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Asking Yourself Good Hard Questions

  • Writer: Anna Santini
    Anna Santini
  • Jan 9
  • 13 min read

I mechanically lifted the dishes out of the dishwasher, and plodded over to the shelf to put them away. Another day, another dishwasher to unload. My mind ran in a thousand directions: the problem du jour, all I had to do that day, and why no one else in the house could do dishes. It wasn’t pretty. And it was sadly the norm. Fortunately, a little bell of insight dinged inside me. What is another way to do this? There is always another way to do everything. I straightened up, and peaked out the window over the sink. Another day, another sunrise over the beautiful hills in the distance. And holy heck - another day with a WORKING DISHWASHER! What a cause for celebration. 

OK, so I shifted to gratitude. But the shift was not in trying to be grateful. The shift was in asking the question. 


Here’s another recent example from my own life. My son was being an asshole to me. Again. Rude responses to simple questions. He is 18, doesn’t know what he’s doing next in life, and regularly spews his angst at mom. I work on a lot of things: I try communication. I try boundaries. I try fun. I try support. I take him to therapy. It is all good. And it still hurts. When I felt the familiar wave of rejection draw my face into a frown, I asked myself: what do I need to stop fighting here? What can I just accept? The truth was clear: he was speaking unkindly to me and there was nothing I could do to stop that. Yeah, consequences. And all the rest. But ultimately, I had no control over how he was going to treat me. I had tried many times to just not let it bother me before. Just let it roll off your back. Just ignore it. That was a kind of fight of a different kind, trying to fight and suppress my reactions. This question was different. What is actually ok about this? 


"We get a larger life by asking larger questions and keeping those questions before us—not from settling for the available answers, which ultimately prove limiting." ~James Hollis, Jungian psychologist, author, teacher, father. 

Why Asking Yourself Good Hard Questions is Important

There is great power in a good question. You could call these “turning questions” as a therapist of mine used to. Turning questions help you flip your automatic thinking and connect with what is true. They’re like a get out of jail free card, opening doors to new possibilities. I like to also call them “steadying questions”, because answering them can bring peace, strength, and stability. In the sea of constant change, it is up to us to keep swimming. Someone else will be relying on you to be the steady one when you are a parent. 


Good questions may be the hardest questions to ask and answer, but they cut to the heart of conflict, tension, and suffering. Questions cause shifts. And they often give us the kick in the butt that we needed to take action. 


The Motherflow journal is more than prompts. It is training during pregnancy in a meta skill that is incredibly important throughout the parenting journey (and life): how to ask yourself good hard questions. Truth is hiding in the questions you are not asking.


When we’re younger, we don’t always do this instinctively. In fact, we do the opposite. We placate, pacify, and rationalize. We skip the hard questions so we can keep doing what’s fun and easy. We avoid the truth so we don’t have to change. 


Once you are a mother, you don’t have time for this bullshit anymore. You have another life, or maybe a bunch, depending on you for their very survival. And it’s not just survival; it is the nurturing of their souls. Science has given us the proof behind what we already know: it is not nature OR nurture. “We have a nature that requires nurture”, as Lisa Feldman Barrett says. 



“Children are not a distraction from more important work. They are the most important work.” Whether by C.S. Lewis, as it is famously attributed, or originating from Dr. John Trainer as the internet now says, this quote refocuses our energy on the deep truth of parenting. Once you become a parent, there is nothing more important than who you are nurturing, and whether they feel safe, seen, and loved in your presence. 


But I’m pointing out the obvious. You already know of the importance of the task of parenting, or you wouldn’t be here. The point is that no one is here to parent us. There are no teachers to circle our mistakes in red pen. There are no coaches giving us pep talks and running us through drills. No bosses giving us quarterly reviews. If we’re lucky, we have a partner by our side to call us out on our blind spots. But we are the ones who have to step into this very adult role of leadership. 


This takes constant re-evaluation. We stop, step back and ask ourselves - 

Whats working here?

Whats not working here?

What could i have done better?

