You know that feeling when you’re going through the motions, day after day, and suddenly wonder if this is really all there is? Maybe you’re stuck in a job that pays the bills but drains your soul. Or maybe your relationships feel shallow, like you’re wearing a mask even with people who should know the real you.
Here’s what most people won’t tell you: change doesn’t happen because you suddenly have all the answers. It happens because you start asking better questions. The right question at the right time can crack open your perspective like morning light through venetian blinds.
What follows are 20 questions that have the power to shift everything. Not because they’re magic, but because they force you to look at parts of your life you’ve been avoiding. Ready? Let’s get into it.
Questions to Ask Yourself to Change Your Life
These aren’t your typical self-help questions that sound profound but leave you exactly where you started. Each one is designed to make you pause, think deeply, and most importantly, take action that moves you closer to the life you actually want.
1. What would I do if I knew I couldn’t fail?
Fear is probably running more of your life than you realize. It’s the quiet voice that says “maybe later” or “that’s not realistic” or “people like me don’t do things like that.” But here’s something fascinating: when researchers study regret in older adults, the things people regret most aren’t their failures—they’re the risks they never took.
Strip away the fear for just a moment. If failure wasn’t possible, what would you attempt? Would you start that business? Switch careers? Move across the country? Ask that person out? Write that book? Whatever jumped into your mind first—that’s your answer. That’s what your gut knows you should be doing.
Now, failure is possible, obviously. But what if you reframed failure as information rather than identity? Every successful person you admire has failed more times than most people have tried. The difference is that they kept asking themselves this question and acting on the answer.
2. Am I living my values or someone else’s?
Your parents wanted you to be a doctor. Your friends think you should buy a house. Society says you should be married by 30. Social media suggests you need to hustle 24/7. But whose life are you actually living?
Take five minutes right now and write down your top five values. Not what sounds impressive or what you think you should value, but what genuinely matters to you deep down. Maybe it’s creativity. Freedom. Connection. Learning. Adventure. Peace.
Next, look at how you spent last week. Where did your time, energy, and money actually go? If someone analyzed your calendar and bank statements without knowing you, what would they say you value? The gap between your stated values and your actual behavior—that’s where your dissatisfaction lives. Closing that gap? That’s where change begins.
3. What am I tolerating that I shouldn’t be?
You’ve gotten used to the dripping faucet. The friend who always cancels plans. The boss who takes credit for your work. The clutter in your home. The chronic back pain you keep meaning to address. The relationship that stopped feeling good two years ago.
Humans are incredibly adaptable, which is both our superstrength and our downfall. We can normalize almost anything if we’re exposed to it long enough. But just because you can tolerate something doesn’t mean you should.
Make a list called “Things I’m Tolerating.” Write down everything, big and small. Don’t judge yourself for the list—it’s not about blame. Then pick the easiest thing on there and fix it this week. Just one thing. Maybe it’s finally getting those running shoes resoled or having that uncomfortable conversation you’ve been avoiding. Small fixes build momentum. Momentum builds confidence. Confidence builds a life where you stop settling.
4. Who do I need to forgive, including myself?
Carrying resentment is like drinking poison and expecting the other person to die. Cheesy metaphor? Sure. Also completely true.
Think about who you’re still angry at. Maybe it’s a parent who wasn’t there for you. An ex who betrayed you. A friend who let you down. A colleague who sabotaged you. And here’s the hard one: yourself, for the mistakes you made, the time you wasted, the person you hurt.
Forgiveness doesn’t mean what happened was okay. It means you’re done letting it take up space in your head rent-free. A study published in the Journal of Behavioral Medicine found that forgiveness is associated with lower stress levels, better physical health, and improved relationships. But beyond the science, there’s this: every minute you spend rehashing old wounds is a minute you’re not building something new.
You don’t need to call anyone or send a letter (though you can if you want). Sometimes forgiveness is an internal shift—a decision to release the grip that anger has on you. Try this: imagine physically handing that resentment back to the person who caused it, or setting it down at your feet and walking away. What would your life look like if you were 20% lighter?
5. What drains my energy, and what refills it?
Energy management matters more than time management. You could have all the time in the world, but if you’re depleted, you’ll still accomplish nothing that matters.
