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.

OK, so that’s how I whittled the pool down to 24. How did I decide on my two hires?

Content Curator

Looking back, I made a few mistakes with the posting for the curator position. I should have been much more stringent about the qualifications and what I wanted. I was expecting maybe 1/3 of the amount of applications I received and for those applicants to be half as qualified as they ended up being.

Out of the original 707 applications, about 625 of them were for the curator position. And upon sifting through the applications, it quickly became apparent that probably about 250-300 of those candidates had similarly high qualifications to one another: college degree, some successful research experience in college, somewhere between good and great writing skills, as well as high enthusiasm for the job.

Fuck.

Talk about high quality problems. After curling into a fetal position for a few minutes, I decided that I needed to redefine my standards for the position. At least 200 of these people would probably be competent at the job. Probably 100 of them would be great. But there was no way I could take 100 to Phase 2. I needed to raise the bar somehow.

To do that it became no longer sufficient to simply be a “good candidate” for the job. That was now the bare minimum. One needed to be not only be a good candidate but to also be a candidate who would likely bring something to my business that I could never bring. I eventually settled on asking myself two questions:

  1. “Can this person research me under the table? Could they read and understand the most dense academic journals without flinching or complaining?”
  2. “Can this person potentially teach me something and/or improve my writing or my business in a major way?”

The first question led me to give heavy preference to people with masters degrees and PhDs, especially if they were in related fields to psychology, neuroscience or biology. An undergraduate degree in psychology with university research/thesis experience basically became the bare minimum on the resume and even a large number of these people were eliminated.

The second question led me to give a heavy preference to people with experience within the publishing industry (editors, agents), previous online business experience, therapy/counseling experience, or professional writing experience (journalists, authors).

I also kept my eye out for a few “wildcard” candidates, basically a few people with off-the-charts raw intelligence and talent, just to see what they might be capable of.

As a result of these new standards, I surprisingly relied heavily on people’s resumes in the beginning of the evaluative process. Whereas the last time I hired I hardly looked at people’s resumes, this time it was the very first thing I looked at. Usually, within a few seconds I had a pretty clear idea what their chances of making it deep into the process were.

Next, it was on to the favorite books. For people whose resumes met the high qualifications listed above, I looked to their books and explanations as a confirmation of these qualifications. If someone had a PhD in anthropology, I looked for books that reflected this level of intellectual depth and research ability.

If a person didn’t meet my qualifications on their resume, their books were an opportunity to make up for that and to prove to me that they had deep intellectual interests and research skills.

I have to be honest. The favorite books list helped few and hurt many. I’m not sure how to say this without people thinking I’m shitting all over their cornflakes — there’s nothing wrong with light fiction or children’s books — I love Stephen King and Dr. Seuss and Dale Carnegie as much as anybody. But if those were your most favorite books in the whole world, then you are not the droid I am looking for.

On the books list I was looking for some deeper intellectual pursuit for no other reason than the joy of that intellectual pursuit. Most favorite books lists lacked this. Lists that were all fiction were a bad sign. As were lists full of some of the more popular self help works. That may sound snobby, but I think people underestimate how much research goes into posts like this one or this one. I don’t just pull this stuff out of my ass. I do a lot of hard reading.

Generally, a candidate needed to have either a highly qualified resume or a good books list. If they had neither, then they were usually eliminated at this point.

Some books lists didn’t hurt or help. You saw a lot of the usual suspects on them. In that case, I usually focused more on the quality of writing in the books explanations and their cover letters. Modest resumes and books lists could be overcome with excellent writing and explanations as well as an excellent cover letter. But this rarely happened.

I’d estimate that maybe 50 people had great books lists. And the selection of particular books could actually raise my estimation of a candidate by quite a lot. One example was The Developing Mind by Daniel Siegel, the founder of Interpersonal Neurobiology. Anyone who chooses to read this for fun, much less understands the implications and gets excited about it, is exactly the type of person I’m looking for. Another example was The Evolving Self by Robert Kegan, famed Harvard developmental psychologist whose developmental model I am an unabashed fanboy of. Another example was Denial of Death by Ernest Becker, a dense, yet mind-blowing, philosophical work. Another was Laws of Form by G. Spencer Brown, a unique philosophical book that integrates mathematics into its prose. Another example was anything written by Tolstoy… because he’s Leo Motherfucking Tolstoy.

Now, you might be thinking, “Well, you asked us for our favorite books, not the best books or the most academic books,” or whatever.

