Nobody should be looking for a "cool job" -- maybe this is just semantics, but jobs aren't "cool". They might be rewarding to varying degrees and offer varying levels of autonomy, but it seems wrong to think about their fashionability (being gainfully employed never goes out of fashion). The Fonzie approach to work seems pretty self-defeating to me. If you are doing something to be cool rather than to simply do whatever it is -- making art to seem like a cool artist rather than because you enjoy making art -- then you are always at one remove from your own activity, self-alienated. (I doubt both can be done simultaneously; the self-regarding pursuit of cool detracts from the pleasures of pure immersion in a task.) Plus the harder you try to establish your cool, the less cool you are. And the degree to which people think your job is cool is often the degree to which you are being undercompensated for doing it. A cool job is usually a matter of someone else insisting how cool it is to be associated with some company or industry, while you slog through the same administrative or managerial tasks you'd do at any job. You end up getting paid in cool instead of cold hard cash, and I know which currency I'd prefer. (No amount of cool is going to pay my electric bill when I'm 64.) Better to never let "cool" come into your thinking and just try to find ways to get paid for doing things you like to do.
Of course that might be what you think of when you hear "cool" -- I just hate to let it stand as a synomym for satisfying or interesting as the following writers do. Nevertheless, via Jane Galt comes some good job-seeking advice from Timothy Burke that readers -- particularly those pursuing liberal arts degrees in hope of landing cool jobs -- may find useful.
The bad news, and I’m not sure liberal arts institutions are always as forthright about saying this as they could be to their current undergraduates, is that the significant majority of immediately post-graduate employment experiences are going to suck. Dilbert’s office would be an improvement over quite a few of the ones I’ve heard about. I think my favorite job experience I’ve heard about in the last six years was the non-profit community group that paid $15,000 a year for a 55/hr week with no benefits or vacation time and was run by a near-psychotic incompetent. But there’s lots like that to go around. I do think we promise payoffs in the longer term from “critical thinking” and the like, so any student who’s listening carefully probably understands the implicit point being made when that’s said.
Thinking about people I know with Cool Jobs who are not academics, broadly speaking I can identify a couple of ways that they got there.
Route 1 to a Cool Job is applying to a Nasty Leftover job and then proving yourself with diligence and creativity to be a Cool Person and being promoted upwards to the stuff in the same workplace or organization that’s satisfying and interesting.
Route 2 to a Cool Job is going to graduate school but in a specific professional field, aimed at very specific technical proficiencies, skills and credentials, NOT a doctoral program aimed at becoming an academic. You’re looking for something that goes straight into a profession or field of employment outside of academia, preferably a program with a strong, proven track record of placing its graduates in employment. The shorter the program, the better.
Route 3 to a Cool Job is making a nuisance out of yourself in a way that feels very very difficult for a lot of folks (including myself)–basically exploiting your family and social networks, writing to strangers, showing up at lots of events and aggrandizing yourself in various ways, brownnosing if necessary, being gutsy and unafraid, jumping into strange situations without looking. The problem with this is not just that it is difficult to do, but that it takes a certain kind of personality and judicious ability to size up social situations to do it successfully. Somebody with the wrong personality or with a consistent inability to judge when and how the moment has arrived is going to do themselves way more harm than good following this strategy.
Route 4 is hanging out your own shingle in some fashion–if you’ve got a serious technical skill, some special area of knowledge, some ability to do creative writing, anything of that kind, you go into business or do consulting or sit down and write. Anything that either produces a concrete output (artwork, writing, programming, technology, a successful small business) or that serves as an effective entree to some larger institution by proving yourself is a good thing. That is, providing what you’re doing doesn’t suck–bad art, lame writing, or technically incompetent independent work isn’t going to help you any, and parasitic just-one-step-above-confidence-man kinds of consulting work may alienate rather than ingratiate. May require a significant other and/or parents you can sponge off of for a while.
Route 5 is basically paying lots and lots of dues, about ten to fifteen years of painfully bad or frustrating jobs where the next job is somewhat higher paying or more responsible than the last job, but not really a Cool Job or even a particularly good one–and then taking the accumulated reputational and professional capital from that and cashing it in to grab a Cool Job.
I think I was so seduced by the fiction of democratic meritocracy that I didn't think making connections and networking was all that important. One could get by on sheer ability. What I didn't understand is that, unless you are specialized in something extremely technical (i.e. you do something "not cool"), the ability to get along with other people is ability -- more important than any other kind of knowledge or skill for most jobs in most bureaucratic organizations. Having an extensive social network is a good proxy for that ability to blend in organizationally. Judging by my experience in publishing, the easiest way to get a job somewhere is to know someone who already works there. I guess that is Burke's route 3.