Pay attention for one week. Notice what leaves you feeling exhausted versus energized. It’s not always what you expect. Maybe that networking event everyone says you “should” attend actually drains you for three days afterward. Maybe the hobby you thought was relaxing has become another obligation. Maybe certain people consistently leave you feeling worse than before you saw them.
On the flip side, what activities make you lose track of time? What conversations leave you buzzing with ideas? What environments make you feel most alive? For some people, it’s being in nature. For others, it’s deep work on a challenging project. For others still, it’s being in a crowded coffee shop observing humanity.
Here’s your action step: ruthlessly eliminate or minimize at least one energy drainer, and deliberately add more of at least one energy giver. Your life will thank you.
6. If I could only achieve three things in the next five years, what would they be?
Unlimited options sound great until you realize they lead to paralysis and scattered effort. When everything is important, nothing is important.
This question forces prioritization. Not ten things. Not “achieve success” or other vague goals. Three specific things. And five years is far enough away to dream big but close enough to feel real.
Maybe yours are: build a business that generates passive income, learn fluent Spanish, and develop a daily meditation practice. Or: write a novel, repair your relationship with your sister, and run a marathon. Or: get promoted to director level, save $50,000, and become someone your kids are proud of.
Once you have your three, everything else becomes easier to evaluate. Does this opportunity move you closer to one of your three goals? If not, it’s probably a no. Does this relationship support your three goals or distract from them? Does this habit align with who you need to become to achieve these three things?
Clarity is freedom.
7. What story am I telling myself about why I can’t?
We’re all walking around with narratives running on a loop. “I’m bad with money.” “I’m not creative.” “I’m too old to start over.” “I’m not smart enough.” “People like me don’t get those opportunities.”
The tricky thing about these stories is that they feel like facts. They’re not. They’re interpretations of your past that you’re projecting onto your future. And every time you repeat them, you reinforce them.
Catch yourself the next time you say “I can’t” or “I’m not.” Then add the word “yet.” I can’t code—yet. I’m not confident speaking in public—yet. That tiny word rewires your brain from a fixed to a growth mindset. There’s actual neuroscience behind this: your brain is plastic, meaning it physically changes based on your thoughts and experiences.
Challenge your limiting stories. Where did they come from? Are they actually true, or are they convenient excuses? What evidence do you have that contradicts them? What would be possible if you dropped them completely?
8. Am I avoiding something I actually need to face?
That doctor’s appointment you keep postponing. The difficult conversation with your partner. The decision about whether to stay in your career. The grief you haven’t processed. The addiction you won’t name.
Avoidance feels like relief in the short term. Long term, it’s a slow-motion disaster. Whatever you’re avoiding doesn’t go away because you ignore it—it grows teeth and gets meaner.
You know what you’re avoiding. It’s the thing that popped into your head when you read this question. The thing that makes your stomach clench. Here’s your mission: do the smallest possible first step toward facing it. Not the whole thing—just the tiniest movement forward. Research the doctor’s number. Write the first sentence of what you need to say. Admit to yourself what’s really going on.
Courage isn’t the absence of fear. It’s acting despite it.
9. What does my ideal Tuesday look like?
Forget “dream life” for a second. That’s too abstract. Let’s get specific.
Walk me through your ideal Tuesday from the moment you wake up. Where are you? Who’s next to you? What do you do first? What’s for breakfast? What work are you doing, if any? Who do you talk to? What do you do for lunch? How do you spend your afternoon? Your evening? What time do you go to bed?
This question reveals what you actually want, stripped of the Instagram highlight reel. Maybe your ideal Tuesday is quiet and solo, or maybe it’s packed with people and activity. Maybe you’re in an office, or maybe you’re on a beach with a laptop. Maybe you’re parenting, or maybe you’re child-free and traveling.
The gap between your current Tuesday and your ideal Tuesday? That’s your roadmap. You might not be able to change everything overnight, but you can start moving in that direction. Could you adjust your current Tuesday by even 10% to make it closer to your ideal? That’s where you start.
10. Who in my life makes me better, and who makes me worse?
Jim Rohn famously said you’re the average of the five people you spend the most time with. It sounds simplistic, but study after study confirms it: your social circle profoundly impacts your habits, beliefs, income, health, and happiness.
List the people you interact with most. Then, honestly assess: does each person elevate you or diminish you? Do they challenge you to grow or encourage you to stay small? Do they celebrate your wins or subtly compete with them? Do they call you on your excuses or enable your self-destructive patterns?
