How To Rehabilitate Your Self-sabotaging Patterns
As a leadership coach, one of the questions I hear most often is:
“How do I stop self-sabotaging patterns?”
It’s asked with a mix of urgency and hope, as though there might be a simple answer, a quick fix that can break years of entrenched habits. I wish I could tell you there was such an answer. But there isn’t.
The Illusion of the Quick Fix
We live in a world that depends on instant results. We are told that if we adopt a new habit, read the right book, or follow a three-step plan, transformation will happen overnight.
But self-sabotage does not reside on the surface. It is not merely about poor choices or a lack of discipline. It is far more subtle and deeply ingrained. Self-sabotage is an unconscious pattern that operates beneath the conscious mind, influencing decisions, relationships, and even our perception of ourselves.
Until we are willing to look inward and identify the recurring patterns we already know don’t work, we cannot truly stop them. They will keep cycling, no matter how much willpower we exert.
What I’ve Learned on My Own Journey
I don’t only discuss self-sabotage from a theoretical perspective; I experience it personally. There were moments in my career and personal life when I knew exactly what I wanted, yet somehow, I kept undermining myself.
For me, the Enneagram was one of the first mirrors that showed me why. It revealed the hidden drivers—the fears, beliefs, and unconscious motivations—that kept me repeating the same patterns. Where I thought I was making rational choices, I was often reacting from my type’s habitual strategies.
Carl Jung’s work deepened this understanding. His concept of the “shadow” helped me realise that what I resisted most in myself—my insecurities, my anger, my need for validation—were precisely the parts I needed to acknowledge and integrate. As long as they remained in the shadows, they controlled me.
The teachings of A.H. Almaas and Warren Munitz provided me with words for something I had sensed but could not express: that self-sabotage is not about weakness or failure, but about a mistaken identity. We become so deeply attached to our ego structures, coping mechanisms, and old narratives that we believe they define who we are. However, they are not. Beneath all of that, there exists an essence—a more authentic self—waiting to be uncovered.
What Self-Sabotage Really Looks Like
Self-sabotaging patterns rarely announce themselves loudly. They often show up in quiet, familiar ways:
- Saying yes when you really mean no and then feeling resentment.
- Putting off what matters most until it becomes a crisis.
- Repeating relationship dynamics you swore you’d never fall into again.
- Distracting yourself with busyness rather than facing the discomfort of stillness.
- Striving for perfection, then collapsing into procrastination when you can’t meet your own standards.
We all have our own versions of these patterns, and we usually know them well. The frustration isn’t that we can’t see them—it’s that we don’t know how to stop them.
The Path Forward: Awareness, Not Force
Here’s what I’ve realised: you can’t bully yourself free from self-sabotage. Force merely intensifies resistance.
The path is awareness. When you can sit honestly with yourself and say, “Ah, here it is again, my old pattern showing up” without judgment, something begins to shift. Space opens up between the trigger and the reaction.
The Enneagram, shadow work, and inner presence practices have all shown me that genuine change comes not from attempting to be someone new, but from bringing compassion and awareness to the parts of ourselves that remain stuck. When you recognise the pattern clearly, you are no longer inside it—you are observing it. And in that space of observation, the possibility of choice arises.
Why This Matters for Leadership and Life
Self-sabotaging patterns not only hinder our personal growth but also impact our relationships, careers, and leadership. When we become trapped in cycles of fear, avoidance, or perfectionism, we cannot lead with clarity and confidence. We react rather than respond. We protect instead of connecting.
But when we begin to recognise and soften these patterns, something profound occurs; we lead from a deeper place. We show up more authentically. We stop confusing control with power and start embodying a leadership rooted in presence.
A Closing Thought
So, how can you break free from self-sabotaging patterns?
Not through force, quick fixes, or pretending they don’t exist. Instead, by turning inward with honesty and courage, seeing what has always been there. By uncovering the hidden recurring patterns and meeting them with awareness rather than resistance.
This is not quick work. It is slow, patient, sometimes uncomfortable work. But it is also the most freeing work you can do.
When your unconscious patterns no longer control you, you are free to fully embrace your potential—not as someone you aim to become, but as who you truly are.
Reflective Prompts for Your Own Journey
If you’d like to begin exploring your own self-sabotaging patterns, here are a few questions you can journal on:
- What patterns do I notice keep repeating in my relationships, work, or personal choices?
- What emotions tend to arise when these patterns show up?
- If I look deeper, what need or fear might be driving this behaviour?
- How do I usually respond when I catch myself in the pattern—do I judge, avoid, or pause to observe?
- What would it feel like to respond with awareness and compassion instead of resistance?
These questions are not about “fixing” yourself. They aim to illuminate the parts of you that have been concealed, so you can see clearly and make different choices.
