Recognize that it’s impossible to learn what you think you already know. Embrace intellectual humility by focusing on what you don’t know and asking questions, as this is a source of wisdom.
Understand your strengths, limitations, weaknesses, and vulnerabilities. Be aware of your personal evolution and how your capacities change over time, as this self-knowledge is an essential form of wisdom.
Clear your mind of ego, biases, prejudices, and preconceived notions to be open to new knowledge. Actively check your ego by asking if it’s distorting your perceptions or decisions, as ego often makes things about you, hindering success in endeavors that are about others.
Practice pausing and reflecting before reacting or forming opinions. Test your emotions, judgments, and views of things rather than going with your first instinct, which is a core Stoic practice.
Cultivate curiosity and actively ask questions, as your life can hinge on the questions you ask or don’t ask. Encourage questioning in yourself and others, realizing that the act of questioning is essential for the journey to wisdom.
Engage with books as a way to have conversations with the wisest people who have ever lived. Learning from books offers efficiency and spares you from painful trial and error that you might otherwise experience on the street.
Develop a system, like a commonplace book or journal, to synthesize and transfer knowledge into an easily accessible and cultivable form. This process of recording and organizing what you learn is crucial, as knowledge not recorded is often lost.
Actively seek out individuals who are further ahead, whom you admire, and who possess wisdom. Cultivate intellectual relationships with patient teachers who can direct and orient you towards the knowledge and experiences you need.
Dedicate long, uninterrupted periods to concentration and focus, as it is essential for learning, understanding, and achieving any kind of wisdom or insight. Engage in practices like journaling to support this focus.
Identify your peak times for mental freshness and quiet, then structure your day to prioritize deep work and creative breakthroughs during these periods, minimizing interruptions like phone use or meetings.
When exploring a topic, commit to multi-year deep dives into its history, legality, philosophical roots, and economic underpinnings. This technical competence and curiosity are integral to wisdom.
As you achieve success, actively seek out accurate feedback and criticism, as access to it tends to diminish. Cultivate a practice and network (like a board of advisors) to ensure you continue to improve and avoid stagnation.
Recognize that real and lasting wisdom often comes from paying for it through suffering, embarrassment, and costly errors. The redeeming quality of these experiences must be the insight and understanding you extract from them.
Accept the complexity, contradiction, and ineffability of things, rather than insisting on simple definitions or understandings. Engage with fiction, poetry, and the arts to grasp truth from different angles.
Strive to distill complex ideas, experiences, and studies into their fundamental essence. Aim to articulate core truths with brevity and impact, much like Lincoln did with the Gettysburg Address.
Reflect on death as an ever-present part of existence, not just an end-of-life event. This fundamental piece of wisdom can be life-changing, helping you to live well in ordinary moments and ultimately prepare for dying well.
Understand that you always have a choice in your actions, as free will is an essential part of the virtue tradition. Your choices define who you are, so choose virtue over vice.
Be aware of how you come off to others and strive to perceive social dynamics accurately. Lacking social intelligence, even with high intellectual capacity, can lead to avoidable negative outcomes.