Self -Sabotage 101: The Subtle Art of Screwing Yourself Over

Ever met someone who just can’t let things be good? Someone who, when life finally gives them lemonade, starts looking suspiciously at the lemons, wondering if they’re genetically modified?

Yeah. We all have that one person that does this. That someone might even be you. It’s okay. We’re all guilty of it at some point, the quiet and utterly chaotic masterpiece that is self-sabotage.

Let’s talk about it, for those at the back of the class.

What is Self-Sabotage?

Self-sabotage is when you, either consciously or unconsciously, get in your own way. You fumble your own bag. You ruin your own peace. You block your own blessings — all while holding the map to happiness in your hand like, “Nope, this is probably a scam.”

And here’s the wild part: it usually doesn’t look like drama. It often wears the disguise of “just being cautious”, “protecting my heart”, or “I know how this ends.” But really? It’s fear. It’s unhealed hurt. It’s the trauma on autopilot with your inner saboteur in the backseat, sipping iced coffee, whispering, “Turn left, let’s ruin everything again.”.

Enter exhibit A: The OG Who Hurts Before He Gets Hurt

He was vulnerable once. He gave his all, opened up, let his guard down, trusted completely and in return, he was left empty. Since then, his unspoken motto has become: “Nobody can hurt me if I hurt them first.”

It’s not that he doesn’t want love; he does. But now, when someone gets too close, he ghosts them. Not because they did anything wrong, but because their consistency makes him uncomfortable. A simple “good morning” text feels too predictable. A thoughtful question feels like a trap. Affection? A red flag in disguise.

He pushes away the people who genuinely care and flirts with those who don’t. He thrives on attention but runs from connection. When someone shows him stability, he labels it “too much,” “too fast,” or “too good to be true.” He’ll say things like, “I’m not good at relationships,” but what he really means is, “I’m still holding on to wounds I never stitched up.”

Underneath the bravado is someone who fears that love is for other people, not him. So he burns the bridge before anyone can cross it, then stands in the smoke and says, “See? I told you it wouldn’t last.” Meanwhile, love is still knocking; gentle, patient, maybe even holding snacks, just waiting for him to open the door.

Exhibit B: The Office Underdog Who Keeps Shrinking

She’s smart, capable, and full of ideas that could transform the way her team works. But when it’s time to speak up in meetings, she hesitates. She tells herself, “They probably already know this,” or “What if I get it wrong?” And sometimes, “Who am I to even be here?”

So she stays quiet. She watches others share less polished ideas and still get recognition. She watches opportunities pass her by. Not because she isn’t good enough but because she’s convinced that staying small is safer than being seen.

And that’s the quiet pattern of self-sabotage: trading growth for comfort, and confidence for caution, all while holding answers no one else thought of.

Does this sound familiar?

Then we have Exhibit C: The “Too Good to Be True” Situation

He is loving, loyal, and communicates openly. He keeps her updated on where he is, what he’s doing, and never leaves her hanging. He isn’t playing games or hiding anything — he genuinely sees her and chooses her. But still, there’s a part of her that struggles to believe it. In the past, she’s been lied to, cheated on, and blindsided by people who smiled to her face and broke her behind her back. So now, she’s built armor, quiet defenses that whisper, “Don’t fall too deep,” and a mindset that says, “If he hurts me, at least I saw it coming.”

As a result, she begins to expect betrayal before it happens. She assumes the worst, even when he’s done nothing to deserve doubt. She mistakes his peace for manipulation and his honesty for strategy. When she gets a strange feeling, instead of checking it gently, she calls it intuition not realizing it’s insecurity wearing the mask of gut instinct. In those moments, she doesn’t see him for who he really is. She sees him through the lens of everyone who failed her before. And that is the quiet tragedy of self-sabotage: not that someone else ruins something good, but that you do because your past made it hard to believe that something good could actually be real.

If you’ve ever felt this way, pause. Breathe.
Take a moment to check in with yourself. Ask: Am I truly protecting myself, or am I pushing away someone who might actually be safe to trust?
Because healing isn’t about fear vanishing overnight. It’s about learning to live alongside your fear without letting it take the wheel.

Fear will still whisper doubts in your ear. But healing means you decide not to let those whispers control your actions or your heart.

So… Why Do We Do This?

Self-sabotage is often survival mode dressed in everyday behavior. At some point in your life, your mind learned that playing it safe even if that meant losing something good, hurt less than risking it all and being deeply disappointed. Maybe it was a childhood lesson, a heartbreak, or repeated betrayals.

The pain of losing something good felt more manageable than the pain of vulnerability or rejection. So your brain developed a protective shield a way to “keep safe” by not fully opening up or by pushing people away before they could hurt you.

But here’s the catch: what worked once as a survival tactic can become a trap. Now, that same coping mechanism is quietly undermining your chances for happiness and connection. It’s keeping you stuck in a cycle that doesn’t serve you anymore.

How Do You Break the Cycle?

1. Name It.
   The first step toward breaking free is awareness. You have to call yourself out gently but firmly. When you feel the urge to push someone away, ask yourself, “Is this really intuition or just my insecurity speaking?” “Is this wisdom or just fear disguised in fancy words?” Saying it out loud can help you separate what’s real from what’s reactive.
   
   

2. Trace the Root.
   Healing asks for courage to look back and gently explore when and where you first learned to expect disappointment. Whose love (or lack of it) taught you that you were hard to love? These early wounds shape your present fears. Bringing them into the light is the first step to softening their hold on you.
   
   

3. Build New Evidence.
   Start noticing when good things happen and don’t fall apart. Pay attention to moments when love, kindness, or success arrive without catastrophe. Document these wins, no matter how small. Allow yourself to receive love and support without overthinking or dissecting every gesture. This builds a new story, one where safety and goodness can coexist with your fears.
   
   

4. Choose Growth Over Comfort.
   Self-sabotage feels familiar because it’s what you’ve always known. Growth, on the other hand, can feel scary and foreign. But ask yourself: if your comfort zone is only keeping you hurting, isn’t it time to step outside it? Growth means being willing to sit with discomfort and uncertainty, trusting that the pain of change is worth the promise of healing.
   
   

Self-sabotage is loud. It shouts, warns, and protects. But healing, true healing, is louder, stronger, and more persistent. Healing is a choice you make every day to believe you are worthy of good things, even when your past tells you otherwise.

You are not broken. You’re simply carrying the scars of what you’ve survived. But those scars don’t define your future. You deserve the best love that feels safe, joy that doesn’t come with strings, peace that doesn’t make your heart race.

So, the next time life offers you something good… maybe don’t question it to death. Instead, try sitting with the discomfort of peace. Let yourself believe, just for a moment, that this time it can be different.

Because what if it’s not too good to be true? What if it’s simply… good?

Sincerely,

Damie Ibegbu