I still remember that conversation with my parents — the moment all my bottled-up anxiety burst open, my worst fears unfolding right in front of me. The words barely made it out before the tears came.
And then, just silence. Me, lying on my bed, staring at the ceiling, wondering... What now?
Have you ever been so passionate about something that you lost track of time? The kind of drive that keeps you up all night, skipping meals, completely absorbed in what you love?
Some people call it obsession. Others call it addiction.
I called it motivation.
For years, I’ve kept this story to myself. Not because I’ve forgotten, but because, honestly, it still stings. It’s a story of failure, of pouring everything into something only to watch it slip away. And when something hurts, the instinct is to push through, bury it, and move on.
But lately, I’ve been thinking about it again, realizing that maybe the wound never fully closed. So today, I want to share my experience with you — not for sympathy, not for closure, but because I believe there’s something here that might help you on your own journey.
Today, we’re talking about self-sabotage.
Built to Fail
In 2012, I knew one thing for sure — I wanted to build something. I wanted to create a company from scratch. At the time, Chile had no strong platforms to support amateur writers in publishing their work and building a readership. Kindle hadn’t fully arrived yet to Chile, and the main alternatives were Wattpad and LeanPub.
That’s how Blumee was born.
Blumee was a platform for writers to publish their stories — similar to what Substack or Medium offer today — but with the long-term goal of allowing writers to package their work into a book (an idea I never fully realized, but hey, maybe Substack should consider it).
I brought some friends on board, hoping to build something together. Some helped for a while, but over time, it became clear that our interests, motivations, and levels of commitment didn’t fully align. Eventually, I was left working on it alone.
Still, the startup scene in Chile was thriving, and that gave me opportunities I wouldn’t have had otherwise. I pushed myself into public speaking, networking, pitching — skills I hadn’t developed before but that became essential as I tried to make Blumee a success. For a while, I felt unstoppable, like I could take on the world.
But reality has a way of catching up.
Blumee wasn’t growing fast enough, and, more importantly, it wasn’t making money. I spent my days coding and networking, but I couldn’t secure funding. Why? Because I didn’t have a proven business model.
That’s when the doubts started creeping in. Every time a funding opportunity appeared, questions flooded my mind: What if this doesn’t work? What if I don’t get the funds? What if I waste years of my life on something that’s doomed to fail?
I now realize those doubts weren’t just thoughts; they were self-sabotage in action. Instead of tackling the real issues — figuring out a revenue model, making the hard pivots — I let fear paralyze me. I stalled. I hesitated. I avoided the decisions that could have saved Blumee.
And then came the hardest conversation I’ve ever had with my parents.
I had just earned my degree, but my work wasn’t bringing in money. My parents asked me a simple but loaded question: What’s next?
I had no answer. I was burned out, overwhelmed, and uncertain. I told them I was working on a plan, but they saw through it. They told me it was time to become independent — to get a job.
That meant shutting down Blumee.
Years of work, gone. Just like that. I knew it was coming, but knowing didn’t make it hurt any less. I broke down in tears. I had built something I believed in, but I had also built it to fail. The self-sabotage had worked.
Fast forward to today — this experience shaped who I am and how I approach the world. It left a wound I’m still working on healing. But not everything is grim. That decision led me to move to the U.S., meet my incredible wife, build a family, and work at companies like Amazon and Block, gaining experience I never would have had otherwise.
Would I do things differently now? Absolutely.
Self-sabotage is often our way of protecting ourselves from failure, yet ironically, it ensures we fail before we even have a chance to succeed. It’s a harsh lesson, but one worth learning.
When You Are Your Own Enemy
“Man is not the enemy of his suffering, but of his pleasure.”
Friedrich Nietzsche
Looking back at how I self-sabotaged, one pattern stands out: I spent a lot of time thinking about what success would look like.
Maybe too much.
My anxiety had me playing mental chess, thinking five, ten, twenty moves ahead — more than I should have. What should have been motivating — the vision of success — became overshadowed by uncertainty. Instead of focusing on what could go right, my brain fixated on everything that could go wrong.
Would I be ready for this?
Could I even handle it?
My anxious mind answered for me: No, I wasn’t ready. And if I wasn’t ready, then why even try?
