“Until you make the unconscious conscious, it will rule your life and you call it fate.” ~ Carl Jung
I was sitting in my therapist’s office when she asked me a question that made me freeze.
“Tell me about the last time something good happened in your life.”
I opened my mouth to answer, then stopped. My mind went blank. Not because nothing good happened, but because I honestly couldn’t remember enjoying any of it.
He was waiting. The silence felt heavy.
Finally, I said, “I got a promotion three months ago.”
“And how did it feel?”
“Horrible, actually. I spent the first week thinking they’d made a mistake. The second week wondering when they’d figure it out. The third week, I started showing up late to meetings.”
He tilted his head. “Why?”
I had no answer then. But looking back now, I know exactly why.
I was sabotaging myself. And I didn’t realize I was doing it.
I couldn’t see the pattern
For the longest time, I thought self-sabotage looked obvious — like dramatically quitting a job, blowing off a relationship, or making some clearly self-destructive choice that you could point to and say, “That. That moment I ruined everything.”
Didn’t look like me.
I was quiet. delicate almost invisible.
It looked like hesitation when I should have been celebrating. I’ve already made overthinking decisions. Things start to feel good as the moment pulls back.
This was the guy I had been seeing for months. Things were easy with him – comfortable in a way that felt rare. We laughed a lot. There was no drama. No red flags. Just… wonderful.
And that’s when I started to find problems.
I will analyze his writings. Read too much into the time it took for him to respond. Create a narrative about how he is possibly losing interest, even though nothing in his behavior suggests so. One night, after a perfectly nice dinner, I picked a fight over a little thing that I can’t remember what it was.
He looked at me, confused. “Where is it coming from?”
i didn’t know All I knew was that Shantae felt somehow wrong. Like I’ve been waiting for the other shoe to drop, and if it’s whatever it is, maybe I should… kick myself.
He ended things a few weeks later. Not because of that one fight, but because I had built so much distance that there was nothing left to hold on to.
And I told myself that I was right – that it would never work.
When the good feels like a trap
I started noticing patterns everywhere.
A friend invited me to join her book club. I said yes, got excited, then spent two weeks convincing myself I’d said something awkward in the group chat and everyone secretly didn’t want me there. I stopped showing up after the second meeting.
I’ll start projects with a lot of energy—a new workout routine, a creative hobby, even journaling—and within a week or two, I’ll just…stop. Not that I didn’t enjoy them. But the moment they started to feel better, something in me would whisper, “This will not last. Don’t connect.”
The worst part? None of this felt like self-sabotage in the moment.
It has been felt:
“I’m just being realistic.”
“I’m protecting myself from despair.”
“Something feels off. I should trust my gut.”
And sometimes this thought is Legit is sometimes your gut is Telling you something real.
But I started using my intuition as an excuse to run from something unfamiliar.
Realize that everything changes
I was on the phone with my best friend, venting about how stuck I was. Nothing works out for me how. How I was “trying so hard” but kept ending up in the same place.
He remained silent for a while. Then he said softly, “Can I ask you something?”
“Of course.”
“Do you remember when you got that freelance opportunity last year? That one you were so excited about?”
i did It was a dream project – creative, well-paid, exactly the kind of work I wanted to do.
“You told me you turned it down because the timeline was too tight. But you also told me you specifically cleared that month’s schedule to make room for new opportunities.”
My stomach dropped.
“And the guy you were seeing—the one you said ‘didn’t feel right’? You told me a week before you ended it that you’d never felt so comfortable with anyone.”
I couldn’t speak.
“I’m not trying to be harsh,” he continued. “But it seems like every time something good starts happening, you find a reason to walk away from it.”
That conversation sat with me for days. Weeks, actually.
Because he was right.
I didn’t get stuck because life dealt me bad cards. I was stuck because every time I got a good hand, I folded.
What was I really defending?
I spent a lot of time trying to find out why.
Why would I sabotage the things I wanted? Why should I run away from peace when I have spent so long chasing it?
The answer, when it finally came, was almost embarrassingly simple.
Good things felt stranger. And strangers don’t feel safe.
I spent so much of my life stressed, worried, and overthinking that they would become my baseline. i’m normal Almost comfortable, in a weird way.
The chaos was predictable. I knew how to navigate it. I knew I was in it.
But cool? Stability? Did things actually work out?
