Matched with my boss

Chapter 4

Chapter 4

Jake

"Sometimes, to win, you have to risk it all, even what you never thought you’d risk."

The elevator glides upwards in complete silence, a metal box gently rising between the building’s glass walls. I glance at my reflection in the mirror occupying one side of the elevator’s back wall, adjusting the knot of my dark blue silk tie. My eyes, a steely gray that many have said seem impenetrable, meet my gaze with calculated calm. Today is the day I’ll finally be presented as the president of Sidle Financial Consulting. The legacy I had distanced myself from for so long, and yet, here I am.

Sidle Financial Consulting occupies several floors of the building. From the tenth to the twenty-eighth, the company’s core spans the structure, housing all the departments that keep this financial, consulting, and strategy machine running. An imposing building of glass and steel, its windows reflect the lights and relentless energy of New York City. My office is on the top floor, the twenty-eighth, precisely where the big decisions are made—the ones that, starting today, will be mine.

The elevator doors open with a soft ding, and I step out into reception. The walls are paneled with dark wood, contrasting with the modern lines of the furniture. Along the lobby, abstract paintings adorn the hallway—vibrant colors that seem to pulse against the reserved decor. The receptionist, a young blonde woman with a polite smile and gray uniform, nods upon seeing me.

“Welcome, Mr. Sidle. The executives are waiting for you in the conference room.”

I nod silently and walk down the hall, where a glass door automatically opens, granting me access to the meeting room. Floor-to-ceiling windows let the morning light flood the room with a warm glow. The meeting table is long and rectangular, made of dark ebony, surrounded by black ergonomic chairs. As I enter, the department heads are already seated, watching me with curiosity.

I recognize many familiar faces, men and women who have been working for the company for the last twenty years, some even from before I left. I see Professor Navarro, one of the company’s oldest and most respected members, whom I’ve known since I was a child when my father brought me along to introduce me to this world. His hair is now gray, and his glasses rest on the bridge of his nose as he gives me a neutral, yet respectful look. Navarro has always been a straightforward man, keeping the company steady during times when my father couldn’t be at the helm.

“Good morning, everyone,” I say firmly as I reach the head of the table. I straighten up, clasp my hands behind my back, and nod, taking a moment to look at each person present.

My father then stands up, slowly. Though slightly more stooped with age, he still carries that air of authority I’ve always associated with him.

“Today is an important day for Sidle Financial Consulting,” my father announces, his strong voice resonating through the room. “I have decided to step aside and hand over the leadership to my son, Jacob Sidle. The time has come for the new generation to take the helm. I trust that Jacob will lead this company to new heights and that each of you will support him as you have supported me.”

A restrained, polite applause fills the room—more a courtesy than a celebration. All eyes turn toward me, and I feel the weight of expectations in those gazes. I take a deep breath and step forward to address the room.

“Thank you all for being here,” I begin, keeping my voice steady and controlled. “I know that my arrival might be seen as a significant change, and perhaps some of you may have your doubts. That’s natural. But I want to assure you that my commitment to this company and to each of you is absolute. I want us, together, to build upon the legacy my father began and to expand it with new approaches and strategies that will propel us into the future.”

I pause for a moment, letting my words sink in. I see a few nods; others still seem to hold some reservations. I continue.

“I understand the responsibility this role entails, and I also understand that, for many of you, my presence might not feel entirely familiar. I’ve been away for quite some time, pursuing other goals. But I’m here now, ready to bring everything I’ve learned to make Sidle Financial Consulting stronger, more agile, and more effective. I’m confident that together, we can achieve this.”

There’s a soft murmur of approval among those present. Navarro looks at me with an expression that’s almost inscrutable, but I’d dare to say there’s a hint of approval in his eyes.

“Now then,” I continue, “I want you to know that my door is open to each of you. This is a team, and I’m here to support you. Times change, and so must we. Let’s keep building on the foundation we already have and take this company even further.”

I finish my speech, letting my gaze drop momentarily to the table as I collect my thoughts before looking back up. A more enthusiastic round of applause fills the room. Maybe that’s a good sign.

