I really don't think life is about the I-could-have-beens. Life

Host: The evening was settling in, the soft glow of the city lights reflecting off the window as the last traces of daylight slipped away. Inside, the quiet hum of a small café filled the space, the distant clinking of cups and low murmurs of conversation drifting through the air. Jack sat back in his chair, a half-drunk coffee in front of him, his fingers absentmindedly tracing the rim of his cup. Jeeny sat across from him, the glow of her phone illuminating her face, but there was something in her gaze — a quiet anticipation, as though she was waiting for something.

Host: Finally, Jack looked up, his eyes a little more thoughtful, his voice tinged with a new weight.

Jack: “You ever hear that quote by Nikki Giovanni? ‘I really don’t think life is about the I-could-have-beens. Life is only about the I-tried-to-do. I don’t mind the failure but I can’t imagine that I’d forgive myself if I didn’t try.’ It’s been on my mind lately. I keep thinking about all the things I’ve wanted to do, but haven’t. All the things I keep putting off because I’m afraid of failing. But then, reading this... I don’t know, it makes me wonder if I’m just holding back for no reason.”

Jeeny paused, her eyes lifting from the screen of her phone to meet his, her expression softening with understanding.

Jeeny: “It’s like she’s saying that the worst thing isn’t failing — it’s not trying at all. Failure can be a lesson, something you can grow from. But the regret of never giving something a shot? That’s harder to carry. It’s a weight that you can’t shake off. We all have those things we want to do, but the fear of failing keeps us stuck.”

Host: The low buzz of the café seemed to fade as their conversation took center stage. The words felt heavy, like they were hanging in the air, asking to be understood. Jack leaned forward, his gaze steady but touched with the quiet frustration of someone who knew the truth but hadn’t yet embraced it.

Jack: “Yeah, but what about when failure feels like a sign that you just weren’t meant to do it? Sometimes, it feels like failing is the universe’s way of telling you, ‘This isn’t for you.’ How do you separate that from just being afraid of trying?”

Jeeny’s eyes softened, her voice gentle but firm as she spoke, as though she had been grappling with this truth herself.

Jeeny: “I think failure is part of the process. Not every failure means you weren’t meant to do something. Sometimes, it means you need to adjust, learn, and rethink your approach. You don’t really know if something’s not for you until you give it a shot. And it’s not about the end result; it’s about whether you tried at all. Regret is about looking back and wondering, ‘What if?’ Not about, ‘I gave it my all and it didn’t work out.’"

Host: The dim light in the café seemed to warm, and Jack sat back slightly, as if trying to let her words sink in. The quiet clink of a spoon against a cup echoed briefly between them before he spoke again, his voice a little more open, but still tinged with hesitation.

Jack: “But what if the risk is too big? What if trying means that everything you’ve worked for could collapse, or that you end up in a place you didn’t want to go? It’s easy to say ‘try,’ but sometimes the consequences feel too heavy.”

Jeeny paused, her gaze steady and full of understanding, but her voice was clear, measured.

Jeeny: “I get that. The risk is real. But sometimes you have to ask yourself: what’s the real consequence of not trying? Living in a constant state of ‘what if’ can eat away at you. It’s like being stuck in a loop of unanswered questions. If you fail, you move on, you grow. But if you don’t try, you never even get the chance to discover what you could be capable of.”

Host: Jack’s fingers rested on the edge of his cup, his eyes distant as he considered her words. The quiet rhythm of their conversation felt like the slow build of something — a shift that was coming, but wasn’t quite there yet. He let the silence sit for a moment before speaking again, his voice quieter, more thoughtful.

Jack: “I guess the truth is, I’m afraid of missing out. I’m afraid that I’ll get to the end of this and look back and wonder, ‘What if I’d just tried? What if I’d taken that risk?’ I think the fear of failure is just a shield I hide behind, because it’s easier than facing the possibility of regret.”

Jeeny’s eyes softened, and her voice was filled with quiet compassion, but also firmness.

Jeeny: “And I think that’s exactly why Nikki Giovanni’s quote resonates so much. It’s not about perfection; it’s about action. Life isn’t about the I-could-have-beens, because those are just empty spaces filled with fear. The I-tried-to-do is where the real growth happens — even if it leads to failure. The real mistake is in not trying at all.”

Host: The room was still, the light from the streetlamps outside casting long shadows on the floor. Jack sat back, the weight of her words settling in the space between them. The sound of the world outside seemed to disappear as he finally let out a long, deep breath, as though a heavy weight had been lifted off his chest.

Jack: “You’re right. It’s about trying, not about always succeeding. If I don’t try, I’ll never know what could have been. I don’t want to live with that kind of regret.”

Jeeny: “Exactly. The only failure is not trying. Everything else is just part of the journey.”

Host: The quiet in the café felt more peaceful now, as if the tension between their words had dissipated, leaving a sense of shared understanding. Outside, the lights of the city flickered, a soft glow against the darkening sky. Inside, Jack sat a little lighter, as if the burden of regret had been lifted, and he was finally ready to try.