Your 20s feel like standing at a crossroads with a hundred different paths branching out in front of you. Some days you feel invincible, ready to take on anything. Other days, you’re lying in bed at 2 AM, wondering if you’re making all the wrong choices.
Here’s something nobody tells you: everyone feels this way. The difference between people who thrive in their 20s and those who just survive? They ask themselves the right questions.
Questions have this incredible power to cut through the noise and get you thinking about what actually matters. So let’s talk about the ones that can genuinely change how you spend this decade.
Questions to Ask Yourself in Your 20s
These aren’t the kind of questions you answer once and forget about. They’re the ones worth revisiting every few months, because your answers will shift as you grow.
1. What does success actually mean to me?
Stop for a second. When you picture “making it,” what do you see?
Is it a corner office with a view, or maybe it’s working from a beach in Bali? Is it having a packed calendar, or having the freedom to say no to things that drain you? Your parents might think success looks one way. Instagram might show you another version. Your college friends probably have their own ideas. But what matters is your definition.
I’ve met people who climbed the ladder their entire 20s, checked all the “success” boxes, and hit 30 realizing they were living someone else’s dream. That’s a tough place to be. Write down what success means to you right now, even if it feels different from what you thought it would be. Even if it seems small or weird or not impressive enough. This is your baseline. Everything else stems from this.
2. Am I spending time with people who make me better?
Look at the five people you spend the most time with. Do they challenge you? Support you? Make you laugh until your stomach hurts?
Or do they constantly complain, pull you into drama, or make you feel smaller than you are? This isn’t about being ruthless or cutting people off. It’s about being honest. The company you keep shapes who you become. If everyone around you is stuck, chances are you’ll stay stuck too. If they’re growing, learning, trying new things, that energy becomes contagious.
Pay attention to how you feel after spending time with different people. Energized or drained? Inspired or discouraged? Your gut knows the answer before your brain does.
3. What am I learning right now that has nothing to do with my job?
Your job skills matter. But they’re not everything.
Maybe you’re learning to cook something more complex than pasta. Or you’re finally understanding how investing works. Perhaps you’re teaching yourself guitar or getting into photography. Learning something just because it interests you keeps your brain flexible. It reminds you that you’re more than your job title.
Research from MIT shows that people who maintain diverse interests and hobbies report higher life satisfaction and better problem-solving abilities at work. That’s because different types of learning connect in unexpected ways. The patience you develop learning an instrument might help you handle a difficult client. The creativity you tap into while painting might solve a work problem you’ve been stuck on for weeks.
Give yourself permission to be a beginner at something. The awkwardness of not being good at something yet? That’s where growth happens.
4. How much of my day am I spending on autopilot?
You wake up, scroll your phone, rush to work, sit in meetings, come home exhausted, watch Netflix, sleep, repeat.
Sound familiar? Autopilot is comfortable, but it’s also how you lose years without realizing it. Try this: for one week, track how you spend each hour. Not to judge yourself. Just to see. Most people are shocked when they realize they spend three hours a day on social media but “don’t have time” for things they claim to care about.
The patterns you build now become the life you live. Small daily choices compound. Spending 30 minutes a day reading means 182 hours a year. That’s the equivalent of a full-time work month. Imagine what that could do for your knowledge, your career, your mindset.
5. What would I do if I wasn’t afraid of looking stupid?
Fear of embarrassment stops more dreams than fear of failure ever could.
Maybe you’d start that blog. Take an improv class. Ask someone on a date. Apply for a job that feels slightly out of reach. Switch careers entirely. But the fear of what people might think keeps you frozen. Here’s a reality check: most people are too busy worrying about their own stuff to judge you as harshly as you think. And the ones who do judge? They’re usually not the people whose opinions should matter to you anyway.
Think about someone you admire. Chances are, they’ve looked stupid countless times. They just kept going.
6. Am I saving money, and if not, why not?
Money in your 20s feels tight. Rent eats a huge chunk. Student loans loom. You want to actually enjoy life too. I get it.
But here’s the thing about compound interest: it rewards people who start early. Even $50 a month invested from age 25 to 35 (that’s just $6,000 total) can grow to over $23,000 by age 65. If you wait until 35 to start, you’d need to invest triple that amount to end up in the same place.
You don’t need to be perfect. You need to start. Set up automatic transfers so saving happens before you have a chance to spend. Pay yourself first. Future you will be incredibly grateful. If you genuinely can’t save right now, ask yourself what would need to change to make it possible. More income? Lower expenses? Different priorities? Identifying the specific barrier is the first step to solving it.
