I get rejected, a lot. Whether it’s for job applications, conferences, startup accelerators, mentorship programs, universities, I have gotten hundreds if not thousands of rejection emails.

Each time they sting a little. I’m not gonna lie. I apply to stuff because I want to be a part of it and it sucks when that application is denied. It’s gotten easier to take rejection as I’ve progressed in my career, but it still sucks.

I don’t think we talk about this enough. About the sheer number of rejections that people get, whether they’re successful or not. I don’t think we normalize rejection enough.

I’ve applied to Jane Street maybe 10 times. I’ve gotten an interview exactly twice. I’ve never gotten an offer.

I’ve applied to Y Combinator multiple times. Some applications were more serious than others. All rejected.

Spotify, GitHub, Stripe, Amazon have never given me the time of day. Heck, I interned at Microsoft and I get auto-rejected by a lot of roles. And I do pretty well with job applications! I wouldn’t be surprised to see very successful people who have 10x the rejections.

Part of the issue is that people’s first real experience with rejection is with college applications. College applications are these big one-shot systems. You spend four years¹ preparing and get one, maybe two tries to get into school.

And in that process, unless you’re one of those kids who applies to like 30 schools, you’re gonna get at most a dozen rejections. Many high achieving students get zero rejections.

Job applications are nothing like that. You can play every year for the rest of your life. Companies encourage it! They tell you to come back next year, email you asking you to give it another shot. Imagine Harvard sending you an email telling you to try again. Imagine being able to get into Stanford at 40.

That’s why I liked job applications. I didn’t feel like I did my college process “properly”. I wasn’t prepared and didn’t know how to play the application game. And by the time I learned it, it was too late. With jobs, I could keep playing and keep learning.

Too many people are stuck in the college application mindset. They see a job application as a singular thing that needs to be carefully written and revised. Which is oddly optimistic. Job applications are very much a numbers game. Assuming you have any control over the situation is very naive. No matter how carefully you craft your cover letter, no matter how much prep you do, there’s a chance Google’s automated system will just throw your application away or a recruiter will just not respond. That isn’t to say you should put zero effort into applications; a well worded email goes a long way. But that effort should be limited in scope.

People also assume that an application is a strong statement about their ability. I’ve been in so many conversations where I encourage someone to apply to XYZ place only to be told “nah man, I applied there last year and got rejected”. It doesn’t help that colleges are very good at selling college admissions as this magical process that can pick out the wheat from the chaff. People can treat admissions as this sacred art that is always correct.

This is a case where privilege matters a lot. If you’re someone who has privilege in the tech industry, which I do as an Asian male, you will probably get less discouraged from a rejection. Putting it in tech terms, you will take it as less of a signal. For many people with privilege², a rejection is just a sign that something went wrong in the application process or the company messed up. For many people without privilege it’s a sign that they’re not good enough.

When I fenced competitively, there were people who were so confident in their ability. They’d fence you, lose to you, and without losing a beat, ask you for another round. I wasn’t like that. I’d want to win in competitions but in practice I’d take the loss. That’s what separated me from the people who got good. I didn’t have that confidence instilled into me that I could beat anyone.

Which does make me wonder, is there a way to put that confidence into people? To set the expectations up that you will get rejected and that rejection is not an indictment on your self. To encourage people to celebrate and talk about rejection. To see rejection as a sign that no, the company fucked up.