9 Questions to Help Understand Life’s Greatest Mystery — You

Space, time travel, pie and other mental exercises to reveal what you value, why you behave the way you do and how to live more intentionally

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In this edition:

• Well, the title pretty much says it all…

I was lost somewhere around the Andromeda Galaxy when things went sideways.

What began as a daring space mission turned into confusion. The planet we’d detected wasn’t where it should’ve been. Suddenly, the ship trembled. A black hole appeared out of nowhere, ready to consume everything nearby, including us.

How could that be? Those things don’t just pop up like fireworks.

“We either go in or hit the escape pod,” my navigator warned. “Which way, Captain?”

Uninterested in being sucked into the unknown, I whistled for my furry sidekick, Astro, and raced to the escape pod. We blasted away, hoping to survive.

Wrong choice. You are too far away to be rescued. You float listlessly across the vacuum of space until your last breaths. The end.

Wait, I’m too young to die. I’m only eight. Ugh. If only I’d not been so quick to jump to what I thougtht was the safest option. I should have known a black hole appearing out of thin air (or space) might be a curious clue worth investigating.

So, I flip back to page 73 and try again.

If you decide to stay aboard the ship, turn to page 88.

Way to brave the unkonwn! Turns out the “black hole” was a cloaking device, hiding what you’ve been seaching for, Planet X. Prepare to land!

Lesson learned: I need to be a little more discerning and a little less fearful…

Know thyself

You might recognize this story as a poor rendition of the “Choose Your Own Adventure” book series, which was popular when I was a kid. They were fun to read because your decisions shaped the plot. Sometimes your choices made you a hero; other times they made you an anacoda’s lunch.

What’s more, as you explored space, jungles, oceans and alternate timelines, you also explored a little of yourself.

Would you take risks? Or, would you play it safe, like me? Would you trust your instinct or take time to think?

Although designed for kids, these adventure stories actually teach something behavioral scientists have confirmed: we don’t fully know ourselves because of cognitive biases and the stories we tell about who we think we are.

Research shows we often have a distorted view of ourselves. One study even found close friends actually rated our observable traits more accurately than we did ourselves.

The psychologist Carl Jung said:

“Who looks outside, dreams; who looks inside, awakes.”

Many of us — like my 8-year-old self and, admittedly, my 43-year-old self — are dreaming. Studies suggest only 10–15% of people are truly self-aware — far fewer than the 95% who believe they are.

Researchers have found self-aware people tend to be more balanced, more confident, maintain more positive relationships and have a greater sense of achievement. Self-awareness is basically having a clearer understanding of what motivates us and of our behaviors and feelings. Getting to know yourself better enables you to make changes, develop new habits and learn new skills.

And that includes money habits.

If you don’t define your relationship with money, it will define it for you. As money is so integrated into all areas of life — work, family, success, even love — it’s not as easy as simply asking, “What does money mean to me?”

Albert Einstein once said, “No problem can be solved from the same level of consciousness that created it.” That’s why it can help to access our inner selves with some imaginative thinking.

So, what if we asked ourselves more creative questions — questions that shift your angle of vision just enough to reveal something new?

Here are what I think are nine good ones I’ve picked up over time. Like a “Choose Your Own Adventure” book, they use imaginative thinking to help you think deeper and more broadly.

1. “If you had to flee Earth, what would you take?”

What do you value?

Value clarity is linked to well-being, motivation and resilience. By honoring our values — family, creativity, kindness, adventure — with our greatest assets — time, money, energy — life can feel more meaningful.

But values also evolve over time, the same way your music taste might drift. One day you’re in a mosh pit at a hardcore show, and the next you’re listening to vinyl jazz records at home with a sleeping cat in your lap. (Life comes at you fast!)

A playful way to uncover your core values is to imagine you have to leave Earth for good. You’re boarding a ship to a new planet but can only bring a few things. What do you take?

Books? Musical instruments? Sports equipment? A family heirloom?

Whatever you choose reveals something, both what you cherish and what you might be surrounding yourself with today that doesn’t actually align with what you value.

2. “What would it look like if it were easy?”

It’s now a legendary business story: A plane is traveling back to the U.S. from Russia. On board are a few men who just had their dreams of revitalizing America’s space capabilities dashed. Among them: Elon Musk.

Buying rockets was too expensive to start a private space company. Undeterred, Musk opened a spreadsheet, ran some numbers and concluded: We’ll build them ourselves.
SpaceX was essentially born from one reframing: What would this look like if it were easy?

It’s the go-to problem-solving question of Tim Ferriss, formulated to change your perspective and consider practical steps and habits for working toward a desired goal. Maybe then another variation of this question would be, “What would Tim Ferriss do?”

So, when you have an ambitious challenge, ask: “What would this look like if it were easy?”

That likely involves looking for a way to simplify the process. One of the best examples in the real world is automatic contributions to a 401(k). You’re essentially building wealth without thinking about it or doing anything.

The goal isn’t to avoid hard work; it’s to make sure your effort is focused where it matters most.

3. “What percentage of the universe is ‘you’?”

The scientist Carl Sagan famously called our planet the “pale blue dot”, inspired by an image taken by Voyager 1, 4 billion miles away.

He said:

“Our posturings, our imagined self-importance, the delusion that we have some privileged position in the Universe, are challenged by this point of pale light. Our planet is a lonely speck in the great enveloping cosmic dark. In our obscurity, in all this vastness, there is no hint that help will come from elsewhere to save us from ourselves.”

