4. Brennan
four
Brennan
Six Months later
M y life is fucking out of control.
Time slips away like sand through my fingers—no matter how tightly I try to hold on, it escapes, leaving me with nothing but the unsettling sense my life is unfolding faster than I can live it.
Days blur into nights. Weeks into months. The quiet existence I used to have is a distant memory.
CognifyAI is at a tipping point. My Board of Directors are pushing hard for us to expand into new markets. They see untapped potential and dollar signs. They’re also spooked by how fast AI is being adapted for everyday use.
They want results
Yesterday .
The problem is, the milestones they expect change with the weather. It’s no way to run a business—but it’s not all up to me. I may be the CEO, but I report to the board, which is made up of our investors who seem to think they know more about the values of my company than I do. So I fight them. They fight back. We compromise.
It's a vicious fucking cycle that has me reeling. Makes me rue the day I ever took VC money.
They’re not happy with me these days because I’ve been increasingly vocal at the stupid things they want me to do. All I see are irreparable cracks forming by trying to expand too fast. Rushing innovation has the potential to backfire spectacularly, which I can’t allow. My entire life has been dedicated to building my company and I’m not about to fail.
So I work. All the fucking time.
Last night I returned home from my eighth trip in four weeks to Silicon Valley. I’ve barely slept all month because I’m constantly fighting fires. This week’s crisis is our Chief Technology Officer is threatening to quit if she doesn’t get a massive raise and additional equity. I don’t blame her, next to me she’s taking the brunt of the investor bullshit.
Ah, fuck. I’m rat-holing. Again .
Tonight, I’m out with my brother, Cillian at my favorite place, the Metropolitan Grill. I’m nursing the same beer I ordered three hours ago. He’s drinking heavily—more than I’ve ever seen him—and it worries me. I can’t watch another family member fuck up his life with alcohol.
When I’m in town, I try to keep a close eye on him, but I’ve not been here much this year. It sucks, he’s my best friend and he’s been through a terrible breakup and started a lucrative but complicated job. The personal toll is obvious, even if he refuses to acknowledge it.
Jesus. We’re two brothers with successful, booming companies who are so stressed out we’re barely able to exchange two words.
Cillian downs another whiskey, his words slurring as he turns to me. “Y’ever think we’re all chasin’ our tails, Brennan? We put s’much into this life, into these people , and…it all blows up in our faces.”
“Yeah.” I nod, swirling the warm beer I have no intention of finishing.
The noise of the bar fades as I, once again, get lost in my thoughts without really responding. I’m snapped back to the present when my phone buzzes. Like a trained monkey, I check my messages. It’s from my brother Connor. Connor: Ran into Astrid. She mentioned she hasn’t heard from you in a while. Everything okay?
Suppressing a groan, I add another task to my list. Astrid and I were supposed to get together a couple weeks after our lunch—apparently, she forgot to return this mysterious item of mine she’s had since high school. For me, I can’t imagine what it could be.
Time fucking flies. It’s been six months since I sat across from her in this very restaurant. Despite my initial misgivings—considering my old fixation on her, part of me wanted to keep my fantasy girl a fantasy—she was easy to talk to, which was unexpected. I don’t always connect well one-on-one. The idea of working on this stupid reunion project kind of blew my mind.
It also reminded me of when I started CognifyAI. The brainstorming. Strategizing. Solving problems. God, I’ve missed it.
“Wassup?” Cillian watches me study my screen.
“It’s Connor.” I pocket my phone. “He ran into a girl from my class. She was asking about me.”
Cillian stares at me, his cynical expression on full display. “So, wait. Are you tellin’ me you haven’t pulled the trigger with her? Y’should definitely go after her. She’d be a hot fuck.”
“Nah, it’s not like that.” I stab my fork into the table in frustration because—let’s be honest—while there’s no hope of any sort of romance with her, it’s not like I haven’t jacked off to her a dozen times since the time in my office.
Cillian laughs bitterly and shakes his head. “Not like that? I’m telling youse to go have some fun. Get your dick wet. Fuck her but don’t fuckin’ love her.”
I’m taken aback by his tone, but I know it’s the hurt talking. He fell hard for a woman who wasn’t who she seemed. It broke something inside him. Now he’s channeling his bitterness into warnings he’d never have given me before. And whiskey. Lots of fucking whiskey.
“I get it, Kill. You’re going through hell. Remember, though, unlike you I’m not cool with casual sex. You know I get too attached.” I lean back in the booth. I love my brother, but he’s not the nicest to be around when he’s drunk.
His head lolls a bit. “Ah, fuck it. The minute y’start thinkin’ somethin’s real, it goes to shite. ’Tis true. Yer not cut out for no-strings pussy, ma wee brother.”