What do i need to do better?


And I’m not talking about continuous self doubt. Yes, that comes with the territory (link to self trust versus self doubt). And - there are real decisions to be made. Real errors we need to course correct from. Real self reflection that has to happen in order to guide our paths forward. 

Benefits of asking yourself good hard questions


  1. Wake up. To not stay stuck, or passive, or just roll with the tides of whatever life brings. To have an active role in living our best as only we can. We don’t get complacent and sleepy and nonchalant. We wake the fuck up. 

  2. Grow up. Asking yourself good hard questions is challenging, and that is the point. We ask the tough questions for the very act of doing a hard thing, just like going to the gym. 

  3. Anxiety Relief. What??? Didn’t I just say to wake the fuck up? And that we’re putting on our big girl pants and doing something hard? And - It's just as hard not to ask the questions (often harder). Avoidance is a major anxiety coping mechanism. Ironically, what we avoid is actually causing us great anxiety. By avoiding it, the consequences are compounding. Face the music. Look the demon in the eye. There is no way out but through. I don’t care what metaphors you use, just do the work. The beauty of this is, while it can be intense and extremely difficult, there is relief on the other side. And sometimes immediately.  Martha Beck’s work on overcoming anxiety is rooted in tapping into our innate curiosity as a direct path out. Turns out, asking questions in and of itself switches on your solution-seeking brain networks and turns down your stuck suffering networks. There is real science behind this, but more importantly - try it for yourself. 

  4. Posterity. If you ever go back and read your journaling of hard questions, say a year later, you may be surprised by the questions, or the answers. You may be surprised at how they're still relevant, or how you completely forgot about them, or how your perspective has turned to a new angle, and you now have a completely upside down question. This sense of surprise is good, because the unexpected is what captures our brain’s attention. This keeps our autopilot mind constantly updating its predictions

Barriers to asking yourself good hard questions


Not wanting to know the answer

Sometimes we don't ask the BIG questions because we don't want to answer. Honestly - we are afraid of the answer. We don't ask ourselves what kind of birth we'd like to have because we're afraid of being disappointed if we don't get it. So we say we don't care and we take what comes. Or you might not really like the answer if it means you have to work hard or change.

Not acknowledging what’s true doesn’t make it go away.


Not knowing the answer

I challenge you to ask yourself the good hard questions for the very act of entering into the challenge. The challenge, in and of itself, is a worthy endeavor, even if you never answer the questions, (my little journals are full of questions, a million questions, and very few answers!). 

When you think you don't know the answer, your mind is totally stumped. That's pretty cool. I love a good mind-stumping question, like the Zen koans. There were phrases and questions that masters asked for that very reason - to get these constantly whirring gears in our head to grind to a halt, if only for a moment.

So you ask the hard question just to rest in the not knowing. Not knowing the answer is a fine place to be. More on that below.  


There's also a very good chance that your subconscious will work on the question under your level of conscious awareness. I have not located the scientific evidence to back this up at the moment, but there is research that confirms it, as I've heard it countless times in various podcasts and books.


“I don’t know.”

One of my mentors, Brooke Castillo, taught a technique called “thought download”, where you just pour the stream of consciousness that's happening in your mind directly onto paper, as a sort of meditation. Then later analyze each sentence and

figure out what feelings, actions, and results each thought contributed to. She taught that if one of your thoughts was in question form, answer it, and analyze that answer as your thought. She taught that we often hide behind questions and “I dont knows”, when deep down we DO know.

Try this - if you’re brain just says “I don’t know” for every question you try to ask yourself, slow down and ask about that answer - “Am I absolutely sure that I do not know?” “If I did know the answer, what might it be?” 

Another idea - just guess. Making up an answer will give you information. You may have a gut reaction of resonance or disgust if you try to make something up, which is a clue to a deeper truth. This is like when you can’t decide something and you flip a coin and realize “oh, that wasn’t the one I wanted”. You didn’t realize you already knew your decision until the coin pointed to the opposite. 


