683 Ways to Fail to Get a Job Offer

Two weeks ago I put up a job posting to hire for two positions, a content curator and a digital artist. Both positions were full-time, both offered the chance to work remotely and essentially live anywhere, and both provided an opportunity for daily creative work on a small web business that continues to grow at a breakneck rate. It was bound to be competitive.


I received 707 applications. Only 24 were invited back to participate in a second round.

Reading over job applications 13 hours a day for four days straight, one quickly develops an eye for what differentiates great applications from sucky ones. You begin to see patterns, themes, variations. You see what makes the good applications good, the bad applications bad, and the ugly applications, well, ugly.

The truth is that there are some basic and common sense principles even already-good candidates could use to improve their applications. And there’s no reason for people to not be implementing these basic, common sense principles. Especially my readers.

(This is part one of a two part article. This part explains general tips and requirements for my job posting or any job posting. Part two is about my specific evaluation process for these two jobs.)

The Bare Minimum

1. Follow directions. I would feel stupid starting this article by telling people to follow directions, except for the fact that I immediately deleted almost 150 applications for no other reason than they failed to do one or more of the following:

  • Submit the application to the proper email address with the proper subject line.
  • Keep their application within the specified word limits.
  • Submit by the appointed deadline.
  • Attach all of the required documents in the requested file formats.
  • Include the letter ‘X’ at the bottom of the application, as instructed.

I buried the instruction to include the letter ‘X’ in a paragraph towards the end of the posting. It was designed to help me sort out people who didn’t read the entire post carefully before applying. And clearly, it worked.

I received emails to the wrong email address, with the wrong subject line, with no cover letters, from people just giving me their phone numbers and asking me to call them, from people with corrupted file attachments or with the wrong file formats. About 15 people submitted their applications late — some multiple days after the deadline. And of course, about 100 people failed to put the ‘X’.

It’s really simple. If you can’t follow basic instructions when applying for the job, why would I ever think you could follow instructions while actually doing the job?

2. Avoid basic errors. For content curators, any typo, misspelling, misuse of grammar, factual error or poor word usage would receive an instant deletion. The whole point of this job is to be conscientious and pay attention to details, to research statements you may not be sure about, and to generate the most professional writing possible. I need someone who can correct my (many) errors, not the other way around.

It felt evil at times, but there were a number of otherwise strong applications that were deleted for no other reason than they forgot an apostrophe or used “then” instead of “than” or got the author’s name of one of their favorite books wrong.

As for the digital artists, I was far more lenient on this stuff. I don’t need them to read or write for me, and I don’t need them to pay attention to details that don’t involve their artwork. But a few artists were automatically discarded for the following: ridiculous file sizes, bad resolutions of images, links to broken webpages or entire missing websites. I don’t need an artist/illustrator to be a web genius, but in this day and age they must have a basic understanding of file types, file sizes, resolutions and uploading their work online.

How to Gain an Advantage

After eliminating the applications that did not meet the bare minimum requirements, I was left with about 450 valid applications for two positions. Here’s how the best applications distinguished themselves from the crowd.

3. This isn’t about you, it’s about me. There’s no way to say this without sounding like a dick, but I don’t care where you live or the fact that you used to want to be a firefighter or that your mom has a stutter and took out her insecurities by making you read Moby Dick when you were 12. I’m sure you’re a nice person and all, but please, save it for the Phase 3 interview.

This application, despite what you may have been led to believe, is not about you. It’s about me.

Tell me how you’re going to make my life easier. Tell me about how you can make my business grow. As a president whose brain exploded once said: It’s not what this job can do for you, but what you can do for this job.

Reading through the cover letters, I noticed a direct correlation to the quality of the application and the ratio between the number of “you’s” to “I’s” that appeared. The more the word “you” or “your” appeared, the better the application. The more the word “I” appeared, the worse the application.

This is a made up example, but this is the type of sentence that would appear in a weak cover letter:

“I really love to research and I am great at it. I researched all throughout my university career where I was an assistant to one of my professors. I’ve always loved to read non-fiction and my friends always tell me that I can summarize ideas clearly and succinctly.”

And an example of a strong cover letter:

“My research skills will take your writing to a new level. My experience in college as a research assistant will allow me to fact-check your articles, dig up sources for your ideas, and critically evaluate your work. You may love me or hate me, but I promise to use my skills to make you an even better writer.”