Perhaps not so obvious as a brightly lit moon on a clear night, there is a lot of hope in Sagan’s words. He called astronomy a humbling and character-building experience. To see our entire planet shrunk to the size of a mustard seed, he said, “underscores our responsibility to deal more kindly with one another, and to preserve and cherish the pale blue dot.”

The pale blue dot: Earth

Instead of thinking life and the world are things that happen to you, what if you’re just a small period or letter in a much greater story? What if you’re not the center of the universe?

That could show up in your life by rejecting the common narrative that you’re supposed to use the world around you to accumulate and broadcast your importance. Instead of using your resources only on yourself, use them to make the world around you better, to make the people around you matter.

It frees you from perfectionism, comparison and the pressure to “matter” in some grand, cosmic sense.

Humility research backs this up: studies show humble people have stronger relationships, less anxiety and better self-control. It’s why the financial journalist Jason Zweig calls humility one of the seven virtues of great investors.

As C.S. Lewis put it:

“Humility is not thinking less of yourself, it’s thinking of yourself less.

4. “If Future You took a time machine back to today, why?”

In an episode of the American version of “The Office,” the character Andy Bernard looks at the camera and says:

“I wish there was a way to know you’re in the good ole days, before you’ve actually left them.”

Chances are the good old days might be right now, but only obvious in retrospect.

So, if you find yourself in a tough spot or feel you’re not getting anywhere, try this thought experiment: Future You travels back to this exact moment, but the side effect is that you don’t know you’ve traveled back in time.

Why would they come back to now?

To experience something they miss? To appreciate something you’re overlooking? To nudge you to change something small that alters something big?

This question doesn’t eliminate problems. But it can help you see things in a more optimistic light, which is associated with a variety of benefits, including longer life spans and better health.

5. “Who’s your idol?”

Arthur C. Brooks plays this game with his students based on St. Thomas Aquinas, who said humans tend to worship one of four things: money, power, pleasure or honor.

What you idolize can reveal where you’re likely to make your biggest mistakes. The writer David Foster Wallace echoed this in his famous commencement speech:

“[I]n the day-to day trenches of adult life, there is actually no such thing as atheism. There is no such thing as not worshipping. Everybody worships. The only choice we get is what to worship… If you worship money and things, if they are where you tap real meaning in life, then you will never have enough, never feel you have enough. It’s the truth. Worship your body and beauty and sexual allure and you will always feel ugly.”

Your idol points to your weaknesses and the illusions you chase. While those things are not evil in and of themselves, if they become your source of being, they can create disorder.

Knowing what you worship is the first step to not being owned by it.

6. “What if everything was perfect?”

Frida Kahlo started painting after a severe bus accident left her immobilized. While recovering from her injuries, she began painting self-portraits using a mirror rigged above her bed to pass the time and process her physical and emotional pain.

She said, “I paint myself because I’m so often alone and because I am the subject I know best.”

No training. No studio. Just the will to start, despite the less-than-ideal conditions.

Maybe for you it’s writing a book. Or asking for someone’s hand in marriage. Or starting to invest.

Often what holds us back is the belief that conditions aren’t right. We haven’t gone through the proper process yet. In other words, it’s not the perfect time. Only later do we regret being so timid. For instance, the top financial regret is not starting to save for retirement early enough.

So, ask yourself: If everything were perfect — the timing, the resources, the confidence — would you take the opportunity in front of you?

If the answer is “yes” under perfect conditions, then the answer is probably “yes” now.

As Frida shows, you can just start. You can just do things.

In a way, perfection is its own limitation. Freedom is getting started.

7. “Do you want more pie?”

The joke goes: What’s usually first prize in a pie-eating contest?

Punchline: more pie.

It’s not even a good dad joke, but it does act as a useful compass.

What do you enjoy doing so much that the reward is simply… doing more of it?

Not for money. Not for status. Just more of the thing itself.

That’s where fulfillment hides.

8. “If someone pulled the story of your life off the library shelf, would it be worth reading?”

In “The Library of Babel,” Jorge Louis Borges imagines a library containing every possible book. That includes the complete book of your life. Now, let’s say someone pulls down the volume with your name on it.

Would they be interested in reading it?

A good story doesn’t need car chases or sudden reversals. But it does need something: intention, movement, curiosity, a choice made. If life so far feels like filler text, this exercise could help create a subtle pressure to edit your own story while you’re still writing it.

It’s a story-framed way of asking: What are you wasting time on? What are you neglecting? What dreams are you letting wither and die?

The writer Bill Perkins, author of Die with Zero, writes:

“In the end, the business of life is the acquisition of memories. So what are you waiting for?”

In one way or another, you’re going to be using your time, money and energy. Even if you do nothing at all. Is it going to the life you’ve imagined, or is the story running on automatic, like the same chapter copied over and over?

9. “Is this the last time?”

Dirty diapers. Another bedtime story. That invitation to go out for drinks. Affectionate kisses. Fist bumps. Reunions. Bowling league. A call home.

There will be a last one of each — and we almost never know when it is.

This is the question I try to remind myself to ask whenever I’m with others and wish to be somewhere else. Maybe I’d rather not spend the money going out with friends, but what if this is the last time? Maybe I’m too tired to play catch, but what if this is the last time my son asks?

We’ll never know when the last time is. So enjoy the ride even as you pursue greater things. Because there will be many great things — things that might annoy you in the moment — that fade along the way. The things we often talk too dismissively about as “just life.”

There will be a last one of everything.

Is this one it? What can you do to cherish it more, to make it last just a little longer?

Was this the last stroller ride? :(

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