I went to art school in Chicago for a year at Columbia College. I

Host: The soft clink of a spoon against a cup filled the background as Jack and Jeeny sat across from each other, the soft hum of the café surrounding them. Jack had been quiet for a while, his eyes focused on the steam rising from his coffee. Jeeny noticed the thoughtful look on his face, as though his mind was occupied with something more than just the present moment.

Host: After a brief pause, Jack looked up, his voice slow and deliberate, as if he was still sorting through his thoughts.

Jack: “I came across something today from Nico Tortorella. He said, ‘I went to art school in Chicago for a year at Columbia College. I had this whole master plan of getting into sustainable development and green architecture and construction, so I wanted to go to business school and then get my masters in construction and development.’ It made me think about how we often have these grand plans for our futures, these ideas of what we’re supposed to do — but then life takes us in unexpected directions. Is it okay to change course like that?”

Jeeny’s eyes softened with understanding as she leaned in slightly, her voice calm and thoughtful.

Jeeny: “I think it’s completely natural to change course. Life isn’t always a straight path, and sometimes we think we know what we want, but as we grow, we realize that maybe our true calling is something else. It’s okay to start with a certain plan — like going to art school or pursuing business — and then adapt when you discover new passions or understandings. The important thing is being open to those shifts, being flexible enough to embrace new opportunities as they come.”

Host: Jack nodded, clearly processing her words. He looked down at his coffee, the steam still rising in delicate spirals, and then back up at Jeeny, his expression thoughtful.

Jack: “But how do you know when it’s time to pivot? How do you know if you’re just giving up on a dream too soon, or if the new direction is the right one for you?”

Jeeny’s smile deepened, and she took a slow sip of her coffee before responding, her voice filled with quiet certainty.

Jeeny: “It’s not always clear when it’s time to pivot, but I think it comes down to self-awareness. Sometimes you have to step back and ask yourself if you’re still passionate about what you’re pursuing, or if you’re just holding onto a plan because it’s what you thought you were supposed to do. If a new direction excites you, if it aligns more with your values and goals, that’s when you start to realize it’s not about giving up, it’s about evolving. It’s about finding the path that feels authentic to you at that moment.”

Host: Jack leaned back in his chair, the thought clearly settling into his mind. The gentle background hum of the café seemed to fade as his thoughts deepened, and he turned to Jeeny, a small realization forming on his face.

Jack: “So, maybe it’s not about sticking rigidly to a plan, but about listening to yourself and adapting as you grow? Following the things that resonate with you, even if they weren’t part of the original plan?”

Jeeny nodded slowly, her eyes bright with quiet understanding.

Jeeny: “Exactly. Life isn’t about sticking to one vision if it no longer fits. It’s about being willing to evolve, to change course when necessary, and to trust that your journey will lead you to where you’re meant to be. Every experience, every shift, is a part of your growth. And sometimes, the new path can be even more fulfilling than the one you originally imagined.”

Host: Jack smiled, the weight of the conversation shifting as the realization took root. It wasn’t about staying locked into one direction but about embracing the twists and turns that come along the way. The world outside the café seemed to fade for a moment as Jack and Jeeny shared a quiet understanding — that life is as much about discovery and adaptability as it is about planning. The journey, it seemed, could be just as important as the destination.