That’s how the excuses started. I found reasons not to fundraise, convinced myself to keep building unnecessary features, told myself I needed just a little more time before taking the next step. Deep down, I wasn’t protecting myself from failure — I was protecting myself from success.
I had made success seem so daunting that maintaining the status quo felt safer. I sabotaged my own momentum, ensuring I never had to deal with the challenges that success might bring.
I burned the bridge before even reaching it.
Nietzsche once said that “pleasurable thoughts about the future can be our enemies”. I didn’t understand this fully at the time, but now I see it clearly: I let my own mind turn a hopeful future into a source of fear.
And I’m far from alone in this. Research shows that 50% of entrepreneurs struggle with anxiety1, and that anxiety often leads to self-sabotaging behaviors2. For freelancers and business owners, the daily pressures of financial uncertainty and leadership responsibilities only amplify these tendencies3.
The mind can be a powerful ally — or a ruthless enemy. The key is learning how to manage the fear before it manages you.
What Causes Our Brain To Turn Against Us?
Self-sabotage might seem completely irrational, but it’s actually wired into us — rooted in both our evolutionary history and brain chemistry.
Our ancestors survived by avoiding threats and seeking safety4. That instinct still runs deep, even though modern "threats" aren’t usually life-or-death. The amygdala — our brain’s built-in fear detector — overreacts to perceived dangers, like public speaking or taking a professional risk, treating them as if they were actual physical threats5. At the same time, our prefrontal cortex, the part of the brain responsible for rational thinking, struggles to override that fear6. The result? We procrastinate, avoid challenges, or retreat into our comfort zones, even when taking the risk could benefit us in the long run.
In other words, our brains trick us into choosing short-term safety over long-term growth — even when we don’t consciously realize it.
But it’s not just evolution at play. Self-sabotage is also fueled by mental health struggles like anxiety, depression, and ADHD789, which interfere with emotional regulation and long-term planning. For instance, anxiety causes the anterior cingulate cortex (ACC) — the part of the brain responsible for monitoring conflict — to go into overdrive, making us overanalyze, second-guess, and spiral into self-doubt10. Depression activates an overactive default mode network (DMN), leading to relentless rumination and reinforcing feelings of inadequacy11. ADHD, on the other hand, disrupts dopamine regulation, making it harder to stay motivated and focused, which often results in impulsivity or chronic procrastination — both classic forms of self-sabotage12.
Then there’s brain chemistry. When stress kicks in, hormones like cortisol flood the system, hijacking the prefrontal cortex and making rational decision-making nearly impossible. Meanwhile, low levels of serotonin and dopamine amplify negative self-perception and kill motivation, creating a vicious cycle where we unconsciously confirm our own worst fears and doubts.
So, in an ironic twist, our brain — trying to protect us — ends up working against us, turning fear into hesitation and uncertainty into self-sabotage. Understanding this is the first step toward breaking the cycle.
How Can We Manage Self-Sabotage?
No man is free who is not master of himself
Epictetus
Self-sabotage is part of being human. It’s wired into us — shaped by both evolution and our mental conditioning. While we may never fully eliminate it, we can learn to recognize when it happens and take steps to minimize its impact. The key is to approach it with awareness and self-compassion rather than frustration or self-judgment. When we understand that self-sabotage is often just a reaction to fear, doubt, or discomfort, we can create space to challenge it instead of letting it control us.
Two of the most effective ways to combat self-sabotage are mindfulness and introspection. Mindfulness helps us notice when self-defeating thoughts and behaviors start creeping in — without judging or getting caught up in them. Introspection, on the other hand, digs deeper, helping us identify the root causes of these behaviors, like fear of failure or feelings of inadequacy. The more we question these limiting beliefs, the more control we gain over them. Simple practices like journaling, meditation, or taking a moment to reflect on our triggers can help build this awareness over time.
Stoic philosophy also offers valuable insight when it comes to overcoming self-sabotage. At its core, Stoicism teaches that we should focus only on what we can control — our thoughts, actions, and responses. This principle aligns perfectly with breaking the cycle of self-sabotage: instead of getting stuck in fear or procrastination, we can take intentional, constructive steps toward our goals. Stoic thinkers like Epictetus reminded us that we’re not disturbed by events themselves, but by how we perceive them. When we reframe setbacks as opportunities for growth and practice self-discipline, we build resilience against self-sabotage.
