Every day, you wake up and make choices. Some are small—coffee or tea, jeans or khakis. Others are big—should you take that job offer, end a relationship, or move across the country. Here’s what’s interesting: most of us handle tiny decisions with ease but freeze up when the stakes get higher.
That hesitation isn’t weakness. It’s your brain trying to protect you from making a mistake. But here’s what often happens instead—you overthink yourself into paralysis, or you rush forward without thinking things through. Both paths can lead you somewhere you don’t want to be.
There’s a better way. By asking yourself the right questions before you commit to any significant choice, you create a mental framework that cuts through confusion and guides you toward clarity. Let’s explore exactly which questions will help you make decisions you can stand behind.
Questions to Ask Yourself Before Making a Decision
These twenty questions will help you examine your choices from every angle that matters. Use them as your personal decision-making toolkit whenever you face a crossroads.
1. What Problem Am I Actually Solving?
Before you can make a good decision, you need to know what you’re deciding about. This sounds obvious, but you’d be surprised how often people jump to solutions without clearly defining their problem. Maybe you’re thinking about buying a new car because yours keeps breaking down. But is the real problem the car itself, or is it that you need reliable transportation? Those are different issues with different solutions.
Get specific here. Write down what’s bothering you or what gap you’re trying to fill. A research study from Stanford found that people who clearly articulated their problem before seeking solutions were 47% more likely to be satisfied with their decision six months later. That’s because they addressed what actually needed fixing rather than what seemed most obvious on the surface.
2. Am I Making This Choice for Me or for Someone Else?
Your life belongs to you. Sounds simple, right? Yet so many decisions get made because of what your parents expect, what your partner wants, or what society tells you is the “right” path. There’s nothing wrong with considering other people’s needs—that’s part of being human. But when their preferences become the primary driver of your choices, you end up living someone else’s life.
Think about your last major decision. Whose voice was loudest in your head? Was it yours? This matters because you’re the one who will live with the consequences every single day. Make sure your own needs and desires have a seat at the table.
3. What’s the Worst That Could Happen?
Fear loves to operate in vague, shadowy territory. When you force yourself to articulate the actual worst-case scenario, fear often loses much of its power. Let’s say you’re considering starting your own business. The worst case probably isn’t homelessness and ruin—it’s more likely that you’d need to get another job and would have lost some savings and time.
Once you identify the genuine worst outcome, ask yourself: could I survive that? Could I recover from it? Usually, the answer is yes. This doesn’t mean you should be reckless. It means you should base your decisions on realistic assessments rather than catastrophic thinking.
4. What’s the Best That Could Happen?
While you’re examining worst cases, look at the flip side too. What if things go brilliantly? What doors might open? What opportunities could unfold? Sometimes we get so focused on risk management that we forget to consider the upside potential.
This question helps you evaluate whether the possible gains justify the risks. If the best possible outcome only makes your life marginally better while the worst case could cause significant harm, that’s valuable information. But if the potential upside could change your life for the better while the downside is manageable, that changes your calculation entirely.
5. Does This Align With My Core Values?
Your values are your internal compass. They’re what you believe matters most in life—things like honesty, creativity, family, independence, or service to others. When your decisions align with these values, you feel grounded and authentic. When they don’t, you experience that nagging sense of unease even if everything looks good on paper.
Take a job offer that pays incredibly well but requires you to compromise on ethical standards you care about. The money might solve immediate problems, but the internal conflict will eat at you. On the other hand, a choice that honors your values tends to feel right even when it’s difficult. That’s your compass working properly.
6. How Will I Feel About This in Five Years?
Time is an excellent decision-making filter. The things that seem urgent and critical today often shrink in significance when you zoom out. That argument with your coworker? Probably won’t matter in five years. The decision to learn a new skill or repair a damaged relationship? Much more likely to have lasting impact.
This question helps you separate what’s truly important from what’s merely immediate. It also helps you gauge whether you’re making a choice based on temporary emotions or lasting priorities. Future-you has wisdom that present-you can access just by asking.
