30 Journaling Prompts for Making a Hard Decision
Sep 29, 2026
I've noticed a pattern in my own life. When I'm not sleeping well, it's often because I'm not at peace. And when I'm not at peace, it's usually because there's a decision I keep putting off.
It follows me around all day. It's still there when I turn off the light.
Almost every time, the decision involves a hard conversation with someone, one that could stir up strong emotions. So I hesitate.
Here's what I tell myself: "I don't want to hurt them." It sounds kind. It sounds responsible. But when I'm honest, that's not the whole story. Often I'm not protecting the other person. I'm protecting myself from the uncomfortable feelings that might show up if I have the conversation.
Here are a few decisions I've put off for exactly that reason:
- Do I share my concerns with them or wait?
- Do I let my guard down, and choose to trust them?
- Do I start producing content that people could criticize?
- Who is the best candidate for the job?
- Do I continue using their services or make a change?
- Do I launch this new service or product?
Some of these involve a hard conversation. Others involve the fear of being criticized. The root is the same: avoiding discomfort.
As a coach and family therapist for three decades, I see this pattern all the time in the people I counsel and coach. Smart, caring people stay stuck, not because they lack information, but because they haven't named the real decision or faced the fear underneath it.
That's what these 30 prompts are for. They're grouped by what's actually keeping you stuck, so you can start where you are. And if you'd like to write in them, get the free printable Decision Journal here.
Why we avoid hard decisions
Avoiding feels like relief in the moment. The conversation doesn't happen, the launch doesn't happen, the feelings don't happen.
But the decision doesn't go away. It takes up space in your mind, your relationships, and sometimes your sleep. Waiting is a decision too, and it's usually the most expensive one.
A quick note: not every sleepless night is about an unmade decision, and if sleep problems are ongoing, please talk with your doctor. But if you're lying awake with something unresolved, it's worth asking what you've been avoiding.
How to use these prompts
- Pick one prompt and set a timer for 5 to 10 minutes.
- Write by hand if you can. Don't edit. Don't solve. Just write.
- Start with the group that matches how you feel right now, not prompt 1.
- Be honest. No one else has to read this.
When you're stuck
Get clear on what you're really deciding.
- What decision am I avoiding, and what do I tell myself instead of facing it?
- If I had to state this decision in one sentence, what would it be?
- What have I already decided deep down but haven't admitted?
- What is the real question underneath this question?
- What information am I waiting for, and is it actually coming?
When fear is driving
Face the fear so it stops steering.
- What am I afraid will happen if I choose wrong?
- How likely is that outcome, honestly?
- If I knew I could handle the worst case, what would I choose?
- What has fear talked me out of before, and what did it cost me?
- Whose voice do I hear when I imagine getting this wrong?
Want these prompts on printable pages, with a decision worksheet and a commitment page? Get the free Decision Journal.
When you're weighing options
Compare what each path really costs and gives.
- What are my real options, including the one I've been ignoring?
- Which option best fits my top three values?
- What does each option cost me in time, money, energy, and relationships?
- Which option would I regret not trying in five years?
- What am I gaining and what am I giving up with each choice?
When other people are involved
Separate your decision from everyone else's expectations.
- Whose approval am I looking for in this decision?
- Who will be affected, and have I talked with them?
- What would I tell a friend facing this same choice?
- Who has walked this road, and what could I learn from them?
- Which part of this is mine to decide, and which part isn't?
If your decision involves a hard conversation
This is the one I have to be most honest about with myself. Before you move on, try these three questions:
- Am I protecting them, or am I protecting me? Both can be true. Name which one is louder.
- Which feeling am I trying to avoid, and can I survive feeling it? Discomfort is not danger. Most of the time, it passes.
- What would a kind and honest version of this conversation sound like? Kindness and honesty aren't opposites. Often the kindest thing is the truth, said with care and at the right time.
When you need the long view
Choose from the life you want to be remembered for.
- Where will each choice put me in one year? Five years? Ten?
- Which choice would the person I want to become make?
- At 80, looking back, which choice would I be proud of?
- Which option fits how I want to be remembered?
- What does my gut say in the first five seconds, and why do I argue with it?
When it's time to commit
Turn clarity into movement.
- What is the smallest step I can take in the next 24 hours?
- What would "good enough" look like so I can stop waiting for perfect?
- If this doesn't work out, what will I do next?
- Who will I tell about my decision so I stay accountable?
- Finish this sentence: "I've decided to ______ because ______."
After you journal: from clarity to action
Journaling gets you clear. It doesn't get you done.
Here's what I've learned: There's no positive change until you "Decide" to change. "Decide" today! Your "Legacy" depends on it.
The path looks like this: Decide → Courage → Confidence → Capabilities. You don't wait to feel confident before you decide. You decide, you act with a little courage, and the confidence and capabilities follow.
And you don't need the perfect decision. You need motion. If you're stuck on getting it exactly right, read [Motion Over Perfection], then take the smallest next step you wrote down in prompt 26.
If fear keeps showing up in your answers, [7 Unexpected Benefits to Facing Your Fears] is a good next read.
Live the life TODAY you want to be remembered for 10 years after you're gone.
Get the free Decision Journal
From Confused to Clear. From Stuck to Strong.
Don't just think about it. Decide. The Decision Journal gives you:
- All 30 prompts on printable pages
- A one-page worksheet to weigh your options, values, and fears
- A "Decide Today" commitment page to turn clarity into your next step
Take the next step.
Buy The Legacy Jar and get 100+ more questions that go deeper to strengthen your relationships more. BONUS: We've included our Shatterproof Yourself Lite course with 7 steps to better mental health.
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