Question: What are the barriers within you that need to be broken?

Framework: The Beginner's Paradox

I have a few core Missions that define my life—everything is aligned around them.

Missions are life journeys with no specific end. Missions are not goals. Missions are infinite games. The power of Missions is found in the clarity they provide: If an opportunity, person, or action does not positively contribute to one of your Missions, you can say no to it.

I have clearly defined a Mission within each of three categories: Professional, Personal, and Health. Clearly defining (and embarking on) your missions is the key to unlocking new clarity, focus, and fulfillment in your life.

Question: What is one tiny action that would create momentum?

Framework: The 2 Types of Knowledge

Question: What am I certain of today that I'll laugh at in 10 years?

Framework: The Bike Shed Effect.

I recently re-read an old Paul Graham essay that got me thinking about the composition of professional time—what "types" of time exist in our workdays and how we can find a more optimal balance across those types.

I identified four types of professional time: Management, Creation, Consumption, and Ideation. Most of us have a lot of Management, a little bit of Creation, and almost no Consumption and Ideation.

Use a color coding calendar exercise to deconstruct your current mix of time. Three tips to improve your balance: (1) Batch Management Time, (2) Increase Creation Time, and (3) Create space for Consumption and Ideation Time.

Question: What would you invest in today assuming you had to hold the investment forever?

Framework: Survivorship Bias.

I just completed my first marathon in 2:57:31 just 6 months after I started running. By achieving the sub 3-hour marathon time, I had hit my Big Goal. It felt great, at first. But then came the rut, one which led to a fundamental change in how I'm going to think about goal setting and achievement in the future.

Big Goals create a perfect storm for unhappiness. If we miss them, we feel like a failure. If we hit them, we feel a temporary satisfaction, followed by an odd darkness brought about by the Arrival Fallacy, purpose dissipation, and their extrinsic focus.

Focus on Micro Goals is my new, favored approach. Micro Goals are intrinsic, avoid the Arrival Fallacy, and create daily purpose. I will continue to have Big Goals, but I will focus my daily energy around these Micro Goals to create a healthier balance.

Question: The 1-Second Decision.

Framework: Maximizers vs. Satisficers.

Dr. Peter Attia uses a framework with his patients called the Centenarian Decathlon to organize physical aspirations for life’s later years. The idea is to choose 10 physical tasks the person wants to be able to do at 100 and then reverse engineer the necessary actions in the present to achieve that future.

Using a similar exercise to look at the broader scope of your life can be very helpful. What does your ideal life look like at age 80? Who are you with? What are you doing? How do you feel? Where are you?

To create that future, what are the necessary actions in the present? What actions, habits, and behaviors do you need to adopt today to create that end?

Question: What does your perfect workday look like?

Framework: The 3-3-3 Method.

A Stanford business professor split her class into groups and gave each group $5 and 2 hours to generate as high of a return as possible. The losing groups bartered with the $5 or used the time to generate income. The winning group sold the ad space of the presentation time at the end of the challenge and generated a 12,000% return.

When faced with a challenge with the potential for outsized rewards, we need to think differently. Three steps to think differently: (1) Avoid the distraction, (2) Ask foundational questions, and (3) Select the leveraged approach.

Remember: Creative, non-linear, asymmetric thinking generates creative, non-linear, asymmetric outcomes.

Question: If everything stays the same, what is the one change that would have the greatest impact?

Framework: The Locksmith Paradox.

Last week, I spent three days with a group of successful entrepreneurs on a retreat in Big Sky, Montana. I left the event with a new energy to grow and a lot of interesting, non-obvious learnings. This piece shares my 10 key learnings from the event.

The learnings: (1) Freedom is the real goal, (2) Environment is everything, (3) Insecurity is natural, (4) Always know the game you're playing, (5) Create value with no expectation, (6) Owned distribution is a cheat code, (7) Success isn't always loud, (8) No one has it all figured out, (9) Entrepreneurial loneliness is a real problem, and (10) Solve the problem by seeing it differently.

My Rule for Life: Find the room where it happens. Get in that room. Once you're in it, help others get there.

John Wooden was the legendary UCLA men's basketball coach who led the team to 10 national championships over a 12 year period. He is most well known for his life wisdom that extended well beyond the court.

Keeping the promises you make to yourself is the highest order purpose in life. Every single time you keep that promise, you are stacking evidence in favor of the type of person that you want to become.

This piece explores John Wooden's 9 Promises for a Life Well-Lived.

Question: What am I avoiding because it's too painful to address?

Framework: Fundamental Attribution Error.

