Problems LiveReal is Working to Solve

article by LiveReal Agents Thomas and Grace

Life confronts each of us with riddles.

It throws them at you, and me, and everybody we know.

This might seem like a strange idea at first.

After all, it’s not like this:

It’s more like the Sphinx.

You probably know the story of Oedipus and the Sphinx.

Long ago (the story goes), a horrifying monster terrorized everyone in the city of Thebes.

The beast had the body of a lion, wings like an eagle, and the face of a woman.

They called it “The Sphinx.”

The Sphinx would swoop down from the sky, grab unsuspecting travelers, and challenge them a riddle. If they answered correctly, they would live. If they answered wrong, well…they soon became a tasty side dish.

No one had ever answered correctly.

Everyone in Thebes lived in a state of terror.

One day, a guy named Oedipus heard about this. And he stepped up. “Hey, Sphinx!” he said. “Why don’t you come pick on me?” (Whether those were his exact words, scholars may disagree.)

(Spoiler alert, if it’s really possible to spoil a story that’s two thousand years old.)

The Sphinx did just that.

It posed this riddle: “What creature goes on all fours in the morning, two legs during midday, and three legs in the evening?”

Oedipus answered (without even Googling): “Humans. As babies, in the morning of our lives, we crawl on all fours. As adults, we walk on two legs. And in old age, in the evening of our lives, we use a cane – three legs.”

His answer was correct.

In some versions of the story, the Sphinx then threw itself off a cliff and died. In other versions, it exploded. For our purposes here, we’ll say The Sphinx stopped eating folks and decided to become Oedipus’s friend and flew him around on its back for the rest of his days.

Either way, the Sphinx stopped bothering the Thebians. Oedipus eventually became king of Thebes, and they all lived happily ever after. (Or for a while, at least.)

But here’s the thing:

We’re all Oedipus.

The “Sphinx” is life.

Life poses riddles to us. And we have to come up with answers.

For Oedipus, the riddles were obvious and straightforward. The questions were spoken, objective, verbal.

For us, it’s a little more subtle.

Life doesn’t assume the form of some kindly old grandmother, sit you down in a padded chair and say, “Hi! Welcome to life! Here’s the list of problems you’re going to need to figure out. Let me know if you have any questions! And here’s a cup of hot tea and some cookies!”


The reality actually goes something more like this:

We’re born, slimy and screaming, utterly helpless and vulnerable, and wondering just what the heck we’ve gotten ourselves into. From that moment on, we’re immersed in a flood of existential problems, like a new tadpole finally leaving its egg in the middle of a tsunami.

After that, it’s game on.

Existentialists describe it as “thrownness” – we’re “thrown” right into the middle of a situation – life – without understanding where we are, or what we’re supposed to do, or why.

From that point forward, life is constantly putting riddles to us.

And we have no choice but to try to solve them. Much of what we do is some form of attempting to answer them.

Even our most basic acts can be understood this way.

A baby crying, for example – is, in a way, an answer to riddles that have already been asked. For example, the riddle of happiness (“a bottle would make me happy!”), pleasure (“I would really enjoy somebody changing my diaper”), even death (“I need food to survive here – can somebody feed me, please?”).

So what are some of the riddles life poses to us?

1. The Riddle of Happiness

How will you find happiness (in a world full of suffering)?

We’re all searching for an experience of something we’ll label “happiness.” Heavyweights from Aristotle to the Dalai Lama agree on this.

Whether we see ourselves as miserable or having already “achieved” happiness, our fundamental orientation around happiness is baked in to our nature. We can’t avoid it. Dogs bark, water is wet, humans pursue happiness. Even if we try to give up pursuing it, we’ll probably realize that even that is still just pursuing it in a different way.

Abe Lincoln once supposedly said something interesting about this: “We’re just about as happy as we make up our minds to be.”

But if that’s the case, why are so many people miserable?

Of course, Big Abe was no slouch, and he was on to something there. Yet if it was as easy as “making up” your mind, then there’s probably more to “our minds” than we usually think. All to say: it’s not a simple matter.

