These are the principles that guide me. They are, like me, a work in progress. I intentionally don’t think of these as core values because that term carries baggage that doesn’t reflect why I take the time to articulate them.

How I Use These

It’s easy to see this as a useless exercise. But at least once a day my I’ll catch my brain spinning on a problem. And I’ll open this document and be reminded of one of these principles and suddenly the path will be clearer. My brain rests. I can physically feel the change.

I also don’t think one can set goals or create a vision for the world without having a sense of who he is and what he values. I have so much data floating around my head that I can’t keep all of these important reminders top of mind. So I write them down and review them often.

Frameworks help me trump emotional anchors and remember what not to do in situations where I’m likely to be thinking less than clearly.

I often suggest people read Thomas Schelling’s 1985 paper “Enforcing Rules on Oneself” to understand the role of primary, anticipatory and precautionary rules. That paper and Charlie Munger’s “Psychology of Human Misjudgement” helped me understand the role of frameworks in overcoming natural tendencies.

The Genesis of These Ideas

I’ve stolen most of my great ideas from other people, mostly dead people.

Many of my principles formed from a combination of experiences and reading. I’ve held some of them for a very long time. To form them I spend a lot of time on postmortems.

You can pieces of them in my massively chaotic Evernote version of a commonplace book (what is a commonplace book) where I keep quotes, marked up articles and book notes. I tag the most potent of that collection as Best Of and reread them often. Like most piles of papers in my life, I generally know where everything is.

In 2016 my world view, my body and mind shifted more than in any year to date. The key sources of that shift can be found in the tag called Catastrophe, so named because these works along with a few conversations shattered my life plan and it took me months to recover.

My principles are, like me, in a constant state of motion. If you have any suggestions please email me.

My Life Principles

The only principles and ideas that matter are ones where reasonable people could disagree. -DHH

Prioritize for interesting over sensible.

The greatest outcomes in my life have manifested as a result of decisions that made no sense at the time but seemed interesting. Leave room for the possible by letting go of the security of sensible. Security is safety from freedom and worry. *Turn back the pages of history and see the men who have shaped the destiny of the world. Security was never theirs*. – Hunter S. Thompson

It is more important to consistently avoid making bad decisions than to consistently make good ones.

Avoid bad decisions. Tools like negative checklists can help us avoid our common biases and trigger reminders of what to avoid in moments where our thoughts may be clouded by biases. Positive checklists are shortcuts based on past data that ignore context and fool us into thinking that we can make good decisions by outsourcing judgment. Positive checklists are to be avoided. All I Want To Know Is Where I’m Going To Die So I’ll Never Go There. – Charlie Munger

Do the work required to have an opinion.

You have no right to an uninformed opinion. Come to the table with deep knowledge. Read. Ask questions. Seek knowledge. Become your most intelligent critic. Have the intellectual honesty to kill some of your best loved ideas. Only when you can argue against your own view better than others have you earned the right to your opinion.

If you do nothing else, seek to be rational.

I am frustrated by how easy it is to live an unhealthy, externally-driven life. Rather than rail on social media about how much I hate it I put considerable focus into learning as much as possible so I can develop my own views about every aspect of living.

Doing this well requires tuning out of a lot of our media culture, confronting uncomfortable truths and developing my own ideas that frequently clash with conventional wisdom. It means learning about how humans think and how we’re conditioned to behave.

This principle manifests in how I eat (specifically in what I choose not to eat), how I choose to focus my professional energy and the decisions I make on a daily basis.

This does not mean I value being different. I don’t. It means I value developing an educated understanding of everything I do and being truthful to myself.

I will not make a decision or offer an opinion unless I can clearly articulate my why, even if that means admitting I’m doing the opposite of what I think is the rational path (like eating ice cream).

Avoid trading time for money.

Prioritize time towards activities that are scalable, whose returns continue to compound when your time is directed another activity.

Dentists trade time for money and their work, while honorable, is by definition unscalable. Avoid this trap.

In daily work with others, this means often stepping back from the question at hand and using the question to develop a principle that answers that question and many others like it.

These activities often take a greater initial investment to begin earning compounded returns but the returns will continue long after your attention is directed elsewhere. This principle is not solely directed towards work activities but is also applicable to relationships, health, learning and so much more.

Examples include learning a new language, writing, healthful eating, equity investments.

Avoid short-term feedback loops.

Minimize dopamine-seeking. Optimize for medium to long-term feedback loops. Short-term feedback and validation loops (likes, applause, most press) are dopamine-triggers. They are like addictive drugs. The high is short-lived and shallow. Over time it gets harder to get high the next time.

Things that matter generally don’t provide immediate feedback. Be uncomfortable. Get off the train. Climb the ladder. This means you generally won’t know if a path is right for a few days, weeks or months. This rule does not apply to a child’s smile. This rule does apply to most conferences.

Leave slack in the system.

Say no to most things to leave room for the unplanned things you’ll wish you had time to do. Slack allows for the option to do something or meet someone interesting on a whim. Slack allows great conversations to continue without the interruption of a next appointment. Slack applies to time with people, meetings, learning, time with yourself, time with new ideas. No stacked meetings. Allow extra time for walks.

In tough situations optimize for how others will remember the experience in a year over how they will feel today.

You cannot control the emotions of others. When delivering bad news, firing someone, saying no, etc. focus your words and actions on how the other person will remember how you handled the situation in a year, once the emotional sting of the news is passed. Over the long-term, that you did hard things honorably will matter more than the next day’s headline or the immediate reactions of others.

