There are pros and cons of experience. A con is that you can't

Host: The office was quiet, almost too quiet — that eerie stillness that comes after a storm of meetings and half-drunk coffee cups. The city lights outside flickered like a pulse, beating through the glass walls of the corporate tower. It was Friday night, long past the hour of productivity, when only the ambitious or the haunted stayed behind.

Jack sat at his desk, his tie loosened, the screen glow illuminating his face in shades of fatigue and reflection. Jeeny leaned against the doorframe, holding a paper cup of cold coffee, watching him the way one watches a man caught between resolve and regret.

The air conditioner hummed, the clock ticked, and the city below never stopped moving, even when he did.

Jeeny: “Andrea Jung once said, ‘There are pros and cons of experience. A con is that you can’t look at the business with a fresh pair of eyes and as objectively as if you were a new CEO. Fire yourself on a Friday night and come in on Monday as if a search firm put you there. Can you be objective and make the bold change?’”
Jack: “Fire yourself? I’ve already been fired by worse people — myself included.”
Jeeny: “That’s not what she meant. She meant stepping outside your own habits, your own comfort — seeing your work like a stranger would.”
Jack: “Easier said than done. You spend ten years building something, and suddenly you’re supposed to pretend you didn’t. It’s like telling a parent to look at their child like a stranger.”

Host: The desk lamp flickered, casting a shifting glow across Jack’s face. His jaw was tense, his hands fidgeted with a pen, spinning it between thoughts. Jeeny moved closer, her voice steady, but her eyes soft.

Jeeny: “That’s exactly the problem — attachment. Experience teaches you how things work, but it also blinds you to how they could.”
Jack: “So you’re saying experience is a liability?”
Jeeny: “I’m saying it can be. It builds walls of certainty. Every ‘lesson learned’ becomes a law you never dare to break again.”
Jack: “And without those laws, you make rookie mistakes.”
Jeeny: “Sometimes mistakes are just unexplored innovations with bad timing.”

Host: The rain started, drumming lightly against the windows, as if the sky itself was applauding her point. Jack looked up, the reflection of raindrops dancing across his eyes, his expression unreadable — half-cynical, half-curious.

Jack: “You know, I used to be bold once. I remember making decisions in five minutes that others debated for months. I thought that was courage. Turns out it was ignorance.”
Jeeny: “And now?”
Jack: “Now I analyze, predict, delay. I call it wisdom. But maybe it’s just fear with better vocabulary.”
Jeeny: “Exactly. That’s the con of experience Andrea was talking about. It teaches you to protect yourself from failure — but also from growth.”
Jack: “So what, I should wake up Monday morning pretending I’ve never made a spreadsheet before?”
Jeeny: “No. Wake up pretending you’re not protecting your legacy anymore.”

Host: The words hung in the air, sharp but true, like a note of music that lingers after the instrument has gone silent. The rain intensified, the city lights blurring behind the window, turning the world outside into a moving watercolor of ambition and doubt.

Jack: “It’s easy for you to say that, Jeeny. You’re not the one with two hundred people waiting for your next move.”
Jeeny: “No, but I’ve been the one waiting for leaders who stopped moving. That’s worse.”
Jack: “Ouch.”
Jeeny: “It’s not an insult. It’s truth. The higher you climb, the smaller your field of vision becomes — until you start mistaking the top floor for the whole sky.”
Jack: “So, fire myself, huh?”
Jeeny: “Yes. Walk out tonight as the man who built this place. Walk in Monday as the one brave enough to rebuild it.”

Host: A flash of lightning illuminated the office, bathing everything in a momentary silver clarity. For an instant, Jack looked younger — not by years, but by spirit — the kind of face that had once dared the world to doubt him.

Jack: “You ever think about how strange that is? To start something with passion, and end up managing it like a patient on life support.”
Jeeny: “Because passion’s messy. It scares investors, it breaks rules, it questions everything you just stabilized. But it’s also the only thing that brings a business — or a person — back to life.”
Jack: “So, what you’re saying is I’ve become… predictable.”
Jeeny: “Comfortable. Which is worse.”
Jack: “You really think I’ve lost my edge?”
Jeeny: “No. I think you’ve covered it in policy.”

Host: Jack laughed softly, though the sound was more resignation than humor. The office clock ticked louder now, as if counting down not the minutes left in the day, but the time left to change.

Jack: “You know, when I started this company, I made decisions that terrified everyone — including me. I hired people with no résumés, sold products that didn’t exist yet. Everyone said I’d crash.”
Jeeny: “And you didn’t.”
Jack: “No. But somewhere along the way, I stopped making moves that scared me.”
Jeeny: “That’s when most companies — and people — start dying. Quietly. Respectably.”
Jack: “You make it sound like death by competence.”
Jeeny: “That’s exactly what it is.”

Host: The rain softened, turning into a steady whisper. The office felt smaller now, more intimate, as if the walls themselves were listening. Jack leaned back, his eyes distant, his fingers tapping the desk rhythmically, like a man about to make a decision that might undo years of safety.

Jack: “If I fired myself tonight, as Andrea said… what would I change on Monday?”
Jeeny: “I’d start with the truth.”
Jack: “Which one?”
Jeeny: “That you’ve been managing to protect your past, not to build your future.”
Jack: “And the bold change?”
Jeeny: “Let your people see you scared again. That’s leadership.”
Jack: “You mean vulnerable.”
Jeeny: “No — alive.”

Host: Thunder rolled in the distance, deep and resonant, as if the universe itself was signing off on the conversation. Jack stood, walked to the window, and looked out — the city reflected in his eyes, chaotic, brilliant, alive.

Jack: “You ever wonder if experience is just another word for memory — and memory is just a way to trap yourself in who you were?”
Jeeny: “Maybe. That’s why we have to forget just enough to see clearly again.”
Jack: “To forget what we know?”
Jeeny: “No. To forgive what we’ve done.”

Host: The room fell quiet, save for the rain’s rhythm and the heartbeat hum of electric light. It was the kind of silence that doesn’t end a conversation, but marks its turning point.

Jack: “You know, if I do this — fire myself — it’ll mean tearing down everything I’ve built.”
Jeeny: “Not tearing down — rebuilding differently. You can’t transform something you’re afraid to touch.”
Jack: “And if it all collapses?”
Jeeny: “Then you start again. Better. Freer. With clearer eyes.”
Jack: “You make it sound easy.”
Jeeny: “It isn’t. That’s why most people stay comfortable — they mistake safety for purpose.”

Host: The clock struck ten, the city lights blinked, and the office felt weightless — like a pause before something inevitable. Jack walked back to his desk, closed his laptop, and took off his name badge, placing it gently on the table.

Jack: “Alright. I’ll fire myself tonight.”
Jeeny: “And come back Monday?”
Jack: “As a stranger who believes again.”
Jeeny: “Then maybe this company — and you — will finally wake up.”

Host: The rain stopped, leaving behind the smell of ozone and possibility. The streets below shimmered, reflecting light like a mirror of renewal. Jack and Jeeny stood in the dim office, two silhouettes against the glass, both changed, both quiet.

And as Jack stepped out into the hallway, his footsteps echoing in the emptiness, it felt less like leaving — and more like beginning again.

Because in the end, experience can either blind or illuminate. And sometimes, to see the truth of your creation, you have to fire the version of yourself that built it.

Only then can you walk back in — not as the one who knows,
but as the one who still dares to see.