His words sting but I can’t entirely dismiss them. Besides, I’ve seen what he’s gone through when he fell hard. The toll it’s taken on him. I’ve never gotten close to someone loving me before I do something to fuck it up.
We fall into a heavy silence, Cillian finishes off yet another whiskey while I give up all pretense of finishing my beer. I watch him get drunker. Worry about how far he’s sinking. Unsure of how to pull him back, though.
It’s troubling because during the workday, he’s functional. His business is booming but the nighttime boozing is fucking with his attitude. Cillian’s bitterness is cracking the carefree facade he’s built and it seems like he’s heading for disaster.
Maybe I’ll talk to my other brothers about what we can do to support him. I’ll see everyone tomorrow at my da’s sixtieth birthday party. For now, though, it’s close to ten and I’m itching to get home.
“Cillian.” I tap him on the shoulder cautiously as we wait for our Ubers. “Maybe you should take a step back from the drinking for a bit. Focus on your work. Take care of yourself.”
He belches loudly, causing the couple waiting next to us to stare in disgust. “What’s there to take care of? Work’s fine. The company’s better than ever. I’ve got everything under control.”
“Yeah, okay.” I sigh as I try to help him stay upright. Memories of my da stumbling home wasted throughout my teenage years fill me with low-level terror. Cillian is not, in fact, okay. Until he realizes it, though, there’s nothing I’ll be able to do. “I don’t want to see you burn out.”
“Don’t worry ’bout me. Focus on yerself. Fuck Astrid, if y’want.” He shrugs, stumbling a bit.
Our Ubers arrive at the same time and I help him inside, making sure he’s settled. “See you tomorrow at the party?”
He nods incoherently, waves me off and shuts the door. I watch as the car speeds off into the night. The tension in my shoulders intensifies as I get into my own vehicle. The odds of me sleeping tonight are zero.
Half hour later, I get home to my townhouse—my parents built a compound years ago and gifted me and each of my brothers our own homes-- pull out my phone and scroll through the messages from Astrid I’ve been ignoring. God, I feel guilty about, essentially, ghosting her.
I’ve got to get better .
Little does she know, I wireframed our idea the day after we met but it’s been pushed to the side as CognifyAI dominates every waking hour.
Or am I making excuses?
Fuck .
I’m trying not to hyper-focus on her but the truth is, I think Astrid might be someone I could care about. It’s hard for me to tell, with so little experience, but I think this situation is very different. What started out as a strange reconnection could be, at least, a friendship. One I didn’t expect.
The truth is, I like her.
I looked forward to getting together after our lunch. Then I got nervous. Aside from an apologetic text a few months ago, I haven’t made any effort.
Let’s be honest, it’s not because she’s done anything wrong. I’m fucking terrified of rejection. Petrified of misconstruing Astrid’s kindness as meaning something else.
It’s happened to me so many times.
“Brennan, you’re so awesome but…”
“Brennan, you’re so intense…”
“I’m so sorry, Brennan. I don’t think of you in a romantic way…”
I can’t hear those words from her. I can’t.
It’d be torture to be around her and, once again, pine like a loser when she friend-zones me. Or, worse, face the humiliation of her recoiling with horror if I had the guts to make a move.
Overthink much?
Have you met me?
On the other hand, she deserves basic courtesy. It’s fucking embarrassing she’s resorted to messaging me through my famous brother. Who the fuck do I think I am? I told her I’d help her with this project, and I’m a man of my word.
Before I can second-guess myself, I send her a text. Me: Hey, Astrid. Sorry I’ve been MIA. Things have been crazy busy on my end. Can we set up another meeting? I’d like to pick up where we left off.
I hear nothing for the next ten minutes so I pull out my laptop and try to distract myself by firing off emails. It works. Until my phone pings an hour later. Astrid: I appreciate the apology, but I’m not in the habit of being blown off. Are you sure you have the time for this?
Wow. I like her directness at calling me out. Very few people, other than my family and my board, have the balls to confront me these days. Me: You’re right and no excuses. I won’t waste your time again. Thursday happy hour? I’ve got some ideas I think you’ll like. Astrid : Let me guess, the Met Grill? Me: Nah, you pick, I’ll come to you. Text me the place. Astrid : Living on the edge, McGloughlin? Me: I’ll take my chances. Astrid : Challenge accepted, nite! Me: Goodnight!
Huh. That was pretty easy.
After returning to my email logjam, hours later I collapse into bed. Exhaustion permeates every cell of my body, but my thoughts keep circling away from my work problems and back to Astrid.
Our text exchange surprised me and makes me feel certain the pleasant conversation we had was real. I close my eyes and concentrate on being fully present. Try to access what I’m feeling. Pinpoint moments of clarity.
It works.
Real connections for someone like me are rare.
This is one I shouldn’t let slip away.