As the saying goes: we have the right to the pursuit of happiness (not the right to actually attain it.)

So we pursue it. But do we ever find it? And if so, how?

That’s a good riddle.

Solving that one would really make us happy.

2. The Riddle of Pleasure

How do you experience pleasure (without winding up in pain)?

When you're young, you eat an ice cream cone, and you think you've solved the meaning of life and happiness and everything in one fell scoop.

Eating + ice cream = pleasure = this is awesome = meaning of life and happiness and everything, solved.


Of course, when you get older, assuming you’re paying attention and are at least partly in touch, you realize it really isn't that simple.

Meaning, too much ice cream can make you fat and sick. (Thanks for that curveball, universe.)

We figure out, sooner or later, that every pleasure has a price. When we're young, we get a grace period. But beyond that, every pleasure seems, in some mysterious way, to be intimately connected to a pain.

Depending on the pleasure, it can become pain almost immediately. (Heroin, for example.) Others take longer.

So: are there good pleasures that don’t lead to pain, but longer-term happiness (#1)?

That’s a riddle.

Cracking that one would really feel great.

3. The Riddle of Suffering

How will you find relief from suffering (in a world full of it)?

Life is hard.

And chock-full of suffering.

It’s the evil twin brother of happiness (#1) and pleasure (#2). We seek them out – happiness and pleasure – but suffering barges in too, like an uninvited and unwelcome guest that takes over the couch and makes itself at home in, right in the living room.

So, what do we do about suffering?

Avoid it? Numb ourselves to it? Distract ourselves? Outsmart it? Overcome it? Cure it? Transcend it?

We’re flooded with “answers” to this everywhere. Pharmaceutical companies sell us pills to solve it. Hollywood offers to help us forget about it for a while. Bartenders help us take the edge off it. Drugs take the edge and sometimes everything else along with it. Stoicism says we should accept and steel ourselves against it. Buddhism talks about a total cure. Christianity suggests a way of embracing and transcending it. And so on.

There are lots of ways to deal with suffering. Some can be effective. Others offer short-term solutions in ways that creates more long term problems.

That’s the riddle: figuring out what to do about suffering.

Cracking that riddle would give us a lot of relief.

4. The Riddle of Meaning

How do you find meaning (in what seems like a meaningless world)?

What’s the point?

We're born, we live, we die. But why?

"All our lives we sweat and save,
building for a shallow grave,
must be something else we say,
somehow to defend this place."
- The Doors, The Soft Parade

Where is it all headed? What’s the goal here? What’s worth giving your life to? What's the point of all this madness? What’s worth dying for? Why are we doing any of this? Why play this game at all? To what end? Why are we here? Is this all meaningless?

This isn't abstract philosophical crotch-rubbing. Like Frankl, Tolstoy, Camus, and others have said well, this is literally a matter of life and death.

We all need a reason to get out of bed in the morning. Without that, we might not.

We need a "why." And a good one. Without that, suddenly, the world can become a treadmill, a hamster wheel, a road to nowhere, an existential cul-de-sac, a tale told by an idiot, full of sound and fury, signifying nothing, nothing at all.

This riddle is intimately connected to the others.

After all, “happiness” (#1) seems meaningful (and might be, depending on how you define it.) But an empty series of pleasures (#2) might also seem meaningless. Death (#7) for some might make life seem meaningless. But maybe that depends on what death means to someone, and their answer to the riddle of meaning in life.

Suffering (#3) at first glance usually seems like something we’d want to avoid at all costs. But when something is meaningful, we sometimes voluntarily, deliberately choose to endure incredible suffering for the sake of it.

Example: having children (#5, relationships.) Kids make parents suffer. A lot. But it’s meaningful suffering. And a lot of parents wouldn’t trade that suffering for anything in the world.

Your approach to the issue of life having meaning, purpose, value, significance, and so on – or, on the other hand, meaninglessness, ennui, nihilism and so on – affects everything: your happiness, relationships, health, your day-to-day…everything.

That’s a serious riddle.

Cracking it would mean a lot. (To see our progress on cracking it, look here.)

