The Trouble with Having Things Figured Out

 When I was a kid, all I wanted was to have life figured out. Adults seemed like they had all the answers, and I craved that kind of confidence and control.

The more I learned, the more I convinced myself I knew. I developed a habit of acting like I had all the answers—even when I didn’t. By the time I was 20, I thought I had life figured out. 

But life has a funny way of showing you otherwise. Experience quickly revealed that many of my so-called answers were wrong. And yet, even now, I sometimes catch myself pretending to know more than I do.

The truth is, we all love that feeling of certainty. It’s comforting. But the trouble with feeling like you’ve got things figured out is that it can trap you, closing off possibilities you don’t even see.

The 3-Card Monte: A Lesson in Confidence

You’ve probably seen the 3-Card Monte, maybe on a street corner or in a movie. The premise is simple: the dealer lays down three cards and mixes them up. Your goal is to find the money card.

(Check out this quick version in my TEDx talk if you're not familiar)

But here’s the thing—it’s not really a game you can win. The 3-Card Monte is an old con game, where the “con” stands for confidence. The dealer’s job is to make you feel certain you can outsmart them. As your confidence builds, you lower your guard and bet your money. And that’s when you lose.

The same thing happens in life. We love the feeling of certainty, but it can blind us to what’s really happening. Overconfidence tricks us into thinking we’ve got things figured out—right before we get blindsided.

Three Ways Overconfidence Trips Us Up

1. It Stops Us from Asking Questions

I once spent hours stuck on a piece of writing, convinced I could figure it out alone. I resisted asking for help because I didn’t want to admit I was stuck. Finally, I asked a friend for feedback, and within minutes everything clicked.

How often do we sabotage our progress just to save face? We avoid asking questions or seeking feedback because it feels like admitting weakness. But by trying to prove we’ve got it figured out, we slow ourselves down.

2. It Builds Walls Between Us

Certainty can isolate us. We see it in the world today—people so convinced of their beliefs that they refuse to listen to others. I’ve lost friendships because I couldn’t admit I might be wrong. We’ve all had bosses or teachers who dismissed our ideas because they were sure they knew better.

When we act like we’ve got all the answers, we stop listening and learning from others. Instead of building connections, we put up walls.

3. It Blinds Us to Opportunities

We’re bad at predicting the future, but we love to think we can. Blockbuster once turned down the chance to buy Netflix for $50 million. Kodak shelved its own digital camera convinced that film was the future. Overconfidence made them blind to opportunities right in front of them.

What opportunities might you be missing because you’re too certain about one idea or another?

But What If Life Already Feels Uncertain?

For many people, the idea of embracing uncertainty might sound overwhelming. If your life already feels unpredictable—whether due to financial instability, personal challenges, or living in a world full of unknowns—the idea of inviting more uncertainty can feel like too much to bear.

I’m not suggesting you dive headfirst into chaos. This isn’t about adding more uncertainty to an already difficult situation. It’s about recognizing where overconfidence might be holding you back—and allowing just enough doubt to open up new possibilities.

You don’t need to question everything you know. But by allowing a little uncertainty, you make space for growth, discovery, and new opportunities.

Embracing Possibilities

Feeling like you’ve got things figured out gives you a sense of control, but it can also keep you stuck. On the flip side, getting comfortable with discomfort—learning to embrace a bit of uncertainty—can open up new possibilities you might not see otherwise.

The next time you catch yourself feeling certain, ask: “Am I missing something? Could I be wrong?” Step back, challenge your assumptions, and explore new perspectives.

You don’t need to live in a state of total self-doubt. But allowing a little uncertainty into your thinking can lead to a world of possibilities and opportunities you hadn’t considered.