While we all want to live in a state of low stress, during certain moments, we need to learn to optimize our stress response—we need to learn to harness stress to our benefit rather than allowing it to derail us.

The Yerkes-Dodson Law says that stress and performance are positively correlated, but only up to a certain point, after which more stress reduces performance.

3 strategies for mastering stress: (1) Reframe threat into challenge; (2) Use science-backed breathing techniques to pull back from the edge; and (3) Place yourself in controlled stressful environments to train your stress response.

Question: If you woke up three years from now and were living your ideal life, what were the three things you did to get you there?

Framework: The Pyrrhic Victory.

Theory: Our belief in our ability to create our own luck exposes us to more good fortune (or at least allows us to see the good fortune amidst a sea of bad).

In an early 2000s study, Dr. Richard Wiseman found that lucky people came across "chance" opportunities, while the unlucky people seemed to miss them. Both groups had equal access to these opportunities, but the lucky group saw what the unlucky group tended to miss.

Our daily thoughts, behaviors, and actions serve to expand or contract our luck surface area, which in turn determines our experience as a lucky or unlucky person.

The Luck Razor: When choosing between two paths, always choose the path that has a larger luck surface area.

Question: Do I actually need more information, or do I simply need to act on the information I already have?

Framework: The Identity-Action Grid

I recently got a message from a 22-year-old reader asking for career advice. Career advice is a topic area that I have always found interesting, probably because I feel it so often misses the mark. I take this as a challenge.

I sat down and synthesized the advice I would have wanted to receive early in my career (or what I would tell my own son if he were just starting out).

The 7 pieces of career advice everyone needs to hear: (1) Swallow the frog, (2) Do the old fashioned things well, (3) Work hard first and smart later, (4) Build storytelling skills, (5) Build a rep for figuring it out, (6) Show up early and stay late, and (7) Dive through cracked doors.

Question: Which thorns do you choose?

Framework: The Question of Nine.

The Wall Street Journal recently released a visual breaking down how people spend their time in retirement. The visual shows that the majority of a retiree's time is spent on sleeping, relaxing and leisure, and watching television.

Most of us create this beautiful image of what retirement will look like, but the reality is (likely) much different. Why? Well, the image we create is based on who we are today, while the reality will be based on who we are at retirement age.

The traditional concept of retirement is grounded in a foundational assumption that there should be a "before and after" within your life. I would propose a reframe: The goal is to design a life that you don't need to retire from.

Question: What are the boat anchors in your life?

Framework: Q1 relationships.

David Brooks first proposed a distinction between Résumé Virtues and Eulogy Virtues. Résumé Virtues are the things you put on your resume. Eulogy Virtues are the things people talk about at your funeral.

What I've resolved: We can build both, but only by focusing on the correct directionality. A purposeful focus on Eulogy Virtues will build Résumé Virtues, but a focus on Résumé Virtues will not build Eulogy Virtues.

If there's one thing I learned last week, it's that life is so very fragile. But no matter how fragile it is, each day, we have a choice of how to live it. Each day is a fresh start, a fresh choice to make. How will you choose to live?

Question: What if your path is a spiral?

Framework: Shu Ha Ri: The 3 Stages of Mastery

Question: The way you treat yourself.

Framework: The Shirky Principle.

The Parable of the Two Arrows: "In life, we cannot always control the first arrow. However, the second arrow is our reaction to the first. The second arrow is optional."

Victor Frankl, the Austrian philosopher and Holocaust survivor renowned for his contributions to existential psychology, has a brilliant framing for this: "Between stimulus and response, there is a space. In that space is our power to choose our response."

To create the space and move forward after a negative event: Pause, Reset, and Choose.

I was recently struck by a realization: The people I read books about are very rarely the people I would ever want to trade lives with. Why? The price of their success was not one I would be willing to pay.

There is a price tag for anything you want to achieve in life. Every single thing you want is an output that requires certain inputs to buy or earn. There's a "list price" (actual, direct price to pay for the thing you want) and a "real price" (List Price, plus the hidden, indirect price in the form of the tradeoffs and opportunity cost of the pursuit).

What I've learned: There are many things in life that look like a great deal based on the List Price, but a ripoff based on the Real Price.

Questions to ask: What is the List Price of the thing you want? What is the Real Price of the thing you want? Are you willing to pay that Real Price?

Question: If I repeated this day for 100 days, would my life be better or worse?

Framework: The 5 Second Rule.

Welcome to the second half of 2023. If you've kept up your New Year's resolutions and feel on track, great! If not, that's ok, because even if the best time to start was 6 months ago, the second best time is today.

Today, I'd like to share a distillation of my 10 favorite ideas from the 52 newsletters I've written so far this year.

