"Intellectual Sparring Partner (Noun): A friend, colleague, or acquaintance whose combination of background, competency, and personality makes them well-suited to strengthen the quality of your reasoning and decision-making via active, grounded discussion and debate."

"Background: Different from your own across a number of vectors. A fundamentally different “map of reality” is ideal."

"Competency: Exhibited clarity and depth of thinking. An analytical mind that is able to deconstruct problems into component parts."

"Personality: Kind (but direct). You want to feel safe with the person and know that they operate from a basic stance of kindness—but that this kindness does not interfere with their willingness to be direct. This is essential."

"Establish structure with regular “sparring sessions”—1 hour on a fixed weekly or monthly cadence, with clear topics and desired outcomes to guide the discussion."

"The Four Idols framework says that everyone is driven by the pursuit of one (or more) of the following idols: Money, Power, Pleasure, and Fame."

"Reminder, there is nothing wrong with any of these idols—they are perfectly natural. The key is to become aware of your idol—to understand the role and influence it has in your decision-making and life, and to realize that chasing this idol will not lead to happiness on its own."

"Money: Financial wealth and the accumulation of resources. Power: Control over others; commanding position. Pleasure: Feeling good. Fame: Admiration of others; approval and respect from peers."

"the things you worship may “eat you alive.”"

"“The insidious thing about these forms of worship is not that they’re evil or sinful, it’s that they’re unconscious. They are default settings. They’re the kind of worship you just gradually slip into, day after day, getting more and more selective about what you see and how you measure value without ever being fully aware that that’s what you’re doing.” - David Foster Wallace, This is Water"

"The key is to become aware of your idol—to understand the role and influence it has in your decision-making and life, and to realize that chasing this idol will not lead to happiness on its own."

"What had they done (or not done) that they had come to regret later in life?"

"Could these regrets have been avoided by heeding this advice?"

"""If you do not change direction, you may end up where you are heading."" – Lao Tzu"

"It forces you to begin with the end in mind."

"List Your Regrets:"

"This is deeply personal—don't write down what you think you should say, write down what you will actually regret."

"Establish Your Values: Formulate a set of 3-5 core personal values that are highlighted by your regret list."

"Determine Your Actions: For each core personal value, determine the actions you can take today to behave in line with that value (and avoid the eventual regrets)."

"Deathbed Regret: Not spending enough time with my kids during the Magic Years."

"Deathbed Regret: Not training my body and mind during my middle years."

"Deathbed Regret: Allowing true friendships to atrophy over time."

"Deathbed Regret: Allowing negativity to linger in my life."

"Deathbed Regret: Letting money control my life."

"Deathbed Regret: Not leaving something that lasts beyond my life."

"I will strive to leave a mark on the lives of those less fortunate than I was."

"My bet is that if I do deep, focused work on projects I consider meaningful, I will create something valuable for others, which implies that the money will take care of itself."

"But true wealth is found not in attaining more, but in discovering your version of enough."

"You're not sure why, but your motivation and inspiration runs dry. Things become very, very difficult."

"It's especially common for ambitious, high-achievers, who tend to default to a state of burning the candle at both ends."

"Step 1: Stop Digging"

"""The most important thing to do if you find yourself in a hole is to stop digging."" ― Warren Buffett"

"Negativity: It's easy to be hard on yourself when you're in a rut."

"Exhaustion: Imagine a car stuck in the mud. Ambitious people assume that they can get the car out of the mud by revving the engine and propelling forward, but the tire spins faster and faster and the car digs itself deeper and deeper."

"Upgrade Your Mindset: Eliminate the negativity and cut yourself a break. If you catch the negative self-talk happening, stop it in its tracks."

"Step 2: Change Direction"

"There are all variety of factors that are outside of your control that may have contributed to you falling into a rut, but this step solely focuses on those within your control."

"Internally: How am I complicit in creating the conditions that I don't want?"

"Externally: How is your environment negatively shaping this reality?"

"As you change direction, focus on your identity: What mental and physical space would the ideal version of yourself occupy here?"