7. What Information Am I Missing?
Sometimes you feel stuck on a decision because you literally don’t have enough information to choose wisely. Maybe you’re considering a career change but haven’t talked to anyone who actually does that job. Perhaps you’re thinking about a major purchase but haven’t researched alternatives or read reviews.
Make a list of what you don’t know. Then figure out how to find those answers before you commit. This might mean conducting informational interviews, reading, experimenting, or consulting with experts. Good decisions are informed decisions. Don’t mistake a lack of information for indecisiveness.
8. Am I Being Realistic About the Time and Effort Required?
Humans are notoriously bad at estimating how long things will take. Psychologists call this the planning fallacy. You think you’ll finish that project in two weeks when it actually takes six. You believe starting a side business won’t interfere with your regular life, but then you’re working every evening and weekend.
Whatever you’re considering, double your estimate of the time and effort it will require. Then ask yourself if you’re still willing to move forward. If yes, you’re probably making a choice with your eyes open. If no, you’ve just saved yourself from a commitment you’d come to resent.
9. Who Will Be Affected by This Choice?
Your decisions ripple outward. They touch your partner, your kids, your parents, your friends, your colleagues. That doesn’t mean you should let others dictate your choices, but it does mean you should consider the impact. Taking that job across the country affects your spouse’s career too. Going back to school might mean less time with your children in the short term.
Being aware of these effects lets you make plans to address them. Maybe you need to have conversations with the people involved. Perhaps you need to find ways to minimize negative impacts. At minimum, you’re making your choice with full awareness rather than being surprised when others respond to consequences you didn’t anticipate.
10. What’s My Gut Telling Me?
Your intuition isn’t magic—it’s your brain processing thousands of bits of information below your conscious awareness. That feeling in your stomach when something seems off? Pay attention to it. That sense of excitement and rightness when you think about a particular path? Listen to that too.
This doesn’t mean intuition should be your only guide. Combine it with rational analysis. But if you’ve done your homework, gathered information, and thought things through, and your gut is still screaming “no,” that’s worth taking seriously. Your subconscious might be picking up on something your conscious mind hasn’t articulated yet.
11. Can I Test This Decision on a Small Scale First?
Not every choice needs to be all-or-nothing. Thinking about a career change? Take a class first. Talk to people in that field. Maybe do some volunteer work or a side project in that area. Considering moving to a new city? Spend a few weeks there first, living like a local rather than a tourist.
Small experiments give you real data about how a bigger decision might play out. They let you fail cheaply if something isn’t right for you. They also build confidence if your experiment goes well. Whenever possible, find a way to dip your toe in before jumping into the deep end.
12. What Biases Might Be Influencing My Thinking?
Your brain takes shortcuts. These mental shortcuts—called cognitive biases—usually help you process information quickly, but they can also lead you astray. The sunk cost fallacy makes you keep investing in something just because you’ve already put time or money into it. Confirmation bias makes you seek out information that supports what you already believe while ignoring contradictory evidence.
You can’t eliminate biases completely. But you can be aware of them. Ask yourself: am I drawn to this option because it’s genuinely best, or because it’s familiar? Am I avoiding that choice because it’s actually problematic, or because it requires change and change feels uncomfortable? Awareness alone often breaks a bias’s hold on your thinking.
13. Do I Have the Resources I Need?
Resources aren’t just money, though that matters too. They’re time, energy, skills, support systems, and emotional bandwidth. Starting a business requires capital, sure, but also countless hours and the emotional resilience to handle setbacks. Going back to school needs tuition money, but also the time to study and the mental space to absorb new information.
Honestly assess what resources your decision demands. Then look at what you actually have available. If there’s a gap, can you acquire those resources? Can you build them over time? Can you find creative alternatives? Sometimes the answer is to wait until you’re better resourced. Sometimes it’s to move forward with modifications. But you need clarity on this before you commit.
14. What Would I Tell My Best Friend to Do?
Here’s a strange truth: you’re often wiser about other people’s lives than your own. That’s because you can see their situations more objectively, without all the emotional noise and personal investment that clouds your judgment about your own choices.
