22. Elliot
ELLIOT
A few days after Elliot returned to Chicago, a box had arrived from Borderless. The neat handwriting on top was Lucy’s, and Elliot knew that the box contained the personal items he’d left behind when he’d departed the Borderless offices at top speed. He couldn’t bring himself to open it, though.
As long as the box stayed closed, it was easy to imagine that his life in New York was still waiting for him to return, even as weeks passed since he’d seen Lucy. He wondered how she was doing. He wondered how she’d felt as she’d packed that box for him. He missed her.
Yet Lucy hadn’t reached out in the last few weeks, and neither had Elliot.
As much as his heart ached, he felt increasingly convinced that letting her go was the right thing to do.
Eventually, she would find someone else.
She would be happy. Elliot would console himself with his company.
Running Keype was the only thing he was truly good at, anyway.
The time they’d spent together had been nothing but a beautiful interlude in a life they were destined to spend apart. It was all as it was meant to be.
Or, at least, that’s what Elliot told himself late at night when the urge to call Lucy grew almost irresistible. If Elliot tried to be part of her life once more, it would only end in heartbreak for both of them all over again. He needed to keep his distance.
One windy Tuesday a few weeks after Elliot had returned to Chicago, Keype announced the hiring of the new maternity-cover CFO.
Elliot reached for his favorite pen to sign the contract — and realized he didn’t have it.
It shouldn’t have mattered. Elliot wasn’t a superstitious man by nature, but the pen was special.
He and Dominic had bought a matching set of pens when they’d started their businesses, and they’d often joked about how those pens were responsible for their successes.
“Is it all right if I sign this a little later?” Elliot asked his assistant.
“Sure.” His assistant put the contract back in its folder. “No rush. We have until next Monday to get it signed. Are you having second thoughts about the candidate?”
“No, he’ll be perfect for the job.” Elliot reached for his keyboard.
“That’ll be all for now.” He didn’t want to admit that he was feeling superstitious about the pen.
After a quick look around his office, he determined that it must be in the box Lucy had sent from New York.
With a heavy heart, Elliot pulled the box out from under the desk, cut through the tape that held it shut, and began unpacking.
On top were a few personal photos, a notebook where he’d kept track of some Borderless affairs, and a stapler that wasn’t Elliot’s.
That must have been a mistake. When he flipped it over, he saw that it was stamped with Dominic’s name, and his heart lurched.
Whether Lucy had sent it along on purpose or by accident, the stapler now felt meaningful.
A little more digging revealed Elliot’s pen, but there was still a lot more in the box.
Elliot picked up a Pura Vida flier, a wine cork from the trip to the vineyard, a rough agenda of the European trip he’d planned with Lucy, and Dominic’s pen, the other half of the set.
Each object made his heart constrict further.
At the very bottom of the box, he spotted an envelope with his name on it.
At first, Elliot thought it might be a message from Lucy, but further inspection showed that the handwriting wasn’t hers.
It was Dominic’s.
Elliot’s heart began to race. In all likelihood, this was an old letter that Elliot had already read, but there was a chance, a slight one, that Elliot was about to hear something from his best friend that he’d never heard before.
Sitting in his desk chair, he used a letter opener to carefully slice the envelope open.
A single sheet of paper slid out. It was covered, front and back, with the spidery handwriting Elliot had always teased Dominic about.
His heart racing, Elliot scanned the first line.
Elliot,
I sure hope you are in my office now and that you find this letter, not anyone else. I’m about to be a little mushy, and I can’t let people know that I have a mushy side. It would completely ruin my reputation, and I can’t have that now that I’m gone.
Elliot’s heart raced faster. This was a new letter.
A letter Dominic had intended for Elliot to find when he took over as CEO after Dominic’s death.
Elliot couldn’t believe he’d never seen it before, but he hadn’t looked through Dominic’s old office very thoroughly.
Lucy must have spotted the letter with his name on it and tossed it into the box without knowing Elliot hadn’t read it. Elliot continued reading.
I know that me being sick was a bummer. And I know that me being gone is a bummer, too.
But I want you to be happy, Elliot. I want you to live the life you want.
That’s why I made both you and Lucy CEOs of Borderless.
I know it might be hard for you to work together, but I also know that there’s something between you.
I saw how you looked at each other in college.
I saw how you looked after Lucy stopped spending time with us. I saw how heartbroken she was.
I should have said something at the time, but I didn’t fully understand what was going on, and I thought I knew better. I was sure you’d both be happier with other people. Then years passed, and neither of you found love. I started to wonder if I’d made a mistake.
I’ve tried a few times, over the years, to get you in the same room again, but you were both hesitant to even be in the same city.
You asked about each other, but no matter what I said, you never seemed ready to see each other.
And I was the last person either of you would turn to for romantic advice.
Well, I knew that there was one request you wouldn’t refuse: mine, after I was gone.
