7 challenging questions to ask yourself that will cut life down to the bone

Perhaps our everyday lives are simply ways for us to ignore difficult questions.

Without bringing those questions to consciousness, though, they control us, ringing unanswered throughout our lives. Our hearts yearn for depth, yet we run away from their intensity.

It takes courage to confront deep questions, to permit the necessary space for them in our lives.

So take heart and ask yourself:

If you met yourself now as a child, what would they say to you?

How would your childhood self view you now? What would they tell you that you have lost or left behind; what feelings or ideas would they say you have unduly taken up?

There is no compromise with the truth that we must be willing to ‘lose our life in order to find it’.
— Bud Harris

When I consider these questions, I see myself as a young child, dressed up like Virgil from the Thunderbirds, wearing boxing gloves and my Dad’s RAF hat. I was a boisterous, joyful, gleeful child.

But that boisterous, abundantly joyful nature is something I rarely observe now. I can see toddler me wondering why this adult refuses to have fun, never seems to smile and seems so serious all of the time.

In fact, when I’ve engaged with my inner child he’s told me exactly the same (tip: try writing with your non-dominant hand).

This question opens up space to consider how we have changed over time. Much of that is useful, as we matured to encounter the conditions of our lives.

But it also points to neglected aspects of our character that would benefit us if expressed. Why is it, for instance, that I cannot freely express my playful nature?

In truth, we surrender aspects of ourselves to society. Sometimes that’s positive, an appropriate scaling down of energies that could harm others, but sometimes it’s the unintentional surrender of a core component of our character or life-force. So:

Where in your life do you surrender what you shouldn't?

We can view our adult selves as a compromise between the call of our inner natures and the need to meet outer conditions. Picture a scale between unadorned narcissism on one side and habitual self-effacement on the other: we balance ourselves between these twin forces.

As our lives proceed, we tend to compromise the integrity of our inner world to placate the outer world.

In time, we may let go of so many parts of our natures that we feel that we have let go of ourselves, losing some core part in others’ demands.

Does this value, practice, or expectation take me deeper into life, open new possibilities of relationship, and accord with the deepest movements of my own soul? If not, then it is toxic, no matter how benign its claim.
— James Hillman

This question asks us to reflect on where we have yielded parts of ourselves to others and to reconsider. We can then redress the balance, address our core and ask:

What seeks to live through you?

There is a thread sewn through your experiences. It’s as thin and strong as a spider’s web, and  — like a fish on a wire — you’re caught on it. The thread runs from your first memories to you — now — as you read these words. It’s the ever-unfurling answer to the largest question in your life: who are you?

I’m fascinated by this question (yes, I'm just another fish), and I’ve noticed that often the way we try to answer it involves sorting: we sort ourselves into groups, into kinds of people who we can relate to and claim an identity as. (I do the same when I call myself an INFJ on the start here page.)

Well, as social relationships go, that’s great — after all, it’s wonderful to find (or form) your tribe of weirdos, and it's great indeed that the internet allows us to meet others so close to us in spirit and character, yet so far away.

Yet there’s something unsettling and counterfeit about this attempt to find ourselves in a group or category. And it’s that we sublimate our character in the group, so that we don’t have to face the distinct thread of our lives.

The truth is, we’ll never find our particular, unique experience in any category.

The unique causes and conditions that gave rise to your life demand a unique answer.

Simply put, you cannot outsource the meaning of your life without sacrificing your power and integrity.

Although the world is full of people who will tell you who you are, what you are, and what you are to do and not to do, they wander amid their unaddressed confusion, fear, and need for consensual belief to still their own anxious journey.
— James Hillman

You don’t need to complete yet another personality exercise. Instead, you need to listen to life and its call on you.

So listen for the question that your life asks of you, rather than looking for answers outside. Listen for the question that surfaces the summons of your soul.

It takes time and patience, but it leaves you with a powerful narrative for your life, a story that transforms the thread of your life into an electrified arc.

And yet, even when we know what we’re here for, life often still obstructs us. If you need an example, just consider this:

Does your work support your soul?

This bites.

In the previous question, we considered the compromise between our inner natures and our outer conditions. Nowhere is this compromise more fraught and heightened than in our working lives.

For some, work helps us to actualise our purpose; for others, work makes us stumble, standing in the way of the question that our lives seek to answer, demanding payment instead of growth.

So for this question, we reflect on work’s place in our lives. In what ways does it support us? Is it simply through money or through human connection? Does it also encourage us to tend the spark of our soul?

No matter how work serves us, we must not treat work as neutral, or underplay the depth of its influence on our lives.

