On the philosophy smoker, Mr Zero asks why he keeps on going on the job market, year after year. He loves the job, and he likes the position he has, which are solid reasons to stay in his NTT position, but he also says "I don't really know how to do anything else", which may be a not-so-good reason to stay. It is a pretty common reason, though - when you specialize for years in graduate school and afterwards to become a good teacher and researcher, the jump to a non-academic position seems difficult and one does not even know how to begin.
I wrote this post for readers of the boot camp who want to try a different career path as landing a tenure track position is becoming increasingly difficult, especially for people from non-elite institutions. Tellingly, my first draft of this post was titled "When to call it quits". I changed the title once I realized it represents a warped view that is unfortunately prevalent in academia, namely that choosing an non-academic career is synonymous to giving up.
A while ago, I interviewed seven post-academic philosophers who have now built out successful careers outside of academia (here, here and here). More recently, I interviewed R Scott Bakker who was in grad school for philosophy, but decided to stop when he was about to defend his dissertation and instead turn to writing. I would encourage readers to read those interviews, as they provide detailed career trajectories of philosophy PhDs who left academia. Still, I do not have first-hand experience on this front, so I would encourage readers who left academia and are now in a non-academic position to share their experiences in the comments section.
Weighing the costs and benefits
While some factors contribute to unhappiness in academia, such as low wages and job insecurity, bear in mind that only you can assess the costs and benefits of staying in your current situation (which can be anything, from a cushy tenured job, adjuncting, a string of VAPS, or graduate school) and the projected costs and benefits of looking for a job outside of academia. What your current job means to you is more important than how other people value it. For instance, it may be that you are happy, or sufficiently happy all things considered, in an adjuncting situation, or that you increasingly regard your tenured position, which other people would give an arm for, as unsatisfying.
One common reason people remain in academia who are unhappy is the amount of time and money they already invested. These are sunk costs, meaning they'll never be recovered. However, if you have evidence your chances of obtaining a tenure track job are poor (e.g., lack of interviews, lack of a competitive publication record), and this was your goal, it is never to late to cut your losses.
Another common reason is that graduate school does not prepare students for non-academic career paths, and increasing specialization further on makes it difficult to move away from academia. This may explain why academia sometimes feels like a cult, and why testimonies of "how I quit academia" read like testimonies of traumatized people finally picking up the courage to leave an abusive cult.
When to look for a non-academic career
Many people think about a nonacademic career after they are unable to land a tenure-track position for a few years and are stuck in adjunct positions, VAPs or postdocs. Even if one manages to be in relatively well-paid full-time non-tenure track positions (in Europe there are many, and most employed PhDs have reasonably paid postdocs with benefits, rather than the precarious adjunct positions), uprooting one's life every couple of years becomes an increasingly alienating experience.
Even if at this point you think that you can only thrive as an academic philosopher, if the insecurity is affecting your wellbeing and mental health it may be a good time to look for a job outside of academia. Often, what makes us happy in employment is not teaching or writing philosophy papers per se, but the sense of autonomy and making a difference in our teaching and research. These things are possible outside of academia, as my interviews indicate.
That being said, the number of years post PhD by itself (the worry of staleness) should not, in my view, be the main reason for giving up on academia. My evidence, which is admittedly anecdotal, is that several people who defended their PhD 5 or more years ago have recently landed tenure-track positions. "Staleness" itself is not the issue; what can become a problem is not having a dossier that is deemed sufficiently strong for someone with several years of post-PhD academic experience. Writing takes time and energy, and it is difficult to get publications while being an adjunct, or a VAP with high teaching load. In the market we face today, one might consider a non-academic career if one is several years post-PhD and does not have a competitive publication record.
Some people already worry about their job prospects in graduate school. This seems justified, given the state of the job market. As my interviewees indicate, you can already take active steps in graduate school to prepare your exit. Nate Smith, a quality assurance engineer at a network security company, already knew around year 3 of graduate school
Somewhere around year 3, I realized that all the hard work to prove myself good enough to get an academic job had no end in sight. It was all pretty stressful, and getting a job was just going to be the beginning. I was looking at years and years before I'd ever even have a chance at getting tenure somewhere (maybe like 10!), and I was starting to dread it. I love philosophy, but I think I just didn't love it quite enough to be willing to subject myself to everything that was going to be required to be successful. I wanted to get on with my life, and pursue other things that didn't have anything to do with philosophy. Academic philosophy was totally consuming my life, and I just didn't like how unbalanced it felt. Then I realized, I don't HAVE to do this to myself. All this, and there wasn't even any guarantee of success.
If you have a tenure-track or tenured job, does this commit you to staying in academia? While most people who have such jobs are happy and wouldn't imagine doing anything else, some people wonder at whether this is really the thing they will do the rest of their lives. One of the people I interviewed, Zachary Ernst had tenure at a solid school (Missouri) and left that position for a non-academic career as software engineer in a Chicago-based startup, Narrative Science. Even when you are tenured or in a tenure-track position, and are feeling dissatisfied, it is not too late to change.