The goal isn’t perfection — it’s about consistently making choices that move us forward rather than holding us back.
The Secret Weapon: Discipline
While mindfulness and introspection help us recognize and understand self-sabotage, the reality is that it won’t just happen once and disappear. Self-sabotage tends to resurface, sometimes subtly, sometimes with full force, depending on our circumstances and emotional state.
There will be moments when we catch ourselves in the act — whether by recognizing the warning signs or anticipating self-sabotaging behaviors when stress or anxiety kicks in. The key isn’t just awareness; it’s what we do next.
This is where discipline becomes essential.
By practicing discipline and self-control consistently, we sharpen our ability to course-correct when self-sabotage sneaks in. The goal isn’t to be perfect but to build reliable systems that help us stay on track. Instead of waiting for motivation or struggling through self-doubt, commit to small, intentional actions that align with your goals.
One strategy I use to combat procrastination, a common consequence of self-sabotage, is the Five-Minute Rule — committing to just five minutes of work on a task to overcome initial resistance. More often than not, those five minutes turn into meaningful progress.
Remember, success builds momentum. The more you take action, the easier it becomes to push past self-sabotaging tendencies and keep moving forward.
Takeaways
We all have aspirations — things we know, deep down, we’re capable of achieving. But then there’s that nagging inner voice, the one that whispers doubts and second-guesses every move. Sometimes, it’s subtle. Other times, it sneaks into our actions, holding us back in ways we don’t even realize.
If there’s one thing I want you to take from this, it’s that you are capable. That inner critic? It’s not the voice of truth. Don’t let it convince you that you don’t deserve success, and definitely don’t let it dictate your next step.
And if fear of success ever makes you anxious, remind yourself: That’s a bridge to cross when you get there. Right now, your energy belongs in moving forward.
How has self-sabotage shown up in your life? I’d love to hear your thoughts in the comments.
Have a wonderful week!
Navigating Entrepreneurial Mental Health: Insights from the Trenches (2024) — https://founderreports.com/entrepreneur-mental-health-statistics
Avoidance of Anxiety as Self-Sabotage: How Running Away Can Bite You in the Behind — https://www.psychologytoday.com/us/blog/overcoming-self-sabotage/201005/avoidance-anxiety-self-sabotage-how-running-away-can-bite-you
6 Self-Sabotaging Behaviors of Entrepreneurs —https://www.thedenizenco.com/journal/6-self-sabotaging-behaviors-of-entrepreneurs
Why We Self-Sabotage — https://www.psychologytoday.com/us/blog/unlock-your-true-motivation/201911/why-we-self-sabotage
Amygdala Hijack: When Emotion Takes Over — https://www.healthline.com/health/stress/amygdala-hijack
Procrastination: It's pretty much all in the mind — https://www.bbc.com/news/health-45295392
Handling Self Sabotage & Anxiety — https://adaa.org/living-with-anxiety/personal-stories/handling-self-sabotage-anxiety
Self-Sabotaging and Depression: The Symptoms — https://peachtreewellnessmh.com/is-self-sabotaging-a-symptom-of-depression
Self-Sabotage and ADHD: Are You Your Own Worst Enemy? — https://www.additudemag.com/self-sabotage-adhd
Simmons, A., Matthews, S. C., Feinstein, J. S., Hitchcock, C., Paulus, M. P., & Stein, M. B. (2008). Anxiety vulnerability is associated with altered anterior cingulate cortex function during affective processing. NeuroReport, 19(10), 1033–1037. https://doi.org/10.1097/WNR.0b013e3283036e34
Hamilton, J. P., Farmer, M., Fogelman, P., & Gotlib, I. H. (2015). Depressive rumination, the default-mode network, and the dark matter of clinical neuroscience. Social Cognitive and Affective Neuroscience, 10(6), 766–774. https://doi.org/10.1093/scan/nsu079
Volkow, N. D., Wang, G. J., Newcorn, J. H., Kollins, S. H., Wigal, T. L., Telang, F., ... & Swanson, J. M. (2011). Motivation deficit in ADHD is associated with dysfunction of the dopamine reward pathway. Molecular Psychiatry, 16(11), 1147–1154. https://doi.org/10.1038/mp.2010.97