I asked my company to give me a 2 month break
big ask
“Why do you dare to ask for something so big?” I felt a knot twist in my stomach.
“It’s uncomfortable,” my roommate replied, “but I still think I’m worth it.”
Alright. Time to drop the bomb. I’m about to ask my startup—a place where people work Monday to Sunday—for a two-month break.
I know how ridiculous it sounds. I’ve been terrified to bring it up. Even though I know I need it, I’ve procrastinated for a month, too afraid to speak. My school counselor finally encouraged me: “Even if it doesn’t work out, you’ll see how much they value you through the conversation.”
Then last week, I found out they messed up my visa, and kept it from me for a month. That was it. I was burnt out, fed up, and I didn’t care anymore. So, I took a deep breath, walked into the meeting room, and asked.
And… it was a disaster.
“Why do you need a two-month break?” they asked.
“I want to rest for a month, and spend another month learning AI,” I answered.
It wasn’t unreasonable. I’d been asking for AI-related projects for months but kept getting sidelined.
Their response?
“Then you’ll have to work more nights and weekends.”
But I already worked nights and weekends for the startup.
“If you finish faster, you can use the extra time to study AI.”
But every time I finished something, more work just piled up.
“You need to be more efficient.”
Wait. Are you saying I’m underperforming now?
“Let’s brainstorm where you’re wasting time during the day.”
And just like that, I was shoved into the hot seat, forced to dissect my life, explain where I was “wasting time.” It was humiliating.
“Uh… I guess dinner with everyone? Sometimes we chat for a while… but I don’t want to cut that. It’s our bonding time,” I muttered.
“Then you can learn to exit the conversation earlier and get back to work.”
I wanted to scream. We don’t even get national holidays off. And now even dinner was being dissected?
In the end, nothing changed. They reluctantly gave me a two-week break, but my boss, clearly furious, slammed the conversation shut: “THIS IS A STARTUP.”
“THIS IS A STARTUP.”
I walked out feeling empty. Not angry. Just numb. I barely even fought back. It wasn’t worth it. My friends were livid on my behalf, but honestly, I’d loved the experience. I gained clarity that I didn’t know working there for the entire year.
Here’s what I learned:
Business always comes before relationships.
No matter how “friendly” the culture seemed, it was clear: I come second to the business. So I have to think for myself, too.I wasn’t as valuable as I wanted to believe.
For a long time, I worried maybe I just wasn’t good enough. But lately, I’ve been receiving validation from outside. This conversation confirmed it: I’m not as valued here as I’d hoped.Their only solution to problems is “work harder.”
That’s their philosophy: more hours, more grind. I don’t believe in that. I believe in working smarter, not harder. And that’s a fundamental mismatch.
These realizations were immensely valuable. No more illusions. No more sweet talk to blur things. I saw the culture, crystal clear. Now it’s up to me to decide whether I can live with it.
Funny enough, a week later, they called me into another meeting. This time, they came in with… a paid time off plan. They admitted they’d been disorganized for too long, and now they wanted to set proper policies.
Turns out… big asks do work.
Here’s what I learned about big asks:
They’re terrifying, but when you’re honest about what you need, the real victory is in asking, not the outcome.
You gain insights you might not uncover in years.
You think it’ll ruin relationships—but sometimes it sparks change for everyone.
Honestly? I’d do it again.
