3 Questions That Will Make You Rethink Your Life

Life has a way of pulling us forward on autopilot. We get caught up in routines, chase the next promotion, and follow paths that once made sense but may no longer serve us. Sometimes we need to hit pause and ask ourselves the hard questions—not the ones with easy answers, but the ones that make us uncomfortable enough to change.

These three questions have the power to cut through the noise and help you see where you stand. They're worth revisiting regularly, especially when you feel like you're drifting rather than steering your ship.

1. If money weren't a factor, how would your life and work change?

Imagine you had all the financial security you could ever want. What would you do with your days? How would you spend the 40+ hours a week you currently dedicate to work?

This isn't just a daydream exercise—it's a reality check. You spend almost half your waking life at work, so it should bring you at least some satisfaction. I remember something a coworker told me during a seasonal job years ago: "You can't have a stressful job, because that means you'll be stressed almost all the time." It was such a simple observation, but it stuck with me.

Of course, financial security matters. It's completely reasonable to take a job that provides stability and pays the bills. But here's where things get tricky: sometimes we achieve that security and keep chasing more—more money, more status, more responsibilities we don't need. We convince ourselves each promotion is necessary when really, we're just trading away our time and energy for money we already have enough of.

The sunk cost fallacy loves to whisper in our ear: "You've come this far, you can't stop now." But what if stopping—or at least redirecting—is exactly what you need?

2. Would your current self be a role model for your younger self?

Think back to who you were at 15 or 16. Would that teenager look up to who you are today? Would you want your kids to follow the path you're on?

This question cuts deep because it's asking: Are you proud of who you've become? Is your life built on integrity, or are you carrying around a quiet sense of shame about the compromises you've made?

Too many of us live in a constant state of "someday." We tell ourselves: "Right now I need to do X, Y, and Z, but once I get through this busy period, once I hit that milestone, once I solve these problems, then I'll have time to become the person I always wanted to be."

But what if that problem-free future never comes? What if the person you're becoming right now, in this messy, imperfect present, is actually who you are?

Your younger self had dreams and values that felt crystal clear. Somewhere along the way, life got complicated. But underneath all that complexity, those core values are probably still there, waiting for you to remember them.

3. What do you deeply regret, and what would you do differently?

When you look back over the last 10 years, what stands out? Not the day-to-day blur of meetings and obligations, but the moments that mattered—both the ones you're proud of and the ones that still sting.

There's a saying that goes something like this: "You probably won't remember how many hours you spent at the office, but your kids definitely will." It's a harsh truth, but an important one. The things we think are so urgent and important in the moment often fade from memory, while the relationships and experiences we neglect leave lasting gaps.

Here's the thing about regret: it's not just a painful emotion to endure—it's information. If you regret something now, there might still be time to change course. The sunk cost fallacy wants you to believe you're too far down one path to start another, but that's rarely true.

Maybe you can't undo the past, but you can decide what the next 10 years will look like. You can choose to forgive yourself for the mistakes and start making different choices today.

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These questions aren't meant to send you into a spiral of self-doubt or regret. They're meant to wake you up. To help you see where you might be sleepwalking through your own life and permit you to make changes—even big ones—if that's what your honest answers are telling you to do.

The goal isn't perfection. It's alignment. It's making sure that the life you're building is the one you want to live.