7. What’s one thing I’m tolerating that I shouldn’t be?
That friend who only calls when they need something. The job that makes you miserable every Sunday night. The apartment that’s cheap but makes you feel unsafe. The relationship that stopped feeling good months ago.
Tolerating things slowly erodes your self-respect. You start believing this is just how life is. That you don’t deserve better. That speaking up is too hard. But here’s the truth: every time you tolerate something you shouldn’t, you’re teaching people (including yourself) that your boundaries don’t matter.
You’re allowed to want more. You’re allowed to say this isn’t working. You’re allowed to change your mind about what you’ll accept. Start small if you need to. Address one thing. See how it feels to stop settling.
8. Who do I need to forgive (including myself)?
Carrying resentment is like drinking poison and expecting the other person to get sick. It doesn’t hurt them. It hurts you.
Maybe someone betrayed you. A parent let you down. A friend disappeared when you needed them. Or maybe you’re the one you can’t forgive because you made a mistake, missed an opportunity, or hurt someone you care about. Forgiveness doesn’t mean what happened was okay. It means you’re done letting it take up space in your head.
This might be the hardest question on this list. But it’s also the most freeing. Therapy helps. So does journaling. So does simply deciding that today, you’re going to try letting go of one small piece of the anger or guilt you’ve been carrying. You deserve that lightness.
9. What does my typical day say about my priorities?
You say health is important, but you haven’t exercised in three months. You say relationships matter, but you haven’t called your best friend in weeks. You say you want to write a book, but you spend two hours a night watching shows you barely remember.
Your calendar and your bank statement tell the truth about your priorities. Not your intentions. Not your wishes. Your actual choices. This isn’t about judgment. It’s about alignment. If there’s a gap between what you say matters and how you spend your time and money, something needs to shift. Either your priorities need to change, or your daily habits do.
10. Am I building skills that will matter in 10 years?
Technology changes. Industries shift. Companies go under. But certain skills stick with you forever.
Can you communicate clearly in writing? Can you learn new things quickly? Can you manage your emotions under pressure? Can you work well with people who are different from you? These abilities matter whether you’re in tech, healthcare, finance, or anything else. They travel with you across careers and industries.
Think about where your field is heading. What skills will be valuable? What’s becoming automated? A study by the World Economic Forum found that by 2025, 50% of all employees will need reskilling. The question isn’t whether you’ll need to learn new things. It’s whether you’re building the foundation that makes learning easier. Stay curious. Stay adaptable. That’s your insurance policy.
11. What brings me genuine joy, not just distraction?
Netflix after a long day? That’s fine. But it’s distraction, not joy.
Joy is different. It’s that feeling when you’re so absorbed in something that you lose track of time. When you finish and feel more alive, not more numb. For some people, it’s creating something with their hands. For others, it’s being in nature. Or having deep conversations. Or solving complex problems. Or making people laugh.
Your 20s are busy. You’re tired. Distraction is easier than joy because joy requires something from you. But a life built on distraction leaves you feeling empty. A life punctuated by genuine joy? That’s what makes the hard parts worth it. Identify what brings you real joy and protect time for it like you’d protect a meeting with your boss. It matters that much.
12. What story am I telling myself about why I can’t do something?
“I’m too old to start.” “I don’t have the right degree.” “I’m not creative.” “I’m bad with money.” “I’m just not a morning person.”
These stories feel true because you’ve repeated them so many times. But they’re often just comfortable excuses. Test them. What if they’re wrong? What if you could learn to manage money? What if creativity is a skill you can develop? What if starting at 27 instead of 22 doesn’t actually matter?
Look for evidence against your limiting beliefs. Find one person who proves the story false. Then ask yourself what becomes possible if you stop believing it. Sometimes the story is the only thing holding you back.
13. How am I taking care of my body?
Your body in your 20s is resilient. You can eat terribly, skip sleep, never exercise, and mostly get away with it. Until suddenly, you can’t.
The habits you form now set the trajectory for the next 60 years. You don’t need to be perfect. You don’t need to run marathons or eat kale for every meal. But moving your body regularly, eating mostly real food, and getting decent sleep? These aren’t optional extras. They’re the foundation everything else is built on.
Poor health will limit every other dream you have. Your 40-year-old self will either thank you or resent you for the choices you’re making right now. Which one do you want it to be?