Exactly.

That was exactly the point. The person who is going to be best for this job is the type of person who reads books about self-affirmation theory for fun and then annoys their friends by constantly talking about it. Yes, it’s nerdy and academic, but that’s the point. In fact, that was part of the job description.

This isn’t to say that all of your books had to be super nerdy and academic texts. The best candidates usually had a nice mix of choices, demonstrating a well-rounded personality. And if someone put some good books that were not necessarily super erudite or dense, I became more interested in their explanations than the book itself. As far as I was concerned, you could put Dr. Seuss (and some people did), and if your explanation rocked (and some people’s did), then that was fine.

But once again, the book explanations hurt many and helped few. Most people’s explanations resembled summaries or book reviews more than a thoughtful explanation. Yes, I know what happens in The Fountainhead. I’ve read it. Yes, I know Fight Club is about masculinity, yet no mention of satire or modern society. Ultimately, I found that few people were able to explain their choices in a truly meaningful or interesting way beyond, “I read this book at this age. This is what it was about. I thought it was cool.”

Ironically, the cover letter was often only read last, if at all. If a candidate’s resume and books seemed to meet the requirements, then I would read the letter to get a good sense of their personality, what they could add to the position, and whether they were “applying for the right reasons.”

With these more stringent standards, it was fairly straightforward to get the candidate pool down from a few hundred to about 40 or so. But from there it became excruciatingly difficult. Of these last 40 people, I often read and re-read their applications multiple times. I had to cut people that I really liked, and give up the chance to work with people I was pretty sure could do an amazing job, only because there were people I was sure could do an even more amazing job.

By Sunday evening I had whittled it down to 15 candidates. The clock was ticking. I had promised to send emails for Phase 2 out by midnight. My original aim had been to pare it down to 10, but that seemed increasingly impossible, both for the sake of time and the sake of my sanity. So I said fuck it and accepted all of the remaining 15 candidates into the next round.

Digital Artist

Screening for the artist/illustrator position was a completely different, and in some ways, far more enjoyable experience.

For one, I didn’t have to worry about all the details — the spelling, punctuation, word usage, research experience — like I did with the curators. In some cases (if they had an amazing portfolio), I even let a missing ‘X’ slip by. For the artists, it really was 80% about the portfolio and 20% everything else.

Second, the majority of artists are either stuck in jobs they don’t want, or they’re dead broke and struggling to make a living off their work. So the sheer joy of the opportunity to be paid to simply do what they already love to do every day made the “applying for the right reasons” check a cinch in most cases. Most of them were ecstatic about the opportunity.

Third, I really didn’t know what I wanted from this position going in. I had a vague concept in my mind, but I was really open to anybody whose work could impress me. So going through these applications was a process of discovery for myself as well. It was fun. And I found some artists who were doing things I couldn’t have even imagined before posting.

About 85 artists applied for the position. My standards were simple:

  1. “Does this person seem professional and reliable?”
  2. “Am I a fan of this person’s work?”
  3. “Can I imagine this person’s work accompanying my writing on the site?”

The majority of the applicants passed the first question easily. Many of them had prior work experience. Many of them customized their portfolios for me and did cool drawings or graphics introducing themselves.

The second question is where it got harder. There were a number of candidates who were clearly talented and very good at what they did, but it just wasn’t my thing. So I had to let them go.

The third question then became even more difficult. Even though I loved their work, could I see it fitting well on my site? Unfortunately, there were a number of people who I thought were awesome but couldn’t imagine their work being side-by-side with mine for whatever stylistic reasons.

Photography in general fell into this category. I wasn’t specific in the job posting and opened it up to photographers, but it quickly became apparent that I didn’t want to work with a photographer. Part of it is how varied I’d like the artist’s work to be. Part of it is how quick of a turnaround time I would like. Part of it is just my personal taste. There were two photographers who were absolutely phenomenal, yet I had to pass them up. I just decided that it’s not the direction I’d like to go with the site.

The other major problem with a number of candidates was that their portfolio was full of excellent work that was made for other websites and businesses that were completely different than mine. Therefore, even though their work was high quality and professional, it was hard for me to get a sense of what they would do for me. Once again, the best applications were from the artists who created work specifically designed for their application based on my site and articles. Looking back, I probably should have made this a requirement for applying in the first place.