The ideas covered: Spotlight Effect, 1-1-1 Method, Eisenhower Matrix, Surfer Mentality, Feynman Technique, 4 Types of Luck, Trap of the Extraordinary, Character Invention, Think Day, and Time Billionaire.

Question: What would this look like if it were easy?

Framework: The wind and the sun.

A mental model is a way to think about the world. It is a tool—a lens through which you can simplify, evaluate, and make decisions in real time as you walk through life.

When faced with any key decision, you effectively choose one of two potential characters: Investor or Borrower. The Investor is a long-term thinker who makes an investment to delay gratification, while the Borrower is a short-term thinker who takes out a loan to experience pleasure now.

Investments compound positively and the future self cashes in on the rewards. Loans accrue interest negatively and the future self is stuck with the bill.

This is the first in a new series of shorts that will cover one question and one framework to get you thinking heading into the weekend.

Question: What are the elements of your ideal life at 80-years-old?

Framework: Self-Handicapping (and how to avoid it). 

What have you changed your mind on recently? Egocentric Bias says that we convince ourselves of the accuracy of our own personal perspective—that we view ourselves as unimpeachable—and therefore struggle to acknowledge any perspectives or data that may alter our understanding of the world.

The parable of The Blind Men and The Elephant tells the story of six blind men who examine one part of an elephant and each come to very different conclusions on what an elephant is. They are all partly right, but also all entirely wrong.

The information you have about the world represents a tiny fraction of the information available, yet you use it to form a view of how the world works.

Remember the Blind Men Razor: "Never attribute to malice, ignorance, or stupidity that which can be adequately explained by different information."

Confession: I am a nervous public speaker. But confident public speaking is a critical skill, so we need a set of strategies to increase our confidence and perform as the best version of ourselves.

Prep Strategies: (1) Study the best speakers and learn from them, (2) Create a clear storytelling structure, and (3) Build "lego blocks" but avoid rote memorization.

Pre-Stage Strategies: (1) Address the Spotlight Effect and ask "so what?" about your worst fears, (2) Get into character and turn on the best version of yourself, and (3) Eliminate stress with a simple breathing technique.

Delivery Strategies: (1) Cut the tension in the crowd at the outset, (2) Use big, broad gestures and avoid touching your pockets or torso, and (3) Move with purposeful, slow steps.

I'm absolutely thrilled to announce that my first book—The 5 Types of Wealth—is officially ​available for preorder​ everywhere books are sold!

For the last three years, I've been working on this in the dark, so I'm excited to finally reveal it to all of you in my incredible community.

Today, I'd like to share a bit more about the book—why I'm so excited for you to read it—and humbly ask that you consider preordering copies for yourself, family, and friends if you've found value in any of my writing in the past.

In the early 1970s, Stanford psychology researcher Dr. Mark Lepper conducted a study with a group of young children that found those who had received a reward for completing a task experienced lower intrinsic motivation to perform that task in the future.

The Passion Paradox: We have a deep desire to chase our passions, but by chasing them, we may actually reduce our passion for them.

Three strategies for escaping the paradox: (1) Keep play as play, (2) Let work be work, and (3) Make work more playful.

You're firing on all cylinders personally and professionally—inspired and motivated. Then, suddenly, you aren't. Things become very, very difficult. You're in a rut.

I've developed a useful set of principles for managing these swings and working out of them. My three-step method to work out of a rut: (1) Stop digging, (2) Change direction, and (3) Create movement.

Ruts will happen. When they do, slow down and allow yourself to work through them. 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.

A Reddit post I shared that read, "PSA: 20 years from now, the only people who will remember that you worked late are your kids" sparked a lot of online dialogue last week.

Our default setting of work worship may be slowly, methodically robbing us of joyful, fulfilling, comprehensively wealthy lives. Perhaps it’s worth questioning the default setting—to begin living by design, rather than by default.

I am of two minds on this: (1) Being present and spending time with those you love is the most important thing in the end and (2) Having the people you love see you work hard on things you care about is a principle they'll remember for the rest of their lives. Understanding, navigating, and balancing the tension across these two minds is how you ultimately "win" the game.

In the 1980s, Microsoft founder Bill Gates began an annual tradition he called the Think Week. Gates would seclude himself in a remote location, shut off all of his communication, and spend an entire week dedicated to reading, learning, and thinking.

While I knew I didn't have an entire week to dedicate to it (due to early career demands, family priorities, etc.), I figured I could adapt something with a similar core ethos and vision. The Think Day was my creation—and I want to share its value with all of you today...

