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Are you a job search drone?

Updated: Mar 11

To upgrade your job search process, skip down to the prompts. Come back up for further explanation.


A client of mine had slipped into catatonic execution mode while trying to find a job – unthinkingly shipping job applications in a dense fog of aimless desperation. Among the numerous aspects contributing to the feelings of intractability, she gradually lost confidence in how to present herself to employers. She became directionless. Interview feedback was non-existent. The folk wisdom of loved ones felt stale seemed to contradict at times. The best articles she could find on the subject also contradicted. She felt completely blown around by the advice she was receiving.


There’s really no shortage of blogs, e-books, paper books, seminars and career centers that want to help in your job search. What’s commonly at hand is status- or experience-driven advice (e.g. “I’m a hiring manager of Google and this is what I think is good and bad), or if we’re lucky, pop psychology articles that prescribe action based on a recently published study or two. And then there are friends, colleagues, counselors and career centers that almost certainly pull from the same grab bag of anecdotal hearsay, or relay xeroxed tropes on finding work. Especially when quality feedback is also hard to come by after submitting applications and conducting interviews, it can all feel very arbitrary. So how can we know what will improve our job search chances?


The crux of this article is a single point: that crisp internal clarity will often straighten the path from “A” to “B”. Applied to this context, self-understanding is crucial to getting a leg up in your pursuits. This is not an airy call to know thyself. The practical implications of this potentially carry innumerable competitive advantages.


A gift by way of example


What is a concrete way that improved self-understanding can boost your chances at landing a desired gig? Well, if I’m determined to use the job search process to sharpen my skills, and learn about myself and the world, one option is to build feedback mechanisms into the process.


A simple way to do this is implementing email tracking if you’re sending out resumes/CVs and cover letters. This single upgrade can deliver valuable feedback on whether your offering is appealing to employers. For example, employers receiving hundreds of applications to a position can’t possibly open all of the applications, or at the very least likely have a cap on the amount they are willing to open. Were you to find, as I did, that employers only tend to open ~50% of my emails, this likely means you’ve been rejected far less than you thought. (2 responses out of 50 suddenly looks much better than 2 out of 100). Furthermore, you can match the opened emails with the employers that reached back out to you and determine your success rate there. If tons of people are opening your emails and you’re hearing nothing back, this also carries a set of potential implications. Some services let you see how many times the recipient has opened your email, which could be indicative of interest level.


Avoiding catatonic execution mode


The log jammed client I mentioned at the outset possesses a highly ‘socialized’ mind when it comes to her job search process, or so a constructive-developmentalist might say. This means that she is heavily dependent on navigating life via external cues. She almost always turns outwards (often deferring to socially-accepted or societally-constructed frameworks) for guidance, understanding and criteria for her decision-making. To be clear, there is nothing inherently bad about having a highly socialized mind. In fact, people who are cleanly in step with their social context are usually successful.


But having a highly socialized relationship to your job search can be hugely disadvantageous. You could be blending in by taking standard advice, bleeding efficiency by taking an unreflective approach, and not actually be addressing the desires of an employer by defaulting to the norm. Most importantly, you can end up very far from what you desire to do by not having a “self-authored” or internally derived sense of what you want.


Consider another case where someone was deciding between different types of work. Most of their justification for considering a career was something like, “well, I am torn because I seem to be pretty good at both operations and research and could be happy doing both. My education was more research-focused, but I find operations more enjoyable.” Compare that to “I realized that operations appealed to me because completing a checklist of tasks feels like tangible progress and growth in my life, which is something I personally crave right now. But ultimately I want to produce work that develops a more intellectual skill set and I want what I produce to endure over time.” For this individual, something genuinely pulling them in two directions was suddenly made quite clear after unpacking goals that were internally derived. From growth and realizations of this sort, entire swaths of potential options can become upvoted or eliminated.


Search yourself before searching for prospects


Below are a list of prompts designed to pry your thought process loose from the common socialized approach in your job hunt. I’ve included more recognizable questions alongside them in the hopes of highlighting the difference. Note: I am not advocating that the ‘socially derived’ questions be discarded in favor of the internally derived, but rather included and incorporated in your overall approach to the job search.


