Why Asking Deep Questions In The Evening Might Hold the Key To Your Problems

Silvia Bastos |

Deep Questions

Being a human being, you probably occasionally face problems in your life that don’t seem to have a solution.

Like feeling anxious for no reason.

Or feeling unhappy in your job, or in a relationship that you don’t know how to fix.

Or perhaps it’s just pure uncertainty about the future—not knowing your next steps, lacking motivation and creativity, and fearing failure.

You’re not alone. I know how it sucks to feel stuck, frustrated, powerless. Believe it or not, we’ve all been there.

girl feeling stuck with lots of problems in her life

Now here’s something that may feel both empowering and scary: when it comes to these kind of big, juicy personal challenges, no matter how much advice you get or how many books you read, the final answer will always be up to you.

You and only you have the power to solve it.

But how?

Well, it’s simple: you already know the solutions to your problems; deep inside, you already know what to do.

You just need to learn how to access that knowledge.

Whether you want to call it self-awareness, intuition, or simply connection, the truth is that we know more about ourselves than we think. The thing is, most of this knowledge is usually hidden in a rarely accessible part of our mind: our subconscious.

ideas, insights and solutions are fishes swimming in the sea of the unconscious mind

The subconscious mind is like the basement of our consciousness, or the bottom of the sea. It’s dark and unexplored, and we don’t know much about it because we rarely go there. But if we want to dig up those big answers, we need to bravely dive in and fish them from the corners of our mind.

One of the most powerful ways to find those deeply buried answers is by asking deep questions.

But wait—there is a catch.

Googling “deep questions” or picking random journaling prompts won’t do it. If you want to penetrate the surface of your conscious mind and find the insights that lie beyond, you need a strategy.

You need to ask the right questions, and you need to ask them well.

And that’s what this article is all about.

‘Most Important Question’: Josh Waitzkin’s Problem-Solving Secret Weapon

Josh Waitzkin is an eight-time US National Chess Champion, a two-time World Champion in Tai Chi Chuan Push Hands, and the author of the book The Art of Learning. The movie Searching for Bobby Fischer was actually based on him.

Nowadays, Josh trains world class performers from a variety of different fields. In an interview with Tim Ferriss, he mentioned one specific exercise he uses to move through major blocks by bridging the gap between conscious and subconscious: he calls it “Most Important Question” (MIQ).

"Out of all that's happened today, what can I turn into my Most Important Question?"

This is how it works: at the end of each day, after you finish work, take some time to reflect and come up with the Most Important Question of your day. You might be looking for a solution, a direction, a feeling—whatever it is, make a question of it.

When you’ve got it, write it down in your journal, and then…

Let it go.

Forget about it.

Take some time to relax with a good book or a meditation session, and go to sleep without it on your mind.

Next day in the morning, right after you wake up (make it the very first thing, that is, before you check your phone or walk the dog), open your journal, look at the question, and spend some time brainstorming it.

step-by-step process of asking Your Most Important Question

Why do it this way and at these specific times?

Your conscious mind is most active while you’re awake, and the subconscious while you sleep. By using your questioning process as a bridge between both, you are engaging the wholeness of your brain in super effective problem-solving teamwork.

This is Your Brain on Deep Questions (and a Good Night’s Sleep)

In his book The Art of Thought, English psychologist Graham Wallas proposes that the creative process involves four stages:

Solving big problems requires creative thinking.

The problem is that, by obsessing and constantly worrying about getting the answers, we often skip an important stage of the process—the Incubation.

"How ideas/solutions are born: Preparation, Incubation, Illumination, Verification"

By allowing your sleeping brain to process your Most Important Question and then coming back to it first thing in the morning (which has been proven to be the brain’s prime time for creativity), you are allowing Incubation to happen during the night, so that Illumination can take place next time you brainstorm.

When we question ourselves in this way, we are also practicing the muscle of letting go (which is crucial in our always-on, hustle-and-burnout culture), and we are learning to focus on the important themes of our lives, which leads to less problems and more progress.

How Evening Deep Questions Rocked My World

I’ve always loved journaling and asking myself reflective deep questions.

However, since I learned about Josh Waitzkin’s way to use these tools as a direct connection between conscious and subconscious, both these practices started bringing me 200% more results.

Let me give you an example.

A while ago, I noticed that a deep melancholy had been surrounding me and everything I did consistently for a few days.

girl feeling sad and melancholy

This was nothing new: I had felt this way a few times before in my life.

But this time, instead of letting myself get dragged down by it (as had happened in the past), I decided to pose a question to my subconscious:

“What is my melancholy trying to tell me?”

In the evening, I wrote down the question in my journal. As I went to bed, I did my best to stop thinking about it until the morning.

Then, when I woke up, here’s what came out of my mind:

“My melancholy is a sign, a prompt for me to access a new level of awareness. I am grateful for it, because it’s putting me in a place of discomfort where I can’t just run away anymore. It’s showing me what is out of alignment in my life in such an obvious way that I can’t look away from it. I have to move on and change.

Now, what does need to change? One thing is time spent in front of the computer. The other is a need for more alone time and self-reflection.

My melancholy is showing me all the fear that lies within me, and how the key is just to be with it and let go. It’s telling me that evolution is necessary. I am no longer satisfied with the way I am living and the things I am doing. I want to feel more passion and do more exciting things that break my routine. I want to feel more fresh and alive. I can do that by being in Nature. Where I am now the canal is a good option. When I go to Wales, Nature will be everywhere.”

girl talking to her melancholy

After that, my relationship with sadness changed immediately. The insights had been planted like seeds. Since then, without even thinking much, I have been taking daily steps to address the problem (going outside more often, breathing more deeply, playing more, journaling more).

This practice has also helped me improve my writing process.