"Step 3: Create Movement"

"Motivation is a natural byproduct of movement. When in doubt, just start moving."

"Movement —> Momentum —> Motivation"

"My favorite method for manufacturing movement: Minimum Viable Progress. Minimum Viable Progress says to just do a tiny bit, as anything above zero compounds."

"Avoid the tendency to think that the movement has to be perfect or robust."

"Staying In The Game"

"Life is a long, long game that all comes down to allowing positive actions to compound for the long run."

"The worst thing you can do is push the engine harder and risk taking yourself out of the game for a longer period than if you had worked through it."

"Am I hunting antelope or field mice?"

"A lion is capable of hunting field mice, but the prize would not be sufficient reward for the energy required to do so. Instead, the lion must focus on the antelope, which do require considerable energy to hunt, but provide a sufficient reward."

"In whatever you are pursuing, are you hunting antelope or field mice? Are you focusing on the big, weighty, important tasks that will provide sufficient reward for your energy?"

"""I have always believed, and I still believe, that whatever good or bad fortune may come our way we can always give it meaning and transform it into something of value."" - Hermann Hesse"

"You cannot control what happens, but you can control your reaction to it."

"Parkinson's Law is the idea that work often expands to fill the time alotted for its completion."

"Open timeframes run counter to our natural procrastinatory instincts! They lead to a lot of movement and very little progress—the ""rocking horse"" phenomenon of busy work culture."

"We tend to be more efficient and productive when constraints come into play. We also tend to focus on the important when pressed for time"

"Leverage Parkinson's Law to make you more efficient in getting through the low-value, but necessary tasks in your professional life."

"Condense the processing into short windows to become more efficient and avoid the negative cognitive impact of task-switching."

"Work on big projects in 60-120 minute focus blocks."

"One common trait I’ve observed: they all legitimately enjoy being wrong."

"They embrace new information that forces them to change their viewpoints—their open mindsets allow them to accumulate and compound knowledge at an accelerated rate."

"This innate desire to be wrong—to get closer to the truth—leads them to seek out people who are willing and able to push their thinking in new directions and to greater depths."

"My own biases and baggage—mainly the deep, misguided desire to have an important sounding title or impressive firm name on my resume—were clouding my ability to make a clear, thoughtful decision about what would be the most enjoyable, energy-creating, and profitable path."

"First off, it’s important to note that there is no such thing as a one-size-fits-all intellectual sparring partner."

"Start by thinking about the existing relationships in your life. You might find that there are a few candidates in that pool that fulfill the above criteria."

"If not, keep looking. This person (or group of people) will play an important role in your life."

"1-3 pre-planned sparring topics. Each person should send the topic with a few bullets on background and framing in advance of the session."

"I would encourage everyone to make a deliberate effort to identify and foster these relationships. Be a great sparring partner for someone else—create value, receive value."

"One intellectual sparring partner can change your life. Find yours—cherish them."

"The most interesting idea I learned during our time together was the Four Idols: a framework and exercise for developing an awareness of your underlying motivations and escaping the hollow, Sisyphean chase that so many people find themselves on."

"The concept of the Four Idols is drawn from St. Thomas Aquinas, who spoke of the four false idols—Money, Power, Pleasure, and Fame—in his Summa Theologica, which was written during his life in the 13th century but published in the late 15th century."

"Money: Financial wealth and the accumulation of resources."

"Power: Control over others; commanding position."

"Pleasure: Feeling good."

"Fame: Admiration of others; approval and respect from peers."

"The downside: As we strive to get “closer” to our idol, we find ourselves on an endless chase for more, incorrectly assuming that this chase will lead us to the promised land of happiness."

"Furthermore, most of us go through our lives completely unaware of the idol we worship:"

"The goal is to develop a conscious awareness of your idol—to become aware of what is motivating and driving you, and to understand the separation between this chase and your lifelong pursuit of fulfillment and happiness."

"I had previously experienced the big swings in emotion that come from the public nature of my pursuits—the high highs of a piece of content resonating with the masses, the low lows of a piece of content driving ad hominem attacks and criticism."

