A handful of insights, wisdom, and guidelines gathered over half a life and professional career, for happiness, prosperity, and wealth. All in convenient slogan form.

Leadership & Management

Guiding others with authority, clarity, and humility.

Clarity from the start.

For anybody joining a new company, the single most important management goal is to provide clarity from the moment they enter. New hires are changing something very important about their life, and they will be seeking structure and certainty in terms of expectations from the beginning. Good managers and executives help provide that.

Authorship over dictatorship.

To maintain an organization, it’s always more empowering to practice authorship—writing things so people can learn on their own—than dictating instructions. The written word lasts longer and is more available than the spoken one, so long as it’s easily discoverable and accessible.

Big ears and short toes.

Listen a lot, learn from others, and don’t be territorial. Allow people to risk stepping on your toes by deliberately making them as short as possible without falling over. Outside of sports, offense is almost always taken rather than given; acting abused when there’s been no abuse is abusive itself.

Take smart chances, and always assume good faith.

Tall people know they’re tall, but short people don’t know they’re short.

Be kind and generous to those who cannot see as far as you (humbly) might be able to. Be aware of people’s strengths but also their limitations, and encourage them always, always to play to the former. Develop teams by amplifying what’s already there, instead of focusing on faults. Emphasizing this makes team diversity a resource.

No one speaks twice until everyone speaks once.

This is one of the principles of the United States Supreme Court, according to Associate Justice Stephen Breyer. Very helpful when meetings get large and most participants remain silent.

Responsive and responsible.

Especially when building teams, always be responsive to suggestions, and always personally be responsible for outcomes.

Transparency earns trust.

There’s no sense in keeping secrets if there’s no reason for a team not to know something—however, protecting people’s privacy and maintaining confidence is equally important.

Choose a CEO based on their decisions.

The CEO of an organization is its executive frontal lobe, and their decisions determine the fate of all involved—company discord is inevitable if the team has no confidence—and this includes you. Set goals on your own, and choose your mentors and leaders wisely.

Truth & Ethics

Honesty, moral reasoning, and the pursuit of what's right.

Engineering is applied ethics.

Engineering is a pursuit and discipline that has far more in common with ethics than mathematics. An excellent engineer is responsible for efficiency and success, yes, but more important is their ability to reconcile two conflicting value systems.

Consider the igloo. If you’re exposed in the tundra, perhaps you might build a snow and ice dome to stay warm. “Warmth” is a value system. But stepping inside, you realize it’s too dark. It turns out that the ability to see is also a value system. Perhaps the solution is to carve a window. But now it’s cold again. We have a conflict of values.

Insulated panes of glass are the engineered solution that brings these two value systems out of conflict. Excellent engineers orthogonalize value systems, so more people can have their cake and eat it too.

What & why before ought & how.

Focus on understanding what currently is the case and why that might be, before thinking about coming up with an “ought” and an action plan. And even so, David Hume’s is-ought problem simply cannot be bridged except, partially, through theology—and even then, not completely.

Possibility and industry are different from the pursuit of aims and objectives, and all of them are contingent on understanding the now. Gain your bearings, and never forget the value of situational awareness.

In pursuit of truth with no hope of proof.

For empiricists and data-driven cultures, articulating the goal and moving toward it never overrides humility. Nothing is certain in science; the aim itself is what is important. Anything learned by observing and experiencing the world cannot be known for certain, but it’s a good start.

To paraphrase Donald Rumsfeld, know what you know, what you don’t know, and be prepared for what you don’t know you don’t know.

Keep ’em honest.

Narratives are often crafted to wield political or social power, and often involve exaggerations or untruths. Know how to separate rhetorical hyperbole from true lies, and beware narrative-spinners who have no respect for truth or facts. These are the people who are interested only in themselves.

Shun shibboleths.

Specific and precise language can be very helpful to aid communication, but using it to be exclusionary is asking for trouble. Better to define concepts early and often to ensure shared understanding and communication.

Pity and contempt are twin born.

To pity somebody is to hold them in decidedly low regard; avoid this at all costs. There are few things more insidiously degrading than expressing pity when one could offer compassion, sympathy, and elevation. Avoid looking at others with concern when you could be lending a hand instead. See a spill? Grab a mop.

Strategy & Thinking

Mental models, decision-making, and navigating complexity.

All models are wrong, but some are useful.

