Most of us go through months like we’re on autopilot. Days blend together, weeks disappear, and before you know it, another month has slipped by without you really paying attention. You wake up, handle your responsibilities, react to whatever comes your way, and repeat.
But here’s what happens when you pause and actually check in with yourself: you start making choices instead of just reacting to life. You spot patterns you’d been missing. You stop drifting and start steering.
Taking time each month to ask yourself the right questions changes everything. It’s like having a monthly meeting with the person who matters most—you.
Questions to Ask Yourself Every Month
These questions will help you reflect, recalibrate, and move forward with more clarity and intention. Think of them as a personal check-in system that keeps you honest and on track.
1. What Made Me Genuinely Happy This Month?
This isn’t about what should make you happy or what looks good on social media. What actually lit you up? Maybe it was a quiet morning with your coffee before anyone else woke up. Maybe it was finishing a project that had been hanging over your head. Maybe it was a random Tuesday conversation that made you laugh until your stomach hurt.
Pay attention to these moments because they’re breadcrumbs showing you what feeds your soul. When you know what genuinely brings you joy, you can build more of it into your life on purpose. Too many people chase happiness in all the wrong places because they’ve never stopped to notice where they actually find it.
2. What Drained My Energy the Most?
Energy vampires come in many forms. Sometimes it’s a person who always needs something from you. Sometimes it’s a commitment you said yes to but regret. Sometimes it’s your own thought patterns eating away at your peace.
Identifying what drains you isn’t about complaining. It’s about protecting your most valuable resource. You only have so much energy in a day, and if you’re constantly pouring it into black holes, you’ll have nothing left for what actually matters. Once you spot the drains, you can start setting boundaries, saying no, or finding ways to minimize their impact.
3. Am I Spending Money in Alignment With My Values?
Look at your bank statement from the past month. Does your spending reflect what you say matters to you? If family is your top priority but you spent more on impulse purchases than on experiences with loved ones, there’s a disconnect. If health is important but you’re spending hundreds on takeout while your gym membership goes unused, something’s off.
Your money shows your real priorities, not your stated ones. This question isn’t about judgment—it’s about honesty. When your spending aligns with your values, you feel better about every dollar that leaves your account. When it doesn’t, you end up with buyer’s remorse and a nagging sense that something’s wrong.
4. Which Relationship Needs More Attention?
Relationships don’t maintain themselves. They fade when you stop feeding them. There’s probably someone in your life right now who deserves more of your time and attention than they’re getting.
Maybe it’s your partner who’s been patient while you’ve been buried in work. Maybe it’s your best friend who keeps texting but you’ve been too busy to respond properly. Maybe it’s your kid who’s been asking to do something together. Whoever comes to mind when you ask this question—that’s your answer. Reach out this week. Don’t wait until the relationship shows cracks before you patch it up.
5. What’s One Thing I Learned About Myself?
Self-knowledge compounds over time, but only if you’re paying attention. This month taught you something about who you are—how you react under pressure, what triggers you, what you’re capable of, where your limits are.
Maybe you learned you’re more resilient than you thought. Maybe you discovered a pattern where you self-sabotage right before success. Maybe you realized you need more alone time than you’ve been allowing yourself. These insights are gold. Write them down. They help you make better decisions going forward because you’re working with accurate information about yourself instead of outdated assumptions.
6. Am I Moving Closer to or Further From My Goals?
Be brutally honest here. Goals don’t achieve themselves through good intentions. They require consistent action in the right direction.
If you set a goal to get healthier but you’ve been skipping workouts and eating poorly, you’re moving backwards. If you wanted to save money but your account balance is lower than last month, the gap is widening. But if you’ve been taking even small steps toward what you want—reading books in your field, having difficult conversations, building new habits—then you’re on track. The key is measuring reality against intention. Most people avoid this question because they don’t want to face the truth, but facing it is exactly what helps you course-correct.
