My Conversation with ChatGPT About Self-Sabotage

I use ChatGPT for a lot of things. Crochet patterns, understanding the Constitution, conversations in French, understanding the Circuit Court system, writing forms for the wine shop, working through the loss of my cat Sera, and a whole list of other things.

AI, for me, is one of many tools I have in my life along with a human writing coach, human friends, Clint, my other two cats, shovels, Google Docs, screwdrivers, spreadsheets, pens, journals, scientists, cameras, experts in the wine and hospitality industry, books, and on and on.

This morning, I was working on my thesis and used my ChatGPT as a thesaurus. I'm writing about my trip to Tokyo as a way to show my university all that I've learned about writing creative non-fiction. When I grow up, I want to be a travel writer. Think Bill Bryson. I'm attempting to add in my usual dry-humor and beef up the sensory details in this first round of edits. In my morning session of writing, I was spending far too much time trying to think of a specific phrase, so I asked ChatGPT. The resulting conversation took a direction I didn't expect, but I thought someone out there might find it interesting. (Useful, even.)

I wrote:

Is there another term like self-destruction? For example, even though I was nervous about learning enough Japanese to go on my trip, I stopped doing my DuoLingo a month before I left.

ChatGPT said:

Yes, there are a few terms that describe that kind of behavior — when someone acts in a way that undermines their own goals or success, even if they want the outcome deep down. “Self-destruction” is one, but here are others that might fit your example better:

1. Self-sabotage

This is the most common and accurate term for what you described. It's when someone consciously or unconsciously creates obstacles to their own success or well-being.Example: You wanted to be prepared for Japan but stopped practicing Japanese—classic self-sabotage.

2. Self-defeating behavior

This is a broader psychological term that includes habits or patterns that work against your best interests. It often overlaps with self-sabotage.

3. Avoidance coping

This is more clinical, but relevant. It’s when people avoid something they fear or feel overwhelmed by (like not feeling “good enough” at Japanese), so they disengage entirely to avoid discomfort.

4. Fear of success

This is less common but intriguing. Sometimes people unconsciously fear what will happen if they succeed — like higher expectations or change — so they sabotage their efforts.

5. Upper limiting (from The Big Leap by Gay Hendricks)

This is a more spiritual/self-help-oriented phrase. It describes the tendency to subconsciously "cap" our own happiness or success when we start to move beyond what we think we deserve.

Would you like help unpacking the specific kind of self-sabotage that might have been at play in your situation?

I responded:

Self-sabotage. That's it. Thank you!

ChatGPT said:

You're welcome! Self-sabotage hits the nail on the head for what you described. It’s frustrating, but also incredibly common — especially when something matters to us. If you ever want to explore why it shows up or how to interrupt it when it does, I’d be glad to help. You're not alone in it.

I said:

I've never heard of this term avoidance coping. I totally relate to that. The fear of success is something I recently (last year-ish) learned about and that describes a lot of my self-sabotage behaviors.

ChatGPT said:

That makes so much sense — and it's powerful that you're noticing those patterns in yourself. Avoidance coping and fear of success often go hand-in-hand with self-sabotage, and recognizing them is a huge first step toward shifting them.

A quick breakdown for you:

🔹 Avoidance coping

This is when we deal with stress or fear by avoiding the source of discomfort instead of facing it directly. It can show up as:

• Procrastination (“I’ll study later…”)

• Numbing (scrolling, drinking, overworking)

• Distraction (doing everything else except the thing you're scared of)

It feels like relief in the moment, but often builds more anxiety over time. The tricky part? It’s not laziness — it’s a self-protective strategy that once worked in some way, even if it doesn’t serve you now.

🔹 Fear of success

It can feel counterintuitive — who wouldn’t want success? But success often means:

• Visibility (people noticing you, judging you)

• Increased expectations

• Change (even good change can trigger anxiety)

• Loss (of comfort, relationships, control)

So, the mind throws up a wall. You might stop short of finishing things, downplay your efforts, or (like stopping DuoLingo) quietly withdraw right before a leap.

Would it help if I gave you a few journaling prompts or reframes that target these two patterns? You're already doing the inner work — we can just sharpen the lens a bit.

I said: (And this is a realization I wasn't expecting...)

That would be great. Honestly, I'm running into this with my wine shop right now. Change and increased expectations is a issue for me. Change in my routine. Not being able to meet the expecations necessary for making the shop a success, and so on.