When the meeting concludes, I exchange formalities and leave the room. I walk down the hallways to the elevator that will take me up to the twenty-eighth floor, to my new office. The doors close, and the view from the elevator window opens up to the city that never sleeps. As I near my destination, I feel a mix of determination and a certain weight in my chest. I’m here for a reason, and nothing will derail me from my goal.

The doors open, and the expansive offices of the top floor welcome me. My space is at the end, across a seemingly endless hallway. On either side, glass-walled offices provide views that stretch to the horizon. My secretary, an efficient woman named Laura, is already stationed there. She nods respectfully as I approach, standing to open the door to my new office for me.

Upon entering, I take a moment to survey the room. My office is spacious, with a large window covering the entire back wall. From here, I can clearly see Central Park and its greenery. The desk is a minimalist, dark marble piece, uncluttered except for a fountain pen and a folder of documents.

The black leather chair behind the desk is comfortable yet firm. I walk over, running my hand along its back before sinking into it with a sigh. From here, everything seems perfect. Everything controlled, everything in place. The illusion of control that life has taught me to value, and ironically, that has always been so easy to lose.

With my elbow resting on the desk, I bring my hand to my chin, reflecting on what I’ve just said to everyone. I’ve committed to leading this company, to continuing a legacy. But I also have my own ambitions, my own plans to take Sidle Financial Consulting to another level. I won’t be my father, and I won’t stay in his shadow either.

I pick up the pen on the desk, spinning it between my fingers as my gaze drifts over the vastness of the city sprawling out before me. There are still many questions, much to confront. But there’s also something in this uncertainty that fills me with energy. The company is mine now, and I have the chance to leave my own mark.

A knock at the door draws my attention, and Ian’s head appears, a mischievous smile on his face. Ian has always had that ability to make me feel less suffocated with his carefree attitude, and today is no exception.

“Hey! All settled in, Mr. President?” Ian jokes as he steps in without waiting for a response.

I chuckle and motion for him to sit across from my desk.

“‘President’ sounds a bit too formal, don’t you think?” I reply, letting my voice drop to a playful tone as I lean back in my chair. “I’m still trying to get used to all this.”

Ian plops down in one of the chairs across from my desk, hands resting on the armrests, as relaxed as ever. He’s a clear contrast to me—not only in how he views life but also in how he presents himself to the world. While I prefer to keep everything under control, Ian has that ease of navigating through chaos as if life were a river and he was simply going with the flow.

“So, what’s it like being the head of a financial empire?” he asks, raising his eyebrows in an exaggerated manner.

I look at him and laugh.

“It still feels unreal,” I replied, setting down the pen I’d been twirling between my fingers, and offered him a smile. “Though I’m sure I’ll get used to it. I guess it’s a bit like climbing a mountain, don’t you think? The hardest part is getting started, but once you’re halfway up, there’s no turning back.”

“Climbing a mountain? Come on, Jake, there’s no way you’ll ever shake off those adventure metaphors, even if they put you in a thousand-dollar suit,” Ian joked, chuckling. “But I’m glad to see you here, really. You look… good. You’re where you’re supposed to be.”

I smiled at his words. Ian wasn’t the kind of friend to openly express deep feelings, but in his small statements, I found true friendship. It was his unfiltered, uncomplicated honesty that had kept me close to him for so many years.

“Thanks, Ian,” I said sincerely but quickly changed the subject, raising an eyebrow. “But enough about me. Tell me, how’s the apartment situation? You said you had everything ready.”

Ian leaned back, crossing his hands behind his head in his favorite disinterested pose.

“Ah, the famous apartment! Yeah, the move is next week. The place is small, but the view is amazing; you’ll see. You’ve got to come by once I’ve got it all set up. I promise I’ll have a good bottle of whiskey ready to celebrate,” he said, grinning.

“Sounds like a plan. You know I’ll never pass up a chance for good whiskey,” I replied, playing along.

“But no, let’s talk about you first, Jake. You’re trying to dodge the subject, but I won’t let you get away with it. Tell me about the mystery woman from the dating app. How’s that going? Have there been more chats?”