14. What relationship needs more attention?
Life gets busy. You mean to call. You mean to visit. You mean to reach out. Then months pass and the distance grows.
Maybe it’s your parents getting older. Siblings you’ve drifted from. A friendship that used to mean everything. Your partner who’s right next to you but somehow feels far away. Relationships are like plants. They need tending. Neglect them long enough and they die, even the ones you thought were permanent.
Pick one relationship that matters. Reach out today. Not tomorrow. Not when things calm down. Today. Send a text. Make a call. Schedule time together. The people you love won’t be here forever. Neither will you.
15. What’s my relationship with failure?
Do you avoid it at all costs? Let it crush you? Pretend it doesn’t hurt? Get defensive and blame others?
Your relationship with failure might be the single biggest factor in how far you go. People who treat failure as feedback get better. People who treat it as a verdict about their worth stay stuck. Every successful person you admire has failed repeatedly. The difference is they kept going.
Start reframing. “This didn’t work” is different from “I’m a failure.” “I need to try a different approach” is different from “I should give up.” Small shifts in how you think about setbacks change everything. Failure is data. Use it.
16. Am I living for today or sacrificing everything for tomorrow?
Some people spend their 20s grinding nonstop, sacrificing health, relationships, and happiness for a future that might never come. Others live so completely in the moment that they wake up at 30 with nothing to show for the decade.
The balance is hard. You need to build for the future while also actually living now. That means saving money but also taking the trip. Working hard but also maintaining friendships. Planning ahead but also being present. There’s no formula that works for everyone.
Ask yourself regularly: am I building a life I’ll want to live in 10 years? Am I also enjoying the life I have right now? If either answer is no, something needs adjusting.
17. What do I need to let go of from my past?
Old versions of yourself. Expectations that no longer fit. Grudges. Regrets. Identities you’ve outgrown. Ideas about who you’re supposed to be.
Letting go is hard because it feels like loss. But sometimes you need to release what you’re clinging to before you can grab onto something better. That dream you’ve been chasing since college but secretly stopped caring about? Let it go. The person you thought you’d become but realize you don’t want to be? Let them go.
You’re allowed to change. You’re allowed to want different things than you wanted five years ago. The past only has as much power as you give it. Choose what you bring forward and what you leave behind.
18. Who am I comparing myself to, and is it helpful?
Social media makes comparison inevitable. Everyone’s highlight reel is on display. That person from high school just bought a house. Your friend got promoted. Someone you barely know is traveling through Europe.
Comparison in small doses can motivate you. In large doses, it makes you miserable. Here’s what helps: compare yourself to yourself. Are you further along than you were last year? Have you grown? Learned something new? Made progress on what matters to you? That’s what counts. Someone else’s chapter 20 might look better than your chapter 8. But you’re reading different books. Let them be.
19. What’s one brave thing I could do this year?
Not reckless. Brave.
Brave is speaking up when it’s uncomfortable. Setting a boundary with someone you love. Quitting a job that’s slowly killing your spirit. Starting therapy. Admitting you need help. Trying something you might fail at. Choosing yourself even when people disagree.
Your 20s are meant for taking risks while the stakes are still relatively low. You likely don’t have kids depending on you or a mortgage tying you down. This is your time to be brave. To try. To fail. To get back up. What’s the brave thing you keep thinking about but haven’t done? That’s probably your answer.
20. What do I want my 30-year-old self to look back and feel?
Pride? Relief? Gratitude? Or regret?
Picture yourself at 30 looking back at this exact moment. What would you want to have done? What risks would you want to have taken? What relationships would you want to have invested in? What would you want to have learned?
This perspective shift helps you see past the immediate discomfort of hard choices. Yes, having a tough conversation is uncomfortable. But 30-year-old you will be glad you did. Yes, saving money means sacrificing now. But 30-year-old you will be relieved you started. Living for future you’s approval is one of the most powerful motivators there is. They’re counting on you. Don’t let them down.
Wrapping Up
Your 20s are messy. They’re confusing. They’re full of questions that don’t have easy answers. But that’s exactly the point. The people who spend this decade asking themselves hard questions end up building lives they actually want to live. The ones who avoid the questions wake up at 30, wondering where the time went.
You don’t need to have everything figured out. You just need to keep asking, keep adjusting, and keep moving toward the person you want to become. These questions will guide you if you let them.
Start with one. Just one. See where it takes you.