5. The Riddle of Relationships

How do you find love (in a world that often doesn’t seem to give a crap about you)?

On the one hand, it’s simple: we want to love and be loved.

On the other hand…well, the reality of it is very not simple.

We fall in love and get our hearts broken. We fall in love and then fall back out of it. We love our friends, kids, family, extended family, neighbors (and these days, celebrities, and strangers we don’t actually know, but think and feel like we know)…and yet all too often, those same people hurt us, disappoint us, betray us, reject us – basically, they treat us like they don’t give a crap about us.

Experience in these matters tends to disillusion us.

But through all this, the basic mission never changes: we want to love and be loved.

OK, so how?

At least part of the trick here is figuring out what real “love” is, and avoiding the phony kind.

This is something many of us learn the hard way: what we think is "love" at first often turns out to be some kind of fool's gold - an imposter, an imitation, a piece of glass when we were hoping for a diamond.

Mix in a lot of Disney-fueled romantic illusion, wishful thinking and a powerful cocktail of hormones, and we're well-groomed to get disillusioned as quickly as possible.

So, how do you “love and be loved” in a world where things are…well, complicated?

That’s a serious riddle.

We would love to solve that one.

6. The Riddle of Knowledge

How do you figure out truth (in a world full of uncertainty)?

When it comes to our lives, certainty seems much better than doubt.

When it comes to questions about how we should act, what we should do, what the nature of the world and ourselves and everything else is, what we should eat for dinner…guesses, probabilities, hunches, best-answers-we-can-come-up-with-at-the-moment don’t really satisfy.

Uncertainty can be tedious, exhausting, and even corrosive. Yet false certainty can be even worse.

How do we base our lives on something solid and truthful – something that won’t let us down?

Until recently, ancient wisdom and religions have traditionally been seen as the authoritative source of truth. Nowadays, science often seems to carry more weight in certain matters. Yet in some cases, we throw away both tradition and science and just do what we want anyway. In other words, we trust ourselves.

Which of these is “right”? One, some, all, none? How do we know?

Life isn’t going to sit around and wait for us to figure all this out. We have to act, decide, live, whether we have full knowledge or not.

So, how do we know what’s real? What’s phony? What’s true, and what’s false?

That’s a really important riddle.

That’s one answer we definitely want to know.

7. The Riddle of Death

How do you plan for the long-term (knowing that eventually, the struggle for survival is pretty much guaranteed to fail)?

We’re struggling desperately to survive in a world where one of the few things we know for sure is that, eventually…well, we won’t.

Two certainties in life, as the saying goes: death and taxes. We can usually figure out the taxes. Yet the other one constantly surprises us.

Thought experiment:

Let’s say we have a ticket for an ocean cruise. Everything is paid for. Some details are fuzzy (exact time of departure, boarding dock, our room number, etc) – but we do know for sure that at some point, we’re going to be on that boat.

What’s the destination?

Don’t know.

Maybe Paris. Maybe Antarctica. Maybe Greece. Maybe down a waterfall.

Most folks in this situation would do something radical:

They would ask questions.

Where is it going? Who will my cabin-mate be? Do I have a say in deciding where we go? Is there a way I can upgrade from a cramped, moldy closet in the bowels of the ship to a first-class, spacious, sunset-view suite with waterbeds? Will it have an all-you-can-eat buffet?

But of course, we all actually do have a ticket for that Cosmic Cruise Ship to the Great Beyond.

Yet few of us seem to ask questions.

We might assume that we already know the answers. Or we might assume that we can’t know the answers. (Connection to #6 – Knowledge.)

Either way, it’s a riddle we’re all confronted with.

We want to solve that riddle or die trying.

8. The Riddle of Sanity

How do you find mental clarity and emotional strength (in a world that seems intent on driving you crazy)?

Depression, anxiety, loneliness, stress, addiction, suicide and so on are everywhere, usually hidden away in a secret corner somewhere. And despite a huge increase in psychologists, therapists, coaches, pills and so on over the past few decades, things seem to be getting worse.

Staying sane in today’s world is a challenge.