7. What Would I Do Differently If I Could Redo This Month?
Regret is only useful if it teaches you something. Looking back at the past month, what would you change? Maybe you’d speak up in a situation where you stayed quiet. Maybe you’d rest instead of pushing through exhaustion. Maybe you’d skip that argument that went nowhere. Maybe you’d take a risk you chickened out on.
You can’t redo the past, but you can apply these lessons to your future. Each “what I’d do differently” becomes a “what I’ll do next time.” That’s how you grow instead of just repeating the same patterns and wondering why nothing changes.
8. Who Did I Help, and Who Helped Me?
Life isn’t meant to be a solo mission. This question reminds you that you’re part of a web of mutual support. Think about the ways you showed up for others this month—the advice you gave, the favor you did, the shoulder you offered.
Then flip it around. Who showed up for you? Who made your life easier, better, or brighter? Gratitude and generosity both grow stronger when you acknowledge them. Plus, noticing patterns here tells you a lot. If you’re always helping but never receiving, you might be blocking support. If you’re always receiving but never giving, you might need to step up. Balance matters.
9. What’s Taking Up Too Much Mental Space?
Your brain has limited bandwidth, and some things rent space in your head without paying their dues. Maybe you’re replaying an awkward conversation from two weeks ago. Maybe you’re worrying about something that hasn’t happened and might never happen. Maybe you’re carrying resentment from years ago that serves no purpose now.
Mental clutter is as draining as physical clutter. When you identify what’s hogging your headspace, you can decide if it deserves to be there. Most of the time, it doesn’t. You can’t always control what enters your mind, but you can control what you let stay there.
10. Am I Saying “Yes” to Things I Should Decline?
Your default response to requests probably needs an update. Many people say yes out of guilt, obligation, fear of missing out, or a desire to please everyone. Then they wonder why they’re exhausted and resentful.
Every yes to something that doesn’t serve you is a no to something that does. When you say yes to that committee you don’t care about, you’re saying no to time with your family. When you say yes to plans you dread, you’re saying no to rest you need. Start getting picky about your yeses. Your future self will thank you.
11. What Habit Is Serving Me Well?
Not all your habits are bad. Some are quietly making your life better without you giving them much credit. Maybe you’ve been consistent with morning movement. Maybe you’ve been reading before bed instead of scrolling. Maybe you’ve been meal prepping on Sundays. Maybe you’ve been texting your mom every week.
Acknowledge what’s working. These positive habits are your foundation, and recognizing them helps you protect them when life gets busy. Too often, the good stuff is the first thing to go when pressure hits. When you know which habits are serving you, you fight to keep them.
12. What Habit Needs to Go?
On the flip side, something you’re doing regularly is probably making your life worse. Maybe it’s checking your phone first thing in the morning and spiraling into anxiety before your feet hit the floor. Maybe it’s staying up too late binge-watching shows you don’t even enjoy. Maybe it’s complaining about the same problems without doing anything to fix them.
Bad habits stick around because they’re comfortable, familiar, or fill a need (even if it’s a need they created). But they’re costing you—in time, energy, health, or opportunity. Pick one to work on. Just one. You don’t need to overhaul everything at once. Small changes compound into big results when you stick with them.
13. Am I Getting Enough Rest?
Rest isn’t a reward for productivity. It’s a requirement for being human. Yet we treat it like a luxury we can’t afford until everything else is done. Spoiler alert: everything else is never done.
Look at the past month honestly. How’s your sleep? Are you taking breaks during the day or powering through until you crash? Are you giving yourself actual downtime or just different forms of stimulation? Your body keeps score, and exhaustion builds up over time. You might be functioning on fumes without realizing it because you’ve normalized being tired. Rest is how you recharge. Without it, everything else suffers.
14. What Progress Am I Celebrating (Even Small Wins)?
You’re probably doing better than you think. We’re wired to focus on what’s wrong, what’s missing, and what still needs fixing. This negativity bias helped our ancestors survive, but it makes us overlook the good stuff happening right now.
Did you handle something better than you would have six months ago? That’s progress. Did you stick with something even when it was hard? That’s progress. Did you try something new, learn something, or improve in any measurable way? That’s progress. Celebrating small wins isn’t about lowering standards. It’s about acknowledging reality and building momentum. Progress fuels more progress, but only if you notice it.
