How to Stop Self-Sabotage and Manage Anxious Attachment

by George Wilse
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If you’ve ever felt like you’re holding yourself back just when things start to go well, you’re not alone. Self-sabotage and anxious attachment often show up together – especially in high-achievers who crave connection but fear rejection or failure. If you’ve searched things like:

"Why do I ruin things when they’re going well?"

"How to stop overthinking in relationships"

"What is anxious attachment and how do I fix it?"

"Why do I push people away then feel alone?"

This post is for you.

What Is Self-Sabotage?

Self-sabotage is when your actions or mindset work against your goals, even when you consciously want success, love, or peace. You might:

Overthink until you talk yourself out of an opportunity

Distance yourself emotionally from people you care about

Fixate on one mistake instead of progress

Avoid asking for help or support

You’re not lazy. You’re protecting yourself. And once you learn what you’re protecting yourself from, you can start to change.

What Is Anxious Attachment?

Anxious attachment is a relationship pattern where you feel overly worried about being rejected, abandoned, or misunderstood. You might:

Need frequent reassurance that you’re loved

Feel anxious or panicked when someone pulls away

Read into texts or social cues

Blame yourself quickly when something feels off

It usually forms from early experiences where love felt inconsistent or conditional. But it can be understood and managed.

How These Patterns Feed Each Other

When anxious attachment meets self-sabotage, you might:

Pull back from opportunities because you fear abandonment if you succeed

Stay in low moments longer because you think you don’t deserve more

Judge yourself harshly and then seek external validation to cope

The result? A cycle that feels hard to break, even when you know it’s hurting you.

3 Ways to Interrupt the Pattern

Name the VoiceWhen self-sabotage shows up, ask: Who’s talking right now? Give that voice a name (e.g. The Critic, The Protector, The Lonely One). This helps create distance from it.

Reclaim the EvidenceCreate two columns. On the left, write what the inner critic says. On the right, write what’s actually true. Challenge your brain to focus on facts, not fear.



Practice Secure Statements When anxious thoughts show up, use grounding reminders:

"I can feel unsure and still be safe."

"One text doesn’t decide my worth."

"Connection isn’t built in a day."


Try This Self-Coaching Exercise (10 mins)


Take a moment this week to journal these:

What am I afraid is true about me right now?

What do I need from myself or someone else?

What’s a more generous explanation for what’s happening?

Then finish with: “What do I want to believe about myself instead?”

You might be surprised what comes up.

You're Allowed to Want More

You’re not broken for feeling this way. You’re human, and you’re learning. These patterns aren’t flaws – they’re protective strategies that helped once but now hold you back. Coaching can help you rewire how you respond to yourself and others. If you’re tired of second-guessing, blaming yourself, or chasing love and validation – we can work on this together.

Next Step

If you're ready to stop sabotaging your success and start building better relationships with yourself and others, book a call. Let's talk about what working together might look like.