Contained in the quippy wisdom of George Box is a reminder to stay aware: any model is an imposition of order where it may not exist, and contains assumptions that may not be appropriate or accurate. In fact, your own models almost certainly do not describe everything perfectly. Choose useful ideas, be wary of statistical measurements, and discard them when needed.

Avoid chronic hypothesislessness.

Always operate with an active and constantly revised working model of the world before you, and how to create the best good for the company, enterprise, customers, or whatever you’re endeavoring toward.

Know your signals and cues.

In animal ethology, a signal is something an animal does to change another’s behavior—a rattlesnake’s rattle warns you to back off. A cue is something an animal does that others can observe and learn from—a rattlesnake coiling up just before it strikes. Signals are intentional; cues are inadvertent.

Distinguish between what people are telling you and what they’re showing you. Actions speak louder than words.

Never read the room.

Instead, know your audience. Do not “go along to get along,” for that is how the leaderless perish as proverbial lemmings. Knowing the people you’re speaking with will take you miles farther as a leader than joining the crowd consensus.

There’s no silver bullet.

While there are commonalities and “main effects,” specific context determines which solutions are most actionable and productive. Always accommodate peculiarities and contingencies of your unique situation rather than whapping a complex system with an all-purpose hammer.

Pith.

Brevity is the vital core.

Go to the source, not to social media.

When interested in knowing about prior work, go directly to the person who created it, whether in books, over email, on the phone, or in person. Various help forums can be useful for a first pass on discovering what might be posing a challenge, but there’s no substitute for contacting the people who have been there before, for any kind of deep technical or operational assistance.

Learning & Growth

The lifelong pursuit of wisdom, curiosity, and mastery.

Vital curiosity.

That need to see the next horizon line, to taste life, to participate in it, to have a mind like a sponge. Without asking questions, without pursuing answers purposefully and diligently, your engine can and will lose steam, putter out, derail, and turn into rust.

Don’t tempt that fate, and never stop asking. Take a cue from the toddlers: they know perfectly well that you never know the real answer to “Why?” until you’ve asked at least five times.

Wisdom over knowledge.

Deep domain knowledge is incredibly valuable to have, but wisdom on how to use it often makes a far larger difference in creating effective outcomes. The wisest among us have been known to appear to be fools; pay attention.

Discretion begets mastery.

In order to understand something well enough to truly pursue it, one needs first to be able to criticize the works of others. This is part and parcel of the ability to formulate one’s own vision. A side effect is being your own worst critic, especially when starting something new. It’s important to embrace criticism in good faith, because the critic may soon be an expert.

Teach a pupil, guide a student, show a scholar.

Only young pupils can be taught. Students need guidance on the learning adventure, and scholars need only to be shown things you yourself have discovered. Never assume any inadequacy in whomever you’re speaking with. All are capable of intuition, knowledge, and growth.

Embrace etymology.

Words have meanings, and humans invented and settled on them for a reason, regardless the tongue. They’re the inherited source code of the human condition. Learn what your utterances mean, what the syllables have meant, and embrace connotation.

See one, do one, teach one.

This is an old credo of the medical profession for learning any new skill. It’s helpful to think and design environments to ensure they are set up so all three steps are available for everybody’s growth.

You become what you practice.

We are not pressure-cookers. We do not “let off steam,” and while the Classical notion of catharsis can be an attractive concept, it’s simply not accurate. Instead, we are by nature learning creatures, and become more facile and much more likely to continue doing what we rehearse repeatedly. Take care not to practice rage or practice mistakes.

Work & Process

How to get things done without drowning in process.

Don’t prioritize; schedule.

From the tradition of Peter Drucker, do not think in terms of priorities so much as goals. Anything and everything could be called a priority, when in fact, there’s always only one priority in the given moment. Think in terms of time management, to ensure the things you might otherwise be juggling actually get accomplished. Preserve a bias toward action rather than “analysis paralysis.”

Make iterative changes iteratively.

The mental carrying capacity for too much change at once is difficult enough, but the real-world complexity that you cannot yet understand is the actual problem. Try modifying one thing at a time, wait to see how that turns out, and then move on to the next challenge. Always point upward and forward.

Steer clear of Sisyphus.

Avoid fleshing out too much fine-grained work long in advance. This only serves to create a deluge that leads directly to stress, and destroys creativity, productivity, and joy. Too much detailed information and planning can overwhelm—the boulder will surely slip. Instead, manage toward decreasing conceptual resolution as the future unfolds, and take action one step at a time.

No BS makes for great DX.