So flip the script. If your best friend came to you with this exact situation, what would you advise? What would seem obvious to you about their decision? That clarity you’d have about their life—try to apply it to yours. This perspective shift can cut through so much confusion and self-deception.
15. Am I Choosing This Because It’s Easy or Because It’s Right?
Easy and right sometimes align. Often they don’t. The easy path is staying in a job that makes you miserable because finding a new one takes work. The easy choice is avoiding a difficult conversation because confrontation feels uncomfortable. The easy option is maintaining the status quo because change requires effort.
There’s nothing noble about making life harder than it needs to be. But there’s also nothing wise about choosing comfort over growth, or avoidance over addressing what needs addressing. Distinguish between the two. Sometimes the harder path is harder because it’s genuinely wrong for you. But sometimes it’s harder because it’s actually the thing that will make your life better in ways that matter.
16. What Opportunity Costs Am I Accepting?
Every choice means saying no to something else. Economists call this opportunity cost. If you spend your Saturday helping a friend move, you’re not spending it with your kids. If you invest money in one opportunity, that money isn’t available for other possibilities. If you commit your energy to one project, you have less available for others.
This isn’t about regret or second-guessing. It’s about clear-eyed awareness. What are you giving up to pursue this option? Are you okay with that trade-off? Sometimes the opportunity cost is worth it. Sometimes it reveals that what you’re gaining isn’t valuable enough to justify what you’re losing. This question helps you see the full picture.
17. Is This Decision Reversible?
Some choices can be undone. You can leave a job, move back to your hometown, or end a business partnership. Others are much harder to reverse—having a child, selling a house in a tough market, or dropping out of school might have lasting consequences even if you later change your mind.
Knowing whether a decision is reversible should influence how much time and energy you invest in making it. Reversible choices can be made more quickly because you can adjust course if needed. Irreversible ones deserve more careful consideration upfront. This doesn’t mean you should avoid irreversible decisions—some of life’s best choices are permanent. But you should approach them with appropriate seriousness.
18. What Does My Track Record Tell Me?
You have a personal history of decision-making. Look at it honestly. When have you made choices you felt good about later? What characterized those decisions? When have you made choices you regretted? What patterns can you identify?
Maybe you’ve noticed that decisions made in anger or fear usually turn out poorly for you. Perhaps choices made after sleeping on them tend to be better than ones made impulsively. Your past decisions are a goldmine of self-knowledge if you’re willing to learn from them. They show you your personal pitfalls and your strengths.
19. Am I Trying to Prove Something?
Sometimes we make choices not because we genuinely want the outcome, but because we’re trying to prove something to ourselves or others. You take the high-pressure job to show everyone you’re successful. You stay in graduate school to prove you’re smart. You make a risky investment to demonstrate you’re bold.
There’s nothing wrong with wanting to prove yourself. But it’s a shaky foundation for major life decisions. When the primary motivation is external validation rather than internal desire, you often end up achieving something that doesn’t actually make you happy. Check your motivations. Make sure you want the thing itself, not just what you think it will say about you.
20. Can I Live With Uncertainty?
Here’s the uncomfortable truth: you’ll never have perfect information. You can’t know for certain how things will turn out. You can do your research, ask good questions, and think things through carefully. But ultimately, every significant decision involves stepping into the unknown.
The question isn’t whether you can eliminate uncertainty—you can’t. The question is whether you can tolerate it. Can you make a choice knowing you might be wrong? Can you commit to a path while holding space for the possibility that you’ll need to adjust later? If you wait for absolute certainty, you’ll never decide anything. Learning to be okay with reasonable uncertainty is part of making good decisions.
Wrapping Up
These twenty questions aren’t a formula that spits out the right answer. They’re tools that help you think more clearly about what matters to you and what your options really entail. Use the ones that resonate with your situation. Skip the ones that don’t apply.
What makes a decision good isn’t that it leads to a perfect outcome—those don’t exist. A good decision is one you make with awareness, intention, and honesty about what you value and what you’re willing to risk. These questions help you get there. The rest is up to you.