"The awareness has made me understand that I need to separate my fulfillment and happiness from that motivation and chase—a healthy separation if you ask me!"

"The Oxford Languages English dictionary defines luck as ""success or failure apparently brought by chance rather than through one's own actions."""

"But all you need to do is perform a simple search of the phrase ""quotes on luck"" to reveal a great many perspectives that differ from this definition:"

"""Luck is where opportunity meets preparation."" - Seneca"

"In it, Dr. Austin proposed that there are four types of luck:"

"Type I: Blind Luck"

"Type I Luck covers the truly random occurrences of the universe."

"Type II: Luck from Motion"

"Type II Luck is derived through the expansion of your luck surface area from simple movement. The increase in collisions opens you up to more lucky events."

"Type III: Luck from Awareness"

"Type III Luck is a result of your awareness and depth of understanding of a specific domain."

"The entrepreneur and investor Naval Ravikant summarized this type of luck beautifully: ""You become very good at spotting luck."""

"Type IV: Luck from Uniqueness"

"Type IV Luck occurs when your unique set of attributes attracts specific luck to you."

"Typically, Type I, Type II, and Type III Luck will arrive in stages:"

"Type I dictates the early years of your life."

"Type II comes into play as you begin to hustle in your 20s."

"Type III sets in as you develop deep experience in your 30s and beyond."

"When choosing between two paths, always choose the path that has a larger luck surface area. Ask yourself: Which of the two paths is more likely to lead to me getting lucky? Act accordingly."

"There is one tool that has been used with near perfect consistency by history's greatest men and women. From artists and inventors to entrepreneurs and athletes, they have all understood the immense power of this one, simple tool: the walk."

"Aristotle founded what became known as the ""Peripatetic"" school of philosophy—a word that literally translates to ""walking"" or ""given to walking about""—given his propensity to walk while lecturing or discussing with students, mentors, or opponents."

"""The moment my legs begin to move, my thoughts begin to flow, as if I had given vent to the stream at the lower end and consequently new fountains flowed into it at the upper."""

"In his famous biography of Steve Jobs, author Walter Isaacson comments that Jobs believed he did his best creative thinking while walking."

"​Stanford researchers found that walkers performed significantly better on tests measuring creative divergent thinking during and after walks. In fact, walking boosted creative thinking by an average of 60% and the benefits lasted well beyond the walk itself."

"University of Hong Kong researchers showed that walking side-by-side led to deeper feelings of connection, implying that walking meetings may actually create better outcomes."

"That 10x increase has unlocked me creatively, spiritually, mentally, and physically—I feel like a completely different person."

"Active Walks: Active walks are 30-60 minutes and are done at a brisk pace with optional technology."

"Passive ""Tech-Free"" Walks: Passive walks are ""atelic"" activities (meaning they are done with no goal in mind). These walks are 30-60 minutes and are done at a slow, leisurely pace with no technology."

"Morning Sunlight Walks: You don't need a fancy morning routine—just go for a 15-20 minute walk."

"Break Walks: As shown in the NYT article above, short walk breaks have a positive impact on your overall wellness."

"I was actually busy, but it also became part of my identity—a weird brag I developed to try to signal my value and improve my own self-worth."

"Our growth orientation also means that we are predisposed to fall into a trap—the Busy Trap."

"Why do we SAY we are busy? Why do we FEEL we are busy?"

"Busy has become the dystopian status symbol of the modern worker."

"If we are busy, it must mean we are extremely valuable and generating prolific output."

"Busy is used as a way to protect ourselves from scrutiny in the workforce."

"It's no secret that we are living in an era of constant connectedness."

"In many ways, connectedness is a paradox"

"We're constantly connected, bombarded by notifications and dopamine hits. But while we have more connectedness, we feel less connected"

"Constant connectedness means we feel busier, but find less meaning in the noise."

"When we constantly seek to optimize, we fill our time with movement (that may be completely devoid of progress)."