It was uncharted territory. And my brain, wired for survival, saw unknown territory as dangerous.
So it did what it does when it senses danger: it tried to bring me back to familiar ground.
Even when familiar ground was the right thing I was trying to escape.
The quiet way I keep myself small
Looking back, my self-sabotage didn’t seem extreme. It looked like this:
A very long wait.
Telling myself I need to research more, prepare more, prepare more – until opportunities pass me by.
Doubting myself mid-progress.
Starting something enthusiastically, then halfway through convincing myself that I’m doing it wrong or that it doesn’t matter anyway.
Easy decisions to overthink.
Spending hours agonizing over choices that didn’t actually require that much thought, then feeling so exhausted by the mental gymnastics that I’d give up.
When things feel good pull away.
Creating distance in relationships, slowing down projects, finding problems where there weren’t any—all because comfort felt like a warning sign rather than a green light.
Start strong, then lose momentum.
The initial excitement would carry me for a while, but as soon as it wore off and things required relentless effort, I would quietly let them fade.
Nothing dramatic. Nothing anyone else would necessarily notice.
But enough to keep me stuck in place, year after year, wondering why I couldn’t move on.
Learning to stop fighting yourself
The shift didn’t happen overnight. And it certainly didn’t come from beating yourself up or forcing yourself to “just do better.”
It started with something gentle: noticing.
I started paying attention to the moments when I wanted to pull back. Don’t judge them. Don’t try to fix them immediately. Just… watching them.
oh I’m doing it again. I’m going to cancel these plans because I’ve convinced myself they don’t want me there.
There it is. I’m thinking of this email in a way where I won’t send it.
I see you, brain. You are trying to protect me by making me believe these good things are secretly bad.
That awareness—without the associated shame—made enough room for me to make a different choice.
Not always. Not quite.
But sometimes.
What actually helped
Discomfort is assumed to mean danger.
This was huge. I spent so long believing that if something felt uncomfortable, it must be wrong. But I’m beginning to see that discomfort can also mean meaning new. And new doesn’t mean bad—it just means unfamiliar.
I’ve shortened things.
Instead of “completely changing my life” I focused on “texting”. “Show the subject.” “Finish this one job.” Self-sabotage thrives on high, overwhelming expectations. Smaller tasks don’t trigger the same alarm bells.
I left needing to feel prepared.
I kept waiting to feel confident before moving forward. But I realized that confidence doesn’t come first—action does. So even when I feel uncertain I start moving. And gradually, with each small step, confidence follows.
I became kinder to myself.
Self-criticism feeds self-sabotage. The harder I was with myself, the more I wanted to hide. So I softened the voice in my head. less “what’s wrong with you?” And more “I see you’re scared. Okay.”
where i am now
I still catch myself doing it sometimes – that familiar pull to back off when things start to feel good.
Just last week, I almost canceled a coffee date with someone I’ve been wanting to get to know better. My brain made up a dozen reasons why I should: I’m too busy, they probably don’t actually want to hang out, it would be awkward, I should wait until I feel more “on.”
But I recognized the pattern. And I went anyway. And it was lovely.
Not life changing. not perfect Just… wonderful. simple well And I let it get better instead of waiting for it to get worse.
That, for me, is progress.
If you see yourself in this
If any of this resonates, please know you are not broke.
You are not lazy or undisciplined or fundamentally flawed.
You are probably just afraid. And that’s people.
Self-sabotage is not about wanting to fail. It’s about trying to protect yourself from pain—even when that protection is causing more pain than it’s preventing.
You don’t have to fight to grow up. You don’t have to force your way forward.
You just have to start noticing, with honesty and a little more kindness than you used to give yourself.
Because the biggest changes aren’t always the most.
Sometimes, it’s just learning to stop standing in your own way.
And let good things be good.
about Dakota J. Dawson
Dakota Jay Dawson writes about emotional sovereignty, healing, personal growth, emotional wellness and self-sabotage recovery. Her work focuses on emotional boundaries, breaking free from self-sabotage, and learning to keep your peace without apologizing. He writes about stoic isolation and the patterns that hold us back—people-pleasing, overthinking, toxic guilt, and the quiet way we stand on our own—and finally offers gentle, practical strategies for choosing ourselves. Get his ebook, Stop letting everything affect you— free here at a promotional price.
