Judging Yourself for Wanting More: How to Turn Self-Judgment into Kindness

This post is a companion to Episode 5 of the Radical Redirection Podcast. If you want to go deeper, listen to the full episode below or wherever you get your podcasts.

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“Who Do I Think I Am to Want That?”

Have you ever let yourself dream for just a second — really let the vision open up, really felt into what it would be like — and then almost immediately pulled yourself back down with a thought like, who do I think I am to want that?

Yeah. Me too. Many times.

Let’s talk about this, because I think it's one of the most important conversations we can have before we ever get to goal-setting, vision boards, or any of the fun, exciting stuff.

Because if we skip this part, all of that other work crumbles underneath us. Every time.

The Voice That Stops You Before You Start

The culprit is self-judgment. And not just any self-judgment — the specific kind that shows up the moment you start wanting something more for yourself. The moment you dare to dream a little bigger than your current reality.

It can sound like: Who am I to start a business? Who am I to think I can change careers at this point? Who am I to want this much? Or it takes a softer, sneakier shape — guilt (others have it so much worse, I should just be grateful for what I have), or fear (if I actually change, everything around me will shift and I don't know if I'm ready for that), or resistance (that would take more energy and time and resources than I currently have available).

And the sneakiest thing about it? Most of the time, we don't even notice it's happening. We just feel deflated. We feel like maybe we were being naive. We close the tab, go back to our day, and quietly file the dream away under "maybe someday."

Why Your Brain Is Working Against You (With Good Intentions)

What's really happening underneath all of this is that the subconscious mind registers change as a threat. Any shift, even a beautiful and deeply desired one, reads as the unknown. And the unknown, to your nervous system, is danger. So it pulls out every tool in its arsenal to keep you exactly where you are — in the familiar, the predictable, the known quantity. Even if that known quantity is quietly making you miserable.

The two most common stories it tells are I can't and I shouldn't. And here's what I've noticed, both in my coaching work and in my own life: these two are often completely interchangeable. When changing feels too hard, the brain invents a moral argument against it — it would be selfish, it's not the right time, other people need me as I am. And when the moral argument feels flimsy, the brain defaults to impossibility — I just don't have what it takes.

Either way, you end up staying put. Either way, the dream gets shelved.

We also judge ourselves for simply wanting. That word — desire — carries so many negative connotations, as if wanting something more automatically makes you ungrateful or greedy or out of touch. We judge ourselves for wanting a different job, for wanting more money, for wanting to become a slightly different version of ourselves. Even jealousy — which is really just a compass pointing you toward what you actually want — gets met with shame rather than curiosity.

when caution, reason, and responsibility is actually fear

I've watched this pattern come up with clients again and again, right at the beginning of our work together when we sit down to create their vision. The critical voice doesn't wait politely. It jumps in mid-sentence. That'll never happen. I've tried before and it didn't work. I don't even know how I'd get there.

And even after we've quieted those thoughts down and built out a genuinely exciting vision together, sometimes after the high comes the low. The fears rush in. The doubts settle. The shame shows up and says: that's so selfish of you. The world is suffering and you're over here dreaming about your ideal life.

We stop ourselves before we even begin. And then we wonder why change is so hard.

I've lived this pattern myself. I sat on the idea for this podcast for nearly a year. I was busy, sure — but I was also methodically working through every single way it could go wrong before I'd let myself take one real step forward. Fear dressed itself up as caution and responsibility, and I almost let it win. In the meantime, my confidence was quietly shrinking. The original spark of inspiration felt further and further away.

I was doing all this "healing work" on loop without ever applying it to the actual thing I wanted to create.

Eventually, the stuckness got louder than the fear. And I finally thought: do I want this or not? I do. So let's just do it.

Here we are.

What To Actually Do About It

So how do we work through this? How do we stop the self-judgment from derailing us every time we try to take a step forward?

We start with a little logic, because the brain does respond to it. The truth is: you having a better life takes nothing away from anyone else. In fact, when you're thriving — when you have more time, more energy, more resources, more joy — the people around you benefit too. You show up differently. You give more freely. You have more capacity to support the people you love. And you quietly become proof to everyone watching that it's possible, that it's allowed, that wanting more doesn't make you a bad person.

But logic alone doesn't reach deep enough. Our unhelpful beliefs live in the subconscious, and dislodging them requires something more than a rational argument. So we get curious. We ask: what am I actually afraid would happen if I went for this? What am I avoiding? How do I not want to be seen?

And then — this is the part that matters most, and the part we most want to skip — we feel it. Not perform it, not analyze it to death. Actually feel it. Fear, sadness, shame, whatever is living underneath the judgment. Name it out loud or on paper. Let it move through you. That's how we process emotions. That's how we stop them from getting stored in the body, from becoming the quiet weight that slows down every next step we try to take.

From there, we start to gently rewrite the narrative. Not with affirmations that feel like lies, but with something smaller and more true. I'm in the process of feeling okay with wanting more. I'm working on letting go of the guilt around this. I want to be a better version of myself, and I'm getting there. Starting with "I'm in the process of" or "I'm working on" is powerful because it's actually true.

You don't have to claim you're already there. You just have to acknowledge the direction you're moving in.

The Groundwork Always Starts on the Inside

Before the strategy. Before the action plan. Before any of the practical, tangible steps — there is this inner work. The work of noticing how you speak to yourself in the quiet moments when you dare to want something. The work of catching the judgment, getting curious about it, feeling what's underneath it, and slowly, compassionately, beginning to choose a different story.

This is the foundation. And without it, everything else we try to build will eventually crack.

You want what you want for a reason. Your desires are not accidents. They are not signs of selfishness or delusion or ingratitude. They are signals — from your soul, from the deepest part of you that knows what you're here to do and who you're here to become.

The question is whether you're going to let the self-judgment drown them out. Or whether you're going to get curious, get real, and start building the inner foundation that can actually carry you forward.

That's where change begins. Every single time.

This post is a companion to Episode 5 of the Radical Redirection Podcast. Listen to the full episode wherever you get your podcasts — we go even deeper into the tools for working through self-judgment in real time.