"The failure to prioritize is the greatest driver of busyness."

"The Short List: There are rarely more than 2-3 things that truly matter at any point in time. Failure to identify and focus on them means we busy ourselves with everything on our 20 item list."

"Urgent vs. Important: Spending too much time on the urgent draws our attention away from the important."

"""Beware the barrenness of a busy life."" - Socrates"

"Failure to Progress on the Important: Busyness is a drain on the mind. It saps our creative energy and forces an inefficient allocation of our precious mental resources."

"Physical Health: When you feel busy, you give yourself excuses to cut corners."

"Mental Health: Feeling busy is a recipe for burnout."

"Gratitude & Enjoyment: When you're busy, you never stop to smell the sweetness in the air. I recently tweeted about the importance of stopping to acknowledge the beauty of a happy moment. When you're busy, you never do this. It's devastatingly harmful to our enjoyment of life."

"""No one pursuit can be successfully followed by a man who is preoccupied with many things…since the mind, when distracted, takes in nothing very deeply, but rejects everything that is, as it were, crammed into it. There is nothing the busy man is less busied with than living: there is nothing that is harder to learn."" - Seneca"

"The first step is to eliminate our desire to say we are busy. We need to remove ""busy"" as a positive signal from our collective consciousness."

"It's not about how many hours you work or how filled your days are with movement. It's about how much output you generate per unit of input. It's about the leverage on your input."

"Be deliberate about identifying what is important in your life and work."

"Make a List: Write down your top-25 priorities on a piece of paper."

"Narrow the List: Go through the first list and circle only the top 3-5 items."

"Split the Lists: Write down the top 3-5 priorities on one list."

"Once you've identified it, be ruthless in focusing on it. If anything new comes up, pull out your list and make a quick assessment of whether it falls into one of your priorities (or if it should be avoided at all costs)."

"Use the simple Eisenhower Decision Matrix as a tool to see how much time you are spending on urgent vs. important tasks."

"This couldn't be further from the truth: Boredom and scheduled free time have long been a secret weapon of history's greatest minds."

"Reframe: Stop taking pride in being busy. Learn to take pride in your output per unit input."

"Use a baseline time horizon of 5 years in the future, but adjust as you see fit. A basic letter structure to follow: (1) Reflections on the Present, (2) Changes to Make, (3) Goals for the Future, and (4) Fun & Crazy Predictions."

"What does that “10x” mean?"

"These are the step-function improvement or growth opportunities."

"My generalized mental model for life is that truly meaningful change is only felt in 10x increments."

"I think too many people jump at every 2x opportunity they encounter in life and thus find themselves too busy or without the mental bandwidth to capitalize on the 10x opportunities when they arise."

"Every year on my birthday, I write a letter to my future self."

"Reflections on the Present—most notably a desire to carve my own way rather than be defined by the impressive path that my older sister had established in high school."

"In writing the first letter on my 25th birthday, the time horizon I decided upon was 5 years."

"Anecdotally, I have found that 5 years is the amount of time in which meaningful life change happens."

"The letter format is mostly unstructured, but I try to have some degree of content consistency across them."

"The four areas I am sure to address in each letter: Reflections on the Present Changes to Make Goals for the Future Fun & Crazy Predictions"

"Review the responses to what is draining your energy, what relationships are toxic, and what habits are leading you away from your goals."

"For every 1 degree a plane veers off course, it misses its target destination by 1 mile for every 60 miles flown. The lesson: Tiny deviations from the optimal course are amplified by time—off by a little now means off by a lot in 5 years."

"You're writing to your future self, so this is the chance to have some fun. These predictions tend to be pretty funny—and wrong!—when you read them in 5 years."

"Life simply changes too much in a 5 year span—especially in your 20s and 30s. Having a 5 year plan is fine if it provides value via structure and focus, but recognize that it's probably going to have to adjust."

"My reflection on the alignment of my systems and habits with my goals was the best predictor of my achievement of said goals."

"The process of writing a letter to your future self forces deep reflection on the present and thoughtful rumination on the future."