Indecisiveness

Exercises & Practices

Self-assessment, growth practices, scenarios, and journaling prompts

Indecisiveness

Exercises & Practices


Is This Me?

These questions aren't a test. Just notice your internal response — what lands, what you want to skip over, what makes you uncomfortable.

  • Do you research decisions long past the point where more information would actually change anything?
  • When someone asks what you want — where to eat, what to watch, how to spend the weekend — do you reflexively say "I don't care, you pick"?
  • Do you find yourself asking more and more people for their opinion, hoping someone will tell you the "right" answer?
  • Have you missed opportunities or deadlines because you couldn't commit to a choice in time?
  • Do you replay past decisions that went badly and use them as reasons not to decide now?
  • When you imagine making the decision, do you feel a knot in your stomach, a tightness in your chest, or a vague dread you can't name?
  • Do you keep both options alive in your head because choosing one means losing the other — and the loss feels unbearable?
  • Are there people whose potential disapproval keeps you from deciding, even when their opinion isn't relevant to this particular choice?
  • Do you tell yourself "I just need a little more time" when honestly you've had enough time — you just don't want to commit?

Questions Worth Sitting With

These don't have quick answers. Sit with them. Let them work on you before you try to answer.

  • What decision have you been carrying that you haven't been able to make — the one that sits in the back of your mind, that you think about in the shower, that you keep putting off?
  • Whose voice is loudest in your head about this decision — and should it be? Is that voice helping you think clearly, or is it noise that doesn't belong here?
  • If you knew you could handle whatever came next — if you trusted yourself to adjust, recover, and keep moving — what would you decide?
  • What is indecision actually costing you right now? Not hypothetically — what are you losing in time, energy, relationships, peace of mind, and opportunities while you stay stuck?
  • Is there something from your past that's speaking into this present decision — a previous choice that went badly, a time you trusted and got hurt? Is this situation actually the same, or are you letting the past decide for you?
  • What would it mean about you if you made this decision and it turned out well? What would it mean if it didn't? Are those meanings true — or are they stories you're telling yourself?
  • If you stopped waiting for certainty and just made the wisest choice you could with what you know right now — what would that choice be?

Growth Practices

Pick one. Try it this week. Notice what happens.

Week 1: Notice. This week, pay attention to every moment you get stuck deciding — big or small. Don't change anything, just notice. When you hesitate at a restaurant menu, when you can't pick what to wear, when you stall on responding to an email. Notice what happens in your body. Notice whose opinion floats into your head. Notice what fear — if any — is underneath. Keep a simple tally or a note in your phone. The goal isn't to fix it yet. The goal is to see the pattern.

Week 2: Try. Pick one low-stakes decision this week and use the framework: define your purpose, list your criteria, rank them, and then decide within 24 hours. It could be something like choosing a weekend activity, picking a gift, or deciding on a home project. Don't ask more than one person for input. Notice what it feels like to use a structure instead of just swirling.

Week 3: Stretch. Take a decision you've been stuck on — a real one — and do the full process. Write down the purpose. Define the criteria. Draw the concentric circles and put names in them. Ask yourself Dr. Cloud's question: "What information do I not have that I still need?" Name the fear. Set a deadline. And when the deadline comes — decide. Even if you're not 100% certain. Notice that you survive the deciding.

Week 4: Hold. After making your decision from Week 3, practice not second-guessing it. When doubt creeps in, remind yourself: "I made this decision with wisdom and good criteria. I can handle what comes next." If someone expresses disapproval, practice not explaining or defending. Just let the decision stand. Notice what it feels like to own a choice.


Scenario Cards

Scenario 1: The Endless Job Search Priya has been looking for a new job for eight months. She's had three solid offers, but turned each one down because something wasn't quite right — the commute was slightly long, the team seemed okay but not amazing, the salary was good but not great. She keeps telling herself the perfect opportunity is coming. Meanwhile, she's exhausted at her current job and her savings are getting thin from all the interview travel. A fourth offer just came in. It meets most of her criteria but not all.

What do you notice about Priya's pattern? What criteria might she need to revisit? What fear might be underneath the pursuit of "perfect"?

Scenario 2: The Family Holiday David and his wife want to spend Thanksgiving with her family this year — they've done his family the last three years running. But David's mother has made it clear she'll be deeply hurt. Every time he and his wife try to finalize plans, David says he needs to think about it more. His wife is getting frustrated. His mother keeps calling. David feels paralyzed.

What's really keeping David stuck? Whose opinions belong in this decision? What would healthy decision-making look like here?

Scenario 3: The Relationship That's "Fine" Aisha has been dating Marcus for two years. He's kind, stable, and everyone likes him. But she finds herself hesitating whenever the conversation turns toward the future. She can't identify anything wrong — she just doesn't feel the certainty she thinks she should feel. Marcus is starting to ask where this is going, and Aisha keeps saying she "needs more time."

Is "more time" likely to give Aisha the certainty she's looking for? What questions should she be asking herself? What might be underneath the hesitation that has nothing to do with Marcus?


Journaling & Reflection

Looking Back

  • Write about a decision you were stuck on but eventually made. What finally got you unstuck? What happened after you decided? What does that memory tell you about your capacity to navigate uncertainty?
  • "The decision I keep avoiding is... and the reason I tell myself I'm avoiding it is... but the real reason might be..." See if you can get underneath your surface explanation to something truer.

Looking Inward

  • When you imagine making the decision you're currently stuck on, what happens in your body? Where does the tension land? What specific fear shows up? Put a name to it — not "something bad," but what exactly.
  • Describe the person you want to become in how you make decisions. What does that person look like? How do they handle uncertainty? What relationship do they have with fear? With other people's opinions? What's one step you could take today to become more like that person?

Looking Forward

  • "If I trusted myself more — trusted that I could handle whatever comes next — the decision I would finally make is..." Finish that sentence and see where it leads.
  • Write about what the cost of staying stuck looks like six months from now. A year from now. What will you have lost? What will you wish you had done? Make it specific and real.

Want to go deeper?

Get daily coaching videos from Dr. Cloud and join a community of people committed to growth.

Explore Dr. Cloud Community