30 Questions Before You Decide

What are you actually deciding between?

Name the options clearly. If you have only two, ask: Is there a third option I haven't considered? The Heath Brothers' research shows most people consider too few options—we get trapped in "whether or not" thinking.

What started this decision? What made it urgent now?

Understanding why you're at this crossroads matters. Sometimes the trigger reveals what you actually care about—or reveals that the urgency is artificial.

If you had to decide in the next 60 seconds, what would you choose?

This surfaces your gut. Don't dismiss it. Research shows gut instincts for major life decisions are often surprisingly accurate—they integrate more information than conscious analysis can process.

What did your gut just tell you? What was the feeling in your body when you read that question?

Relief? Dread? A sinking feeling? Excitement? Pay attention to this. Your body often knows before your mind catches up.

What would you decide if no one ever knew?

This separates your genuine preferences from social pressure. The gap between this answer and what you're considering reveals how much you're deciding for others.

What would you decide if everyone knew—and you had to explain it publicly?

Sometimes our private choices wouldn't survive public explanation. This isn't always bad—but the tension is worth examining.

What version of this decision have you been avoiding naming?

Often the real choice hides behind a more palatable framing. "Should I take this job?" might actually be "Am I ready to leave this relationship?"

What information are you waiting for that you think will make this easier?

Do you actually need it? Or is waiting a form of avoidance? Research shows we often delay decisions seeking certainty that will never come.

What's the cost of deciding nothing and staying exactly where you are?

Inaction is a decision too. Not choosing is choosing the status quo—and that has consequences that accumulate over time.

Is this a one-way door or a two-way door?

Jeff Bezos distinguishes between irreversible decisions (one-way doors) and reversible ones (two-way doors). Most decisions are two-way doors. If you can reverse course, you can afford to move faster.

What is the worst realistic outcome of each option?

Not the catastrophic fantasy—the actual worst case. Most fears, when examined, are survivable. This is Tim Ferriss's "fear-setting" exercise: name the fear, then defang it.

If that worst case happened, what would you do to recover?

Having a mental recovery plan reduces the fear's grip. You're more resilient than you think—and most failures are not permanent.

Which worst-case scenario could you live with more easily?

Sometimes the question isn't which path succeeds—it's which failure you could tolerate. This reframe often provides unexpected clarity.

Whose opinion are you weighting too heavily in this decision?

A parent? A partner? Society? Your past self? Identify them. Their voice in your head may not represent your actual best interests.

What would you choose if that person's opinion didn't exist?

This isn't about dismissing others. It's about separating your judgment from borrowed fears.

What's the fear under the fear? What is this decision really about?

Fear of failure often masks fear of judgment. Fear of commitment masks fear of foreclosing options. Fear of leaving masks fear of being alone. Go one layer deeper.

Are you continuing down a path because it's right, or because you've already invested so much?

This is the sunk cost fallacy—one of the most well-documented decision errors. The time, money, or effort you've already spent is gone regardless. Only future costs and benefits matter.

If this decision fails spectacularly, what will you wish you had known or done differently?

This is Gary Klein's pre-mortem technique. Imagining failure in advance helps you spot blind spots your optimism is hiding. Research shows this generates 30% more risk factors than traditional analysis.

What assumption are you making that might be wrong?

Adam Grant's research shows the smartest people question their assumptions. What are you taking for granted that deserves scrutiny? What would change if that assumption were false?

What would you tell a close friend who was facing this exact decision?

We are often hypercritical and fearful with ourselves but wise and compassionate with others. Take your own advice. This question bypasses the noise of self-doubt.

How will you feel about this in 10 minutes? In 10 months? In 10 years?

Suzy Welch's 10-10-10 framework. Decisions that feel urgent often aren't. What matters in 10 years rarely matches what feels pressing in 10 minutes.

When you're 80, looking back on your life, which choice will you regret not taking?

Jeff Bezos's regret minimization framework—the question that made him leave a lucrative job to start Amazon. Research confirms: we regret inactions far more than failed attempts.

Which choice leads to better stories?

Not better outcomes—better stories. The path that stretches you, challenges you, puts you in rooms you've never been in. Even if it fails, it becomes a story worth telling.

Which choice is more aligned with who you're trying to become?

Not who you were. Not who others expect. Who you're becoming. The best decisions are identity-consistent—they reinforce the person you want to be.

What would the version of you that you most admire choose?

Your future self. Your role model. The person you'd be proud to become. Channel them. What do they see that you're missing?

What must you give up if you choose this path? Can you grieve it?

Every yes is a no to something else. This is opportunity cost—and it's real. Name what you're releasing. Honor it. Then decide if the trade is worth it.

Is there a smaller version of this decision you could test first?

Can you pilot it? Prototype it? Date before marrying, freelance before quitting, visit before moving? Experiments reduce risk and reveal information.

Who haven't you talked to who might have useful perspective?

Someone who's made this choice before. Someone who sees you clearly. Someone outside your usual echo chamber. One good conversation can shift everything.

When you imagine having decided—and it's done—where do you feel relief in your body?

Close your eyes. Picture yourself six months from now, having made the choice. Which choice brings the exhale? That sensation is data.

What do you know now that you didn't know at Question 1?

Don't skip this one. The answer is often the decision itself.