Avoid placing unnecessary administrivia into workflows out of habit or convention, when people can be trusted to innovate and work on their own. No bullshit creates an inspirational developer experience.

When in doubt, cut it out.

With respect to process—if anybody’s unsure why they’re doing something and nobody exactly remembers the origin of the organizational or process element, it’s better to eliminate it first and restore it later when (and if) the need arises.

Take time to do it right or make time to do it twice.

Maintain consistently high standards in anything in life, as you never want to find yourself removing band-aids and duct tape later. Worse yet, if you’re building systems of people or things, one failure point can make everything crumble, especially if a solid foundation has not been laid. Rubber bands, paper clips, and chewing gum might work for MacGyver, but not for a founder of a company or a pursuer of a life.

Never skip the retro.

Any opportunity to learn from mistakes and improve things because of them shouldn’t be skipped, no matter how irritating the process may be. These are the times we all commit to a better future.

Teams & Organizations

Building companies and teams with purpose.

Enterprise, Company, Organization, Business, Firm.

Whatever your goal, especially the adventure of a lifetime, you can create it. An enterprise is an endeavor or goal. A company are the people you choose to take with you. Organization is simply how everybody communicates. A business (“busy-ness”) is what the group does day to day as individuals and collectively. A firm is the security you can create for all involved.

We don’t have a single word in English for this, because it’s life itself.

Seek autonomy and alignment.

For creative and innovative cultures, everybody thrives with the freedom and ability to generate ideas. Without enough agency, there is little strength in numbers, only sitting on hands waiting for commands. Keeping a team targeted toward the most important challenges is the key contribution of effective leaders.

Hire for “cans,” not “haves.”

Character, horsepower, and personality disposition make all the difference in hiring decisions when assembling a company. A “proven track record” is often a good indicator, but who wants to do the same things over and over again?

If you’re hiring people to spend a majority of your waking hours with, you’re concerned with what happens next. Choose your company for the future, not for the past. You’ll often be quite surprised. (See also: The vector exceeds the point.)

Teams have goals, not functions.

A team is never composed of people with identical skill sets; it is made of people with common purpose. Embrace e pluribus unum and design organizations accordingly. Allow functional training to be achieved through cross-team mentorship. If atop an organization, find your peers among those similarly situated to you—they are unlikely to be on your immediate team.

“Product” is the art of the desirable. “Engineering” is the art of the possible.

The two classic functions in technology-creating companies are that of “product” and “engineering”: roughly, the architects and the builders. One group focuses on people’s needs, and the other on bringing these to life. While requirements documents are helpful to coordinate effort, all players involved are best off when in frequent back-and-forth conversation—constantly communicating, refining, and coordinating—while fully appreciating one another’s strengths and experience.

Maintain meetings.

Meetings should exist (and only exist) for a clearly defined reason. If you find yourself designated to lead a meeting and cannot be present, never cancel the gathering. Instead, delegate responsibility to somebody else. They gain the experience, the team is not blocked by your absence, and you can always read the minutes to catch up.

Resilience & Perseverance

Endurance, direction, and the hard road to excellence.

Easy Street is a dead end.

The hard road is where excellence is truly forged. There is no path to lasting success or happiness without trial, error, failure, and putting in the effort. Failing is not shameful, nor is coasting admirable. Roosevelt’s “Man in the Arena” has already succeeded. True growth demands rigor, calculated risks, and a genuine willingness to tackle complexity head-on.

Shave your yak, but don’t draw blood.

Be prepared for the journey. Take care to value yourself and your experience enough to be proud of it. Have the tools you need, and none that you do not.

In software engineering, getting your environment set up for maximum productivity is the name of the game. But obsessive yak shaving causes damage (four out of five Tibetans agree!), just as people can worry and groom a skin ulcer into existence, or pluck their eyebrows to the verge of extinction.

Balance and intent win the day. Don’t put yourself in a position to paint your eyebrows back on.

If the ground swings first, duck.

Some eventualities are not worth fighting. Keep your bearings, and know when to self-protect if the world takes a whack at you for whatever ridiculous reason. You cannot fight the ocean, but you can surf the waves.

Time is your only limited resource.

Do not waste it trying to “catch up” with people—spend it with them together. Money can always be made again, and reputations can always be rehabilitated or re-established. Time is to be spent consciously and wisely.

Matriculate at the university of hard knocks.