Protective Mechanisms  

We have complexes. We all have protective parts of our psyche that sometimes don't let us answer these hard questions. Uh-uh. Can't go there. Facing the answers would be too painful, or cause too much cognitive dissonance, or just challenge our present reality too much.

Internal Family Systems can be brilliant for getting at truths and perspectives that parts of your mind cannot face for whatever reason. You can do parts work with a trained IFS therapist, or on your own once you are familiar with the process. Martha Beck teaches a simplified self applied process in her book Beyond Anxiety


Trying too Hard

Sometimes the reason we can't answer the good hard questions is because we're trying too hard. We don't need to “think about it” and analyze it and get the right answer as on a test at school. 

Obviously there is no right answer. What I find more freeing and often more accurate,

is a process that I also learned from various spiritual teachers, which is to just sit with the question in silence and not use the thinking part of your mind at all. Relax in brain and body and just rest and sit and wait until something pops into your awareness. It might be a direct answer to the question, or might be something seemingly unrelated.


Gently ask the question in your mind and then feel down into your body, your heart or your belly and see if an answer spontaneously arises. You don't need to sit for hours

formal meditation to do this, (and you won't have time to). Just give yourself a minute, literally 30 seconds to a minute, just in silence, stillness, and space. Maybe all you feel is fear clenching in your belly. That’s OK. Maybe you just feel a not knowing, a blank openness. Isn’t this the great mystery that the wisdom traditions teach? Asking a good hard question is a way to get to peace. 

My favorite ways to ask the good hard questions.


  1. Journal. Obviously, writing is a wonderful tool for self reflection, and its benefits are abounding. Blah blah blah the science, just WRITE. Try it out for yourself. Some tips to get you started will follow. 

Here’s a real truth about motherhood: Even if we know journaling is beneficial, even if we know the evidence and have experienced it firsthand, we still often don’t have the time or space to devote to journalling. 

Good news - that does not stop us from asking ourselves the good hard questions. 

*Try a mini journal, one of those pocket size ones. Just write one question, on one page. Let it live there. You don’t need to fill the page, or three, or write for 15 minutes. Or scribble one question on a post it. Writing can be informal, on the fly, and done in seconds, not hours.

  1. Talk. Many of us experience that we are verbal processors. We talk things through in order to find clarity. It isn’t until we put words and names to things that some sense begins to emerge. I once heard talking it out described as finding your way around an unknown room, blindfolded. As you explore and move around, you end up sensing what is there. Talking is also what we’re drawn to in our culture. At the first sign of confusion or distress, we call a friend. This is valid and wise. We need others to help us regulate our nervous systems and talk through our issues. Therapy is also a reliable way to get help if and when you need it. Just because there is no guidebook to this thing called parenting and life, doesn’t mean we don’t need help. Just because we’re grownups doesn’t mean we don’t genuinely want and need parent figures, coaches, and teachers. Therapy is a useful tool in our toolbox. And- we cannot rely on therapists and friends to ask or answer our deepest questions. No one is in here with us. We can talk all day and night, but then we still have ourselves to deal with. At a soul level of growth, you must face yourself, by yourself. That is why the great Hero’s Journey myths have Luke Skywalker entering the cave and battling the enemy who turns out to be himself. So for “talking”, don’t forget to talk to yourself. Voice recordings on your phone are brilliant for this. Even if you never go back and listen or respond to it, the act of pressing ‘record’, tricks us into feeling heard, which tricks us into opening up and let all truth pour out. Sometimes more truth than we would allow with a real person. 

Sidenote - am I alone in not always having or wanting to spare the $$ for therapy? Feel free to just start talking to yourself and see what comes up.

