Chapter 2 - The Algorithm of RegretThe first-class cabin was quiet, bathed in the soft, amber glow of overhead reading lights. Across the aisle, a Wall Street banker in a charcoal suit was snoring softly into a neck pillow, completely dead to the world.
I sat rigidly upright in seat 2B, my phone clutched in my sweating palm.
Right before airplane mode locked down my signal, a new notification had flashed across the screen:
“Board meeting convened in Denver. Calder is in the room. He’s offering cash up front. If you aren't here to sign by midnight, Merritt Systems goes to him. Don't blow this, Damon.”
Seven hundred and eighty million dollars. The crowning achievement of my career. The ultimate vindication of every late night, every missed holiday, every sacrifice I had made since I was twenty-two years old and swore I would never be poor, powerless, or insignificant again.
Three hours earlier, that message would have sent my pulse racing. I would have been hammering out counter-offers to my executive team, ready to tear open the fuselage with my bare hands if it meant getting to Denver fifty seconds faster.
Now? The text message looked like flat, meaningless lines of code on a dead screen.
Twenty rows behind me sat two children with my face. Two children whose first steps, first words, first birthdays, and scraped knees I had missed because I was too busy building an empire.
Why didn't she tell me?
The question burned like acid in my chest.
When Cassandra and I broke up three years ago, it hadn't been a quiet, amicable parting. It had been an absolute war zone of ambition versus stability. I had just secured our first major venture capital round, and I was working eighty-hour weeks, sleeping on the office couch, missing dinners, and treating our relationship like an inconvenient meeting on my calendar. Cassandra had begged me to slow down, to remember why we moved to San Francisco together, to build a life rather than a balance sheet.
In my arrogance, I told her she didn't understand the cost of winning. I told her that if she wanted a predictable, middle-class life with a husband who came home at five o'clock, she was looking at the wrong man.
So she walked out. Or rather, I let her walk out, convincing myself that love was a distraction and that emotional attachments were just liabilities on a financial ledger.
I hadn't looked back. I bought her out of our apartment lease, transferred a lump sum into her bank account to clear my conscience, blocked her number, and plunged headfirst into the shark tank of Silicon Valley.
And all the while, she had been carrying my children.
I turned my head, staring through the narrow gap between the first-class privacy divider and the galley curtain. In row twenty-eight, illuminated by the dim reading light, I could see the top of Cassandra’s head. She was leaning over, whispering softly to Luke, who was tracing patterns on the plastic tray table with his red crayon.
The little girl, Violet, was curled up asleep against Cassandra’s chest, her tiny fingers tangled in her mother's sweater.
My throat tightened. A heavy, suffocating wave of shame washed over me—a feeling so foreign and intense it made my physical chest ache. I had spent millions of dollars funding medical research to save premature babies, yet I had been completely blind to the two tiny lives my own flesh and blood had brought into the world without my knowledge.
“I tried,” she had said when I asked why she didn't tell me.
What did that mean? Did she call my office? Did she send an email that got filtered out by my aggressive executive assistants? Did she try to reach out, only to find a wall of cold corporate secretaries and blocked numbers?
The realization hit me with terrifying force: I had built such an impenetrable fortress around myself that even my own family couldn't scale the walls.
Suddenly, the plane shuddered violently.
A sharp drop in altitude threw my stomach into my throat. The "Fasten Seatbelt" sign chimed loudly above us, followed immediately by the captain's voice crackling over the intercom:
“Ladies and gentlemen, we’ve just hit an unexpected pocket of severe turbulence as we cross the Rockies. Please remain seated and ensure your seatbelts are securely fastened.”
Outside the windows, the black night erupted into violent white turbulence as we slammed into a wall of winter clouds. The aircraft banked sharply, groaning under the stress of the wind.
From twenty rows back, a sudden, piercing shriek cut through the roar of the engines.
It was Violet. The sudden drop had clearly terrified her out of her sleep.
