This month’s reading list centres around a single theme: finding solace in doubt and uncertainty. These books explore the relationships that didn’t work, the mistakes we made, the consequences we didn’t expect, the job we didn’t get, the moments that we missed, the imperfections that make us human. We become desperate for meaning. We delve into trying to be better. As Oliver Burkeman said, we are becoming constantly obsessed with discovering how to master the situation of being a human, and that we won’t be able to relax into our lives until we do.
We need discovery, don’t get me wrong, but not around mastering how to be human. I don’t think there is an answer to that. Rather, the type of discovery we need is in embracing uncertainty and life’s inherent chaos. As the academic Wilfred McClay once pointed out, real wisdom doesn’t lie in getting life figured out; it lies in grasping the sense in which you never will get it completely figured out. It lies in learning and accepting. In our relentless pursuit of achievement and perfect outcomes, we miss the beauty of our journey, and what it meant for us to be part of it. Outcomes are so subjective, relying on the thousand things that need to happen or could have happened. We get confused by the outcomes. The more precise your vision of an outcome, the more likely you are to be disappointed. As Boyd Vardy wrote, going down a path and not finding a track is part of finding the track. It’s “the path of not here.”
Yes—things usually don’t turn out as planned. But you don’t need to abandon your dreams; just don’t let them get in the way of noticing what’s taking place. I hope you enjoy my reading list this month!
The Castle by Franz Kafka - I visited the Franz Kafka museum in Prague recently. Despite writing over a century ago (1883-1924), Kafka’s insights feel startlingly contemporary, especially his grasp of how life constantly slips away from our desires and control. “Kafkaesque” was developed as a concept to describe situations that are nightmarishly complex, bizarre, illogical, and disorienting, often leading to a feeling of helplessness and oppression. The Castle is his unfinished masterpiece, where Kafka writes the story of a man who arrives in a village for a duty that he struggles to clarify. Through complex characters and mounting frustrations, Kafka explores how individuals navigate a society that succumbs not only to oppressive authority (the castle) but to their own collective imagination of power. It brings up rules that were probably never written, letters that get lost in transit, cards and communications that arrive late or never at all. It’s a disturbing view of our own versions of reality. It rewards patient reading, drawing you into its labyrinthine world. One of my favourite quotes comes from K., the individual in question, who says that “ridiculous confusions, in some circumstances, can determine the course of a man’s life.”
The Wisdom Of Insecurity by Alan Watts - I am admiring more and more Watts for how he blends philosophy and metaphysics with insights about our collective consciousness. Last month I read The Book On The Taboo Against Knowing Who You Are, and I found it fascinating for its existential metaphors as wandering souls, explaining that by trying to find meaning across tribes, we have become invariably divisive and quarrelsome, brushing the world from magic. In his effort to show this paradigm, he pushes us to lean into self-knowledge, open-mindedness and exploration as the beginning of a solution. In The Wisdom of Insecurity he explains in simple terms that time itself is a creation of the restless mind, that so long as the mind is split, life is perpetual conflict, tension, frustration, and disillusion. Suffering is piled on suffering, fear on fear, and boredom on boredom. But the undivided mind is free from this tension of trying always to stand outside oneself and to be elsewhere than here and now. Each moment is lived completely, and there is thus a sense of fulfillment and completeness. This book has a bold title that echoes one of our deepest feelings and fears. I’d recommend this book over and over as a very interesting and meaningful read.
Radical Focus by Christina Wodtke - I used to read a lot of self-help, business and economic books back to back; now I find it much better to read other genres including biographies, philosophy, memoirs, fiction. As Steven Pressfield said once, sci-fi is a technological spin on a philosophical or metaphysical problem. I think reading openly has made me a stronger critic of business books, and I have to say that I was deeply satisfied with Radical Focus. Starting with a business fable that hits close home, she addresses the biggest pain points that a large group or team of individuals has when building up an idea: priorities. Under the scheme of differentiating objectives and key results, Wodtke was able to reflect some of the most important things that a manager needs to grasp to get a team towards the finish line. I found it very helpful to see examples of the different dynamics and ways to achieve results, the concept of “half-build strategies”, 2x2 charts, and what the ideal system should contain in three steps: inspiring and measurable goals, a sense of progress, and cadence for accountability.
Tomorrow and Tomorrow and Tomorrow by Gabrielle Zevin - In my quest to read more fiction, I got this book recommended by a meaningful friend and then by another. It wasn’t long after I started reading that I couldn’t believe I let this sit on my bookshelf for so long. 478 pages that I couldn’t put down and therefore finished in three days. This book explores deep complexities around relationships, virtues, ambition, dreams, philosophy, creative endeavors, addictions, tragedy, and above everything, love. I would recommend this book to anyone, regardless of their walk of life, as both entertaining and educational. A quote that stuck with me is “this life is filled with inescapable moral compromises. We should do what we can to avoid the easy ones.” Yes, it’s hard to face life in different circumstances and find ourselves making choices that could be ethically imperfect: taking a shortcut, ignoring a principle, benefiting from something or someone. But can we avoid those decisions that we can see clearly? Not speaking up when we need to, pretending it’s not your problem because you’re not in the spotlight. So I read once that when everyone is sick, we no longer consider it a disease. What are the decisions that we can change for the better, today?
Govt. Cheese by Steven Pressfield - I am a fan of Pressfield. I think I quote something from him in almost everything I write. For me he is a literary hero, a warrior, an imaginary mentor when I sit to write. He is as close to raw humanity as he can get. He emerged from life’s darkest valleys and published his first novel at fifty-two, becoming Hollywood-famous with it. Much later, he published The War of Art, one of my favourite books about overcoming creative resistance. This is his memoir. In meaningful snippets, he describes categorically and harshly the different circumstances of his life and how he was deeply lost and wandering through it. “Me? I’m nobody,” he replied to others more than once, throughout his different circumstances. Quoting from the back of the book: “he worked 21 jobs in seven states including schoolteacher, attendant in a mental hospital, tractor-trailer driver, oilfield roustabout, migrant fruit picker, advertising copywriter and Hollywood screenwriter. None of this was intentional.” When I read this, how can I accept my own excuses for not pursuing what I truly want? What is anyone’s excuse not to achieve what they want? I enjoyed this reading not because it’s a story of challenge and success, but because it felt deeply honest, painful and human.
I’d love to hear your thoughts on these ideas. The best books you can read come to you through word of mouth, so if you know good titles that relate, please share them! If any of these resonate with you, pass them along.