Why You Might Self-Sabotage When Things Are Going Well

Sometimes things finally start falling into place—you’re doing well, feeling good, things are calm.

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Then, out of nowhere, you pull away, mess something up, or talk yourself out of it. It doesn’t make logical sense, but it’s a real thing. Self-sabotage isn’t always intense or dramatic. Sometimes it’s subtle, slow, and even justifiable. However, one thing’s for sure: it usually shows up right when you’re about to level up or get comfortable. Here’s why you might start pulling away when things are actually going well.

1. You’re waiting for the other shoe to drop.

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When good things happen, it can stir up anxiety, especially if you’re not used to stability. You start thinking, “This can’t last,” or “Something bad must be coming.” That expectation of loss can feel worse than the thing itself, so you preempt it by pulling the plug first.

It’s a defence mechanism. If you ruin it yourself, at least you’re in control. Of course, deep down, you’re robbing yourself of peace that’s real and available because your nervous system hasn’t quite caught up to the idea that things can be okay without falling apart.

2. Success doesn’t feel safe to your nervous system.

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If chaos or struggle was your baseline growing up, then ease might feel unfamiliar, or even unsafe. You’re not chasing stress on purpose, but your body’s used to it, so calm feels like a setup rather than a reward. You might start creating friction just to get back to what feels “normal,” even if it’s not healthy. This isn’t about logic; it’s about the patterns your system trusts, even when they don’t serve you anymore.

3. You don’t believe you deserve good things yet.

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When you’re still carrying guilt, shame, or low self-worth, good things can feel like a mistake, or a trick. Instead of letting them in, you start subconsciously sabotaging them to match the version of yourself you’re used to seeing. You might downplay compliments, pull back from a promising relationship, or procrastinate on an opportunity. It’s not because you don’t want it; it’s because some part of you doesn’t think you’ve earned it yet.

4. You’re afraid of what success might change.

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Even positive change can feel threatening. What if success distances you from people you care about? What if more visibility leads to more pressure? Growth often comes with unknowns, and unknowns can feel like danger. So, instead of leaning into opportunity, you hold back. You convince yourself it’s safer to stay where you are, even if part of you is craving more. The fear of change can override the excitement of progress if you’re not aware it’s happening.

5. You’re more comfortable in the fixing role than the thriving one.

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Some people spend so long surviving, hustling, or healing that they don’t know what to do when things finally calm down. They identify more with the struggle than the stability, so when life gets good, they feel restless or misplaced. You might start looking for problems to solve, or even create new ones, just to feel useful or purposeful again. Thriving requires a whole new self-image, and that can be more uncomfortable than people expect.

6. You’re more afraid of being seen than being stuck.

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Success often comes with visibility, whether it’s emotional openness, public recognition, or people simply paying more attention. And for some, that spotlight feels more terrifying than failure. If being noticed has ever led to criticism, rejection, or betrayal, you might start shrinking yourself just to feel safe. Staying small feels familiar. Stepping into your light feels risky, even if no one’s trying to hurt you this time.

7. You associate calm with boredom or stagnation.

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If your life’s been full of intensity, calm might register as dull. You might mistake peace for emptiness, and unconsciously stir up drama, chaos, or urgency just to feel alive again. However, rest doesn’t mean you’re stuck. It means you’re safe enough to take a breath. Learning how to be okay with “nothing’s wrong” can take time, especially when your body’s used to always being on edge.

8. You’re secretly testing whether people really care.

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When things go well, some part of you might start pushing boundaries—flaking on plans, picking fights, withdrawing—to see if people still show up. It’s not manipulation. It’s fear trying to test love and loyalty. If abandonment or inconsistency is part of your past, you might self-sabotage just to find out if people will stick around. The hard part? Sometimes they don’t, and it reinforces the very fear you were trying to soothe.

9. You’re uncomfortable with ease because it feels like you didn’t earn it.

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If you’ve internalised the idea that anything worth having must come through struggle, ease can feel suspicious. You might downplay your wins or sabotage your momentum because it all feels “too easy.” However, ease isn’t laziness, and struggle doesn’t make something more valid. Letting things flow doesn’t mean you’re cheating the system—it means you’re finally aligned. That’s worth leaning into, not backing away from.

10. You’re afraid of losing what you finally gained.

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Sometimes, the fear of loss is more powerful than the experience of having something. You finally get the love, the job, the peace, and then the panic hits: “What if it all disappears?” That fear can be so intense that you sabotage the situation just to soften the blow. If you lose it by choice, at least it wasn’t taken from you. Of course, in doing that, you miss the chance to fully enjoy what you’ve built.

11. You mistake self-protection for wisdom.

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You might tell yourself you’re just being careful or realistic, when really you’re bracing for disappointment that hasn’t happened. You keep your joy on a leash, convinced it’s only a matter of time before things go sideways. That cautious mindset can look smart on the outside, but inside, it’s driven by fear. It stops you from fully participating in your own success because you’re too busy preparing for its collapse.

12. You’re still carrying a past version of yourself.

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Growth is strange because it asks you to let go of who you used to be. That can stir up resistance, especially if your old identity was built around struggle, survival, or smallness. You might self-sabotage just to feel like yourself again—not your evolved self, but the one you’ve always been. But here’s the thing: you’re allowed to change. You’re allowed to become someone who lets good things stay.