That’s why you’re both CEOs. You deserve another chance, because I’ve never seen either of you happier than you were back in college.
You deserve to be happy. And I like thinking that the two of you might be together someday, sharing the same jokes you shared with me, traveling together, and continuing my legacy.
Tears pushed at the back of Elliot’s eyes, tears he hadn’t even spilled at Dominic’s funeral. Elliot never cried. Never. Yet today, he wasn’t sure he could hold back. Half crying, half laughing, he continued reading.
Now, I know you might not really be right for each other, and I’ll accept that. I have to. But if you think there’s any chance you’d be happier together than you are apart, please give it a try. Don’t let fear hold you back. Don’t let me hold you back, either.
I know you love your work. I know you think that’s the most important thing in your life.
But take it from me, when you reach your final days, you won’t remember the time you spent at work.
You’ll remember the people you loved and the people who loved you.
You’ll remember the wonderful days you spent together.
You’ll remember the times you made each other laugh.
You’ll remember the adventures you had. A life isn’t measured in work.
It’s measured in love. I know, laugh at me all you want, but it’s true.
So, enjoy your time leading the company I loved and reach for the future you want. Use everything you learned running a business and put it into your future, because that’s where you’ll need it. I’m rooting for you. Both of you. It isn’t too late.
Punches and love,
Dominic
Elliot read the letter once, then a second time, then a third time.
The letter sounded so much like Dominic that Elliot could practically hear his best friend’s voice in the back of his mind.
The sign-off, especially, brought back memories of college days when they’d trade punches and high fives instead of hugs and affection.
It felt like Dominic was still with him.
And, as always, Dominic didn’t hesitate to give Elliot the “real talk.” And, as always, the “real talk” hit Elliot hard.
Because Dominic was, somehow, still spot-on in his analysis of what was happening in Elliot’s life, even though he was no longer here. Tears pressed at the backs of Elliot’s eyes again as he imagined his friend pouring all his hopes for Elliot’s future into this letter.
Yet Elliot had gone completely against what his friend had wanted for him — and what he wanted for himself.
Instead of sticking with the CEO job and giving his relationship with Lucy a real second chance, he’d walked away the moment things had gotten difficult.
Dominic was right: Elliot’s work was meaningful, but it was no longer what he thought about in the quiet moments.
Now, Elliot remembered the time he’d spent with Lucy.
He had made a terrible mistake when he’d walked away from her.
He should have figured out another solution.
At the end of the day, Dominic was right that a life was measured in love, not in work.
Elliot should have tried harder with Lucy.
He should have realized that what they had was more meaningful than Keype, more meaningful even than Borderless.
Carefully, he folded the letter and slid it back into its envelope.
He set it onto his desk, along with the other things from the New York office, and picked up the cork from the vineyard trip, spinning it between his fingers.
He would never again drink wine without thinking of Lucy.
There wasn’t much he could do at all without thinking of her.
Another sentence from Dominic’s letter flashed through Elliot’s mind.
It isn’t too late. Of course, his friend had been talking about Elliot and Lucy’s second chance.
He hadn’t foreseen how badly Elliot would mess things up.
He hadn’t foreseen that Lucy would be avoiding him all over again, and he her.
Yet maybe, just maybe, Dominic was still right.
Elliot’s heart began to race, and he stood, pacing around his office.
The Chicago skyline stretched in front of his window, with the lake in the far distance.
In that moment, Elliot would have traded the coveted office with its gorgeous view for a small New York restaurant with Lucy at his side in a heartbeat.
Lucy didn’t want to talk to him. That much was clear.
Elliot wasn’t sure he’d want to talk to himself after how abruptly he’d left.
He remembered the heartbreak he’d felt when Lucy had ended things with him back in college and felt all the worse.
If she cared about him, even a little, she was probably going through the same thing now.
So, what could Elliot do? His first thought was to return to New York and ask for another chance, but he dismissed that idea quickly.
After how they’d ended things last time, Lucy wouldn’t trust him easily.
They wouldn’t be able to fall into each other’s arms the way they had at the vineyard.
No. Elliot needed to prove that he was serious this time.
He hadn’t told Lucy how he felt about her back in college, and he hadn’t told her how he felt about her this time, either.
It was time to finally be fully open and honest, not about how he’d felt in the past, but about how he felt now.
He needed to show her that he was ready to put in the work to make their relationship a success.
After all, Dominic had said that Elliot could apply his business skills to his future, and maybe he was right. Maybe the same hard work and dedication that had made Keype a success would help make his relationship with Lucy all it could be, all it should have been.
Elliot wasn’t going to live in fear anymore. He would tell Lucy everything. He would prove to her that he cared and that he was willing to do whatever it took to make things work. Then, it would be up to Lucy to say what she wanted to do next. Elliot just had to hope that she felt the same way.