20. Elliot
ELLIOT
E lliot took a taxi straight to the airport. That evening, he was back in his condo in Chicago. By phone, he contacted his New York landlord and canceled his lease. Just like that, his time in New York was over. His time with Lucy was over.
Because it was, wasn’t it? They both knew it.
Elliot still wanted to be with Lucy, but he had no idea how to be a good boyfriend to her while living in another city and being CEO of a different company.
Lucy, meanwhile, no longer seemed to have any interest in a relationship with him.
She’d been clear that she wanted him to leave, and by the time their conversation ended, Elliot had been ready to go.
After all, it seemed like Lucy was just fine with him leaving — though a little mad that he’d given his notice without consulting her, perhaps. Which was fair.
Maybe it was all for the best. After all, Elliot had never been a man for serious relationships.
Since dating Lucy in college, he’d tried a few times, but it had never worked out, at least not for long.
A part of him had always thought that if he were going to have a long-term relationship with anyone, it would be with Lucy.
And since it hadn’t worked out with Lucy…
Elliot ran a hand through his hair. He just couldn’t believe that everything had gone so wrong, again.
He didn’t know how to make things right.
He didn’t even know what making things right would look like.
He could apologize to Lucy for leaving without telling her what was happening, but he’d already done that, and it was clear that she didn’t want to talk to him anymore.
Elliot got up from the couch, where he’d sunk with his head in his hands first thing after arriving at his apartment.
He brushed a hand through his hair and made his way to the kitchen, where he poured himself a glass of wine from an old bottle a colleague had given him as a gift.
It tasted… well, Elliot wasn’t entirely sure what it tasted like, but it was good, and it reminded him of Lucy and their wonderful vineyard trip.
He still couldn’t believe that he’d lost her. Again.
Maybe they were never meant to be. Maybe Elliot needed to throw himself back into his life, his real life, and do his best to forget about her. Again.
Some part of him held out hope that Lucy would take the time she needed and would eventually reach out to him, but Elliot knew that was probably not going to happen. She clearly felt betrayed by his departure. And she’d been ready to end their relationship because of it.
His thoughts spiraled in an endless circle of regret and sadness until, finally, he downed the last bit of his wine and went to bed.
The next morning, his alarm went off at six, and he was up quickly.
He changed into athletic clothes and headed to the condo complex’s gym, his feet following the familiar route down the stairs even as his mind drifted back to New York and Lucy.
He threw himself into exercise and managed, at least momentarily, to put Lucy out of his mind as he rotated through bench presses and back rows.
After a quick shower, Elliot headed to work.
He’d been in Chicago just last week, so it wasn’t much of a shock to step back into his offices.
His employees greeted him with friendly smiles, which Elliot returned.
He attended the usual Tuesday morning all-hands meeting, looking out at the familiar faces of programmers and HR staff and copywriters.
It used to make him proud to see all his employees together, but today he didn’t feel that.
Next, Elliot went to his office, where he spent the morning deep in work, with only quick pauses for sips of coffee.
He’d put out most of the fires last week, so today was spent on his usual work of company management and future planning.
Over lunch, he had a productive meeting with his CTO about future investments in R&D towards a new product with great growth potential.
It was exciting stuff, exactly the kind of thing Elliot would usually have been completely consumed by. Today, it barely held his attention.
The afternoon passed in a blur of meetings, including a few interviews with candidates to cover the CFO role while his current CFO was on maternity leave in a few weeks.
That was exciting, too, as Elliot usually loved to be involved in the hiring process.
Today, though, he listlessly flipped through resumes and cover letters.
Evening included a dinner spent at Elliot’s desk and a few drinks at a local bar with friends who’d missed him while he was in New York for the last few weeks.
It was nice to see them, but Elliot couldn’t stop thinking about how hollow everything felt.
His Keype work felt like… business. Whereas the time he’d spent working at Borderless with Lucy had been creative in a different way.
Sharing his successes and ideas with her had made everything feel ten times more exciting and impactful.
Evenings spent at her side, eating dim sum or watching movies or just talking, had been far more meaningful than evenings spent at his desk, even when his work was interesting and productive.
Elliot had been certain that he’d made the right call by stepping back from Borderless.
But more and more, as the day went on, he wondered if he’d made a mistake.
Perhaps Lucy and Borderless had been his one chance at happiness, and Elliot had thrown it all away for a company that no longer felt as special to him as it once had.
After all, Keype made Elliot money, lots and lots of money, but it didn’t enrich his life in the way his time with Lucy did. Money didn’t seem as important anymore.
Elliot did his best to put the doubts out of his mind, but it was difficult.
“So tell me,” his friend Greg asked, lifting a glass of beer. “How did you like being CEO of two companies at once?”
“It was… a challenge,” Elliot said, sipping his own drink. He’d unconsciously chosen wine, which reminded him of Lucy all over again. “But a good one.”
“And how was your co-CEO?” Greg pressed. “She must have really been something, given how long you stayed away from Chicago.”
“True,” his friend Shaun said, grinning. “Almost nothing can keep Elliot away from Keype.”
“She was wonderful,” Elliot said. He sighed. “But it wasn’t meant to be.”
His friends rolled their eyes in unison.
“That doesn’t sound like the Elliot I know,” Greg said. “Not meant to be? From the man who built a multi-billion-dollar company from scratch? The man who never gives up until he has what he wants? I don’t believe it.”
Elliot shrugged and shook his head. It wasn’t like he could make his relationship with Lucy work through sheer dedication, the way he’d grown Keype. Love was much more nuanced than that, and Elliot couldn’t see a way to make things work out between them.
“Tell me about your girlfriend,” Elliot said, hoping to change the subject. “Melody, right?”
“Oh, she’s great.” Greg launched into a story about the wonders of Melody, and the conversation moved on. Elliot’s thoughts didn’t, though.
Slowly, days turned into weeks, and Elliot settled more and more into his old Chicago routines.
He hit the gym, went to work, and ate most meals at his desk.
His rare free time was devoted to more work and, occasionally, reading up on Borderless’s successes.
Elliot had been right: Lucy was an excellent CEO all on her own.
All the news from Borderless was positive, highlighting innovative new strategies, employee satisfaction, and sustained growth.
No one had bought the shares Elliot put up for sale yet, but sooner or later, someone would.
And, though he didn’t want to, Elliot would probably make great money from the sale since Borderless was such an exciting company.
As more and more time passed with only positive news from Borderless and no word from Lucy herself, Elliot realized that he really had missed his chance.
Even if he regretted choosing Keype over Lucy and Borderless, he couldn’t go back.
Lucy didn’t need him. Borderless didn’t need him.
If Elliot tried to insert himself back into her life, they’d both end up getting hurt a third time.
It was better that Elliot let Lucy live her life and try to move on with his own.
Despite Elliot’s malaise, Keype continued to thrive under his leadership.
With the crisis that had drawn him back to Chicago averted, it seemed more and more that running his own company was the only thing Elliot could do right.
So, he would focus on Keype. He would stay in Chicago.
He would watch Lucy’s successes from a distance, just as he had after college, and content himself to life as an eternal bachelor.
At least Dominic would have been happy.