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Deep Thinkers · Apr 11, 2026

A Conversation With the One I Hate Most (Part 2)

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Deep Thinkers · Deep Thinkers

This is Part 2 of a two-part series on shadow work and radical honesty. If you haven’t read Part 1, you can find it here.

“To own one’s own shadow is to reach a holy place—an inner center not attainable in any other way. To fail is to fail one’s own sainthood and to miss the purpose of life.” — Robert Johnson

To me, the journey home, back to inner harmony and peace, is the most important task of our lifetime. Without it, we are haunted by the sense that something is always missing. Contentment feels out of reach, elusive and fleeting. But like anything worth having, this journey demands courage. It calls us to reckon with the darkness that lives within us all. Put another way: you cannot reach the pinnacle of your potential without first accepting the ruin within your own capabilities.

Once we understand this, the floodgates open, and we can finally walk the path meant to take us back home.

Below is the rest of the conversation between my Shadow and me. It’s a transcript from a journaling exercise that helped me understand why, after all these years of committing to personal growth, I was still left feeling empty, and how I nearly lost the person I love most.

At its core, this is a reckoning. It’s about radical honesty—doing what you say you will do, accepting the undesirable side of yourself, and finding the path back to a place of inner harmony and true authenticity.

The Conclusion:

The air has grown cold again, colder even. I am physically uncomfortable—hearing these words, my words, feels like a betrayal, like someone I don’t recognize has taken control. This is the rot I pretended wasn’t there. This is me. It’s everything I’ve buried, now staring back at me from the page. I want to run, but I don’t. I stay…because the only way out of this is through it.

Shadow: Confess? Why? What’s the point? Things are better now between you and her. Why screw it all up by bringing that up?

Ego: “Because she deserves to know… and…”

Shadow: And what? What kind of idyllic nonsense are you gonna spout now?

Ego: “Well, I need to get this off my chest. I just know I won’t feel right until I confess—until I am honest about what I’ve done and who I’ve been.”

Shadow: Sounds like this is all about you again. Do you ever get tired of being so selfish? Just watch—you’re going to break her heart. You confess, and then what? She sees you for who you really are, and then everything I’ve done was a waste.

Ego: “It’s selfish to keep this to myself.”

Shadow: Is it? Sounds like you’re the one who can’t handle a little secret, so you want to toss it onto her and hope for absolution just so you can feel better about yourself. I don’t know…sounds pretty selfish, if you ask me.

Ego: “Why do you do that?”

Shadow: Do what? Tell it how it is? Hit you with facts?

Ego: “No. Why do you spin everything in a way that eventually leads to doing nothing? Every justification you propose, when I really think about it, serves only one purpose: to stay exactly as I am. The funny thing is, I don’t think you’re 100% wrong. It’s true that one of the reasons I feel the need to be honest is that I’m trying to find some kind of peace…for me. But that’s all you can fixate on. It doesn’t matter what you say, I know that our relationship can’t go any further than this without truth. She deserves to decide if she can forgive me and move forward. There would be no chance for us if I held onto this.”

Shadow: But why bring it up now? Why not wait? Things were on the verge of collapsing, and now they’re better. And you want to do this? I don’t get it. If the guilt is too heavy, you know the way out. You have the remedy right there. Use it, go to sleep, and see how you feel tomorrow. See if you still feel the need to do this incredibly stupid thing.

Ego: “Nah, I’m good. I’m done running. Done distracting myself. If I want honesty, it starts with me. Feel how you feel, but I’m doing this. I meant what I said. I won’t keep you locked away anymore, but that doesn’t mean I have to do what you say. I don’t ‘own’ her, so I can’t ‘lose’ her. If she leaves, would I be sad? Of course. But if I never say anything and she sticks around, I won’t be able to live with myself. This is how it goes from now on. I will try to understand you. I will give you the space to express yourself—within reason—but ultimately, I’ll decide what to do. Self-preservation won’t be the only thing I live for anymore. Like it or not, this is the way it goes.”

Shadow: Hmph. We’ll see if you’re singing this same tune once she leaves you. We’ll see how long you stay clean when things really take a nosedive. It’s really easy to talk all this integrity and bravery bullshit right now, but I want to see if you can truly stand just as you are under a mountain of despair. I doubt it. Anyway, it doesn’t matter. Since you’ve let me into your little circle here, you’ll hear plenty from me. When it all comes crashing down, I’ll be right here.

Rather than answer, I give a brief nod. I look to the horizon, just beyond the break in the valley, and see the light moving closer to the darkness. I notice that neither is trying to consume the other. They both remain, and at the center where they meet is a connection that seems to be telling me something.

Tears hit the journal pages as I wonder if any of this matters in the long run. Part of me thinks it’s all pointless. But there is a pulse of something very real beneath the cynicism, a sensation I can’t ignore—a faint, but material lightness. A micro fracture in the constant pressure inside me. The valley air feels a shade warmer, the chill finally pulling back…for now.

There is still so much work to do, but there is an understanding here. Where things go now rests solely on my actions, on who I am, not who I claim to be.

Until we understand why we do the things we do, we’ll repeat the same patterns and blame the universe for our struggles. For me, denying my own darkness led me down a path of self-sabotage and a decimated sense of self-worth. I resigned myself to a bleak fate long ago. The things I wanted most were things “people like me” didn’t get to have. I accepted this narrative and made it my identity. To suffer—needlessly at that—was what I was meant to do.

Unconsciously, I acted in ways that took me further from my deeper desires and toward this fabricated narrative of what I deserved. Soon, a pit opened in my heart, one that felt like a constant thrum of despair that would never leave. To numb this pain, I turned to anything that could help me forget. Anything that could pull me from reality into a fantasy of false bliss. But these escapes aren’t free. Each trip outside the border of your reality steals a piece of you. Eventually, you are no longer a person, but a hollowed-out shell masquerading as one.

