Chapter 3
We took seats opposite each other on the train, and Natalie dove into her social media feed on her phone.
Since moving to an in-house job, she’d started a page about her favorite New York restaurants.
She was always our go-to person for restaurant recommendations, so it was fun seeing her turn her foodie hobby into an actual side business.
While she scrolled and tapped away, I looked out the window and ruminated about why this party—and seeing Chris—had made me feel so off.
Even though I was glad I went, for some reason, it spurred an uneasy feeling in my bones—a disquieting, uncomfortable doubt, like I thought I knew where I was going, but somehow, I got lost.
Chris and I broke up for the last time right before I started my first year at the firm.
Even in school, it was always on-again, off-again.
Chris alternated between showering me with love and praise and withholding it.
Every time he withheld, I would eventually get fed up, we’d break up, then after not enough time had passed for me to get over him, he’d come back, say he still loved me, and pull me back in.
But when we moved to New York, where he was from, after law school graduation, it became clear he only wanted me to be a part of his law school life.
He was always going out with his friends—men and women—and never invited me.
It didn’t feel right to me. I was his girlfriend, the woman he was supposed to love, why wouldn’t he want me around?
I got so upset one time we fought that I asked him if he still even loved me.
It took him so long to answer that I stormed out, saying I was leaving for good.
Even then I hoped he’d stop me, hoped he’d apologize and do better.
But he didn’t. I never heard from him again.
It wasn’t just losing him that hurt, it was losing the future I’d pictured for us: moving in together, getting married, starting a family.
Seeing him while being surrounded by friends and acquaintances our age that had gotten married and started families was a brutal combination.
I still wanted those things, but I hadn’t had a boyfriend—or even connected with anyone in a meaningful way—in over five years.
It was hard to picture a future that included those milestones when I didn’t have anyone to picture doing them with.
I didn’t have time to go on dates with any regularity because of my job.
And who would want to date a stressed-out workaholic like me, anyway?
I’d come to terms with the fact that Chris wasn’t the one. But the depth of the rejection I felt when he ended our relationship was so overwhelming that some part of me still wasn’t over that feeling. He made me feel like I wasn’t good enough.
So, like every other time I’d felt like I wasn’t good enough, I coped by working harder.
In reality, I could attribute some of my high performance at Peters & Dowling to Chris.
After the breakup, I threw myself into work.
I had the highest billable hours in my associate class for the first two years, and got a reputation as a go-to associate, some partners telling me I was partner material as early as my fourth year.
The validation I felt each time I received praise for my work and my hours helped me build back a bit of my self-confidence, even though it wasn’t quite the same.
And for a while, I found the work interesting enough, thrilling enough—analyzing companies, figuring out what they had to offer, locating the skeletons in the corporate closet, thinking through how to solve them.
I liked negotiating, and loved the feeling when we got our way on a particular point and the client was happy.
I’d worked on early investments in dozens of companies that went on to become household names.
I’d negotiated mergers between major corporations for hundreds of millions, sometimes billions, of dollars.
Each time I would send the closing announcement press releases to my parents and Drew, they were enthusiastic.
This is amazing, congrats! Mom and Dad would say.
Very impressive, Drew would say.
I did it, I would think every time another big deal closed or another partner expressed enthusiasm about my future at the firm.
I proved everyone wrong that had ever doubted me.
I was smart, talented, and accomplished.
I made great money. After just six years, I’d paid off all my law school debt.
And in three more years, I could be a big law firm partner with a million-dollar paycheck.
The success I had wanted—needed—since the day I got my rejection letter from Franconia Academy was within reach. Mine for the taking.
But in six years, I hadn’t stopped to ask myself: Once I got that promotion to partner, would I finally feel content?
When would it be enough?
And what was I missing out on to get there?
In answer, the image of the unadulterated smile on Tyler’s face as he watched his daughter play at her second birthday party flashed through my mind.
“Eek! The literal chef of the restaurant I featured on my page last week commented on my post!”
My gaze whipped from the cloudy train window to my friend.
She was wiggling in her seat, grinning ear-to-ear like she won a trip to Bermuda.
My cheeks tugged upward. “That’s awesome, Nat.”
“Now I have to decide what to say.” She wiggled again and settled back into her phone.
My hand reached for my own phone in my bag, but I stopped myself. Checking it didn’t bring any joy. I didn’t have a passion or a hobby like Natalie did. And if I was being honest with myself, I didn’t love my work anymore. I wasn’t sure if I ever had.
I think I just loved the validation.
Watching Natalie, I felt a pull to do something I loved, too. But what? Did I have anything in my life that I genuinely, truly loved to do?
No.
When we got to my apartment, I caved and checked my email. A jolt of terror shot through me when I saw John had emailed thirty minutes ago with an attachment containing his comments on the purchase agreement.
John Adler: Here are my comments. Please incorporate and send to the client ASAP.
Natalie noticed the consternation on my face.
“Work? Do you need to handle it now? Because I can head home…”
I thought for a moment. It was already 8:00 p.m., and even if his comments were light, it would still take me several hours to get the full draft polished and ready to go to the client.
It was Saturday night, I was with my best friend, and I was inebriated.
He said ASAP but I chose to believe he meant ASAP, tomorrow.
“Nope, I’m going to handle it tomorrow morning.” I forced a smile, already partially doubting my decision. But the client asked for the draft by Monday, and at this rate, I would have it to them by Sunday afternoon, well ahead of the deadline. That should be more than fine.
I replied to John: Received, will do!
“Remember that snowstorm party in law school?” Natalie asked.
“We all went to Tyler’s house and sang along to music videos on the TV, dancing on the couch, yell-singing into our beer bottles like they were microphones.
We were so loud that someone called the cops with a noise complaint.
” We were sprawled on my couch and had already finished another bottle of wine since getting back from Mina’s birthday party.
“Probably because it was a Tuesday!” I said.
Natalie giggled. “The cops show up thinking they’re busting an undergrad party, only to find out we’re all in our mid-twenties and we’re just maniacs that sing so loudly someone called the cops on us.”
We devolved into uncontrollable laughter at the memory.
“We were such goofs,” I said.
“We were happy,” Natalie said.
“We were drunk!”
“That’s true, too.”
“Oh, you know what we should do?” I asked.
“Put on the Hamilton soundtrack?”
“Yes! Mind reader.” I furrowed my brows, feigning concern that she’d read my mind, even though this sort of thing happened with us often.
She laughed as I stood to turn on my speaker.
We were happy back then, during school. When was the last time I felt like I did that night?
Totally unencumbered, so in the moment. This came close—wine drunk on the couch with my best friend.
But it was different. Deep down, I was worried about that stupid email and all the work I had to do tomorrow, likely with a hangover.
I frowned to myself, my body angled away from Natalie as I called up the Hamilton soundtrack on my phone.
You don’t have to keep doing this, my own voice slurred inside my head as the familiar notes wound their way into my tiny living room.
Don’t I, though?
I’d come this far. What would people think if I gave up now?