The landscape of the modern world is littered with – how can we say this? – stuff that isn’t good for us.

Just one example (out of many candidates): commercials, ads, and all forms of marketing have advanced to the point of nearly being weaponized. It’s so evolved that we don’t even notice it much of the time (one reason why it’s so effective.) We just wind up wondering where our money went, and why we have a lot of stuff we don’t need.

Another example: sugar: you literally can’t check out of a grocery store without walking through a wall of candy.

The answer to all this, of course, isn’t to rewind back a few hundred years or so before you could spend decades of your life couch-surfing Netflix or chainsmoking video games.

The answer is that the weapons you need to guard your sanity have to evolve as well.

It’s a mental arms race. And the rest of the world has built up a pretty huge arsenal.

Keeping your sanity these days can be a dogfight.

How do you stay sane? And not just sane, but mentally and emotionally strong, healthy, vibrant?

That’s a riddle worth solving.

To ignore it – well, that would just be crazy.

9. The Riddle of Becoming Yourself

How will you become yourself (in a world that seems to be deliberately trying to prevent you from doing that)?

Who are you?

What are you?

Are you a body, a soul? An evolved animal, a spiritual being? Are you an insignificant, accidental, temporary clot of cosmic dust, a haphazard bag of genes controlled by brain chemicals…or are you something unique, special, one-of-a-kind, important in some fundamentally real way?

Or on the more personal level: are you able to fully develop your talents so they blossom and flower, and will soon reach full bloom? Or are you a cog in a machine, an easily replaceable part in some lumbering, impersonal, goliath machine that, if it ever learned that you existed, wouldn’t care?

Do you sense that you’re on your way to becoming somebody, and something in the world is trying to squash that?

All this points to a key challenge for us: to find our unique place in a world that seems determined to hammer us into something – anything – else.

Bosses try to make us into workers. Politicians try to make us into voters. Businesses try to make us into customers. Hollywood tries to make us into celebrity-worshippers. Even friends and family, sometimes with the best of intentions, try to shape us into their ideas of who or what we should be. (And, as if that wasn’t tricky enough, sometimes they’re right.)

“I wanted only to live in accord with the promptings
which came from my true self.
Why was that so very difficult?
- Hermann Hesse

Figuring out how to become ourselves – instead of what the world is trying to shape us into – isn’t easy.

That seems like a riddle worth solving.

And only you can solve it.

10. The Riddle of Authenticity

How do you find what’s real (in a world full of phonies)?

We want “real” stuff. Real love, real happiness, chocolate, sanity, spirituality, ice cream, intimacy, friends, and so on.

But there are phony versions of all these, and the world seems to constantly offer it to us. Usually with a lot of hype, flash, glitter and fanfare.

“Buy this! It’ll solve all your problems!” “Do this, and it’ll change it all!” “Understand this, and that’s it!” “Solve all of life’s problems forever in 3 seconds or less!”

All too often, we discover that what we thought was “real” was a counterfeit.

If we fall for counterfeits, we wind up with things like “solutions to happiness” that make us miserable. Solutions to sanity that drive us crazy. Solutions to relationships that drive us apart. Solutions to pleasure that cause us pain. We want priceless treasures but often wind up with booby prizes.

And so on.

What we want, in other words, is to Live Real.

(Sorry. Shameless self-promotion slipped in there.)

It’s a real problem.

And it deserves a real solution.

Less Sphinx, more Whack-a-Mole.

Now that we’ve covered these ten riddles, we should probably clarify a few things.

For example: unlike Oedipus, we aren’t asked just one riddle.

Life asks us a lot of them. We’ve only covered ten here, but there are plenty more.

Another key difference between our situations: unlike the riddle the Sphinx gave Oedipus, our riddles don’t necessarily have one single “right” or “wrong” answer. They might have multiple-choice answers. Several of which could “work.” (Although some might work better than others. More on this below.)

Another difference: if a traveler would answer the riddle incorrectly, the Sphinx would eat them immediately, right there on the spot. But if we answer “incorrectly” (we’re assuming that’s possible for now), we might not find that out for years. Life often takes a while to give us feedback.

