5 reasons selling yourself is hard

Riddle me this: While I'm the same job candidate that I was a few months ago--i.e. no additional positions or skills on my resume--I am much more likely to get hired than than I was four months ago. But how could this be, since nothing substantial about my experience or skills--the things most relevant to any potential future employer--has changed?

The obvious (in retrospect) answer: I'm more employable now because my ability to market myself has improved.

It turns out that in addition to getting the skills you need to become a good job candidate, there's this whole separate process you go through in order to actually land a job: that of becoming a good job applicant. While I sort of assumed at the beginning of my job search that becoming a good applicant is constitutive of my acquired experience and skills, I've found it's much more than that. Because the employer can't actually test my skills directly (like for instance by hiring me temporarily, or putting me in some sort of simulator), they attempt to figure out whether I've got the necessary skills and experience based on my resume, cover letter, and interviews, all of which are supposed to demonstrate my aptitude (or lack thereof) for a given job. But while the resumes and interviews are all about Andrew as worker, they're still representations of the thing, not the thing itself. So how you represent your experience, personality, and work ethic is really important.

Up to the moment of solving the paradox a couple months ago I'd been undervaluing the role of selling myself in my job search. I'd just been assuming that good job candidates (like good products) sell themselves, because it doesn't feel like I get convinced to buy anything. Rather, what making a buy/don't buy decision feels like is this: I look at a description of the features (candidate's resume), assess whether it meets my needs (job description), and weigh the cost of the item against those needs (are they worth what I can pay?). But what that model neglects is the fact that humans don't make rational decisions; on the contrary, we make emotional decisions. And it's the two-fold job of marketers to 1. Influence emotions, and 2. Create post hoc rationalizations for the emotional decisions made (plus, somebody's got to write the feature descriptions).

Anyway, I've been focusing more on "selling myself" these past couple months. But it's pretty hard. Here are a few reasons why:

• Working and looking for work are not the same thing. Making the shift from work to self-marketing is tough (Unless you work in PR or marketing, I suppose) since they don't have a whole lot in common. Resumes and interviews are two of the most un-work-like things I can think of, as my ability to perform well at those tasks has little to do with the jobs I'm applying for (except, arguably, the content/writing jobs, where a spotless and compelling resume is likely taken as a sign of my writing ability). Heck, there might not be any correlation between quality of marketing and quality of product. I mean, it takes a pretty smart person to figure out how to put together a slick resume and really kill it in an interview, but there's certainly no logical correlation between the two things. In theory, you could be massively ineffectual while still an excellent interviewee, as long as you were paying close attention while real work was getting done and could insert yourself into key points in the narrative (assuming of course that your references didn't give you away). This is probably why things like degrees and credentials are so heavily weighted; they stand in for complicated, time-consuming assessments that the employer either cannot or would rather not do. But anyway, with regard to the question of correlation: we'll probably never know, since no employer is going to A/B test that just for posterity.
• Resumes are hard to write. Like, literally. So are cover letters. And interviews x10! They take a ton of effort, and they're paradoxically both inductive and anti-inductive (I'll explain).
  • Inductive: They're inductive in the sense that they take experience to learn how to do. For example, I just had a phone interview for a job during which they asked a question I was totally unprepared for. So I more or less flubbed it. But now, since I know it's a question that might be asked, I'm prepared.
  • Anti-inductive: the resume/cover letter/interview triad is anti-inductive in the sense that it's hard to stand out from the crowd. Anti-inductive in this context (see section II here for some great examples) means that the more people know about it, the less useful that information is. So for example, while there's tons of material out there about how to "hack" your resume or a job interview, once that information is out in public on the internet, you're more or less guaranteed that a bunch of people are trying it, diluting the "I'm special!" signal you're trying to send, and blending you back in with the hoi polloi.
• Resumes trivialize your experience. Reducing years of work to a few bullet points and a handful of stories for an interview feels a bit trivializing. Sure, it's all meant to represent your work, not replace it, but during the distillation process it loses some of the magic. Sort of like writing the Cliff's Notes to a story and attempting to pass it off as the original. You can't help but feel like you're doing your experience a disservice. Or, if you're padding your stories a bit to make them into linear narratives, like a charlatan.
• Many things are out of your control. Did the recruiter just get off the phone with a complete a**hole? Or did they just get back from lunch, and they're feeling fat and happy? The sort of attention (or lack thereof) that your resume gets hangs in the balance. People are lazy, or not so smart, or so inundated with smart people that they have trouble differentiating them, or just really busy and make a mistake, or at the very least (see next bullet) rife with cognitive biases that get in the way of rational action. If even one persons takes the extra time to really fine tune their accomplishment statements in such a way that catches a recruiters eye a little more than yours, or makes them feel warm and fuzzy because they share an alma mater, or catches them right after lunch...then maybe they have the job, and you don't. Worrying about this stuff is paralyzing, making it difficult to know what sort of effort would be the most effective.
• Even more things out of your control: "The marketplace for people and jobs is broken", says Laszlo Bock, Google's head of HR. There's massive information asymmetry associated with job searching, or as he dubs it, the "color blue problem". Does the person reading your resume have the same dictionary for industry jargon that you do? Does the recruiter even really know what the job requirements are, or are they just passing resumes through a keyword matching tool? Since you're distilling your experience onto a resume (just like the hiring manager is distilling the job requirements into the JD), it's hard to know what you need to make explicit, and what can stay implied.
• Your brain is sabotaging you. I'm really interested in cognitive biases, so I know there are a whole host of ways in which we are our own worst enemies; our brains are often leading the way sabotaging our efforts toward productive self-marketing. Here are some general themes regarding human non-rationality.
  • Blind spots: how to best communicate aptitudes and capabilities is a bit of a blind spot for people (this is why getting a good editor for your resume and possibly an interview coach is so important). If you're good at your job, then people at your job give you feedback about how you're good at your job, so you just sort of expect that other people will be able to tell that you're good at your job too. But in reality it doesn't quite work that way.
  • Pride: it's easy to internalize a script like: "I'm smart and capable and how could anyone not see that!? So I don't need to be super careful about my resume, or practice responses to common interview questions, cause I'm smart and capable and it should be obvious to other smart and capable people." 99 times out 100 you'll fall flat on your flat with that sort of attitude. Also, an easy to protect yourself from the pain of rejection (lets dub non-responses in the age of the Internet job application "rejection by crickets") with self-validating, indignant responses like "how dare they reject me! They must be stupid and therefore I'm better than they are and I didn't want to work there anyway."
  • Fixed mindset: This means thinking that innate talent (as opposed to effort) is what qualifies one for a job. A fascinating book I read recently, Mindset, does a great job explaining this. Like I mentioned earlier, job searching in inductive, so it takes time to learn, and rejection is just a part of the game. It's a signal that should cause learning. However, even though every interview is a learning experience (abstractly positive), rejection feels intimately bad (concretely negative), and it's all too easy to interpret it as a disconfirmation of your ability to do the job itself.

I continue to peel back the layers of what makes this difficult, and attempt to slay the dragons of my own creation that are getting in the way of putting my best foot forward. At the end of the day I'm staying positive, becoming a connoisseur of my own mistakes, and interpreting rejections as learning experiences, not signs that I'm not qualified. All you job searchers: hang in there.

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I'm Andrew. Thanks for reading. I'm looking for an interesting place to land doing Product/Program Management or Writing/Editing. Biasing toward finding a great company, rather than an ideal position.