This is where I found myself: an empty shell, sleepwalking through the day only to saunter into a cavern of escapism at night. The constant shame did nothing but fuel the cycle, day in and day out. I lived on autopilot, and my only goal was to keep the hurt as far away from my consciousness as possible. I wish I could tell you I had a grand spiritual epiphany that woke me from my trance. The truth was much simpler: It was love. Only when I faced the real possibility of losing the person I loved most did I finally see the man I had become. And I couldn’t stand the sight of him.

I understood (finally) that until I learned to sit with my feelings—to see my reality for what it was and my role in its creation—nothing would change.

That is the struggle of the 'quiet rooms'. When you are addicted to thinking—hooked on the hit of rumination—a quiet room becomes the loudest place imaginable. It always felt easier, instead, to lock the noise away in a cage. But running away only leads you to the very ruin you’re trying to outrun. Stagnation becomes destiny. Every instant of numbing only assures that the noise will be louder when the comedown inevitably hits.

And so, exhausted by the whiplash of chasing nirvana only to wake up in the pits of hell, I finally asked the question:

What in me do I not want to admit exists?

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I kept pruning leaves while the roots were rotting. I kept thinking that ‘more light’—more healthy habits, more optimization—was the right answer.

Traits we deny in ourselves do not disappear because we deny them. They wait in the dark, growing stronger and pulling our strings from within their exile. For a long time, I dismissed shadow work as another “woo-woo” practice, choosing the disciplined, visible work of the Stoics. I wanted tangible growth, which I did see, to an extent. But I was wrong to think that’s all there was and that something like shadow work couldn’t help me. It took reaching the end of my rope to understand that the shadow is the most tangible force of all, and its impact on our reality is absolute.

Without shadow work, it’s impossible to know yourself. We are all capable of evil, capable of becoming the exact opposite of the person we convince ourselves we are. This refusal to see our potential darkness is often the source of repeating the same destructive patterns.

I see with clarity now how often I’ve been the main obstacle between me and my goals. I turned away from the things I claimed I wanted most because more was being asked of me than I felt comfortable giving. Vulnerability scared me, so I would keep my walls up. I was more concerned with survival, with self-preservation, than I was with experiencing true connection.

I kept pruning leaves while the roots were rotting. I kept thinking that ‘more light’—more healthy habits, more optimization—was the right answer. Society teaches us to see our shadow traits as undesirable, to keep them hidden rather than channeled. It praises the light and urges us to run from the dark. Yet the traits we exile do not lose their influence; they only lose their direction.

The problem isn’t the traits themselves, but the schism between the person we pretend to be and the person we actually are. In the end, it’s how you channel that energy that defines you—not how effectively you’ve managed to reject it.

In his Substack, Deep Fix (one of my favorite recent finds—can’t recommend enough), Alex Olshonsky explores a concept coined by Malcolm Ocean: Towardness vs. Awayness. Alex argues that many of us spend our lives in ‘Awayness’—running from financial ruin, toxic relationships, or loneliness. This way of living is reactive and exhausting—and ultimately, aimless. What we need instead is ‘Towardness.’ That is, the clarity to identify a North Star and the discipline to move in alignment with it.

For most of my life, my focus was only on survival. I avoided big responsibilities and ran from commitments in the name of self-preservation. I thought I had goals, but I was just trying to avoid getting hurt or being disappointed. My “goals” were almost always fueled by running away from something.

I was moving, but I wasn’t going anywhere. To break the cycle, I not only had to understand what I was afraid of, but I also had to ask what I was built for.

If the shadow is no longer allowed to dictate the terms, then it’s up to me. I feel a sense of clarity I’ve never had before. My shadow will always have his doubts, will always have his fears. But my job isn’t to silence him, but to understand that I have the final say in how I live my life, in what I actually move toward.

Without a plan, clarity is useless. Without practical ways to integrate the parts of yourself you’ve exiled, nothing will change. If you don’t face your shadow and honor it with a healthy outlet, then it will find its own expression—usually at the exact moment you can afford it least.

Practical ways you can start honoring your own shadow today:

  1. Sit with a journal and allow your shadow to speak to you with no filter (as I’ve shared in these transcripts). Don’t judge the voice, just write what you hear.

  2. List the traits you hate most about yourself and figure out how they were trying to protect you. When you recognize that “distrust” was once a survival tool, you honor the shadow’s intent.

  3. Establish rituals that give repressed traits an outlet. Competitive sports for rage or intense isolation for distrust.

  4. Ask yourself: What in me do I not want to admit exists?

  5. Pay close attention to the people who irritate you most. The specific traits you despise in others are sometimes the very traits you have exiled in yourself.

  6. Look for the traits you admire in others but feel you lack. I’ve heard it said that you cannot recognize greatness in another unless the seed of it lives in you.

  7. When you feel a surge of shame or irrational anger, locate it in your body. Breathe into that area of tension and ask it what it’s trying to say. Don’t try to rationalize the feeling away.

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None of this work is easy. I have broken down more times than I can count. But as I’ve told myself countless times now: You cannot give up on yourself. None of us is permanently broken. We are simply living fractured lives, and peace cannot live in a fractured home.

I know how painful it is to have to look at your darkest traits without the veil of self-delusion. But I also know the quiet that follows when you finally see yourself as you truly are. More importantly, I have felt the peace that comes from being honest with those you love.

I spoke the truth to myself, and then I let that truth out. The disasters I replayed in my head on a loop never came. The sky didn’t fall; instead, I found hope. I’ve been given a second chance.

This time, I won’t waste it.

I’m grateful you stuck around until the end. This essay is free to read, and the best way to help it grow is to share it with someone who might need to hear it today.

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