The Worst Way to Apply for a Job You Really Want

About 10 years ago, when I was trying to move to New York City, I really *really* wanted to work for a certain company. Let’s call it Dragon Co.

I’m telling you, I was a little obsessed with the idea of working at Dragon Co. I loved their interactive approach to design and team-building, and I relished in the relatability in how they communicated. I looked at all of the people who worked there as walking heroes, future mentors, or lifelong friends.

Every few months, I’d check their job board to see if there were openings in the area that interested me. And then once, in the fall of 2010, I struck gold: They were hiring in an area that interested me.

I knew if I wanted to really stand out, I’d have to do something extra clever in my application process. I’d read on message boards that hundreds of people applied for jobs. Without knowing anyone there personally, I racked my brain trying to think of the perfect way to stand out.

I decided (in my overthinking mind) that the anybody could just apply to a company, but what would really stand out would be to somehow get their attention IRL in the office.

Given that I was living in Philadelphia at the time, I knew this was going to be tricky to manage. But I decided to concoct something crazy and try anyway.

This, by the way, is where the story goes off the rails. DISCLAIMER: DO NOT TRY THIS AT HOME. IT WILL NOT WORK.

The offbeat application

When applying to my very first job out of school, I learned via an email that a writing job I really wanted had 292 other applicants. Clearly, a fresh-out-of-college 22-year-old wouldn’t stand out without a miracle, so I knew I needed to think fast in my next step.

So, the following day, I showed up at their office in Philadelphia with an anonymous note. It said:

“Hi Everyone.

Thank you for the update about the status of the application process for this role. Good luck getting through all 293 applicants.

I hope to hear back from you soon.

All the best,

Applicant #94"

(Of course, I didn’t know I for sure that I was the 94th applicant; this was just a number that I liked.)

At the end of the day, after scouting and let’s call it “strategically visiting” (aka: stalking) other companies where I had sent resumes in the city, I returned to that office at the end of the day. That time, I just walked in the office and left behind a binder I’d prepared the night before. When you opened up the binder, it said:


I’m applicant #94.

(But you knew that already.)

Here are some things about me that you don’t know.”

And inside I had included tons of side projects, writing projects, and little tidbits that you never can quite find room to include within the constraints of a cover letter. I felt that, unlike my email form application, that binder was a truer depiction of myself and my personality.

Turns out that they agreed. I didn’t even make it down the street before the door to that small consulting firm swung open, and one of the founders raced after me down the street.

“Wait right there!” he shouted. “Do you have time for a coffee? Now??”

I ended up meeting with both of the founders of the firm on the spot and getting hired the next week.

The worst way to apply for a job

Perhaps overconfident from this early version of cleverness, I decided to up my game in a serious (and, in retrospect, painfully awkward) way.

What would stand out to a group of high-profile New Yorkers, I thought? How can I get their attention in real life and then direct it back to my application?

I decided on a complicated, multi-step puzzle.

  • First, I designed an image with my name, phone number, and email address on it and a short note.
  • Then, I took this image to a local craft store and turned it into a 12-piece puzzle.
  • Last, I split that puzzle into six different packages, wrote six different letters, and mailed the bits to six different people who I thought all worked on the same team that I was applying to join.

In the fantasy-land version of how this story played out in my head, each of them would get these letters on the same day, which all included instructions like, “Find the other people on your team who received this puzzle, too!” and they would gleefully put it together, then get so excited by my creativity that they, too, would hire me on the spot.

I’m sure it won’t surprise you at all to learn that I never heard back from Dragon Co. Not one peep. Not one “we’re sorry, your application is not what we’re looking for.”

I was pretty depressed about this at the time. But in retrospect, it’s probably a good thing that this company didn’t bend over backwards trying to dig up some random girl who was sending them weird spam mail from Philadelphia.

Now, of course, it’s very clear what I should have done:

Looked up someone who knows someone who worked there and reached out via email. (Like a normal human.)

In the end, I wound up getting another job, from a friend who literally put my resume on the top of a pile of other temp applications and said to her manager, “Hire this girl. She went to my school.”

Sometimes, it pays to be clever. But most of the time, it’s better to just be direct.

Originally published at Dry Erase.

GM @USV, alum of @StackOverflow and @NorthwesternU, board member at @CompSci_High and @NUalumni, co-founder of #BeyondCodingNYC

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store