Getting prepared for a non-academic career
Academia's very competitive, but high-end jobs in non-academic environments are too. There are two common, mistaken assumptions about the transferability of a PhD in philosophy to non-academic careers. One is that a PhD is totally useless, the other that a PhD is immediately applicable. The real situation is that employers outside of academia won't care about your PhD title or even about the articles or books you wrote, or your solid teaching evaluations. Rather, these things only matter to the extent they provide transferable skills. Writing articles requires the ability to research a topic in-depth, writing skills, and organization of content, for instance. Giving conference presentations have helped you to make presentations (make reasonable powerpoints, organize materials, present dry material in an engaging way) which is useful outside of academia.
As Zachary Ernst remarks,
As a professional philosopher, if you haven't gotten over-specialized and narrow, then you've got really good analytic and communication skills. So you've got the ability to learn quickly and efficiently. You're also in the habit of being very critical of all sorts of ideas and approaches to a variety of problems. And if you've taught a lot, then you're probably pretty comfortable with public speaking. Those skills are very rare in almost any workforce, and they're extremely valuable.
Additionally, If you have a skill set outside of philosophy and academic skills, don't let them atrophy (this applies for both graduate students and others). It may seem like a waste of time, but even if you do land the coveted tenure-track job, it is conducive to human flourishing to have interests that are not only related to your work or work aspirations. If you know how to code, keep it up and take some further courses (which you can do online), if can draw or paint, commit yourself to regularly creating an artwork, if you write short stories, or are working on a novel, go for it, and make a couple of hours a week time specifically for this purpose. If you are active in volunteer work, keep it up, and so on.
Your total skill set of academic and non-academic capacities is by itself, not enough to land a non-academic job. You need to convince non-academic employers that you possess the requisite skill set. For instance, you need to rewrite your CV into the format of a resume (see here and here how to do this). Briefly, a resume is short and emphasizes the skills you've gained through work experience. It is not a place to list things like publications, which are valued on academic CVs. You can also use LinkedIn to create a profile, list your skills and experience, and ask (former) colleagues to write endorsements for you.
What can you do concretely outside of academia?
When my sister received her PhD in medium-energy physics, she decided to leave academia and is now working for the Royal Belgian meteorological institute. She still gets to do research, albeit applied rather than fundamental (building weather models). Her skills in programming, knowledge of physics and mathematics were attractive to many employees. PhDs in the sciences have a lot of options; humanities PhDs have more difficulties finding a satisfying non-academic job.
In my experience (I am not sure if there are any statistics), many humanities PhDs who end up in non-academic careers take something that is still quite closely related to academia. For instance, Claartje van Sijl, whom I've interviewed, became an academic counselor for humanities grad students and PhDs. Dan Fincke is a philosophy PhD who teaches private online courses (not massive online courses, but personalized and small-scale face-to-face via google hangouts). Rebecca Schuman (not a philosopher, but a German scholar) is quite well known as a Slate writer on academia. These careers suggest that one's knowledge about academia is immediately transferable into a non-academic job.
Some of my interviewees had careers that were not immediately related to their PhD in philosophy, although there are indirect connections: consultant, computer programmer, television writer. Such jobs require significant additional training and practice, which you will need to find time for next to your present occupation if you are considering them (see above).
As I found in the interviews and in many other discussions with people who left academia, you will probably not land a non-academic job (or create your own job) by waiting around for opportunities to materialize. If you want an exit, you need to do probably all of the following: obtain further training, network with people outside of academia, apply for jobs that may be suitable (non-academic jobs are advertised all year round). There are online resources to get you started, e.g., here.
You don't need to make a definite decision
Once you start thinking of a non-academic career, this does not mean you should stop considering an academic path altogeher. Here's something that happened to a friend of mine: he had his PhD more than 5 years ago from a well-ranked university. In spite of this and a strong publication record, he did land a tenure-track job, but instead got a string of temporary lectureships and postdoc positions.
Becoming increasingly frustrated with having to move every couple of years and the insecurity of the job market, he decided to learn several programming languages (both in online and offline courses), and use his skills in formal philosophy to become a programmer. He started applying to non-academic programming jobs, and landed a few interviews. In the meantime, he continued applying for academic jobs. He got an interview for an attractive tenure-track position, and was offered the position. He accepted it. I've often thought that if he had received an offer for a programming job, he would now no longer be in academia.
To conclude
From the people I interviewed, and other people I talked to, I know that non-academic jobs can be rewarding. Compared to most NTT positions and even to many TT positions, they are often significantly better in terms of pay, geographic control (which is very important, and a reason for many people I talked to for leaving academia), and in terms of personal autonomy and happiness, the only significant downside being that one has to give up doing fundamental research. However, a non-academic job will not simply materialize; you need to get additional training and familiarize yourself with the culture of the non-academic career path of your choice.