This isn’t about being cold or transactional. Some people in your life—family, old friends—aren’t going anywhere, and that’s fine. But you can be intentional about how much space they occupy. You can also be deliberate about adding people who inspire you, support you, and expand what you think is possible.
Spend more time with the people who make you want to be better. Spend less time with everyone else.
11. What would I do if money weren’t an issue?
Money is usually the first reason people give for why they can’t pursue what they really want. But often, it’s not actually about money—it’s about fear wearing a money mask.
So let’s remove the variable. You have enough money to live comfortably for the rest of your life. No debt. No financial stress. What do you do with your time?
Some people say they’d travel. Others would create art, volunteer, learn new skills, spend time with family, or work on passion projects. Very few people say they’d keep doing exactly what they’re doing now, which tells you something important.
Now here’s the follow-up question: is there any version of what you just described that you could start doing now, even in small ways? If you’d travel, could you explore your own city like a tourist this weekend? If you’d create art, could you spend 30 minutes this evening with a sketchbook or musical instrument? If you’d volunteer, could you commit to one Saturday a month?
You might not have unlimited money, but you have more freedom than you’re using.
12. What am I pretending not to know?
Your gut knows. It’s been trying to tell you for months, maybe years. But you keep pushing the knowledge down, changing the subject in your own mind, staying busy enough to avoid hearing it.
You know your relationship isn’t going to work out. You know your current path won’t lead where you want to go. You know you need to quit or you need to apologize or you need to get help. You know.
Pretending not to know feels safer than dealing with what you know. But that pretense costs you. It costs you peace, authenticity, forward momentum, and self-respect. Every day you pretend is a day you’re lying to yourself.
Stop pretending. Sit quietly for ten minutes and ask yourself: what am I pretending not to know? Then listen. Really listen. What comes up might scare you, but at least it’s the truth. And the truth, even when it’s hard, is always the foundation for real change.
13. How do I want people to describe me at my funeral?
Dark question? Maybe. Also incredibly clarifying.
When you’re gone, what do you want people to say about who you were and how you lived? Successful? Kind? Brave? Fun? Generous? Creative? Present? Authentic? Someone who made others feel seen and valued?
Write down five words or phrases. Now look at your current life. Are you living in a way that would generate those descriptions? If you want to be remembered as kind but you’re impatient and dismissive with people, there’s work to do. If you want to be remembered as brave but you’re playing it safe in every area, something needs to change.
This question cuts through all the noise about what you should want or what looks good on paper. At the end, none of that matters. What matters is whether you became the person you hoped to be and whether you loved the people around you well.
Let your desired eulogy guide your daily choices. It’s a morbid thought, but it works.
14. What would I attempt if I had more confidence?
Confidence is a funny thing. Most people think it comes before action: get confident, then do the thing. But it actually works backward: do the thing, then get confident.
Still, it’s useful to identify what you’d do if confidence weren’t an issue. Would you ask for a promotion? Put your art online? Start a podcast? Join a social group? End a relationship that isn’t working? Speak up in meetings? Set boundaries with family?
Here’s what you need to know: no one feels completely ready. Everyone successful you see felt scared and uncertain when they started. They just decided to act anyway.
Pick one thing from your “if I had confidence” list. Now commit to doing it badly. Not perfectly—badly. Give the awkward presentation. Post the imperfect art. Have the uncomfortable conversation. Send the application even though you’re not 100% qualified. Action creates confidence. Waiting creates more fear.
15. What habit would change everything if I did it consistently?
You don’t need to overhaul your entire life. You need one keystone habit—a behavior that, when consistently practiced, triggers positive changes in other areas.
Maybe it’s waking up 30 minutes earlier. Or exercising four times per week. Or reading for 20 minutes before bed. Or meal prepping on Sundays. Or meditating daily. Or putting your phone away during meals. Or tracking your spending.
The right keystone habit creates a ripple effect. People who start exercising regularly often naturally start eating better, sleeping more, and managing stress more effectively—not because they’re forcing it, but because the habit creates a positive cascade. People who start their morning with a clear plan often find they’re more productive, less anxious, and more intentional all day.
Choose one habit. Just one. Make it small enough that you can do it even on your worst day. Then commit to it for 30 days. Watch what else shifts.
