Insight and Outsight

Preparation for your next step in your career journey involves balancing four different stages of information gathering.  Each of these builds upon the previous- building an arch connecting where you are to where you want to be one piece at a time.  The keystone of this arch is your decision.  


In previous posts I’ve mentioned being proactively mindful.  It’s a process that we’ll touch upon again here, as it’s key to self-improvement and growth beyond just the career arena.  The capability and practice of self-mindfulness- self-awareness- is an important type of insight.  By actively turning your eye within, you’re re-examining and re-assessing your goals, methods, and path.  Do you still want the same things?  Have you achieved your goals in your current position?  What tradeoffs (such as location, salary, responsibilities, or title) are you prepared to make to enable that next step? I’ve found writing down these questions and answers to be helpful.  Not just for the current decision point, but also to be able to assess how you’ve changed at each career decision point.

Each job change along your career path is a vector.  The move has more than one component.  While there’s a strong argument that your career path takes place in a higher-dimensional space, I’ll repress my inner math nerdism and stick to the classic “direction and magnitude” definition.  

Ask yourself not just where you want to move next, but also ask how far you’re prepared to go to get it.

Once you’ve taken your self-mindful inventory- your skills, your experiences, your desires, and what you’re willing to trade for the investment- it’s time to take a look at the landscape.


Good careerists should always keep up-to-date with their field, but it’s not usually a priority until we’ve decided to actively look.  At that stage, you should carefully examine how the field has changed- new employers, new technologies, new approaches to the workplace, new forms of compensation- before you begin actively looking for your next move.  The workplace is changing at an increasingly rapid rate and it’s easy to fall behind at just the worst time to do so.  Outdated information will only lead you to outdated opportunities.  Some of these changes are obvious, especially in technical fields.  Things such as new operating systems, new languages, or even new design paradigms render old roles obsolete even as they produce new ones.  Some changes are more fundamental, however, such as employers’ increasing willingness to support or even encourage working from home.  An option like that can have a significant impact in your search and selection.  

Don’t fall into the trap of only using career search sites to search for the next step in your career.  They’re only tools, and fairly simple ones at that.  The options they present are breadcrumbs intended to lead you somewhere one piece at a time.  They will not and cannot position you to achieve the career goals you’ve established.  The key to this step is to learn more about the state of your industry as a whole, so read industry journals, blogs, magazines- anything that helps you graft new insights onto your old understanding.


The key benefit to practicing outsight is the ability to be receptive- to consider opportunities of which you weren’t aware when you performed your self-assessment.  Paradigm changes such as cloud architecture in software have ripple effects across industries and yesterday’s skills can be today’s history.  Being receptive is prerequisite for being perceptive because reception is about the removal of assumptions.  Once you set aside your old expectations and “common sense” rules, you’ll free yourself from confirmation bias.  If you actively search (perceive) first, on the other hand, you open yourself up to frustrations such as looking for job options have have become OBE (overcome by events).  It’s true that languages and technologies can have a long half-life (COBOL is the classic example), but they’re not growing fields. Dead-end (or soon to be dead-end) skills are probably not worth adding to your arsenal as you grow your career.  

There is a caveat here, one that many software developers fall into- leaping before they look.  Put more concretely, learning new skills and technologies simply because they’re new.  There are two common reasons for this: the desire to get ahead of “the next big thing” and satisfying intellectual curiosity.  A brief survey of failed startups (in any industry) can show you the perils of guessing incorrectly on the next big thing.  If you’re making a job change out of the need for short-term novelty, chasing bright and shiny objects certainly fulfills that.  If you’re more interested in making the next move for your career, restrain your ardor and invest in skills that the industry is investing in.


Equipped with the results of your research, you’ve identified the next rung in your career ladder- the skills you want to learn, the new responsibilities you’re willing to undertake, and the contexts within which you’ll thrive.  Now it’s time to actively search.

I’ll explore the details of a job search in a future post- right now I’d like to focus on the what, where and when rather than how and what.  You should already know the why– it’s whatever triggered this step.  Actively searching is the most labor-intensive and frustrating part of the process, so use every resource at your disposal: your network, professional associations, job aggregator sites, recruiters, and even cold calling.  

There are two theories- one economic and one political- that you should keep in mind during your search: rational expectations theory and rational choice theory.  The first affects what you should look for and the second, ironically, what you should expect to encounter.

I’ll let Wikipedia dive into rational expectations in detail and restrict my comments to the context of your job search: make your choices rationally, using all available information and your past experiences.  Put more simply, don’t let your reach exceed your grasp.  You’re looking for the ideal next step!  Don’t try to skip it and apply for positions for which you’re not yet prepared.  The rejections will frustrate you, no matter how well-deserved they may be.  Changing jobs isn’t buying lottery tickets; you’re not going to “hit it big” by spamming employers with unqualified applications.  Be logical, be rational, and manage your expectations.

Employers, at least good ones, recruit using rational actor theory.  Wikipedia has a decent summary of the rational actor model built upon this theory.  The key relevant element is that companies will always recruit in their own best interests- writing a great job description, considering every applicant, and selecting the most qualified candidate.  The point I’m trying to make is that companies will not take chances during recruiting.  Forbes has an excellent description of the true cost a a bad hire.  Companies aren’t going to lower their expectations to take a chance on you.  They may take into account factors such as an internal referral, but at the end of the search they’re going to choose the best candidate for the company.  There’s no emotional consideration in their decision making, so don’t rely on one. 

Your application- resume, cover letter, and interviews- are your venues to make yourself appealing.  They will not necessarily make you qualified.  This is why you need to create and maintain rational expectations during the process.  One step at time and don’t make leaps.

Do your research, write cover letters, and follow up!  The worst thing that can happen is that they’ll say no.  If you’ve started your search at the right time, you’ll be benefiting from one of the most basic adages of job hunting: The best time to look for a job is when you have a job.  You have nothing to lose; another opportunity is just an email or call away!


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