Flatland - Edwin Abott. On the possibility of phenomena that are beyond our current ability to understand and what progress toward understanding may look like.
Rejecting the Ideal of Value-Free Science - Heather Douglas. Strips away layer after layer of value-ladenness that shapes our sense-making.
On the Very Idea of a Conceptual Scheme - Donald Davidson. Even when it seems like science is limited by incommensurable conceptual schemes, we share one conceptual reality in which we can learn to better navigate.
The Structure of Scientific Revolutions - Thomas Kuhn. Rather than dripping along discovery by discovery, science jumps in paradigm shifts, each creating a new map that shapes our interpretation of the world.
The Philosopher’s Toolkit - A Compendium of Philosophical Concepts and Methods - Peter Fosl. Gives a brief overview of the different tools at our disposal when making sense of the world.
Opacity: Lindy Effect & Psychological Findings - Nassim Taleb. On scientific heuristics.
The Oxford Handbook of Philosophy of Social Science - Harold Kindcaid. A good overview of major themes in the philosophy of science.
Chaos: Making a New Science - James Gleick. On factors that complicate our attempts to bring order into the chaos of reality.
The Open Society And Its Enemies - Karl Popper. On the importance of openness in society, science, and technology for resilience and progress.
The Weapon of Openness - Arthur Kantrowitz. Argues that openness is our best shot for dealing with civilizational risks and problems as they arise.
The Use of Knowledge in Society - Friedrich Hayek. On human civilization as a superintelligence composed of individual problem-solving entities.
The Meaning Of It All - Richard Feynman. Collection of three lectures on the relationship between science and society. If you have superstitions to let go of, also read Cargo Cult Science.
The Ghost in the Quantum Turing machine - Scott Aaronson. What physics can tell us about free will, chaos, the arrow of time, the holographic principle, Newcomb's paradox, algorithmic information theory, and more.
A Beautiful Question- Frank Wilczek. Uses the history of science, from Plato to quantum physics to answer the question if the world embodies beautiful ideas and what, if anything, this means for reality.
The Big Picture: On the Origins of Life, Meaning and the Universe itself - Sean Carroll. Science-based exploration of the human position and history in the universe, including implications for our sense of meaning.
Scale - Geoffrey West. On the fractal-like scaling laws that govern anything from cells to cities.
The Best Books on Every Subject - LessWrong. List of books on various subjects, many of them scientific.
Creon's List of Profound Books - Creon Levit. Ordered according to math, physics, etc.
Bookshelf, People - Patrick Collison. Lists books and people, many with a science-focused long-termist bend.
Santa Fe Institute - A research organization exploring the frontiers of complex systems science. Santa Fe Institute Podcast - The science podcast, Complexity, explores the Universe's deepest mysteries, while on Alien Crash Site, every guest imagines one alien technology that could change the course of human advancement.
WaitButWhy - A long-form, stick-figure-illustrated blog about future-relevant themes.
Kurz Gesagt - Short explainer videos on questions of importance for humanity.
Philosophy Bites - An intro level podcast that is good for staying up to date on “current topics” in ethics and philosophy.
The Journal for Evolution & Technology - Journal for futurist publications.
Astral Codex, Astral Codex Podcasts - A blog on science, futurism, and rationality.
After-On - Podcast. Intros and interviews on science and technology.