16. What belief about myself is actually limiting me?
Your beliefs about yourself operate like an invisible cage. You can’t see the bars, but they’re there, keeping you in a smaller space than necessary.
Common limiting beliefs: “I’m not a morning person.” “I’m bad at math.” “I’m too introverted for leadership.” “I’m not tech-savvy.” “I’m too old/young.” “I’m not disciplined enough.” “I’m just not lucky.”
Pick one belief you hold about yourself. Now ask: is this actually true, or is this something I decided was true based on limited evidence? Is this a fact about my fundamental nature, or is this a skill I haven’t developed yet? Am I using this belief as a shield against having to try?
Replace each limiting belief with an empowering alternative: “I’m learning to be a morning person.” “I’m developing my math skills.” “I’m discovering my own leadership style.” “I’m becoming more comfortable with technology.”
Your beliefs shape your actions. Your actions shape your reality. Change the belief, change everything.
17. What boundary do I need to set?
You teach people how to treat you. If you don’t set boundaries, others will set them for you—and they’ll set them in their favor, not yours.
Where are you overextending? Where are you saying yes when you mean no? Where are you tolerating behavior that makes you feel bad? Where are you giving more than you have to give?
Boundaries aren’t mean. They’re not selfish. They’re the recognition that you can’t pour from an empty cup and that you have the right to protect your time, energy, and peace. Good boundaries actually improve relationships because you show up more genuinely when you’re not resentful.
Identify one boundary you need to set. Practice saying it out loud: “I can’t take on another project right now.” “I need you to stop commenting on my appearance.” “I’m not available after 8 PM on weeknights.” “I need advance notice before you visit.”
Setting boundaries feels uncomfortable at first. Do it anyway. Your future self will thank you.
18. What brings me joy that I’ve stopped making time for?
Life gets busy and serious. Responsibilities pile up. Before you know it, you’ve stopped doing the things that make you feel alive.
Think back to what used to light you up. Maybe you loved painting. Or playing guitar. Or pickup basketball. Or baking elaborate cakes. Or reading fiction. Or dancing. Or photography. Or having long conversations over coffee.
When did you stop? Why? Probably because other things felt more important or because you told yourself you’d get back to it later. But “later” keeps not arriving.
Joy isn’t frivolous. It’s fuel. It’s what makes the hard parts of life bearable. It’s what reminds you that you’re alive, not just surviving.
This week, do one thing that used to bring you joy. Even if it’s been years. Even if you’re rusty. Even if you feel silly. Just do it once and see what happens. You might remember who you are underneath all the obligations.
19. If today were my last day, what would I regret not doing?
Another mortality question, but this one focuses on regret. When Dr. Bronnie Ware worked in palliative care, she recorded the most common regrets of the dying. The top one? “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”
Others included: working too hard, not expressing feelings, losing touch with friends, and not letting themselves be happier. Notice what’s not on the list: not making more money, not buying a bigger house, not being more successful by conventional measures.
If you only had today, what would you wish you’d done differently? What would you wish you’d said? Who would you wish you’d forgiven? What experiences would you wish you’d had? What risks would you wish you’d taken?
You don’t have just today. You probably have decades. But living like you might not have tomorrow creates urgency and clarity. It stops you from putting off what matters most.
20. What’s one small step I can take today?
All this introspection means nothing without action. You can think yourself into circles, but at some point, you have to move.
Look back at your answers to the previous 19 questions. Pick one that resonates most. Now ask: what’s the smallest possible action I could take today—right now—that moves me even slightly in that direction?
Maybe it’s sending a text. Making a phone call. Doing ten push-ups. Writing one paragraph. Researching one program. Saving $5. Saying one difficult sentence out loud. Throwing away one thing that doesn’t serve you.
Small actions compound. They build momentum. They prove to yourself that change is possible. You don’t need to have it all figured out. You just need to take the next step.
So take it. Right now. Before you close this tab and forget, before you talk yourself out of it, before life gets in the way—take one small step.
Wrapping Up
These 20 questions aren’t meant to be answered once and forgotten. They’re meant to be revisited, wrestled with, and used as tools for continuous growth. Your answers will change as you change, and that’s exactly how it should be.
Life change doesn’t happen because you suddenly figure everything out. It happens because you ask yourself hard questions, get honest with the answers, and then take action—however small—based on what you discover. You already have everything you need to start. The only question left is: will you?