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Chapter 1
Chapter 1: The Google Doc Heard Round the World
The spreadsheet was beautiful.
Penny Landsworth had spent fourteen hours building it over the previous weekend, and now, at 6:47 a.m. on the morning of her thirty-sixth birthday, she sat in bed admiring it on her laptop the way some people admired sunsets or newborn babies. It was a five-year financial projection with color-coded tabs for savings, investments, projected salary increases, and—this was the part she was proudest of—a conditional formatting scheme that turned cells from green to yellow to red based on variance from target.
She had tabs for everything. Grocery budgets. Vacation planning (one trip per year, domestic, booked at least six months in advance). A retirement projection that went out to age seventy-two, because Penny believed in being realistic about modern life expectancies.
Her phone buzzed on the nightstand. She glanced at it.
*Kevin Roth shared a document with you: "Us — A Conversation"*
Penny frowned. Kevin was her boyfriend of four years. He was a systems analyst who appreciated her spreadsheets, or at least tolerated them, which in Penny's experience was practically the same thing. They'd met at a networking event for data professionals, bonded over a shared disdain for people who used pie charts when bar charts would do, and settled into a relationship that was comfortable in the way that a well-organized filing cabinet is comfortable.
She opened the Google Doc.
It was formatted with headers and bullet points, which she would have appreciated under different circumstances. The title was centered and bold: **Us — A Conversation (One-Sided, Sorry).**
*Penny,* it began. *I've been thinking about this for a while, and I think the most respectful thing I can do is be clear and organized about my feelings, since I know that's a language you understand.*
She felt a small chill start at the base of her neck.
*I care about you deeply. You are the most capable, organized, and reliable person I have ever met. You are also, and I say this with genuine affection, like dating a very sophisticated calendar app.*
The chill spread to her shoulders.
*I've started seeing someone. Her name is Britt. She teaches improv comedy. I know that probably sounds like a parody of this situation, and I'm sorry about that. She makes me feel spontaneous in a way I didn't know I needed. I should have talked to you about this in person, but honestly, Penny, I was afraid you'd make a pro/con list in front of me, and I couldn't handle that.*
*I've already moved my things out of the apartment. (I left the label maker. I know how you feel about the label maker.)*
*I'm sorry. Happy birthday.*
*— Kevin*
*P.S. I left comments enabled in case you want to respond.*
Penny stared at the document for a full ninety seconds. Then, with the precision of a surgeon, she highlighted the entire text, changed the font to Comic Sans, and closed her laptop.
She sat in the silence of her apartment—*their* apartment, until apparently sometime in the last week when it became just hers—and tried to identify what she was feeling. Her therapist, Dr. Wanda Jeffries, was always asking her to "sit with her emotions," a phrase that made Penny picture herself on a park bench next to a sulky toddler version of her own psyche.
What she felt, she decided, was confused. Not heartbroken. Not yet. Mostly confused about the logistics. When had he moved his things? She'd been at work until seven every night this week. Had he hired movers? Had he *tipped* them? Kevin was historically a bad tipper, and Penny found that more distressing in this moment than the actual breakup, which probably said something about her that she wasn't ready to examine.
She showered, dressed in her standard work outfit (charcoal slacks, cream blouse, sensible flats that a coworker had once described as "aggressively practical"), and drove to the offices of Lakewood & Associates Insurance Group, where she had worked as a senior actuary for eleven years.
The office was on the thirty-second floor of a glass tower on Wacker Drive, and Penny loved it with the quiet, steady devotion that other people reserved for pets or children. She loved the hum of the fluorescent lights. She loved the predictability of the elevator schedule. She loved that her desk was positioned exactly six feet from the window, which gave her natural light without glare on her monitor.
She was settling into her chair, attempting to lose herself in a mortality table, when her manager, Gerald Huang, appeared in her doorway.
Gerald was a soft-spoken man in his fifties who wore the same three ties in rotation and had once described his management philosophy as "trying not to bother anyone." He looked, at this moment, like someone who was about to bother everyone.
"Penny," he said. "Conference room. Five minutes. All hands."
"Is this about the quarterly projections? Because I finished those last—"
"It's not about the projections."
He walked away before she could ask anything else, which was unusual. Gerald typically lingered in doorways, making small talk about weather or public transit, like a man who'd been told that managers should be personable and was doing his best.
The conference room was already full when Penny arrived. Forty-two employees packed into a space designed for thirty, the overflow leaning against walls and perching on the heating unit by the window. At the front of the room stood Margaret Cho—not that Margaret Cho, as the company's Margaret Cho was fond of clarifying—the CEO, who had flown in from the New York office.
"I'll keep this brief," Margaret said, which was the corporate equivalent of a doctor saying "you might feel some pressure."
