The Questions You're Avoiding Are the Ones That Will Set You Free

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We all say we want to change. We want to feel better, live more authentically, break free from the patterns that keep us stuck. But here's what I've noticed in my years as a therapist and mindfulness teacher: most people want the transformation without the discomfort of actually transforming.

The truth is, real change requires us to look at what we'd rather not see. It asks us to sit with questions that make us squirm, to acknowledge truths we've been running from, sometimes for decades. We get so caught up in the perceived pain of this inner work that we forget what's waiting on the other side - the freedom, the clarity, the lightness of finally putting down what we were never meant to carry.

I know this intimately because I've lived it. Time and again, I've discovered that I was the one causing my own suffering, standing in my own way without even realizing it. My fears, my doubts, my insistence that life should look a certain way - these were the real sources of my pain, not the circumstances themselves.

When Everything Becomes Your Teacher

Matt Kahn is a heart-centered spiritual teacher whose work I deeply respect. In his book Everything Is Here To Help You, he offers a profound reframe: what if every experience, even the difficult ones, is actually here to help you evolve? What if your challenges aren't obstacles but invitations to reconnect with the wisest, most authentic part of yourself?

To support this shift in perspective, Kahn provides a series of penetrating questions designed to expose the hidden beliefs and fears that keep us contracted and suffering. These aren't comfortable questions. They're not meant to be. But they are, I believe, some of the most valuable inquiries you can make if you're serious about transformation.

How to Work With Deep Inquiry

Before we dive into the questions themselves, let's talk about the process. This isn't about finding the "right" answers or fixing yourself. It's about creating space for truth to emerge.

Here's what I invite you to do: find a quiet place where you won't be interrupted. Take a few deep breaths and let yourself settle. Place your hand on your heart if that feels supportive. Then, as you read each question, don't rush to answer it intellectually. Instead, drop down into your heart and simply listen. Ask the wisest part of you - that deeper knowing beneath the noise of fear and conditioning - what wants to be revealed.

When insights arise, write them down thoughtfully. Not everything will come at once, and that's okay. These questions are meant to be lived with, returned to, deepened over time. What matters is your willingness to be honest with yourself, to meet whatever arises with compassion rather than judgment.

The Questions That Found Me

Out of Kahn's extensive list, these are the ones that stopped me in my tracks, the ones I keep returning to in my own practice:

What am I afraid to admit I could lose or gain? This question gets at the heart of our resistance to change. Sometimes we're more afraid of success, of actually getting what we want, than we are of failure. What would having that relationship, that career, that peace of mind actually mean for how we see ourselves? And what are we terrified might slip away if we stop vigilantly protecting it?

What am I afraid to admit will be true about myself when things don't go my way? Here's where we uncover the hidden beliefs driving so much of our behavior. Maybe you're terrified that if you fail, it will prove you're not good enough. Or that if someone rejects you, it confirms you're unlovable. These unconscious conclusions run our lives until we bring them into the light.

What am I afraid is true about me that makes me feel ashamed and compelled to over-compensate in life just to prove that belief wrong? This one cuts deep. So many of us are exhausting ourselves trying to disprove something we secretly believe about ourselves. The over-achieving, the people-pleasing, the constant striving - often it's all an attempt to outrun a painful story we've been telling ourselves since childhood.

What's the most painful thing I believe about myself when no one is looking? In the quiet moments, when the distractions fall away, what verdict do you pass on yourself? This is where we find the root of so much suffering - the harsh inner judge/critic that never seems satisfied, no matter what we accomplish. For me, it was shame, a fate worse than death, that I could change things and didn't, because I failed to take action. Fortunately- this work helped me become aware of this truth so I could deal with it, which is the whole point of sharing this. There is hope, so stay positive and optimistic. 

What defines my sense of self that I am most afraid to lose? Who do I think I'd be without it? We construct identities around our roles, our struggles, even our pain. But what if your sense of self doesn't depend on being the successful one, the helper, the person who has it all together, or even the person who's been through so much? Who are you beneath all of that?

If I imagine facing the worst thing I'm afraid to encounter - whether that's a disease, an enemy, death, or any form of adversity - what conclusions would I draw if it actually happened? Our minds spin catastrophic scenarios, but rarely do we follow them all the way through. What are you really afraid would be true if the worst happened? And is that conclusion actually accurate, or is it another story you're telling yourself?

How does life change when I see a challenge as an individual experience, rather than what it personally symbolizes or means about me? This is the gateway to freedom. When you can separate what happens from what you make it mean about you, everything shifts. You're no longer at war with life. You can finally see that circumstances are just circumstances - and you are so much more than any single experience.

The Practice

Here's what I'm inviting you to do this week: choose one or two of these questions and sit with them. Not all at once - that's too much. Just one or two. Write them down. Carry them with you. Let them work on you in the background as you go about your day.

When you have quiet moments, return to them. Drop into your heart and listen for what wants to emerge. You might be surprised by what you discover - not because you've found some profound new truth, but because you've finally admitted to yourself what you've known all along.

This is the work that changes everything. Not because it's comfortable, but because it's real. And on the other side of that realness is the freedom you've been seeking.

The suffering you're experiencing isn't a sign that something is wrong with you. It's a signal that something within you is ready to be seen, acknowledged, and finally released. These questions are the doorway. All you have to do is walk through.

If you'd like support in exploring these questions more deeply, I offer individual counseling and mindfulness-based coaching designed to help you move beyond limiting beliefs into the life you want to live. You can learn more about working with me at JourneyMindfulness.com