Here’s my problem: with almost every article I write, I eventually hit a block.

I always get to this point in my writing process where I hate everything I wrote, or I feel like a fraud, and it can take me days to find out how to move forward. The article becomes an obsession, and I become miserable.

Asking myself deep questions about my creative process (such as “What message do I want to convey with this piece?”, or “Which part is not fitting in with the rest?”, or “What do I really want to write about?”), plus taking a break, and then coming back to it, has unlocked ideas that I didn’t even know I had inside me (an example: some of the illustrations in this article came from MIQs!)

But what I gained from this exercise doesn’t end there.

A few more benefits I got: amazing ideas to bring more closeness into my intimate relationships, directions to strive towards (for example, noticing that I tend towards rigidity, and want to aim towards flexibility), solutions to deal with my anxiety and fears, clarity on my life’s purpose, and so much more.

I found that sometimes it can be hard to convince my mind to switch off and let go of the problem in the evening, but this is a crucial part of the process. Ask deeply and honestly, rest, and only then answer.

When I manage to do that, the insights are sure to come in the morning.

How To Find Your Most Important Question

girl looking into the sea of her subconscious mind

Josh Waitzkin uses the MIQ technique for different purposes, such as “big, thematic questions”, “tactical questions”, or even more moral and personal questions, such as getting a “clear read” on how he “intuitively feels about somebody”.

You can use this process to ask deep questions about any area of your life (personal, professional, interpersonal, spiritual, etc.) Josh recommends using it for “areas of stuckness”—in other words, this is the perfect weapon to slice through big, hairy, scary blocks.

most important question pointing a sword at a big scary problem

Now, how do you find your own MIQs every day?

The answer is: there is no one-size-fits-all formula.

Part of the beauty of this technique lies in the fact that it’s highly adaptable and unique to each person; you are the only one who can define what is important for you to tackle each day.

There are, however, a few tips that I have found really helpful when brainstorming my MIQs.

1. Ask More Questions

a link of questions each leading to each other

There is no pressure to find your perfect MIQ every single day.

Most of us are not used to doing this kind of thinking, so you might have to feel the ground and do a bit of exploration first.

And that’s okay. If you don’t know what’s the most important thing you can focus on that day, start by investigating with some preliminary questions, such as:

“Where do I currently feel stuck?”

“What event/pattern has been repeating itself in my life lately?”

“In which area do I currently have a strong desire to grow?”

“What has happened today that has left the deepest mark in me?”

Asking any kind of deep questions will always lead you somewhere good. You will see certain topics and patterns coming up, and that will give you a good idea of where to focus on when asking your MIQ.

For example: you might notice that something that really stood out for you that day was a piece of negative criticism from a friend, which left you feeling really hurt and offended.

From there, you might come up with MIQs such as:

“What does my pain in receiving negative feedback tell me about myself?”

“What can I learn from this?”, or even

“How do I imagine other people feel when I offer them negative criticism?”

If you don’t know what to ask, ask something else—you will get there eventually.

2. Go Deep

girl diving into the sea of her subconscious

As we have mentioned before, if you want to access valuable insights from the depths of your subconscious mind, you need to dive in for it, go beyond the surface.

In other words: make sure your questions are deep questions.

One way to do this is by trying to identify the deeper source of your problems.

For example, let’s say you want to start a passion project, but you’re constantly getting frustrated because of your lack of motivation and your procrastination. Here are some examples of questions you could ask:

“What is the real reason why I am avoiding starting this process?”

“Which of my core beliefs am I disrespecting by not acting in alignment with my deepest desires?”

“When have I last been through/felt something something similar, and what does that tell me?”

Another way to make sure you’re diving deep is by being very specific.

For example, if you have been feeling stuck with a specific work assignment for weeks, you can try to dig around for details and hacks:

“What is one thing I haven’t noticed that is preventing me from progressing?”

“What five-minute change can I make that might help me unlock my mind?”

“What is one thing that’s working well in this project, and how can I take more advantage of it?”

Finally, you can explore the meta, big-picture questions around the topics you’re facing.

For example, if you find yourself in a conflict with a colleague or a loved one, you can ask yourself:

“What is my purpose in connecting with other people in my life?”

“Which parts of me (emotions, moods, needs) are out of alignment when there is tension or conflict between me and others?”

“What is my definition of love/friendship?”

3. Get Inspired

girl reading a book called "The Art of Asking Deep Questions"

If you are not used to asking these sort of questions, you can start by getting inspiration from people who do.

In other words, yes, it’s okay to Google “deep questions for self-reflection” or “questions for self reflection” to learn how to formulate them, but it’s always more powerful to then adapt them to your own current circumstances.

Here is a list with some of the best ones we have collected so far at Journal Smarter.

4. Let Go

clouds and sky mixing up with water

This is probably the most important part: in order for this exercise to work effectively, you need to let go of the obsession with finding answers immediately.

Don’t ask your question right before you go to bed; give yourself space to unwind before going to sleep, and try to keep your mind away from it while you’re in bed.

Once you get enough practice, you can do the exercise in smaller intervals, several times throughout the day, such as asking a question before you go to the bathroom or take a tea break, and then coming back to it. The key is to alternate between work and rest, tension and relaxation, conscious and subconscious, instead of always remaining on one of the sides.

How To Start This Evening Ritual Today

You don’t have to feel defeated every time you encounter a tough challenge: you can harness the full potential of your mind to find the solutions that are already available to you.

Try it for yourself. Tonight before bed, grab your journal, do a bit of evening reflection, and find your Most Important Question.

Write it down and read it a couple of times. Let it sink in deep. Then stop thinking about it, relax, and have a good night’s sleep.

Right after you wake up, take five minutes to write down the answers. Freely. Naturally. Let it flow.

Remember: go deep, let go, and let the insights arise.

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