Seek out disconfirming evidence.

Humans have a tendency to seek out information and people that help them confirm that they are right. Strive to look for the opposite so you develop a deeper understanding of what is truly right versus what you want to be right.

Seek those who disagree with you, the ideas that don’t confirm your beliefs, explore them deeply.

As conditions change, your view can change.

Shut up and work.

What you’ve done in a year is more important than what you say you’re going to do today.

Maintain an optimal balance between breadth and depth. 

I believe that in every distinct aspect of our lives such as work, learning, relationships, etc., we have the capacity to go deep or go wide.

It’s easiest to think of these things in the form of a fish tank. You ideally want to maximize the surface area which is the breadth of ideas, people, experiences, projects, etc. you expose yourself to. A higher variety increases the chances you will be exposed to unexpectedly positive things. The most powerful opportunities in my life came as a result of this approach rather than as a result of methodical planning.

Doing more things requires stretching the tank. But when you stretch the tank you end up with less depth. Bigger fish tend to avoid shallow pools. So you must find an optimal balance.

Maximizing breadth is the easiest way to live in our connected world. But this is an inherently bad approach as you are likely to become someone who:

  • Is a jack of all trades and a master of none

  • understands the summary of many ideas but none deeply

  • is marginal at a lot of things but good at very little,

  • someone who has a lot of acquaintances but few friends.

Conversely if you go deep on less then you are more deeply exposed to a smaller number of things which comes at the cost of diversity of ideas, investments, etc.. This approach is not inherently bad but it is sub-optimal.

The ideal life is one lived in balance between depth and breadth where you constantly adjust the axes so as to maximize the diversity of your exposure so as to be exposed to the most opportunities but go deep when and where it matters.

Be willing to seem ignorant about some things to be brilliant at others. Sometimes you’ll choose the wrong stuff.

Minimize super-dependence on single points of failure.

In any well-functioning system it is critical to minimize potential points of failure. I believe it is more important to be in control of your fate or at least distribute risk control over it. For example, this means that instead of building a company whose continued existence is dependent on the permission of a few investors, I prefer to “distribute” that discretion to a large group of customers.

In a more philosophical sense, this principle applies to my sense of self and other foundational aspects of my life I have, historically, allowed the approval of others to control. I’m not totally cured of this ego-driven way of living but I concentrate heavily on developing my own foundation.

Nassim Taleb calls this the Barbell Strategy.

Strive for self-sufficiency.

Minimize the amount of time, money or other obligations to others that decrease your ability to be flexible to changing conditions. By minimizing extraneous, short-term obligations you maximize your ability to focus on the long-term.

Strive to have multiple paths to success.

Redefine success to include outcomes other than the specific thing you are setting out to do. Make things so that you cannot fail or are at least less likely to do so.

Rube Goldberg machines fail with the slightest wobble. By reorienting yourself to include multiple paths to success, life is more enjoyable.

This principle also has the added benefit of forcing a mind trick where I become more open to adjusting course along the way towards outcomes that I couldn’t have predicted before starting down a path.

If you can only be successful if x, y and z happen perfectly, you’re in a bad position. Always be able to imagine at least a handful of positive outcomes. Risk is good, delusion isn’t.

Be willing to lose anything built on an inauthentic foundation.

Risk losing something for being your authentic self rather than keeping something by being your projected self. As long as you are coming from a place of warmth and growth, don’t filter.

Be the one who is calm.

Cultivate an inverse relationship between the stress of the situation and your reaction to it. Calm breeds clarity of thought.

Never be like them.

The loud, bitchy people on planes. The lemmings in suits at a hotel bar. The erratic driver on the highway. The hoarder sitting on the front porch. Never be like them.

Be driven by a love for solving complex, systemic, real world puzzles.

It is important to know why you do what you do.

I find that I’m happiest when solving complex, systemic problems that impact the physical world. In many ways I’m a six year old who loves solving really, really big puzzles.

I don’t have an interest in solving puzzles for the sake of solving them. I like very messy, complex ones that, when solved, create a flywheel impact that becomes a foundation piece for building another puzzle.

This is how I define impact. And I crave problems that, when solved, have systemic impact.

This is my why. Because I love it.

Does this move you forward?

Most of life’s debacles come from forgetting what you are actually trying to do. Winning an argument or proving someone wrong isn’t success. Play the long game and ignore squabbles of nonsensical items of little importance. Be mindful of situations where radical honesty in the short-term could make it harder to be honest over the long-term. Do not resort to your primal tendencies to puff up your chest and fight.

Ask yourself, does this course of action move me forward, backward or laterally.

Smile. Just fucking smile.

There’s a magic to a smile, especially in moments of chaos and with people who are frequently abused or overlooked (airline employees, retail clerks). You can change the trajectory of a person’s day by simply showing a warm, genuine smile.

This approach also has a tendency to encourage others to do nice things for you. But do it because you can, not because you want to manipulate.

Ignore information that provides no context.

Traffic reports tell us bits about traffic incidents when we really want to know how long it will take to get to work. It’s like having cereal and no milk. Such things trick us into believing we know something when in fact we only know details without context. More information is not always better.

Most information (news, industry hype, etc) lacks context and is irrelevant to decisions, at least in real-time. It plays to our need for stories and confirmation when events that are, in reality, random. Only seek information that compounds or influences your immediate decisions, otherwise ignore and wait for context to form.