With the help of my girlfriend (who used to work in design and advertising), I worked the candidates down to nine. As with the curators, deleting the last few was excruciating. Some of them were insanely talented. But having that many people in Phase 2 just seemed to be asking for more headaches later.

Other Comments

English as a Second Language. In the initial job posting, I requested that the content curator must be a native English-speaker. A number of readers challenged me on that, saying that despite it being their second language, they were highly fluent in it and had even earned degrees in English. I relented and changed the requirement to people who could speak English with high fluency.

Let me say this: of the non-native English applicants, no one’s English was bad; but most (not all) were eliminated due to some basic grammar or usage errors. They didn’t misspell anything. They wrote well and they made sense. They just occasionally used words that didn’t sound “normal” to a native ear. And sorry, but for someone who will be editing and revising my writing every day, I can’t have that. I need someone who can not only catch my linguistic flubs, but who can also mimic my voice, use humor and irony effectively, understand slang and colloquialisms, and generally make me a better communicator. If I’m having to edit them, then that defeats the whole point of the position.

Highly Overqualified People. Ah, yes. The doctors, corporate lawyers and finance big-timers. These continue to make me uneasy. Part of the reason is the “applying for the right reasons” check mentioned yesterday. But part of it is that these people, even if their intentions are totally aligned, best-case-scenario they’re still taking a massive cut not only in their pay, but also in their prestige and social recognition. Their lifestyle will be turned upside down. And their family and friends will likely think they’ve gone insane.

I’m not convinced one could make this transition without it getting a little bit messy. An unemployed college graduate needs a good reason to want the job. One of these people needs a great reason. An aspiring graphic designer who is stuck bartending is likely to see this job as salvation. A former Google software engineer or brain surgeon will see it as what? A downgrade? A life raft? A mid-life crisis? Sorry, but unless there’s an excellent explanation, I can’t take that risk.

Most Common Books. The Alchemist by Paulo Coelho came up the most often by far. And I still don’t know if that’s a good thing or bad thing (I’m not particularly crazy about the book). Ayn Rand’s books were very common. As were Malcolm Gladwell’s. As were Herman Hesse’s.

The high school perennials popped up quite a bit: 1984 by George Orwell, Catcher in the Rye by JD Salinger, and Brave New World by Aldous Huxley. A lot of men put Fight Club by Chuck Palahniuk, No More Mr. Nice Guy by Robert Glover, as well as Bukowski’s books. A lot of them put my book, Models: Attract Women Through Honesty, and then immediately apologized for putting it.

On the self help side of things, How to Win Friends and Influence People by Dale Carnegie, The Four Agreements by Don Miguel Ruiz, and The Power of Now by Eckhart Tolle were extremely common. Alan Watts made many appearances as well.

Only one person mentioned Ken Wilber. And only one person mentioned my favorite book of all-time: War and Peace, by Leo Motherfucking Tolstoy.

Stupid Stories. The stupid stories were surprisingly less entertaining and informative than I had hoped. I included the requirement for a few reasons — to see how honest and open a person was willing to be; to see how well someone processes their mistakes and failures; and finally, to keep myself amused while I sifted through billions of applications.

Most of the stories of stupidity were predictable — bad relationships, bouts of drunken nonsense and/or violence, being a child and doing stupid child things. There were a few that were heartfelt and personal: deaths or traumas, regrets and things left unsaid. And then many were just classic embarrassing moments we all feel from time-to-time. Some were funny. Some were sad. Some were well-written. Some were not.

A lot of people laughed off their stupid moments or noted that they didn’t regret it because they learned a lot from it. That was nice and usually a good sign of character. Some chickened out of the question by intellectualizing what “stupid” actually meant. And then some clearly wanted to get the question over with as quickly and least-embarrassingly as possible.

There’s Always Tomorrow. In 2012, I posted a position to hire two interns. I received about 70 applications, of which I selected eight people for round two interviews. One of those interviewees was insanely qualified and smart, but wasn’t a right fit for that job. He was getting a PhD in neuroscience. I needed someone to install forum software. It just didn’t make sense.

But I told him that there would likely be job postings in the future and he may be a better fit next time. He applied again and he’s now one of the candidates in Phase 2 for the content curator position.

This business continues to grow. And as it grows it has become clear that I need to look no further than my own readership for the team I need. If you applied for one of these positions and failed to make Phase 2, it’s very likely that it’s just a mismatch in qualifications and skills and has nothing to do with you personally. So please stay tuned, as there are likely to be more opportunities on the horizon.