20 Questions to Ask Before Making Any Big Decision

Asking yourself the right questions before making a big decision can bring clarity, confidence, and peace of mind.

Sophia Zapanta
February 6, 2025
6 min read

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Big decisions can feel overwhelming, but the key to navigating them lies in asking thoughtful, personal questions. These questions help you uncover your true motivations, anticipate outcomes, and avoid regrets. This guide covers 20 simple yet powerful prompts to help you pause, reflect, and decide wisely.

1. What’s the real problem I’m trying to solve?

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Big decisions often hide a root issue—figure that out first. This clarity can prevent you from addressing symptoms instead of the cause. No one wants to build a bridge over a puddle. Dig deeper to understand the “why” behind your choice—it’s the difference between patching cracks and fixing the foundation.

2. How does this align with my long-term goals?

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Every choice nudges you closer or further from your big dreams. Check if this decision fuels your vision or distracts you. Long-term wins are worth short-term discomfort. Think of your goals like a GPS—if this choice doesn’t move you closer to your destination, it’s probably a detour.

3. What’s my gut telling me?

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Your instincts are smarter than you think—listen to them. If something feels off, it probably is. Your intuition’s like a secret advisor who doesn’t yell but always knows. Don’t dismiss that inner voice; it’s often based on experience, even if it’s hard to explain.

4. Who benefits from this decision, and who doesn’t?

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No choice happens in isolation; someone always gains or loses. Be honest about who’s on each side and whether you’re okay with that. Decisions are rarely neutral. Understanding the ripple effect of your choice helps you gauge its fairness and impact on your relationships.

5. What’s the best-case scenario here?

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Picture the happiest possible outcome—does it excite you? Knowing the upside can keep you motivated through tough steps. Dreaming big isn’t just for optimists; it’s practical, too. Visualizing success helps you figure out whether the reward justifies the effort.

6. What’s the worst-case scenario, and can I handle it?

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If things go sideways, what’s the damage? Assessing risks honestly makes you braver, not paranoid. If the worst-case is survivable, you’re in better shape than you think. This exercise also helps you prepare contingencies, so you’re not blindsided if things don’t go as planned.

7. What are the hidden costs?

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Big decisions often come with sneaky price tags: time, energy, reputation. Look beyond the obvious expenses. You can’t budget for what you haven’t noticed. Whether sleepless nights or sacrificing hobbies, understand the non-monetary toll before committing.

8. Am I doing this for me or someone else?

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It’s easy to mistake other people’s expectations for your own desires. Pause and sift through what you truly want. Life’s too short to live someone else’s idea of success. People-pleasing might win short-term approval, but your happiness shouldn’t be collateral damage.

9. What does my future self think about this?

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Fast-forward a year—are you grateful you said yes, or are you cringing? Channeling your future self is like sending advice back in time. If the future you wouldn’t thank you for this decision, it might not be the right call.

10. Am I saying yes out of fear or guilt?

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If a yes is driven by obligation or panic, reconsider. Strong decisions come from confidence, not avoidance. Guilt fades, but the consequences of a bad call can linger. Ask yourself: Would I still choose this if I wasn’t scared or feeling pressured?

11. Who can I talk to for perspective?

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Sometimes, you’re too close to see clearly. Trusted friends or mentors can highlight blind spots. Just pick people who care more about you than their opinion. A fresh set of eyes or a wise word can help you step out of the fog.

12. What if I did nothing?

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Sometimes, doing nothing is the wisest move. Evaluate if waiting gives clarity or if indecision adds risk. A non-decision is still a decision, after all. It’s not about avoiding action but giving space for the right answer to emerge.

13. How does this impact my values?

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If it clashes with your core beliefs, it’s probably a no-go. Your values are your compass—don’t ditch them for a shiny shortcut. Peace of mind isn’t for sale. When decisions align with your principles, you feel grounded no matter the outcome.

14. What am I afraid of losing?

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Fear of loss often paralyzes good judgment. Call out those fears by name—are they as big as they seem? Sometimes, the fear is scarier than the reality. Understanding what’s at stake helps you weigh whether the potential gain is worth the risk.

15. Do I have all the information I need?

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Decisions based on half-truths or assumptions rarely end well. Fill in the gaps before committing. Google it, ask questions, or read the fine print—your choice deserves it. The more informed you are, the fewer surprises you’ll face later.

16. What’s the opportunity cost?

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Saying yes to one thing means saying no to something else. Weigh what you’re giving up against what you’re gaining. Even great choices have trade-offs. If the alternative you’re sacrificing feels bigger, it might be time to rethink.

17. How will this affect my mental health?

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The wrong decision can drain your emotional reserves. Prioritize your peace—even the best opportunities aren’t worth your sanity. Think of your brain as a battery, not a bottomless pit. A drained mind leads to burnout, and no decision is worth that price.

18. Am I rushing this decision?

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Urgency can cloud judgment. If there’s no real deadline, take a breath. Haste makes waste, and a cool head makes better calls. Deadlines are important, but don’t let a false sense of urgency push you into the wrong choice.

19. Am I okay with this decision being permanent?

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Some choices can’t be undone. If the stakes are high, think twice. There’s no “CTRL + Z” in real life. Consider if you’re ready to live with this choice long after the excitement (or panic) has worn off.

20. What does success look like to me?

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Define your version of winning before you decide. If you don’t know what success looks like, how will you recognize it? Your happiness is the goal, not someone else’s scoreboard. A clear definition of success makes every step feel purposeful and rewarding.