Chapter 4
BLAIR
I should roll over and go back to sleep because I have absolutely nowhere I need to be. No meetings, no calls, no crises demanding my attention. The freedom I thought I wanted feels more like a prison now, and the bars are made of endless, empty hours.
Now I lie here willing my brain to shut off, to let me sleep until eight or nine like a normal person with no obligations.
But my internal clock is merciless. Every morning, same time, wide awake whether I want to be or not.
It's become a daily reminder of everything I've left behind, this biological alarm system that no longer serves any purpose.
Six months ago, my friend Dougie and I sold our company for an amount that still feels surreal when I think about it.
We built it from nothing—just two friends from college writing code in a cramped apartment, surviving on pizza and the belief that we could make money if only we tried hard enough.
Dougie handled the business development while I focused on infrastructure.
I was the one who lived and breathed the actual security protocols, the one who could see attack patterns that others missed.
Our company grew and thrived but Dougie fell in love and eventually wanted out to slow down and spend more time with his girlfriend. I suppose I wanted to slow down too.
By the time we sold, we had six hundred employees across four countries.
The buyer was a massive tech conglomerate that wanted our AI-driven threat detection algorithms. They'd been trying to develop something similar internally for three years and failed.
We'd cracked it in eighteen months, and they paid enough to ensure we'd never have to work again.
The problem is, I'm starting to realize I do want to work.
Dougie bought a vineyard in Napa and sends me photos of his first grape harvests like he's discovered the meaning of life.
His girlfriend is pregnant and they're getting married next year.
He seems to know exactly what came next.
Me? I've spent the past six months discovering that unlimited freedom is just another word for having no idea what to do with yourself.
I swing my legs over the side of the bed and pad to the kitchen.
The espresso machine—a ridiculously expensive Italian contraption—hums to life with the press of a button.
While it warms up, I check my phone, scrolling through the usual collection of overnight emails that don't require responses, news alerts about investments I sometimes monitor, and social media notifications I tend to ignore.
But there's something unexpected waiting for me. A text from a number I don't recognize, sent at 3:47 AM, from an American number. The timestamp alone makes me curious—not many people I know send messages at that hour.
The message makes me smile.
Hi this is Olivia from coffe shop. Were you seriou about the offer? Do you really need the mony? And are you free on the weekend of the 12th?
I read it twice, my grin widening with each pass. The typos are so unlike the polished, controlled woman I met the other day. This message, with its drunk-texting spelling errors, feels like seeing behind the curtain.
The espresso machine beeps, but I ignore it for a moment, staring at the message.
She's reaching out. After our coffee shop encounter, after my ridiculous offer to be her fake girlfriend, she's actually considering it.
Drunk-considering it, but still... The right thing would be to tell her the truth—that I don't need the money, that I was just entertained by her predicament and offered on a whim.
Instead, I find myself typing: Yes, I'm struggling to pay my rent this month, and I'd still love to be your 'Sailor'. Free that weekend.
The easy lie should probably concern me more than it does. But there's something appealing about the deception, about playing a role. With nothing to fill my days, the idea of being someone else, even temporarily, is irresistible.
I send the message and wait. No immediate response, which isn't surprising given the hour she sent her text.
She's probably sleeping off whatever she drank to work up the courage to contact me.
I pour my espresso and carry it to my living room that overlooks Central Park.
Joggers are already out, tiny figures moving along the paths like ants following predetermined routes.
When Dougie and I were building the company, I became confident, decisive, always three steps ahead.
That version of me could walk into a room full of investors and convince them to write seven-figure checks.
She could make split-second decisions that affected hundreds of employees.
She could project absolute certainty even when everything was falling apart behind the scenes.
But that Blair doesn't exist anymore. Without a company to run, without crises to solve, I'm just a woman with too much money and too much time. Playing Sailor seems like a nice distraction from my uneventful life.
My phone stays silent for the next hour. I shower, dress in the same clothes I've adopted since retiring—athletic wear. I could visit the Metropolitan Museum, take a spontaneous trip somewhere, call one of my few friends who aren't buried in work. But none of it feels worthwhile.
I've tried joining clubs, going to networking events for entrepreneurs, even dating apps specifically for high-net-worth individuals.
But every conversation feels like an interview for a job I don't want.
People want to know what I'm working on next, what my investment strategy is, whether I'm looking for partners in some new venture.
Nobody wants to just have drink without an agenda.
I'm finishing my second espresso when inspiration strikes. If I'm going to play the role of a struggling woman who needs money, I should probably lean into the character. I pull out my phone and start typing another message.
Just realized I don't have a suit and can't afford to buy one. (Sorry, I don’t wear dresses) We should probably meet up to discuss that being part of my 'package.'
I hit send and chuckle. It's a calculated move—creating a problem that requires us to spend time together, giving me something to do while advancing whatever this strange arrangement is becoming.
This time, I don't have to wait long for a response. My phone buzzes within ten minutes.
Morning. Sorry about my drunk message. How much do you need for a suit?
I write, Around $300 for a rental, maybe? More if you want me to look like I actually belong at your sister's wedding.
The response comes back almost immediately: I’ll buy you one. Meet me at Bergdorf Goodman at 2 PM. Women's formal wear, fifth floor.
Bergdorf Goodman. Of course. She's not messing around with budget rentals or off-the-rack options.
She wants me to look like a successful finance director, which means she's willing to invest in the costume.
I'm curious about what this wedding is going to be like if she's this concerned about appearances.
Great! See you at 2, I reply, then add, I'm Blair, by the way.