I’m not paying you to make your life better (although that’s obviously a desirable side effect), I’m paying you to make my life better. So please, convince me that it is going to be better.

4. Don’t tell me, show me. The following words mean nothing: “go-getter,” “self-starter,” “born leader,” “team player,” “passionate,” “think outside the box,” “think on my feet,” “organizational skills,” “deep thinker,” “tough-minded” and on and on. These words are worse than useless. They are so abstract to the point that anybody could argue them to be true about themselves depending on the situation (and by the way, most people did).

A rich man doesn’t have to go telling people he’s rich. A poor man does. The best candidates showed me their best traits, either through their resume, their favorite books, or the actual quality of writing of the application itself. They don’t have to tell me they have organizational skills, their application proves it. They don’t have to tell me that they can “think outside the box,” their cover letter proves it.

Tons of people told me they were creative thinkers and then proceeded to write drab, boring cover letters that sounded exactly like everyone else. Tons of people told me that they loved researching serious intellectual topics and then listed nothing but puffy fiction books in their favorite book list. Tons of people told me that they were organized and obsessed with details, yet they had unorganized CVs and screwed up the formatting in their attached DOCX files.

Show, don’t tell. When you plaster vague terms all over your resume, all that tells me is that you couldn’t come up with anything relevant to say, so you just said a bunch of stuff that sounded nice. I realize you probably put those words because some college career counselor told you to put them. But guess what? They suck.

The best applications did the following:

  • They attached or linked to copies of their previous work for me to look at even though I didn’t ask for it.
  • They custom designed their application materials to match the design of my website and even used the same font on their resume.
  • They built entire WordPress sites to act as their application, with separate pages for their cover letter, resume, favorite books and so on.
  • They included lists of errors they had already found within my articles and suggested corrections.
  • They came up with design and illustration ideas to accompany my current articles without me asking.

If you’re creative, proactive, and a problem solver, then prove it. Send something I would want but didn’t ask for. Suggest improvements I never thought of. Write something that surprises me.

5. Want it for the right reasons. The greatest predictor of your future actions are your prior ones. I had a strong bias towards people who have been long-time readers, people who already work remotely or from home, and people who I have interacted with previously. The simple reason is that this job and this business are unconventional and over the years I have found that it is easy for people who are perhaps a bit disgruntled on their current path or who feel a little bit aimless at the moment to project all sorts of things onto this job or lifestyle — projections, mind you, that often turn out to be far from reality.

For this reason, I was particularly skeptical of people making large career leaps from law or medicine or finance to me when they haven’t been reading my site for a long time or don’t seem particularly familiar with the lifestyle that this job entails. I’m sure a lot of these people were honest and genuine in their feelings, but for me it’s a liability to take on someone who only recently became interested in this type of work and whose entire life history reflects choices made from different values.

I was also skeptical of anyone who emphasized their own personal development too much in their cover letter. That may sound odd considering this is a website that focuses largely on personal development. But again, people have a tendency to project or idealize an unconventional job or lifestyle as some panacea for all of their emotional problems. And I don’t need that.

Having run two rounds of job openings now, and having read close to 800 applications in total, I’ve discovered that showing genuine passionate interest for the position, or rather, “applying for the right reason,” is something that cannot be forced when it’s not there, nor can it be prevented from shining through when it is. The example that stands out in my mind is a woman who, in her cover letter, described her emotional reaction the first time she ever read one of my articles. It was touching. And it was something that could not be fabricated, not because she wrote it so well, but on the contrary, because she wrote it as if she were writing about what shoes she had worn the day before. It was just something that was a part of her.

I hired my current employee almost two years ago. I hired him from a job posting similar to this last one. About 70 people applied. And from the moment I read his application all the way until when I offered him the job permanently, he was the front-runner for the position. And it wasn’t just because of his qualifications or his work ethic. It was also because he stated in his application that this is what he wanted to do with his life anyway. And he had the track record of life choices to prove it. Everything he had done had been leading up to a career in an online psychology/self-development business. He was going to try to do it with or without me. So it might as well be with me.

Ultimately your life is defined not by what you said or what you represented but by what you actually did. And if there’s yet another argument for digging deep within yourself and finding the authentic reasons behind why you choose to do what you do, it’s this: The best way to get a job doing what you love is to start doing what you love to begin with.

Part Two will be posted tomorrow, and describe what I specifically looked for in each candidate and how I narrowed the selection from 450 down to 24.

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