Immediately, Cassandra’s voice rang out, soft and soothing, trying to calm her daughter over the violent shaking of the plane.
—It’s okay, baby, —Cassandra crooned, her voice trembling slightly. —The clouds are just dancing with us. They’re playing hide-and-seek with the moon.
Hearing those words, a forgotten memory flashed through my mind like lightning.
Ten years ago, during our very first winter together in a drafty apartment in Seattle, a massive windstorm had blown through the city, shaking the windows and cutting our power. I had been terrified of thunder as a kid, and I must have looked tense because Cassandra had taken my hand, smiled in the dark, and whispered: ‘Don't worry, Damon. The clouds are just moving their furniture around.’
She had used that exact same gentle metaphor to comfort our daughter.
I couldn't sit still anymore. The corporate deals, the board meetings, the $780 million acquisition—none of it mattered. Nothing mattered except getting up out of this leather seat, walking down that aisle, and sitting beside the woman I had wronged and the children I never knew.
I reached for my seatbelt buckle.
Instantly, the flight attendant stationed near the galley lunged forward, her hand shooting out to block me.
—Sir! The seatbelt sign is on! You cannot get out of your seat!
—Get out of my way, —I said, my voice dropping into the cold, commanding register I usually reserved for hostile board takeovers.
—I don't care who you are, sir, the turbulence is severe—if you stand up now, you'll break a bone! Sit down!
—There are children back there! My children! —I shouted over the roar of the engines, the facade finally cracking completely.
The flight attendant froze, her eyes widening as she looked from my furious, desperate face down toward row twenty-eight, where Cassandra was struggling to calm both crying children as the plane dropped another fifty feet.
For a fraction of a second, her professional strictness melted away.
—Then... then stay seated until the captain turns off the sign! —she pleaded softly. —As soon as we clear this pocket, you can go. But not a second before!
Those twelve minutes of turbulence felt longer than any boardroom battle, any hostile shareholder meeting, or any venture capital pitch of my life. Every time the plane dropped, my heart slammed against my ribs. I sat with my hands gripped so tightly around the armrests of my first-class seat that my knuckles turned paper-white.
Finally, with a gentle shudder, the aircraft leveled out.
The captain’s voice chimed: “Flight attendants, please prepare for cabin service. We’re through the worst of it.”
The moment the red sign clicked off, I didn't wait for permission. I stood up so fast my seat tipped backward, shoved past the galley, and strode down the narrow aisle toward row twenty-eight.
Passengers twisted in their seats, staring at the abrupt intrusion.
I stopped right beside Cassandra’s row.
Cassandra looked up, her breathing shallow, one arm wrapped protectively around little Violet—who was still sniffling against her shoulder—while Luke clutched her pant leg with his other hand.
An elderly woman across the aisle abruptly lowered her magazine, pretending very hard not to listen.
I looked down at Cassandra, my chest heaving.
—May I sit? —I asked, my voice barely audible over the hum of the ventilation system.
Cassandra’s jaw tightened. She stared at me for three long, agonizing seconds, her eyes searching my face for any sign of malice, arrogance, or deceit. Finding none, she slowly shifted her weight, moving toward the window seat just enough to clear the aisle.
I slid into the middle seat next to her. The space was impossibly cramped, smelling faintly of apple juice, baby wipes, and lavender.
Luke stared up at me with those big green eyes, tilting his head.
Violet buried her face back against Cassandra’s neck, clutching her gray stuffed elephant.
I turned my head toward Cassandra, lowering my voice so only she could hear.
—Cassandra, I need the truth. All of it.
She looked down at the children sleeping in her arms, her lower lip trembling slightly. Then, she raised her chin, meeting my gaze with a quiet, devastating dignity.
May you like
—They’re yours, Damon. They’ve been yours from the very beginning.
And then, with trembling fingers, she reached into the canvas diaper bag at her feet, pulled out a worn, manila folder, and handed me something that made my blood run instantly cold.
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