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13 journal prompts for self-sabotage

Reclaim your life goals by investigating your triggers. Try these 13 journal prompts to help you heal from chronic self-sabotage.

13 journal prompts for self-sabotage
POV: You're journaling about spending money you don't have

Back in 2019, I had just started dating a man who lived across the pond in London some 5,300 mi (8,600 km) away. I was 29, with a remote-friendly job that earned just under six figures. Given my circumstances, all I’d have to do is move out of San Francisco, arguably the most expensive city in the US, and I’d be living good.

Except there was one other problem: I had a teensy little propensity towards sabotaging myself, financially.

“You’ve gotta spend money to make money!” crowed the primordial finance gurus of the 90s. “Fake it til you make it!” said my Boomer godmom — who, now that I think of it, has never given me a sound piece of life advice in her life.

Sure, several people might have set me up for failure early in life, but at 29 years old, I had plenty of time as a grown adult to un-learn some bad habits and discard bad advice, right?

Wrong. And that’s why I ended up in a Lebanese restaurant in London with my new boyfriend on Christmas Eve, crying into my flatbread after my roommate back home called: my rent check bounced, our landlord was furious, I’d never been more ashamed in my life, and it was all preventable.

What is self-sabotage and why do we do it?

Self-sabotage is the perplexing and frustrating behavior of undermining your own success. The behavior can be unconscious, or an active, conscious choice; I, for one, definitely knew rent was due when I bought that plane ticket, for example. Avoidance — sticking your fingers in your ears and pretending rent is not due — stifles your progress, growth, and sometimes reputation.

Other common forms of self-sabotage include:

  • Procrastination: Delaying a task or decision until the very last minute, or until it’s too late.
  • Negative self-talk: Criticizing yourself until your self-esteem is so shot, you bail out of the task entirely
  • Substance abuse: Escaping into alcohol, drugs, or other substances to cope with stress or difficult emotions which, left unchecked, can derail your goals personally and professionally

Unproductive or self-destructive behavior has been a part of my lived experience for decades. Some people can remember the exact moment that activated the critic in their heads. For me, the activation of my “money isn’t real” demon was gradual: a violent single mother who lashed out from the stress, then bought my forgiveness with gifts, while also insulating me from financial literacy entirely. (My future husband should handle that, after all.)

A decade or two of mixed messages and now, here we are: buying plane tickets with our rent money!

Is overcoming self-sabotage possible?

Of course it is! Is it easy, though? Depending on the situation you’re in, it might be on the of the hardest things you’ll ever do.

But imagine living without it. The peace. The stability!

If you can identify your triggers quickly enough, unconscious self-sabotage can be interrupted by passively and matter-of-factly describing the emotions you’re feeling before the self-sabotaging behavior takes place. Something like, “I am nervous about taking this jiu jitsu class because I have never done anything like it. I feel compelled to have a beer.” Sometimes, just catching yourself in the act is all it takes.

It isn’t always that simple, though. For other situations, you’ll need to spend some time investigating.

Overcoming self-sabotage requires patience, persistence, and self-compassion; beating yourself up will only build up more shame and potentially make the behavior worse. But approaching your behaviors with curiosity — with trusted friends, a therapist, or your journal — can help you develop strategies to cope with them, and maybe even heal them entirely.

Journal prompts for self-sabotage

So what do you say? Let’s make like an archeologist and go digging for treasure (aka, probably trauma)! Here’s a handful of useful journal prompts to help you understand what’s going on in that mind palace, so you can be one step closer to solving the riddle that is your self-sabotaging patterns.

Overwhelmed? I recommend starting with what I call the Shot and Chaser method — one prompt that feels “light” or easy to answer, and another that makes your skin crawl a little. Do them in either order. If self-awareness is a muscle that you build over time, think of the “chaser” like a stretch before the real workout, or a cooldown after.

Onto the prompts…

  1. When was the last time I self-sabotaged? How did it happen? How did not achieving my goals make me feel?
  2. Who was the first person to criticize me for successfully doing the task I’m now avoiding? Are they still part of my life today?
  3. What limiting belief about myself am I preserving by not taking action on my goals?
  4. How can I make my goals feel more accessible?
  5. What are 3 small steps I can take toward my goals this week?
  6. Some of the warning signs that I’m about to self-sabotage are…
  7. What makes me feel confident?
  8. Who or what do I blame when I don’t succeed?
  9. What limiting beliefs follow me around from day to day? Where did I learn them from?
  10. What are five things I can remind myself of when I start to self-sabotage?
  11. Do I believe I’m able to learn new things?
  12. Is my locus of control internal or external? (Do I feel like I’m more or less in control of my own life, or is life mostly “happening” to me?)
  13. When I catch myself self-sabotaging, I will…

Give one, some, or all of these a try, and hopefully you’ll identify some baby steps you can take to more or less reprogram yourself. Give yourself time. Believe in your ability to change and grow. You’re the hero of your own personal story; overcoming the villain in your own mind sounds pretty badass, doesn’t it?

You’ve got this.

With love,

Aubrie Johnson profile image Aubrie Johnson
Aubrie is a neurodivergent artist, tarot reader and art therapy student. When not making stuff, she's birdwatching or out buying a book (knowing full well she has a tbr stack at home).