Where to start – socially derived

  • How do I get employed?

  • What should I apply for given my previous roles, experience and education level?

  • What positions and level of seniority is commonly understood to be sensible for me to apply for?

  • How long does it typically take other people to find a job? What amount of time searching/without a job would reflect badly on me?

  • How would others go about job searching? How can I distinguish myself among all the others?

Where to start – internally derived

  • How does employment square with how I want to spend my life?

  • How does this job search square with how I want to spend my time?

  • How close can I come to searching effectively and spending exactly as much time as I want to on this?

  • What kinds of work would advance my goals, values and principles?

  • What kind of work would I enjoy doing given a sharp understanding of my overarching goals and personal preferences? (Prompts for discerning this below):

– What personal needs and desires must I fulfill with my work? To clarify, what would fulfilling these look like at the height of my career? (e.g. creative outlet, financial stability, clear separation between work and leisure time)

– What capacities/skills would I like to develop on the job?

– What were my most rewarding work experiences of the past? (Work in this sense can be defined widely as sustained application to a project of some sort)

– What kind of past work/experiences put me into a state of flow?

– What kinds of work and subject matter am I naturally drawn to?

– What skills/experience do I want to ramp up?


Resume/CV Writing – socially derived

  • Am I writing/formatting this the right way?

  • Am I writing/formatting this like a competitive candidate would?

  • How would this compare to other candidates?

  • How can I incorporate all or most of the feedback I’m getting?

  • What do I think the reader of this application will be looking for?

  • How do I think the reader will interpret what I’ve written?


Resume/CV Writing – internally derived

  • What is the most accurate and attractive way to present myself that is congruent with how I want to be?

  • What information about myself do I believe it is vital for the reader to know?

  • How can I format this in order to highlight what I believe is most important for the reader to know?

  • Bonus: why do I think other candidates gravitate towards particular approaches in presenting themselves? In what ways do I think that is warranted? In what ways should I deviate from that and why?


Job Search - socially derived

  • Which organizations/roles would seriously consider me based on my previous roles, experience and education level?

  • What could be a good fit for me given my previous roles, experience and education level?

  • What have other people said I should look into given my stated interests, previous roles, experience and education level?

  • What have I heard before that people with my previous roles, experience and education level would be a good fit for?

  • What timeframes and rate of ascendancy within an organization is reasonable given what I know about my field of work?

  • What is the maximum amount of money/highest status role that I feel I can “get away with” being hired for? / What position do my previous roles, experience and education level suggest I am ‘worthy’ of having?

  • What is the value of my work according to others and external metrics?

  • Am I on the right track?


Job Search - internally derived

  • Which organizations/roles would I seriously consider based on my goals, principles and values?

  • Is submitting a resume/engaging in the standard hiring process the best way to get the outcome that I want?

  • What can I learn about myself and the world in undergoing this process?

  • How can I conduct this process in order to learn more about myself and how the world functions?

  • What are my beliefs about what the job entails and whether I could thrive in it?

  • What can I learn along the way during the hiring process?

  • What role do I feel that I genuinely deserve and could provide value in? What are my thoughts around being worthy/deserving of different status roles/amounts of compensation?

  • How do I derive the value of my work according to internal and external measures?

  • How would I know whether I’m on the right track? How can I come to know whether I’m on the right track?


Hiring Process - socially derived

  • What can I display to impress them/show that I am value-aligned?

  • How can I display that I would fit into a company’s culture?

  • What is the socially acceptable way to move through this process so that I have the best chances of getting selected? (ie what shape do I need to make myself in order not to be disqualified?)

  • What about me do I think they would respond to?


Hiring Process - internally derived

  • How does the hiring process reflect on the organization and those doing the hiring? Does that accord with my expectations and projected needs/wants in this role?

  • What kinds of principles/values do I want an organization to have?

  • What kinds of principles/values do I want those who I work with/work for to possess?

  • How would I design a hiring process if I were optimizing for a specific type of person? Does my simulation of this reflect what I’m seeing from this organization? Am I comfortable being what they seem to be optimizing for?


That’s my introduction on this. Please feel free to reach out to let me know whether this was useful for you.

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