Coffee Talk: Navigating Decisions and Life

Ben: Hey Liam, I’ve been noticing you pushing out those new projects lately. Every time I open my feed, you’ve got something new going on. How’s it all coming together?

Liam: Yeah, man, I’ve just been winging it a bit, you know? Not everything’s mapped out. Sometimes overthinking just ties you up in knots. You spend so much time planning that you miss the moment.

Ben: You’re always so gung-ho. I admire that. Meanwhile, I still like to think things through—really look at it from every angle before I take a single step. I need to know what I’m walking into.

Liam: Totally get that. Thinking things through is important, no doubt. But sometimes, if you get too caught up in the “what ifs,” you end up stuck. My rule of thumb? If it feels right, if it’s within my reach, I go for it. We’ll figure out the rest as we go. Cross that bridge when we get to it.

Ben: Man, you’ve got nerves of steel. I always find myself thinking, what if things go south? What’s the fallback? The Plan B?

Liam: Oh, don’t get me wrong—I’m not out here running around like a bull in a china shop. I do a quick scan of the situation, weigh the major risks. But if I wait around for a perfect plan, I’ll probably miss the opportunity. Life doesn’t always give you ideal conditions. Time doesn’t pause for you to draw up a 10-step strategy.

Ben: Yeah... I’ve definitely missed chances because I couldn’t stop thinking everything through. Paralysis by analysis, right? But the idea of just diving in, like you do—it still makes me nervous.

Liam: That nervousness? That’s human. But the fear of failure can’t be the thing that dictates your every move. You’re gonna fall sometimes. That’s inevitable. But you fall, you learn, you get back up. Of course, I only take the kinds of risks I know I can recover from. I’m not betting the house every time.

Ben: Makes sense. Nothing’s completely black and white. Being overly cautious or completely reckless—neither works long term.

Liam: Exactly. It’s about knowing when to pause and when to leap. Some moments demand preparation, sure. But others? You just have to go for it and trust that you’ll adjust on the fly. Adaptability is half the game.

Ben: But what happens when things don’t go the way you hoped? Do you ever look back and think, Maybe I should’ve thought this through more?

Liam: Yeah, sometimes. I’m human too. There are moments where I think, “Damn, maybe I could’ve handled that better.” But that pang of regret? That’s just feedback. I try not to dwell on it. Regret is only useful if it helps you grow. If not, it’s just noise.

Ben: I respect that mindset. You're action-oriented, but not impulsive. You move, but you’re always course-correcting.

Liam: That’s the goal. Make the best decision with what you’ve got, then own it. Good or bad, that choice is yours. I’d rather live with decisions I made, than regret the ones I was too afraid to make.

Ben: You know, hearing you talk like this makes me think… maybe I should stop waiting for the stars to align. Maybe I need to just take that leap sometimes. See where it takes me.

Liam: That’s the spirit. You don’t need to have it all figured out before you start. Just make sure you’re not blind to the risks—but don’t let those risks stop you. Take the shot, adjust your aim along the way.

Ben: Yeah. This chat’s been eye-opening. I’m still not wired exactly like you, but I think I could loosen up a bit. Try more, worry less.

Liam: We’re all learning as we go, man. None of us have it all together. We’re just figuring it out, step by step. Anyway, you up for another coffee?

Ben: Absolutely. Let’s go.