During a recitation class in my sophomore year of college, I overheard another student’s conversation with our TA. Rachel* was asking the TA for a couple points back on her assignment. 

TA: It’s just two points out of 25. This assignment is like one out of fifteen this semester, and your assignments are only worth 10% of your total grade. 

Rachel: I know, but two points here or there could mean the difference in a letter grade at the end of the semester. Can you check if my answer was correct? 

TA: *looks over the paper* Sure okay, I’ll change it if you really care that much. 

As mundane as this conversation seems to me now, at the time I couldn’t stop thinking about it. I was nearly halfway through college, and I had never asked for a regrade on anything, even under circumstances that would’ve been really meaningful. The possibility never even crossed my mind — I’d grown up believing that authority figures made final decisions. Even when the TA initially pushed back, Rachel stayed firm and ultimately received the outcome that she wanted. I was gobsmacked. It seemed… so impossibly simple.



Rachel was the type of girl I admired to an almost embarrassing degree. I’d heard that she had a >4.0 GPA as a CS major. She also went out a lot, and she was always eating salads and jogging around campus. She seemed effortlessly disciplined, confident, social, beautiful, and down to earth. I wanted to be like her.  

As someone who grew up in the laidback PNW, at Cornell I quickly grew to admire the assertive, over-confident independence of affluent students from ‘the city’ (new york). Whatever drawbacks there were to this personality type, there was also something I could obviously learn.

I started noticing that these students regularly asked for extra ‘consideration.’  They asked professors for regrades when they felt things were unfair. They asked for assignment extensions when they felt that they needed them. They asked alumni for informal conversations or even internship opportunities, when they simply wanted them. And frequently, they received what they asked for.

Watching Rachel’s conversation with the TA was an aha! moment; it dawned on me that not asking for things, out of respect (put politely) or cowardice (put more bluntly) was doing me zero favors. Students weren’t making ‘special’ requests at all; their asks were the norm.  It was an element of the game that I hadn’t invested in learning.

Asking for things is almost always an asymmetric bet. The expected cost is near zero — you risk only a rejection (net zero) and a small amount of personal discomfort. In contrast, the upside is not only nonzero, but often very significant. There’s therefore only one rationale choice; to take the bet. Timidness was a trait I’d benefit from unlearning.

Looking back, the points on Rachel’s assignment were probably meaningless, but the practice of advocating for herself was extremely impactful. Each individual assignment extension or regrade could collectively represent something significant. Every slight advantage — a tiny GPA bump, an initial interview opportunity — compounds over time. They wedge open doors for internships, which open doors for job opportunities, which open doors for promotions, and so forth. I learned that I could have all these things too, if I asked for them. And slowly, I did.

…

Fast forward a few years later.  My APM class at Twitter had just finished our first rotation. We learned a lot in our first year, and also experienced some common challenges. Some of my classmates wanted to provide feedback about the program to the leadership team, suggesting changes that we thought could make it better. Even though it’s something I agreed with in theory, I struggled with my natural aversion to asking for more. I initially pushed back on proposing program changes, which included the possibility of a faster promotion timeline than the program originally specified.

“They’ll think we’re entitled! “ I protested.

“Do you think it’s entitled to ask for something, if we share our reasoning? They can always just say no” my classmates challenged. 

This went on for a few days. We had mutually agreed that everyone had to be onboard with the proposal, since the request would represent all of us collectively. Eventually, with enough nudging and encouragement from my peers, I begrudgingly acquiesced. 

Ultimately, the leadership team was incredibly receptive to our feedback — they responded with deep empathy and support. Of course in retrospect, I feel a bit sheepish for my negativity. The skill of asking for things is something I'll always have to work on. I’m continuously grateful for the privilege of learning from my APM friends and classmates, who I’ll always admire and respect.

…

Over the years, I’ve reached out and requested things an uncountable number of times. I’ve also been rejected or ignored far more times than I can remember. Although of course I know that these rejections happened, it's funny how I don’t remember any of them in detail. I do, however, vividly recall every time that someone said yes.