I sighed, but a smile crept onto my lips despite myself. I leaned back in my chair, looking out the window as the words came out slowly.

“Yeah, honestly, it’s going pretty well. I won’t lie—I didn’t expect to meet someone so interesting. She’s smart, Ian. We always have something to talk about, something that connects us. And on top of that… she’s beautiful!” I admitted, feeling warmth rise in my face just from saying it aloud. “I don’t know, when I talk to her, time just flies by.”

Ian looked at me with a teasing smile, but there was also a touch of tenderness in his gaze.

“Seriously, Jake? You’re acting like a lovesick teenager! When was the last time I heard you talk like this about someone?”

“Save it,” I said, though my smile contradicted the seriousness in my words. “It’s strange, I know. After so long without wanting to get involved with anyone, I thought maybe it was impossible to find someone who genuinely interested me like this. But this girl… she has something.”

Ian nodded, resting his elbows on his knees while watching me with a mix of curiosity and sincerity.

“Look, man, I’m not one for sentimentality, but I can tell you this: if you feel that, you should keep exploring it. You have nothing to lose. And honestly, how long has it been since you let yourself enjoy something like this?”

I looked at him, considering his words, and nodded slowly. There was something in what he said that resonated within me, like a bell echoing in an empty room. It was easy to disconnect from yourself when the sole focus was reaching the top of the mountain.

“Maybe you’re right,” I finally said, relaxing a bit more in my chair. “I’m not saying it’ll be easy, but there’s something about her that makes me want to try.”

Ian shrugged and let out a laugh.

“There you have it—that’s my Jake. Always calculating risks but willing to jump into the void if something’s worth it. Tell me, what’s she like? Come on, give me all the details.”

I laughed and then sighed, narrowing my eyes as I tried to sum up how I felt about her.

“She’s… hard to describe. She’s a mix of determination and sweetness. She’s not easily intimidated, and I can tell that even through messages. She has opinions and isn’t afraid to defend them. She’s the kind of person who can talk about anything: from art and philosophy to mundane stuff like TV shows or the coffee she had that morning. I love that about her—I never get bored.”

Ian leaned back, crossing his arms over his chest with a smile.

“That sounds amazing, Jake. I know you’ve always been looking for someone who can challenge you, someone you can have something meaningful with. And it sounds like this girl might just be it. Have you thought about asking her out again?”

My smile turned into a pensive look.

“I’ve thought about it, but I want to take my time. I don’t want to rush and mess things up. You know how I am,” I replied, though a part of me was eager to see her again. But there was something in her mystery, something that drew me in but also made me feel a bit vulnerable.

Ian stood up and walked over to the window, gazing at the view of the city before us.

“Well, either way, if she’s as special as you say, she’s worth the risk. And speaking of risks, why don’t you ask her out before things go cold?”

I laughed, nodding as I stood up and joined him.

“You’re right. I’ll see when the time feels right,” I said as we both looked out at the city.

Ian turned his head towards me, his smile returning to that mischievous tone he was known for.

“Just make sure to keep me updated. I want all the juicy details of your romantic financial journey,” he joked, giving me a light slap on the shoulder.

“You first tell me if you manage to move into the apartment without breaking anything, and then we’ll talk about juicy details,” I replied, grinning broadly.

The mood between us relaxed again. Ian was one of the few people who knew every detail of my life and had always been there for me. I knew I could trust him to talk about anything, even something as complicated as this new mysterious woman who had come into my life.

“Speaking of which, I’ll keep you posted on the move,” Ian said as he turned back to me. “Who knows, I might need a strong hand to lift a few boxes.”

We both laughed and returned to lighter topics for a while. Yet that brief conversation about her, about the woman from the dating app, lingered in my mind. I felt like Ian was right; maybe it was time to be a bit less calculating and just let things take their course, without so much fear of what might happen.

I couldn’t help but think about the next time I might get to talk to her. I didn’t know how things would unfold, but I did know one thing—I didn’t want to lose the chance to keep getting to know her.