No-one should be neutral or indifferent to his work or workplace. It is very important for a person to have a careful look at the kind of work he does. He should try to establish whether the work he does and his workplace is actually expressive of his identity, dignity and giftedness. If not, difficult choices may need to be made. If you sell your soul, you ultimately buy a life of misery.
— John O'Donohue

The uncompromising everyday dullness of work sparks indifference not only to the work but to life itself. It dulls our minds, our hearts and our senses, so that we forget the questions that previously inspired our lives.

Amid such drudgery, we need a reminder of the transcendent. We need the strangeness and wonder of reality to break through to us again. Ask yourself:

How are you in touch with the numinous?

As Nietzsche proclaimed, we have buried God, but as Jung intimated, the gods haunt us.

Despite the many ways we distract ourselves from the mystery of mortal human life, comforting ourselves with technology and a culture designed to keep us sheltered from a bewildering world, we continue to be faced with mysteries that eclipse our lives.

Why are we here? What happens after death (if anything), or what does death mean? Is there a god or are there gods? What is consciousness, or time? Why is there something, rather than nothing? Do our lives contain meaning? Are weird things really real?

To speak of a signal of transcendence is neither to deny nor to idealize the often harsh empirical facts that make up our lives in the world. It is rather to try for a glimpse of the grace that is to be found “in, with, and under” the empirical reality of our lives.
— Murray Stein

Contemplating mysteries may stir us to search for answers through routes such as traditional religion, New Age spirituality, science, philosophy or psychology.

Or such paths may divert us, cloaking our confusion, so that we don’t give ear to the heavy questions that the world demands.

To touch the numinous, we turn to mystery — to questions that eclipse our lives — and pay attention. Though such questions may make us feel small, we become joined to deeper truths by attending to them, as we sense the connection and wonder inherent to life.

And it’s from that recognition of the connection and wonder inherent to life that we can consider anew:

How will you choose to live, given how rare and precious your life is?

Our lives are bookended by great mysteries. In-between, we choose what energies we will bring to life — how we will live.

It may sound as if this question is answered by the third one, What seeks to live itself through you? But the truth is that your life’s purpose is entwined with your lives’ conditions, merged with your friends, family and responsibilities, forming a complex amalgam.

The heart of the matter is, you should never belong fully to something that is outside yourself. It is very important to find a balance in your belonging. You should never belong totally to any cause or system. Frequently, people need to belong to an external system because they are afraid to belong to their own lives. If your soul is awakened then you realize that this is the house of your real belonging. Your longing is safe there.
— John O'Donohue

How you will choose to live, then, is a complex reconciliation between what seeks to live itself through you, your responsibilities to your loved ones and the wider social milieu, and your response to the mysterious or numinous.

No one can honestly circumvent the need to find a path through this complex web and we cannot fault any person for their particular way to reconcile these competing forces.

In the end, you yourself determine how you honour and serve the energies that centre themselves in you.

And — by the end — we are brought to a final great mystery:

How will you meet death?

From Horace's carpe diem, to Buddhist reflection of the decaying body, to the medieval memento mori, we are wisely exhorted to reflect on our deaths, what they might mean  and how we might respond to them.

Thus, we are always split. Nature follows the archetypal path of transformation: life, death, and rebirth. Jung, paraphrasing Goethe, described the path as one of, “Formation, transformation, Eternal Mind’s eternal recreation,” and Hegel intellectualized this process into thesis, antithesis, and synthesis. But feeling/thinking humanity experiences this natural process as punishment, torment, death, and transfiguration—and fears it.
— Bud Harris

Life is a leading up to death, as Heidegger intimated, and reflecting on death serves as a way to bring us closer to our lives.

So asking yourself how you will meet your death is not a question for your deathbed.  Instead, it's a question for right now: one that immediately resets your outlook.

You may flinch when you picture the decay of your body. But that flinch straightens out your attitude:  it forces you to pay attention to the critical, essential elements in your life.

So if you knew you were going to die tomorrow, how would you act today? What would you do? How would you — through how you act — show who and what is important to you? How would you show up in your life, when you know you’re running up against its end? And if you’re not acting that way now, why not start immediately?

Conclusion

To sum up, then, here are the questions:

1. If you met yourself now as a child, what would they say to you?
2. Where in your life do you surrender what you shouldn't?
3. What seeks to live through you?
4. Does your work support your soul?
5. How are you in touch with the numinous?
6. How will you choose to live, given how rare and precious your life is?
7. How will you meet death?

These questions may challenge you, but reading them without also reflecting on them will never expand the psychological territory you allow yourself to roam.

So there can be no conclusion here that comes from me: you must bring yourself to these questions and reflect sincerely.

Questions like these will remain with you throughout your life’s journey, not because you remember my words here but because similar questions bubble up from the soul of each of us. I urge you not to ignore or to forget their call.

I will leave you with a capstone question, though — one that condenses the others:  how would you live your childhood again if you entered it with the understanding that you now have as an adult? The wisdom that you bring to this question tells you how you should live right now.

Yours on the journey,
James