Deep Spiritual Questions to Ask
Twenty questions about belief, practice, forgiveness, suffering and death, written in the first person for journaling, a retreat, a long walk, or a small group that has agreed not to give each other advice. They are ordered so the easier ones warm the ground for the harder ones.
The questions
Open any question for the note
When did I last feel genuinely at peace, and what was going on around me?
Why ask it
Answering with the circumstances rather than the feeling is what makes it repeatable. If the only example is a holiday from years ago, that says something about the current shape of a life rather than about peace.
What does my spiritual practice look like on an ordinary Tuesday rather than on a retreat?
Why ask it
A practice that only survives in special conditions is closer to a mood. Honest answers here are usually far smaller than people expect: four minutes, a walk to the car, or nothing at all this month.
Which of my beliefs did I inherit without examining, and which did I choose?
Why ask it
The inherited list is normally longer, and the inherited items are the ones defended hardest. Sorting them is the whole value; deciding which to keep can wait.
What word do I use for God, and what does that word carry that another one would not?
Why ask it
The chosen word, whether God, the universe, or nothing at all, usually tracks the room someone grew up in more than what they now think. Seeing that gap tends to loosen it.
Who taught me what reverence looks like?
Why ask it
Reverence is picked up by imitation, usually from one specific person who never discussed it out loud. Naming them explains habits that otherwise look arbitrary.
What am I most grateful for that I did nothing to earn?
Why ask it
Gratitude for achievements is easy and slightly self-congratulatory. Ruling those out pushes the answer toward luck, inheritance and other people, which is harder to sit with.
Where do I go when I need to feel small in a good way?
Why ask it
Most people have such a place and have never said so aloud. The answer is usually unglamorous: a stretch of road, a particular hour of the night, one pew at the back.
What do I think happens after I die, and how honest am I being about not knowing?
Why ask it
The second half is the real question. A fast confident answer is often a recited one, and it tends to wobble when asked which part is actually believed.
What do I keep asking forgiveness for without ever accepting it?
Why ask it
Repeating the same confession usually means one of two things: absolution is wanted without change, or forgiveness is believed to apply to everyone else. Which one it is changes what to do next.
Who am I still refusing to forgive, and what would I lose by letting that go?
Why ask it
The second clause is what makes this answerable. A grudge is nearly always doing a job, often holding a boundary or a version of events, and naming the job beats resolving to be nicer.
When suffering came, what actually helped, and what only sounded like it should?
Why ask it
People often find that the phrases they now offer others did nothing for them at the time. Separating the two changes how they behave at the next funeral.
What do I give that costs me something, and what do I give that costs me nothing?
Why ask it
The costless column is usually longer and contains most of what gets called service. The point is not to feel bad about it but to see the ratio clearly.
What would I do differently if I assumed I was being watched with affection rather than judgment?
Why ask it
The answer shows which picture of the divine is actually running, whatever the stated theology. Anyone raised on judgment often cannot picture the alternative at all, which is itself the finding.
Which of my convictions would I still hold if nobody I love agreed with me?
Why ask it
This separates belief from belonging. A short list is not a failure, but it does explain why certain disagreements feel less like argument and more like exile.
What am I afraid I would find if I sat in silence for an hour with nothing to do?
Why ask it
The specific fear matters more than the general discomfort. Boredom, grief and self-reproach are three different answers calling for three different responses.
Where is the line between faith and wishful thinking in my own case?
Why ask it
Almost everyone can draw this line for other people and stalls on their own case. Watch for the answer that redefines the terms rather than applying them.
What have I called a spiritual insight that was mostly relief?
Why ask it
Relief is a strong feeling and easy to misfile as revelation. Reviewing old certainties by asking what problem each one solved at the time shows which ones held up.
What am I still trying to control that I claim to have handed over?
Why ask it
The gap between stated surrender and actual behavior shows up in something small and concrete: a calendar, a bank balance, another person's decisions. Abstract answers here mean the question has been dodged.
If my life were the only argument for what I believe, what would it be arguing?
Why ask it
This moves things from doctrine to evidence, and the honest answer is rarely flattering. It usually also names the one habit worth changing first.
What question in all of this am I avoiding, and why that one?
Why ask it
Kept for last because it only works once the others have warmed the ground. The avoided question is normally already known; the reason for avoiding it is the more revealing half.
How to work through these questions
Practical guidance for the conversation itself
Working through them alone
One question per sitting
Take a single question and write for ten minutes without stopping to improve the sentences. Trying to cover several in one session produces summaries rather than answers.
Date every entry
These questions are more useful as a series than as a one-off. Coming back to the same question in six months shows what has moved, which is information you cannot get any other way.
Note what you skip
If you pass over the same question twice, write down that you did and nothing else. Question 20 exists because of this pattern.
Using them in a group
- Agree before you start that no one responds to an answer with advice, scripture or a correction.
- Whoever suggested the exercise answers first, and answers something they have not rehearsed.
- Go once around the circle before anyone gets a second turn, so the quickest talker does not set the depth.
- Make passing explicit and free. A group where nobody ever passes is a group where people are performing.
- Keep sessions to four or five questions. Beyond that the answers get shorter and more agreeable.
When answers stay abstract
Abstraction is the standard defense with questions like these, and it is easy to mistake for depth. Three follow-ups pull an answer back to ground: when was the last time, where were you, and what did you actually do next. If the reply is still general after those, the topic is not ready and pushing it will only produce a better-worded evasion.
What goes wrong
Recruiting instead of asking
If you already know which answer you are hoping for, the other person can tell, and you will get that answer without learning anything.
Treating grief as a topic
Questions 8, 10 and 11 can land on a live loss. If they do, stop the exercise and stay with the loss. Returning to the list afterward is optional.
Repeating it later
Anything said in this kind of conversation should not resurface in a different room, and certainly not as leverage in an argument. One breach ends the practice for good.
Mistaking a settled answer for a finished one
People who answer all twenty smoothly are usually reciting positions they arrived at years ago. Ask what has changed since, and when.