15. What Fear Am I Avoiding?
Fear is a liar, but it’s a convincing one. There’s something you’re scared of right now, and instead of facing it, you’re probably distracting yourself, procrastinating, or pretending it doesn’t exist.
Maybe it’s fear of rejection, so you’re not putting yourself out there. Maybe it’s fear of failure, so you’re not starting that project. Maybe it’s fear of being vulnerable, so you’re keeping people at arm’s length. Maybe it’s fear of success and the changes that would bring. Whatever it is, avoidance only makes the fear grow bigger. Naming it shrinks its power. You don’t have to conquer it today, but you do need to acknowledge it’s there.
16. How’s My Physical Health?
Your body isn’t just a vehicle for your brain. It affects everything—your mood, your energy, your clarity, your confidence. But it’s easy to ignore physical health until something breaks down.
How are you actually feeling? Not “fine” as a reflex answer, but truly feeling. Are you dealing with aches and pains you’ve been brushing off? How’s your energy level throughout the day? When’s the last time you saw a doctor or dentist? Are you moving your body in ways that feel good? Your physical health deserves regular check-ins, not just emergency intervention when something goes seriously wrong.
17. Am I Learning or Just Consuming?
There’s a difference between learning and consuming. Consuming is passive—scrolling through articles, watching videos, listening to podcasts without retention or application. Learning is active. It changes how you think or what you can do.
Think about all the content you took in this month. What actually stuck? What did you apply? What changed because of information you absorbed? If you can’t point to specific ways you’re different because of what you consumed, you’re probably just entertaining yourself while calling it self-improvement. Real learning involves discomfort, practice, and transformation. If it’s too easy and comfortable, you might not be learning much at all.
18. What Legacy Moment Did I Create?
Legacy isn’t just what happens after you die. It’s what you’re building right now in the small moments that make up your days. A legacy moment is any time you do something that matters beyond yourself—something people will remember, something that makes a difference, something that reflects who you want to be.
Maybe you taught your kid something important. Maybe you stood up for someone who needed it. Maybe you created something meaningful. Maybe you showed kindness to a stranger who was having a terrible day. These moments add up. They’re what people remember about you. They’re what you’ll remember about yourself when you look back. If you can’t think of any from this month, that’s information. Make one happen this week.
19. If I Died Today, What Would I Regret Not Doing?
This question cuts through all the noise. Most of what we stress about daily doesn’t matter in the big picture. But some things do matter, and we keep putting them off because “someday” feels safer than “now.”
Would you regret not telling someone you love them? Not taking that trip? Not starting that business? Not mending that relationship? Not being more present with your kids? Not pursuing your creative dreams? Whatever comes to mind—that’s what deserves your attention. You probably won’t die today, but you’re not guaranteed tomorrow either. Stop living like you have unlimited time to do the things that actually matter.
20. What’s One Bold Move I Can Make Next Month?
Steady progress is great, but sometimes you need to shake things up. What’s one thing you could do next month that would stretch you, scare you a little, and potentially change your trajectory?
Maybe it’s having a difficult conversation you’ve been avoiding. Maybe it’s applying for a job that feels slightly out of reach. Maybe it’s ending something that’s no longer serving you. Maybe it’s starting something you’ve been talking about for years. Bold moves don’t have to be huge—they just have to require courage. They’re the moments where you choose growth over comfort, possibility over safety. Pick one. Put it on your calendar. Do it scared.
Wrapping Up
These twenty questions aren’t meant to overwhelm you. They’re meant to keep you connected to yourself and your life in a real way. Pick a specific day each month—maybe the last Sunday, maybe the first morning after payday—and sit down with these questions.
Some months you’ll breeze through them. Other months, certain questions will hit hard and require more time.
The magic happens when you do this consistently. Patterns emerge. You see yourself more clearly. You make better choices because you’re actually paying attention to what’s working and what’s not. Life stops happening to you and starts happening with you.