  1. Creativity. The act of asking questions IS a creative act, by its very nature. You are tapping into your questioning mind, your “right brain” (figuratively, the way scientists now know that it is not a real division as we once thought), your resourceful and curious beautiful openness. And, words might not give you the answers you seek. If you feel stuck in your mind when you hold a pen and see a blank sheet of paper, consider trying these out:

    • Sing. OK, this one might be a bit out there. But it is something I have actually used a lot in my parenting life, and so I am including it here even though it may sound weird. Yes, you can ask yourself good hard questions by singing. Sometimes our brains are just tired, so tired, of trying to figure everything out. The mental load is real. For many years, a little practice I kept was to take a walk in the woods and sing to myself. Like a kid, just kind of making rhymes, and putting my thoughts and feelings into humming tunes. I often got some good questions and answers that way. 

    • Art. Try asking yourself a good hard question, and painting or drawing what comes to you or what you feel in your body.

    • Dance. Do you feel a lot, but don’t know what it means or what to do about it? Sometimes you need to feel the feelings more to get clarity and move into rational processing. Try asking yourself a good hard question, and then moving your body how it wants to move. Maybe a despair or rage or grief will be noticed that you weren’t aware of before. It might not even look like dance, but more abstract movements like rolling, stomping, or writhing. 


Your turn

Here are some ideas for good hard questions to prime the pump for you. Ultimately, you have to craft your own good hard questions as well as your own answers. 


  • What is the most important thing give my attention to today/right now? 


  • What does _______ (my child) really need from me?

  • What is life asking of me here? What is the task being asked of me here?(Thank you to James Hollis for his many teachings and rephrasing of this powerful question)

  • What could I learn or change to make __________ better?

  • Who has lived through something similar that I could get help or guidance from?

  • What is another way to look at this situation:  _________? 

  • How could I do _________ differently?

  • What would it be like to stop fighting ______.

  • What am I deeply longing for?

    • What is one tiny action that I could take towards meeting that need?

  • What is funny about this situation? What will I laugh about in 5 years?

Good Hard Question Tips

  1. Start small. Dip your toe into asking yourself questions with relatively small questions. Let your goal be to simply face the question, and answer honestly

*These are seemingly small, but mighty questions to start with: 


  1. Don’t stop after the first answer. When you can, dig a little deeper. Ask yourself - 

    • What else? 

    • What else? 

    • Why? 


  1. Try question categories. If you have time to devote to a solid reflection session at the start of a new year or season, try asking yourself your own good hard questions in the following categories.

*Sample good hard starter question for each category: “Why do I have the results that I do about ______”

  • Money

  • Work

  • Parenting

  • Relationship/Partner

  • Friends

  • Fun

  • Meaning and Purpose


  • Flip worries into questions. Since genuinely curious questioning stops anxiety, this is a practice you can turn to for everything. 

    • What is the worst case scenario? What is the best case scenario?How could I handle that?

    • Might there be an opportunity here that I’m not seeing?

    • Is there anything useful I can do about this right now?


  • Use questions to take action. Take something you are dreading or avoiding, and face it:

    • “What is the first, tiniest action I could take now about this? 

      • Is there a good reason to not do it now? 

      • When will I do it?

    • What is another way that I could take action on ______ that might feel more effortless?


  • Drop the victim mindset (link). Blaming others, and poor me is a rampant human tendency. Do the best you can to be aware of it. And that goes for the self judgement too. *The Tell - victim questions aren’t really questions. They are moaning groaning statements. Rephrase your questions until they are more open, less complaining, and touch genuine curiosity.

    • “Why does he treat me this way?” => “I wonder what he is struggling with or feeling pain about that influences his behavior?”

    • “Why am I always late?” => “Is there a pattern can I notice on days I leave the house late?”


In parting, 


I want to acknowledge that this is a very broad topic. Good hard questions can be applied to everything from the most mundane minutiae, to the grandest philosophical quests. 

Keep it simple. Just make it a habit to ask yourself good hard questions. If you are pregnant, the Motherflow pregnancy journal helps you to do just that. Try using principles to craft good hard questions (link).


I’ll tell you what questioning is all about - it’s about bringing things into your awareness that weren’t there before. This might be pure self awareness. Or a discernment or decision about which way to go. Either way, useful stuff. 


Be well and be you,

~Anna


 
 

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