Competence is created through experience, not through credentials. Adversity and failure are the best teachers of all—they impart lessons that no classroom or textbook could ever replicate. Seek challenges, seek hard problems, give an attempt, endure the bruises, and trust that this kind of tuition pays more dividends than any other.

Your work is for hire; your journey is yours.

Take care to journal, record, and preserve your history and your contributions—should a reduction in force remove you from a position, the company is incentivized to immediately revoke access to company systems. Keeping personal records is not theft of intellectual property: it is crucial to self-understanding and communicating your story. If 90% of what you produce is stored in company-owned platforms, a single unexpected layoff means you’ll have immediately lost track of most of what you’ve accomplished.

Don’t let another’s “passion” become your “project.”

Independence of thought and mind is always necessary, and should you find yourself being exploited in any way, it is time to take a step back. “Never let anybody take advantage of you” is among the best pieces of advice you’re likely ever to receive.

Simple ain’t easy.

Simplicity is a thing of pure beauty—of elegant perfection—but it is incredibly hard to find and achieve. What is easy is within reach without much effort. Know the difference between complexity and complication. Simplicity is the goal, complexity is an aspect of the universe, and complication is what people do to make situations worse. (With credit to the great Rich Hickey.)

The vector exceeds the point.

Never dwell on where you are in the moment; focus on direction instead—motivation is the vector, and cannot be waited for. “Motivation” is what describes being in motion, not what causes it, so focus on pursuing direction and jump-starting your movement. It is a verb, not a noun.

Skate to where the puck is headed, and when possible, put it where you want it.

Life & Philosophy

Joy, perspective, and the bigger picture.

Harmony, Flourishing, and Abundance.

Take a crash-course in the 道 (dao) and the ॐ (om) of pursuit, achievement, and success. Faith has many traditions worldwide and certain discoveries are indeed universal. It is well worth the time to get a global, cross-cultural perspective on the theological and the divine.

There is no shame in being broke, and no virtue in being poor.

Being poor is a state of mind, a culture, and a choice. Being broke is merely a situation of circumstance. Your friends, family, and colleagues cannot help you if you’re poor, but they can when you’re broke. Return the favor to them when they need it, and you will never be poor yourself.

Jerks get what they deserve—and enjoy it.

There are people in the world whose only sense of fulfillment is brute power in the domination and control of others. Don’t wrestle with pigs in the mud. You both get dirty and the pig likes it. When real jerks get their just desserts, few people truly mind, and nobody feels guilty. Do not avoid conflict, but walk away when it’s senseless. You can’t win fights, only honest arguments about disagreements.

When you’re in the right and act on it, you’ll have no regrets. Though full resolution may take some time, the universe keeps score.

Choose your venue.

Be strategic about the time and place in which communicating or acting on something will be most effective. After all, people tend to become irritated when you try to golf at the shopping mall.

Learn to take a joke.

Don’t tolerate vapid business-ese, shibboleths, or offense-taking—people who do are missing the point. Life is a joy, not an excuse to be angry. If a person or a company can’t laugh something off, they’re not confident and joyful enough to be worth your time. Celebrate levity; collect and tell witty jokes, not cruel ones. The humerus isn’t only a funny bone in your arm.

With credit to Groucho: Time flies like an arrow. Fruit flies like a banana.

Bring back thorn (Þ, þ)!

On second þought, maybe þat’s not þe best idea. When conducting business, clarity of communication in the now is always better than torches carried for bygone causes, no matter how clever or how nostalgic. Never forget that communication with others is designed to change their knowledge, thoughts, and behaviors, and humans are notoriously prickly about being told what to do. (See also: Choose your venue.)

Nurture your passion.

Passion is our most valuable resource—there are innumerable temptations to squander our passion, and it takes deliberate effort to sustain it. Never, ever, neglect that which sustains you and keeps you engaged, excited, and moving forward.

Peace, Love, and Waffles.

While life may be rough, pursuits frustrated, and demands insurmountable, there’s always a resplendent joy to be found in the moment, and a deep satisfaction in the mundane. After winding up and executing mightily, or stubbing one too many toes per foot, you can always take the time to indulge in the near and the now, with extra syrup.

Be a Martian naturalist.

The best way to understand people, their actions, and their behaviors is to approach everything with a clear head and a clean slate—especially when considering group behavior or average trends. When things seem confusing or you’re too close to a situation, take a step back and for at least a moment pretend to be a visiting scientist from Mars. Simply describe to yourself what you actually observe, without assumptions or emotional baggage.