And another difference: for each riddle, we aren’t asked only once. We’re often asked the same riddle several times, and in many different ways.

It works more like Whack-A-Mole game.

Life pops up like a little mole, and poses a riddle. Pop! (“Hey, what’s the point of all this?”)

Then we answer it. WHACK!

But then another mole pops up out of another hole (Pop!) and poses that same riddle to us again in a slightly different form. (“Where is all this going?”)

Then we whack it again. WHACK!

And the game continues. Life seems to be a series of riddles that pop up like moles, and our job is to whack them back down. Until our time runs out.

Or…maybe those pesky mole-riddles keep popping up until we answer the riddle “correctly.” And then they leave us alone.

Because maybe these aren’t regular moles.

Maybe these are keys to unlock our view of the universe.

Maybe these questions are tiny little portals.

Maybe, if we get curious, and explore a little (“follow the white rabbit!”) and peek through some of these portals, we get glimpses of a bigger world. Maybe it’s Wonderland. Maybe it’s life outside The Matrix.

Or maybe it’s more simple than that. Maybe these questions are prompts that pop up to remind us to upgrade our mental software every so often. Because we’re programmed to evolve. Which is a good thing, because hopefully we can operate on a higher level – whatever that might mean – and get more out of life than we currently are.

However you want to slice it: our answers to these questions are really important.

Their impact on our lives is dramatic and powerful.

Our answers to these riddles could mean the difference between a happy marriage or a divorce. Whether our typical mood is depressed or inspired. Whether we have inner strength and power over ourselves, or inner weakness that gives others power over us.

Our answers to these riddles can enrich or impoverish the quality of our day-to-day experience.

Maybe these riddles are like big metal jet thrusters that we carry around inside us.

If those jet thrusters aren’t working – if we avoid them, or don’t use them properly – they just weigh us down. We struggle under the burden of their weight.

But if we get them working, they help us fly.

Some answers are better than others.

If somebody’s answer to the riddle of happiness is heroin, then – trigger warning – their answer sucks.

If their answer to the riddle of suffering is “just avoid it!” then – trigger warning – their answer sucks.

If their answer to the riddle of death is “it’s not going to happen to me!” – well…life doesn’t usually bother with trigger warnings on that one.

Life tends to correct our answers, one way or another, eventually.

And sometimes it’s pretty brutal about it.

Maybe it’s impolitic to say out loud, but some answers are better than others.

Some answers set us up for unnecessary suffering. Some even create unnecessary suffering by themselves.

So the key trick here is improving your answers.

Because the good news is this: our answers are totally in our control.

We tend to grab whatever answer is closest to us, and assume we’ve settled the matter forever.

But unless you’re lucky enough to be standing next to the mother-of-all-Answers at the moment you asked, well, there are probably better answers out there.

This should be encouraging. This means that we can improve, evolve, upgrade our answers.

And these answers – that may be portals to a better life – well, we can do something about these.

And that’s what we’re doing.

Here at LiveReal, we’re searching for better answers to all these riddles.

We’re conducting an active and ongoing investigation.

We’re gathering evidence, examining clues, checking out leads, following the trail wherever it takes us. All to complete the mission of answering these riddles in the best possible way we can.

We use every available tool we can get our grubby little mole-pounding hands on. Hammers and handsaws, microscopes and machetes, bulldozers and bayonets, from modern science to ancient wisdom and everything in between…we don’t care. We’ll use the kitchen sink and the bathroom toilet if we have to. Call it “Guerilla seeking.” We’ll take nuggets of wisdom from wherever we can to crack those riddles.

We try out answers. We test them. We sort through them, find ones work and sniff out ones that don’t. We make discoveries. We dig up treasure, find out that it’s a pile of fool’s gold, and then keep digging…and then find real treasure.

It’s a heck of an adventure.

It’s not easy. It’s not safe. It’s not predictable, guaranteed, sanitized.

No good adventure ever is.


Let’s face that Sphinx. Let’s whack those moles. Let’s answer those riddles in ways they’ve never been answered before.

And then, let’s ride.

If you liked this, check out:

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