Lakewood & Associates was consolidating. The Chicago office, along with the satellite offices in Denver and Atlanta, would be merging into a single centralized location. The new hub would be in Omaha, Nebraska. Employees would have sixty days to decide whether to relocate.
"Omaha has a wonderful cost of living," Margaret added, with the enthusiasm of someone reading from a brochure. "And the steaks are incredible."
Penny sat very still in her chair while around her, colleagues erupted into whispered conversations, muffled profanity, and at least one person's audible gasp that sounded like it came from a Victorian novel.
Omaha.
She had nothing against Omaha. She had nothing *for* Omaha. Omaha existed in her mind as a vague, flat concept, like the idea of Nebraska itself—somewhere between "the middle of the country" and "a place people are from but never going to."
She pulled out her phone and opened her calendar. In the 2:00 p.m. slot, like a small beacon of normalcy, was her standing Thursday appointment with Dr. Jeffries.
At least something in her life was still on schedule.
---
Dr. Wanda Jeffries' office was on the fourth floor of a brownstone in Lincoln Park, decorated in the soothing earth tones that all therapists' offices seemed to share, as though they all shopped at the same store called Feelings & Furniture. There was a white noise machine outside the door, a box of tissues on every flat surface, and a framed print of a lake that was probably supposed to be calming but always made Penny need to use the bathroom.
Dr. Jeffries was a tall woman in her sixties with silver-streaked hair and reading glasses that she wore on a chain around her neck, deploying them like a weapon when she wanted to study Penny's face more closely.
"Happy birthday," Dr. Jeffries said as Penny sat down.
"Kevin broke up with me via Google Doc, and my company is moving to Omaha," Penny said.
"I see." Dr. Jeffries put on her glasses. "And how are you feeling about all of that?"
"I changed his breakup letter to Comic Sans."
"That's not a feeling, Penny."
"It felt like one at the time."
Dr. Jeffries leaned back in her chair. She had a way of creating silences that felt like they had weight, like the air itself was waiting for Penny to say something meaningful. Penny had spent four years learning to outlast these silences, treating them as a kind of competitive sport.
Today, Dr. Jeffries broke first.
"Penny, I want to be direct with you."
"You're always direct with me."
"More direct than usual." She removed her glasses, cleaned them on her cardigan, and put them back on. This was her tell. Penny braced herself. "In twenty-three years of practice, you are the most emotionally constipated client I have ever treated."
Penny blinked. "Is that a clinical term?"
"It's a Wanda term. You have spent four years in this chair describing your life like you're reading an actuarial table. You assess risk. You calculate outcomes. You plan for contingencies. But you don't *feel* things, Penny. Or if you do, you've built such an elaborate system of spreadsheets and schedules around yourself that the feelings can't get through."
"That seems like it's working, then."
"Your boyfriend just left you for an improv comedian."
"Via Google Doc."
"Via Google Doc. And your response was to change the font."
"It was a *devastating* font choice."
Dr. Jeffries smiled, but it was the sad kind of smile, the kind that made Penny feel like she was being pitied by someone who genuinely liked her, which was worse than being pitied by a stranger.
"Something needs to change," Dr. Jeffries said. "I'm not telling you what. But something."
Penny drove home through rush-hour traffic on the Kennedy Expressway, which moved at its customary speed of "geological," and thought about the word *constipated*. It wasn't wrong, exactly. She could acknowledge that much. She had always been a person who preferred order. As a child, she'd alphabetized her Halloween candy. In college, she'd scheduled her social life in fifteen-minute increments. She'd chosen actuarial science as a career because it was, literally, the math of predicting what would go wrong—and there was comfort in that, in knowing the odds, in being prepared.
But somewhere along the way, preparing for what could go wrong had become the same thing as not letting anything happen at all.
She parked in her building's garage, took the elevator to the seventh floor, and opened the door to an apartment that was now noticeably emptier. Kevin had taken the coat rack, the second set of bookshelves, and—she checked—the good can opener. He'd left the label maker on the kitchen counter, as promised, like a parting gift from a relationship that had been, in hindsight, approximately as passionate as a shared Netflix password.
Her phone rang. The screen showed a photo of a woman with wild curly hair and a tank top that read NAMASTE IN BED.
"Happy birthday, you beautiful disaster," said Donna Kimball.
Donna was Penny's best friend, a title she'd held since they were college roommates at the University of Illinois, thrown together by a housing algorithm that had apparently decided the most anxious person on campus should live with the least. Donna taught yoga at a studio called Breathe Easy on North Avenue, a business that operated on a financial model best described as "vibes and optimism." She was warm, chaotic, perpetually broke, and the only person in Penny's life who could make her laugh until she couldn't breathe.
"Kevin left me," Penny said.
"I know. He texted me to say he was sorry and that he hopes we can all still be friends. I told him to eat glass."
"Donna."
