“Progress is almost never linear. Ups and downs and bursts.”
Nassim Taleb
Thursday, 6th of April marked a turning point in my life: Quitting my job working as a full-time teacher. After leaving my position for personal, professional, and situational reasons, I entered a period of scrutinising and re-evaluating my career. During this time, I have been working as a casual relief teacher to pay the bills, and have been writing, reading and re-reading, in an effort to get re-acquainted with some of the philosophies I’ve let fall by the wayside.
“Remember why you’re here” was the first thing my mentor teacher taught me when I was on my first placement for my Master of Teaching degree back in 2015. Seems easy to remember, and for the longest time it worked for me, until earlier this year when it didn’t. The question as to why I was there was one of many I had asked myself during the final weeks of my job. I had simply hit a wall in terms of growth.
The existentialists often talk about bad faith, or the attempt to avoid the responsibility of understanding oneself, replacing the process of introspection and self-discovery with external norms and pressures. I would say, during the final months of the job, that I revelled in bad faith, complicating my life unnecessarily, feeling like I had to stay because it’s what a good teacher should do. I was no good to anyone – students or colleagues – in that kind of headspace. So, after thinking about it for months, I made the decision to step aside.
At that point, if you were to ask me what I was really doing, you would have drawn a blank stare.
I’d like to think I have a better grasp on it now, having left the job and everything that went with it. Like a pointillistic painting, sometimes one needs to take a few steps back to see things in full. Which in turn raises further questions. Will I stay casual or go back to full-time work? Did I do the right thing by stepping away? Or would it have been worth it to stay at that job, navigating the problems at the back end as they kept piling up? What was I missing that a better teacher might have seen?
But I’m fine with that. At least I have that luxury of being able to mull over those questions, whether they need answers or not, while I continue to re-assess my direction. Will I be working as a classroom teacher twelve months from now, or will I take on a different role, such as education support or admin? Or will I be in a different industry altogether? It might seem strange, but I find myself feeling weirdly unconcerned about it all. It’s not life-or-death, it’s a first world problem.
I’ve heard about and from colleagues, friends, or friends of friends at the crossroads of their careers, debating if it’s worth staying or changing things up. Some of these people have been in the same workplace for years, while others have travelled all around the world, depending on their field.
When I’m in that kind of transitional period, I know what I like to do. I like to stay productive, and make myself useful.
But in terms of input, or my information diet:
First, ignore the legions of influencers and e-celebs currently glutting the market, and read books. Physical books, Kindle, audiobooks, whichever suits you. But I would say, specifically, get into the classics. The classics are important because everything has a precedent. And for a text to survive for centuries before the internet and viral marketing is a clear indicator that there’s something there. Call it survivorship bias, but if the alternative means taking the word of some twenty-something e-celeb who has been nowhere and done nothing, I’ll gladly take it. So, next time someone asks if there’s a point to studying history, it should be that. If there is a quote on learning from failure, or feeling like you’re a few steps behind where you need to be, then I’d rather get it from a philosopher than some flavour-of-the-moment influencer.
Second, don’t just read books, but re-read them. “A good book gets better at the second reading,” the philosopher Nassim Taleb says. “A great book at the third. Any book not worth rereading isn’t worth reading.” There are few things I enjoy more than opening a book I’ve already read and finding something I missed the previous time. It never gets old.
What I’m recommending here is not a “best books” list (I’m not a fan of listicles), but rather a small selection of what works for me, what I turn to when I need to pause and take stock. With this in mind, I would recommend the following:
Letters from a Stoic, by Seneca.
Stoicism has really enjoyed a revival of interest in recent years thanks to Ryan Holiday, and for me, Letters from a Stoic really hits home. Seneca was a teacher to Nero, and gave tons of advice to his friends, whether it be on life, loss, work, power, or wealth. He knew what it meant to lose everything, since he was banished to Corsica and sentenced to death by the Senate. And while he is considered a Stoic, he wasn’t afraid to borrow from other schools of philosophy. He really is like a guiding voice, something that is desperately needed in an age of stick-your-chest-out Cosby-esque pseudo-wisdom.
I would follow Seneca’s Letters with his essay, On the Shortness of Life. The book is small enough to carry in your pocket, plus a quick Google search will easily find you a PDF version.
Essays, by Michel de Montaigne.
One can draw an almost straight line from Seneca to the essays of Montaigne. Influenced by the Stoics, he spent pretty much the entire second half of his life withdrawing and looking inward, asking questions on all manner of topics, including death, sex, people, animals, whatever came to mind. He was also Epicurean in how he figured pleasure and happiness, despite the bleak reality of France at the time. Add in a sense of humility than managed to impress Christians and Sceptics alike. All that concerned Montaigne was what worked and had practical value in his life.
But most importantly, all this time spent in self-reflection would be worthless without something to show for it. Montaigne’s withdrawal from public life granted him not only a better understanding of himself, but thousands of pages of this understanding that he could refer to whenever he needed to (and that we can refer to now). After all, philosophy is more than just spending time in one’s own head. Articulating what you find and turning that into something tangible is key.
Some call this practice the keeping of a commonplace book – a collection of quotes, passages, or thoughts of the day that you keep and draw on when needed. Montaigne’s essays are one such collection, though how you organise your notes is up to you. Robert Greene and Ryan Holiday have used notecards extensively when researching for their works, filed away in boxes.
I’m going for a sort of hybrid system, writing some things down on paper while slowly but surely going digital with others. Book quotes and passages are typed up and saved, while thoughts of the day remain on paper. I might go the digital route fully, but I’m sticking with this approach for now.
I would pair reading Montaigne’s essays with Sarah Bakewell’s biography, How to Live: A Life of Montaigne in One Question and Twenty Attempts at an Answer. Her account of Montaigne’s life in the context of the French Renaissance, and her own commentary on his philosophy, are just excellent. I don’t always find the classics easy to follow, and Bakewell is the one you want when you need a guide for the path of Montaigne.
Incerto, by Nassim Taleb.
Taleb is a Lebanese-American essayist and statistician and something of an avant-garde thinker, and his Incerto spans five volumes: Fooled by Randomness, The Black Swan, The Bed of Procrustes, Antifragile, and Skin in the Game. Described as “an investigation of opacity, luck, uncertainty, probability, human error, risk, and decision making when we don’t understand the world,” Incerto is essentially one long essay on the limits of our knowledge (especially that of academics, media outlets, specialised institutions, and think tanks).
The best thing about Incerto is that you can read these volumes in any order. The Black Swan was my introduction to Taleb’s philosophy, and it was as good a starting point as any of his works. I’m not ranking them from best to worst (whatever that means), because so much of a book’s value depends on personal context.
What have I taken from these works? Many things, but in particular: Humility in the face of things I can’t control, contentment with the results of what I can.
Also, the chapters of Skin in the Game are available for free on Medium, so that can also be a possible starting point. It’s something I would love to have had years ago, previous to the luxury of book-hoarding (although, now that I am book-hoarding, I have the deluxe edition box set and it’s beautiful).
Like with Seneca and Montaigne, he is one of those authors I can return to over and over again.
The existentialists are a great guide on where not to be, but I won’t get into that.
Your mileage may vary.
Lawrence Deveney 