ChatGPT said:

That’s a deeply honest reflection — and exactly the kind of awareness that breaks the spell of self-sabotage.

You’ve built something real and meaningful with your wine shop, and now that you’re stepping into a new version of yourself — business owner, public-facing, leader — it’s completely normal for your nervous system to want to slam on the brakes. Not because you’re lazy or incapable, but because…

"The part of you that’s resisting change believes it’s protecting you."

Let’s work with that part — not against it.

✍️ Journaling Prompts to Explore Avoidance Coping + Fear of Success

You can treat these like warm-ups or go deeper if something clicks.

1. “What’s the worst that could happen… if I succeed?”

• What changes?

• What might I lose (comfort, time, relationships, freedom)?

• Who might not like me anymore?

• What would I expect from myself if I pulled this off?

Look for hidden fears like burnout, isolation, being "found out," or losing control.

2. “What is success asking me to give up?”

• Old routines?

• Time alone?

• An identity (like being ‘the one who starts things but doesn’t finish’)?

This helps uncover why success might feel threatening on a subconscious level.

3. “What am I avoiding, and what does it protect me from feeling?”

Examples:

• I avoid checking the finances — it protects me from feeling panic or shame.

• I avoid posting on Instagram — it protects me from feeling judged or exposed.

Avoidance is emotional protection. When you name what it shields you from, you can offer yourself that safety in a healthier way.

4. “What do I want to be true about me, even if I don’t fully believe it yet?”

This prompt gently shifts identity.

• “I want to be someone who can grow something beautiful and sustainable.”

• “I want to trust that my pace is enough.”

• “I want to believe that I can change without losing myself.”

5. Finish this sentence: “I’m afraid that if I really try, then…”

Let it all out. No censoring. Sometimes the most irrational statements hold the biggest truths.

~

This is where I stopped to copy and paste this into my blog. I thought, "Holy shit. How many people out there might experience these same kinds of thoughts?!"

Much like the reason why I opened the wine shop to begin with, I'm sharing this because it's self-serving. These things help me, so I assume they might help someone else. Also, there's probably a part of me that wants to know that I'm not alone in these kinds of thoughts even though ChatGPT said I wasn't alone. (Like I said at the start, AI is a tool. It's not the be-all-end-all. No one thing is for me.)

Transparency and authenticity are important to me. This was true when I taught yoga and had my own yoga studio, it was true when I was doing Thai Massage, it was true during my time in Healthcare IT, and it's true for this wine shop.

The truth is, opening this wine shop is a HUGE step in vulnerabilty for me. I knew from the start that there would be aspects of this whole adventure that would test me. I'm a woman and so get treated a certain way. I'm new to the restaurant and wine industry. There is a LOT I don't know. There's a balance I have to stand firm on when it comes to acknowledging I need and want help while also sticking to my vision for the place. The vision of this place is very important to me and is a window into nearly everything that I am. By showing you (strangers, friends, people who might agree with me, people who might disagree with me) who I am, it's a financial risk, a social risk, an emotional risk. This requires that I trust that there are more decent people out there than crappy people who want to hurt me - either by hurting my business or by hurting me directly.

I'm not trying to be a hero here, but I want to admit to everyone my fears. Not because I want you to pity me and spend money at my shop, but because I've seen the affects of lack of conversation. Lack of transparency. And no, I'm not just talking about the state of our country. Actually, this all goes back to the lack of conversation around my mother's mental illness. Denial and avoidance exacerbated it. It created shame and fear in her. Because of my mother, one of my soapbox topics is openly discussing mental health. We all have something we're hiding, avoiding, fearing, etc. If we admitted it, we'd realize we weren't alone.

For me, fear of success is a real thing. In my life, I've committed a ridiculous number of acts of self-sabotage because of it. It was a big step for me to finally quit my consulting IT job this year to fully lean into the wine shop. To trust that Clint would be there to support me. To trust that I could actually do this. And now, as I think about how to grow the business to make it successful, I have to trust enough in myself and my vision of this place to ask strangers to work for me. I feel like I'm asking my staff to be human shields, truth be told. I don't want anyone to be negatively impacted because I'm trying to start a business - and to do something that's a bit different for Petersburg.

I'm writing this article, in case there are others out there that might relate to my fears and who might benefit from the suggestions ChatGPT gave me.

I'm writing this because I'm not a unicorn. I know I'm not alone.