"Fine, I told him to eat *recycled* glass. I was polite about it." There was a rustling sound, like Donna was rearranging herself on a couch. "Are you okay? Actually okay, not Penny-okay, where you say you're fine and then reorganize your spice rack at midnight."
"My spice rack is already organized."
"That's what I'm afraid of. Listen, I'm coming over. I'm bringing wine and those disgusting cheese puffs you pretend you don't like."
"I don't like them."
"You ate an entire bag last New Year's Eve."
"I was under duress. It was a leap year."
"That doesn't—never mind. I'll be there in twenty."
Donna arrived in twenty-three minutes, which by Donna Standard Time was practically early. She swept into the apartment carrying two bottles of wine, a family-size bag of cheese puffs, and a energy that suggested she had a plan. Penny had known Donna long enough to be both comforted and alarmed by this.
They settled on the couch—the couch Kevin had, mercifully, not taken—and Donna poured wine into the glasses Penny kept in the cabinet above the refrigerator, the ones she'd bought for dinner parties she never threw.
"So," Donna said, tucking her legs under her. "Tell me everything."
Penny told her. The Google Doc. Britt the improv comedian. Omaha. Dr. Jeffries and the word *constipated*. She told it all in the flat, factual tone she used for everything, the tone that Kevin had apparently found comparable to a calendar app.
Donna listened without interrupting, which was unusual enough to be noteworthy. When Penny finished, Donna set down her wine glass with the deliberateness of someone about to propose something unhinged.
"I have an idea," Donna said.
"No."
"You haven't heard it yet."
"Your ideas once got us banned from a Costco."
"That was a misunderstanding about the sample policy, and they lifted the ban. Mostly." Donna leaned forward. "Okay. Here's what I'm thinking. A Year of Full Permission."
"I don't know what that means."
"For twelve months, starting right now, you say yes. To everything. Every reasonable opportunity, invitation, impulse, whatever comes your way—you say yes."
Penny stared at her. "That's insane."
"That's the point. You've spent your entire adult life saying no to things, or saying 'let me check my spreadsheet' to things, which is basically the same as no. You've optimized all the fun out of your own life, Pen. And now your life has blown up anyway, so what exactly are you protecting?"
This landed with more force than Penny expected. She took a long drink of wine.
"There would need to be parameters," she said.
"God, you're exhausting. Fine. Parameters. Nothing illegal. Nothing that would cause bodily harm. Nothing that violates your actual moral code, whatever's left of it. But everything else? Yes. Someone invites you to a party? Yes. Someone suggests a weird hobby? Yes. Your gut says try something? Yes."
"And what's the point?"
"The point is to find out who you are when you're not hiding behind a five-year plan." Donna's voice softened. "Pen, I love you. You're the smartest person I know. But you're also the most afraid, and I think those two things are related."
Penny looked around her apartment. The label maker on the counter. The empty spaces where Kevin's things had been. The laptop with its beautiful spreadsheet that had predicted everything except the thing that actually happened.
"You said you'd document it," Penny said slowly. "What does that mean?"
Donna's eyes lit up. "Social media. I'll film stuff, take photos, write posts. We'll make an account. 'The Yes Experiment.' People love this kind of thing—watching someone blow up their comfort zone. And honestly?" She gestured vaguely. "The studio could use the publicity."
"So I'm a marketing strategy."
"You're a *journey*. The marketing is a bonus."
Penny thought about Dr. Jeffries saying *something needs to change*. She thought about Kevin and his improv comedian. She thought about Omaha, sitting out there on the plains like a threat.
"If I hate it, I can stop?"
"If you hate it after giving it a real shot, sure. But you have to actually try. No half-measures. No saying yes and then finding a scheduling conflict."
Penny picked up a cheese puff. She looked at it. She ate it.
"Yes," she said.
Donna screamed so loudly that the neighbor knocked on the wall.
"Sorry!" Donna yelled toward the wall. Then, to Penny: "This is going to be the best year of your life."
"Or a complete catastrophe."
"Those are often the same thing."
Donna pulled out her phone, opened Instagram, and created an account on the spot: @TheYesExperiment. She took a photo of Penny on the couch, cheese puff in hand, looking like a woman who had just agreed to something she didn't fully understand.
The caption read: *Day 1. She said yes. God help us all.*
Sixteen people liked it by midnight. Fourteen of them were Donna's yoga students. One was Penny's mother, which was alarming because Penny didn't know her mother had Instagram.
The last one was Kevin, which Penny chose not to think about.
She lay in bed that night staring at the ceiling, trying to calculate the probability of this being a terrible mistake. The number she arrived at was high. But for the first time in a long time, she didn't reach for her laptop to build a spreadsheet about it.
She just lay there, in the dark, in the wreckage of her color-coded life, and let the uncertainty exist.
It was horrible.
But it was something.