Pick one day each month (or quarter) to step back from all of your day-to-day professional demands. Seclude yourself (mentally or physically), shut off all of your notifications on your devices, and put up an out-of-office response. The goal is to spend the entire day reading, learning, journaling, and THINKING.

While in Omaha at the Berkshire Hathaway Annual Meeting, I got into a long conversation with a friend and mentor on one particularly impressive facet of the show: The effortless air about Buffett and Munger's entire performance, the ease and elegance with which they operate in what looks like a pressure-packed situation.

The term sprezzatura has come to be defined as a "studied carelessness" in the modern English language. I think of it as earned effortlessness.

The Paradox of Effort: You have to put in more effort to make something appear effortless. Effortless, elegant performances are often just the result of a large volume of effortful, gritty practice. Small things become big things. Simple is not simple.

We all struggle with some degree of self-doubt and fear of failure. It's particularly common among ambitious high-achievers, who, by definition, are constantly putting themselves in situations that are on the edge of their current competency level.

Character Invention: Create a character in your mind who can show up in the way you want to and teach yourself to "flip the switch" to become this character when necessary.

Character Invention in three steps: (1) Identify the situations where you'd like to show up as the best version of yourself, (2) Envision the character you would like to embody in each situation, and (3) Get yourself some reps by turning on this character in those situations.

Investor Graham Duncan coined the phrase "Time Billionaire" as someone who has over one billion seconds to live.

To me, being a “Time Billionaire” isn’t necessarily about having the actual time, but about the awareness of the precious nature of the time you do have. It is about embracing the shortness of life and finding joy in ordinary daily moments of beauty.

Treat time as your ultimate currency—it’s all you have and you can never get it back. Spend it wisely, with those you love, in ways you’ll never regret.

We live in a culture that endlessly promotes and celebrates the achievement of the extraordinary—of those who accomplished some supreme feat in a single, narrow domain.

The Trap of the Extraordinary is that we conflate success with the achievement of the extraordinary. Winners are those who achieve the extraordinary, losers are those who do not.

To escape the trap, there are two mindset shifts to focus on: (1) It’s not about achieving the extraordinary, it's about finding purpose, joy, and fulfillment in the ordinary along the way; and (2) The prize is not the achievement you strive for, but the striving itself.

The Spotlight Effect is a common psychological phenomenon where we overestimate the degree to which other people are noticing or observing our actions, behaviors, appearance, or results.

Pre-conditioned fear of placing yourself in "spotlight situations" means you shrink yourself down from your true potential. This is a tremendous drag on growth.

To fight back: (1) Develop an awareness of the Spotlight Effect and when it may hit, (2) Focus on being interested rather than interesting, and (3) Ask "So what?" to confront your fears.

The Learning Pyramid indicates that teaching is a much more effective driver of retention than reading or lecture. The goal should be to move rapidly to teaching in order to cement new learning.

The Feynman Technique is a learning model that leverages teaching and prioritizes simplicity to help you develop a deep understanding of any topic.

The four key steps of the Feynman Technique: (1) Set the Stage, (2) ELI5, (3) Assess & Study, and (4) Organize, Convey, & Review.

Question: What would you do if you had zero fear of judgment?

Framework: Truth Tellers

The 1-in-60 Rule says that a 1-degree error in heading will cause a plane to miss its target by 1 mile for every 60 miles flown. Tiny deviations from the optimal course are amplified by distance and time. A small miss now creates a very large miss later. This highlights the importance of real-time course corrections and adjustments.

The end of each calendar quarter presents us with a valuable opportunity to reflect on the quarter that was in order to make any necessary adjustments to our goals and systems that will ensure the next quarter is better than the last.

The Personal Quarterly Review involves three steps: (1) Reflect, (2) Assess, and (3) Adjust. You can download a free printable PDF of the template at the link in the newsletter.

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.

We make most of our daily decisions based on our worship of our idol. The downside: As we strive to get “closer” to our idol, we find ourselves on an endless chase for more. We incorrectly assume that this chase will lead us to the promised land of happiness.

We do not need to reject our idol. 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. 

The Four Idols exercise is simple: Use a process of elimination to identify your primary idol. 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.

Complexity is a silent killer of focus, clarity, and performance. This statement is true for businesses, but even more so for your work and life. It's easy to let complexity and disorder slowly seep in—we tend to add, but rarely subtract.

The Simplicity Audit examines four key environments of your life: Physical, Digital, Mental, and Social.

For each item in each environment, ask: (1) Is this necessary? (2) Is this creating energy? If "Yes" to both, keep it. If "No" to both, remove it. If "Yes" to one, think on it.