Self-sabotage: Why Do I Keep Doing It?

If you’ve ever found yourself wondering why you keep tripping yourself up, you’re not alone. Many of us with dyslexia or ADHD feel we’re our own worst enemy at times—sabotaging plans, missing deadlines, or talking ourselves out of success. In this episode, we dive into why that happens and what might be going on under the surface.

It’s not always comfortable to talk about self-sabotage, but it can be oddly familiar. This conversation looks at childhood experiences, low self-esteem, and the thoughts in our heads that tell us we can’t do it. I share how I’ve explored my own self-sabotage and what I’ve discovered. You’ll hear personal insights on how dyslexia and ADHD can feed these patterns, plus a few practical tips to lessen their impact.

Understanding Self-Sabotage

Self-sabotage is often fuelled by a feeling that we’re “not good enough.” We might worry our wins are flukes, or that success would be too much pressure. At times, it’s easier to say, “I’ll mess this up anyway,” rather than put in the effort and see what happens.

This mindset can show up in small habits like ignoring tasks until the last minute or deciding we don’t need help. It can also pop up in bigger ways, like quitting on a dream project because we’re afraid of failing. We might not even realise we’re doing it, because we’ve lived with these patterns so long that they feel normal.

“Why do I keep self-sabotaging myself? Do I hate myself? Was I traumatised as a child? Is this just what was meant to happen to me?”

That question—why do we do it?—is the focus of today’s podcast. When we sit with it, we start to see that it’s not about hating ourselves. It can be about not trusting ourselves, or fearing what happens if things actually go well.

Looking at Our Past

Many of our self-sabotaging behaviours have roots in childhood. It doesn’t mean we carry deep emotional scars. Sometimes, it’s a simpler pattern of being told, “You’re lazy,” or “You’re not trying hard enough.” Over time, we absorb subtle messages that we must be flawed.

When our brains are wired differently, we might struggle in the traditional classroom. Others can label us as slow or rebellious. We grow up believing there’s something wrong with us. But those labels are inaccurate. Our minds are just working in a different way.

It’s worth examining how words from our past have shaped our present. For instance, if teachers repeatedly criticised your spelling, you might feel triggered every time you write an email. That old anxiety can lead to procrastination, which then looks like self-sabotage. Realising this helps us see we’re not broken—we’re carrying old weights we never asked for.

Building Self-Awareness

One of the most powerful ways to interrupt self-sabotage is self-awareness. When we notice the patterns and name them, they lose some of their power. We can start asking ourselves questions like, “Is this really true, or is it an old story playing on repeat?”

Here’s what helps me personally:

• Journalling: Writing down anxious or negative thoughts, even briefly, can highlight patterns and keep them from spinning in my mind.
• Mindful breaks: Taking a short pause during the day to notice emotions. If I’m stressed or feeling useless, I try to observe it without judgement.
• Talking to a friend: Sharing doubts with someone I trust can quickly expose unhelpful thinking and remind me that not everything I feel is fact.

When you learn to identify that self-defeating voice, you can question it. You might realise it’s just an echo of someone else’s words, or a fear that’s never been challenged. Knowing this changes everything.

Finding a Way Forward

Overcoming self-sabotage starts with replacing old habits with kinder ones. It’s a process of retraining the brain, putting ourselves in situations where we can succeed, and showing ourselves we’re capable. This can mean:

• Setting fewer goals at once, so we don’t feel overwhelmed.
• Breaking tasks into smaller steps, making them more doable.
• Scheduling regular check-ins with a coach, therapist, or friend.

Take small steps and celebrate each win—no matter how tiny it looks. If that means opening a blank document to start a project, that’s a win. If you managed to plan your week on a Sunday night, that’s another. Our brains are wired to latch onto accomplishment, so these small victories help crowd out feelings of self-doubt.

I’ve also found that forgiving myself is key. We all have moments when we slip up, miss an appointment, or forget an important birthday. Rather than beat ourselves up, we can learn to bounce back faster. That bounce-back skill breaks the cycle of self-sabotage and reminds us we’re human. We’re doing our best with the minds we’ve got.

Embracing New Perspectives

Changing a life-long pattern of self-sabotage isn’t a quick fix. We are dealing with habits carved by years of misunderstanding our own brains. The good news is that awareness is half the battle. Once you see the pattern, you can work on ways to disrupt it.

Sometimes, these changes feel uncomfortable. We might lose the familiar identity of being the one who always misses the bus or leaves everything until the night before. That’s when a supportive community, mentor, or friend can help remind us that we do deserve to shed old labels.

I like to think of it this way: our unique minds are blessings in disguise. Dyslexia and ADHD give us alternative ways to solve problems and connect ideas. Sure, they come with challenges, and it’s easy to feel a bit sorry for ourselves from time to time. But by digging deeper and recognising our strengths, we open doors we never saw before.

Self-sabotage is just one aspect of the puzzle. It can be discouraging when you’re in the middle of it, but awareness and baby steps forward can light the way. Over time, you build a foundation that feels stronger and more stable. You’ll still have off days—it’s part of being human. The difference is that you’ll learn to carry on without giving up on yourself.

• Look into past triggers to see if they’re behind your self-doubt.
• Get comfortable questioning negative thoughts.
• Use tools like journalling and mindful breaks to track your progress.
• Celebrate small wins often, to reinforce positive change.
• Allow yourself grace and forgiveness when you slip up.

These insights are just a taste of what we cover. If you want to hear the full discussion and get more practical tips, tune in to the episode above. I talk about shifting our mindset and embracing the quirks we’ve got. The podcast dives deeper into real-life stories and strategies that can help you step out of your own way.

If you’re ready to explore this more, I’d love to have you listen to the full episode at the top of the page and share your thoughts. And remember, you can always reach out to me directly at Truth About Dyslexia. Let’s keep learning and growing together.