Good judgment comes from experience and experience comes from bad

The city lights blinked in the distance, casting long, crooked shadows across the room where Jack and Jeeny sat. The faint sound of traffic and the occasional horn echoed in the background, but inside, there was an almost serene quiet — the kind that only comes after a long day of words shared, of thoughts processed. Jeeny was sitting on the couch, her legs tucked beneath her, while Jack leaned against the window, looking out at the skyline, his face thoughtful but distant.

Host: The room felt still, yet there was an undeniable tension, a weight in the air between them, not because of anything said, but because of what was left unspoken. The evening stretched out, just a moment of pause before they dove into a conversation neither of them knew they were about to have.

Jeeny: “I was thinking about what Fred Brooks said: ‘Good judgment comes from experience and experience comes from bad judgment.’ Do you think that’s true, Jack? Do you think we really need to make mistakes to learn how to make better choices?”

Jack: He turned from the window, his eyes narrowing slightly as he processed the question. “I mean, I think it makes sense. Most of what I’ve learned, I learned by screwing up. The times I’ve failed, they’ve been the moments that taught me the most. But it’s hard to say if you need bad judgment. I mean, it feels like there should be a better way to learn, right? Why can’t we just learn from other people’s mistakes?”

Jeeny: She smiled softly, her gaze steady and calm. “I think that’s the thing, Jack. We can learn from other people’s mistakes, but we don’t always. It’s one thing to hear about someone else’s bad judgment and think you’ll avoid it. It’s another to face those same decisions yourself. Experience comes with a cost, but it’s also what shapes our judgment. When we make mistakes, we understand the value of making better choices.”

Jack: “But what if the mistakes are too big? What if the cost of bad judgment is too high? You can’t always just bounce back from everything. Some mistakes can ruin things forever.” His voice had a slight edge to it now, the familiar frustration surfacing again. “I don’t know if I can agree with the idea that we need to make mistakes to get better. Bad judgment can leave scars.”

Jeeny: “I don’t think Fred Brooks is saying that we should go out and make mistakes just for the sake of it. What he’s saying is that we learn through our mistakes because it’s through those moments that we really understand the consequences of our choices. Yes, some mistakes have bigger consequences than others, but it’s the very act of making a choice and seeing how it unfolds that shapes the judgment we have for future decisions.”

Jack: He sighed, walking over to the table and running his hand over the edge of the wooden surface. “I get that, but it feels like I’ve been learning the same lessons over and over again. It feels like I should have figured it out by now. Sometimes I think I’ve learned the right things, but then something comes along, and I feel like I’ve missed something crucial. So, maybe I’m just not good at making decisions in the first place.”

Jeeny: She stood up, moving closer to him, her voice softer now but filled with a quiet strength. “You’re not alone in that, Jack. Good judgment isn’t about being perfect. It’s about being willing to grow, to understand that every mistake doesn’t define you. The experience you gain from bad judgment doesn’t make you worse, it makes you wiser. It’s like we’re all just trying to figure it out as we go. The key is to stay open to learning, even when the lessons are hard.”

Host: The room felt a little less heavy now, the weight of their conversation shifting just slightly. The uncertainty still lingered, but it was no longer as oppressive. Jack stood still, his hands loosely folded in front of him, the beginnings of an understanding settling in, though it wasn’t complete yet. Jeeny’s words were beginning to break through the walls he’d built around his frustration, and the truth was slowly starting to seep in.

Jack: “I don’t think I ever really gave myself credit for what I’ve learned. Maybe it’s not about avoiding mistakes — maybe it’s about understanding that the lessons are part of the process, even when they suck.” He gave a small, almost reluctant chuckle, as if realizing something he hadn’t wanted to face. “Maybe I need to stop being so hard on myself.”

Jeeny: She smiled, her eyes filled with a quiet pride. “Exactly. We’re all just doing the best we can with the experiences we have. The important thing is to keep moving forward, knowing that every step, every choice, is part of what helps us grow. Good judgment isn’t about being perfect, it’s about being willing to learn and adapt.”

Host: There was a moment of quiet between them, a silence that wasn’t filled with uncertainty but with something gentler, something more accepting. The world outside continued, but inside the room, something had shifted. Jack didn’t have all the answers yet, but the weight of his frustration had lightened. He didn’t have to be perfect. He just had to keep moving forward.

Jack: “Yeah. I think I can live with that. It’s about progress, not perfection.”

Jeeny: “Exactly.”

Host: The evening wore on, and as the conversation turned to lighter topics, a shift had quietly taken place. Jack’s frustration had found a quieter space, replaced by the understanding that mistakes weren’t failures. They were part of the journey, part of learning what it meant to make better choices. He wasn’t alone in the struggle. None of them were. The path to good judgment was one of trial and error, but each step, each experience, brought them closer to becoming the best versions of themselves.

The night wrapped around them, a quiet witness to the change unfolding within.