The Journal Prompt That Will Help You (Actually) Move on, Based on Your Enneagram Type

As decades of breakup songs remind us, moving on is hard. Whether it’s a breakup, a career misstep, or the fallout of a relationship, letting go of the past can feel mindbreakingly difficult.

We might repeat Pinterest mantras or scroll through Instagram’s hustle posts to convince ourselves we’re healing (“Flowers come after the rain”), but when our heads hit the pillow, the past still haunts us. We keep blaming the same people and clinging to self-limiting beliefs.

So how do we actually let go? One of the most powerful tools is journaling. Writing down our hardest thoughts makes them less intimidating and breaks the cycle of negative thinking.

Every Enneagram type can benefit from a journaling prompt tailored to help them finally move forward — for real this time.

Type 1: “How can I show more forgiveness to myself and others?”

As a One, your strong sense of right and wrong often works in your favor. You can objectively analyze situations that might be too painful for others — breakups where both parties were at fault, mistakes you could have prevented, or trust you wish you hadn’t given. Your objective morality lets you view suffering through a clear lens.

But this strength can turn into unforgiveness when you can’t let go of what should have happened. If you get stuck on someone else’s mistakes, you risk becoming self-righteous and unforgiving. When you fixate on your own missteps, you struggle to forgive yourself. Remember, you grow best out of self-acceptance, not self-hatred.

Don’t hold grudges as if staying angry will fix the past. Let go of the belief that holding on will make things right. Today, journal about how you can offer forgiveness to yourself and others, even if it’s just a small step at first.

Type 2: “What boundaries do I need to set to protect my well-being?”

When you are in distress, Two, it is natural for you to seek validation and support from others. You are community-oriented and lean on loved ones to cope. While accepting help is important, be mindful not to rely too heavily on others. Some healing needs to be a solo sport.

After a falling out at work, for example, you gain nothing by holding stilted conversations with coworkers to assess who is on your “side.” And inserting yourself into others’ lives just to draw attention to your own pain is only an attempt to control the situation.

Remember, other people’s actions have little to do with your own healing. True growth comes from within. Today, journal about the boundaries you need to set to focus on your own well-being and growth.

Type 3: “How can I show myself compassion daily?”

As a Three, your drive for constant self-improvement can sometimes keep you stuck. After a breakup or mistake, you tend to overanalyze every detail, searching for ways you might have caused the problem. Because if you can take responsibility for what happened – even if it wasn’t your fault – you won’t have to face that some things are out of your control.

“Self-compassion” might sound indulgent, but it’s not. It’s about letting go of resentment toward yourself for real or imagined mistakes. It means accepting that it’s okay to have human reactions to life’s challenges.

Release the habit of self-criticism. Today, journal about ways you can be kinder to yourself. Maybe it’s resisting the urge to check your ex’s Instagram, or letting yourself unwind with a favorite movie. Whatever it is, allow yourself these moments without guilt.

Type 4: “How do I usually process negative feelings? How can I handle them in a healthier way?”

As a Four, you’re always seeking an aesthetic. You turn life into a story where you’re the main character. While this romanticizes your experiences, it can also keep you stuck. By ruminating over negative feelings and seeking to turn them into an aesthetic, you stay stuck in the healing process for longer than necessary.

Contrary to popular belief, aestheticizing pain isn’t about feeling too much, but too little. By turning your struggles into art, you distance yourself from the reality of your suffering instead of facing it head-on.

The cycle breaks when you see suffering for what it is: negativity that threatens your well-being. Staying stuck in the drama of it might feel cathartic, but it’s not sustainable. In your journal, identify the ways you cope that keep you stuck, and brainstorm healthier alternatives. To put your pain in perspective, make it a point to get out of the house and connect with the world. Consider talking to a counselor for an outside viewpoint and extra support.

Type 5: “How may I be intellectualizing my suffering?”

Fives, like Fours, are experts at understanding pain without truly processing or moving past it. While Fours tend to ruminate, you cope by intellectualizing — turning difficult emotions into mental puzzles.

On paper, you understand what happened to you perfectly. Maybe you know exactly which of your flaws led to your relationship’s breakup, or why a bereavement is keeping you from moving forward and upward at work. You’re self-aware and understand why you feel how you do, but may feel helpless to actually heal.

In your journal, write about the ways that you might be intellectualizing your suffering. 

Use this exercise to explore how you can move beyond analysis and allow yourself to truly feel your pain. Only then can you take steps toward a better, more fulfilling life.

Type 6: “How can I cope with anxiety right now?”

As a Six, you carry a million little fears waiting to come true. Maybe it’s a fear of abandonment that intensifies after a breakup, or anxiety about change that surfaces after a job loss. When events seem to confirm your worst worries, you need to remind yourself of the truth of the situation, because anxiety lies.

In your journal, brainstorm ways to cope with anxiety. Try stepping back from the news or waking up earlier to enjoy quiet time before work or school. These small habits may seem minor but can calm your mind.

Also, learn to recognize when negative thought patterns are forming and interrupt them. For example, if a friend betrays you, lean on safe, trusted relationships to counter the fear that everyone will eventually abandon you. Work on accepting change instead of hiding from it.

Type 7: “In what ways is my life ‘happy’ right now?”

You, Seven, prioritize your quality of life. Happy relationships, the freedom to pursue hobbies and financial stability all fuel your contentment. But these are sources of circumstantial happiness. When challenges disrupt them, you can feel untethered and lost.

Your healing process starts when you remember that you still have control over your intrinsic joy, even as circumstances shift. Don’t wait for life to get “better” to feel happy again. Instead, journal about the things that still bring you delight. Appreciate the small moments — a sunset walk to the store, family dinners, or a refreshing shower after work. Noticing these joys helps you stay grounded, no matter what changes around you.

Type 8: “How may my ego be altering my perception of what happened?”

While many people blame themselves for things beyond their control, Eights often have the opposite challenge — not accepting enough responsibility for what is within their control. As an Eight, you may walk away from conflicts convinced you’re right, even when that’s not the full story.

Admitting fault or accepting blame you don’t think you deserve feels deeply uncomfortable. You’re determined not to carry burdens that aren’t yours to carry. But this mindset can keep you stuck in old patterns, unable to move on or grow if you are adamant about being right all the time.

Start by talking things through with trusted loved ones who will be honest and impartial. Then, reflect in your journal: Are there perspectives you haven’t considered? Is there blame you’ve placed on someone else that you could take responsibility for? Honest reflection is the first step toward real growth.

Type 9: “I wish I had the guts to…”

Today, I’m asking Nines to be bold. In your journal, list the things you desperately want to do but feel you can’t — whether it’s out of fear of hurting someone or because you are scared to face how you actually feel about something.

Then, if it will help you grow, choose one item from your list and take a step toward it.

When you’re in painful circumstances, you tend to limit yourself to what you think you’re “allowed” to do. After a breakup, you might hold back from seeing new people out of loyalty to your ex. Or you might stay in a course of study you dislike because you don’t want to disappoint your parents.

But deep down, you know it’s fear that keeps you stuck — fear of upsetting others or claiming your own autonomy. Your new life is waiting on the other side of those fears. Once you write down what you wish you could do, and the reasons you think you can’t, you’ll likely realize you’re more capable than you thought.

Allow yourself to move forward. Take the risk.