Anyone can point at something and say it’s broken, corrupt, or destined to fail. The real challenge? Building something better. The cynic sees a proposal for change and immediately lists why it won’t work. They’re usually right about specific failure modes — systems are complex, and failure has many mothers. But being right about potential problems differs from being right about the whole.

The cynical position feels sophisticated. It signals worldliness, experience, and a certain battle-hardened wisdom. “Oh, you sweet summer child,” the cynic says, “I’ve seen how these things really work.” But what if this sophistication is itself a form of naïveté?

Cynicism comes with hidden taxes. Every time we default to assuming the worst, we pay in missed opportunities, reduced social trust, and diminished creative capacity. These costs compound over time, creating a self-fulfilling prophecy in which cynical expectations shape cynical realities.

Pattern recognition is valuable — we should learn from history and past failures. But pattern recognition becomes pattern imprisonment when it blinds us to genuinely new possibilities.

Why spend years building something that could fail when you could spend an afternoon critiquing others’ attempts and look just as smart? The cynical stance is intellectually rewarding but culturally corrosive.

The alternative to cynicism isn’t unquestioning optimism. It’s more nuanced: a clear-eyed recognition of problems coupled with the conviction that improvement is possible. Call it pragmatic meliorism — the belief that while perfect solutions may not exist, better ones do.

things are broken, AND they can be fixed; people are flawed AND capable of growth; systems are complex AND can be improved.

Here’s a more charitable reading of cynicism: it’s not an intellectual position. It’s an emotional defense mechanism. If you expect the worst, you’ll never be disappointed. If you assume everything is corrupt, you can’t be betrayed. But this protection comes at a terrible price. The cynic builds emotional armor that also functions as a prison, keeping out not just pain but also possibility, connection, and growth.

Not all domains benefit equally from cynical analysis. Some areas — scientific investigation, financial planning, and security systems — benefit from rigorous skepticism. Others — creative endeavors, relationship building, social movements — often suffer from it.

What would it look like to embrace pragmatic meliorism instead of cynicism? Acknowledging problems while focusing on solutions Learning from history without being imprisoned by it Maintaining high standards while accepting incremental progress Combining skeptical analysis with constructive action

When you feel the pull of cynicism, ask yourself: Is this helping? Is this default skepticism making you more effective or just more comfortable? Are you choosing the easy path of criticism over the harder path of creation?

Forget trying to decide what your life’s destiny is. That’s too grand. Instead, just figure out what you should do in the next 2 years.

Try to define yourself by what you love and embrace, rather than what you hate and refuse.

Where you live—what city, what country—has more impact on your well being than any other factor. Where you live is one of the few things in your life you can choose and change.

Once a month take a different route home, enter your house by a different door, and sit in a different chair at dinner. No ruts.

Every now and then throw a memorable party. The price will be steep, but long afterwards you will remember the party, whereas you won’t remember how much is in your checking account.

Most arguments are not really about the argument, so most arguments can’t be won by arguing.

invent your own definition of success. Shoot your arrows first and then paint a bull’s eye around where they land. You’re the winner!

There should be at least one thing in your life you enjoy despite being no good at it. This is your play time, which will keep you young. Never apologize for it.

You have 5 minutes to act on a new idea before it disappears from your mind.

The patience you need for big things, is developed by your patience with the little things.

When you are stuck or overwhelmed, focus on the smallest possible thing that moves your project forward.

For steady satisfaction, work on improving your worst days, rather than your best days.

Your decisions will become wiser when you consider these three words: “…and then what?” for each choice.

If possible, every room should be constructed to provide light from two sides.  Rooms with light from only one side are used less often, so when you have a choice, go with light from two sides.

There is a profound difference between thinking less of yourself (not useful), and thinking of yourself less (better).

Always ask yourself: what would change my mind?

Becoming one-of-a-kind is not a solo job. Paradoxically you need everyone else in the world to help make you unique.

If you need emergency help from a bystander, command them what to do. By giving them an assignment, you transform them from bewildered bystander to a responsible assistant.

The most common mistake we make is to do a great job on an unimportant task.

Don’t work for a company you would not invest money in, because when you are working you are investing the most valuable thing you have: your time.

Fail forward. Failing is not a disgrace if you keep failing better.

Do not cling to a mistake just because you spent a lot of time making it.

For small tasks the best way to get ready is to do it immediately.

What others want from you is mostly to be seen. Let others know you see them.

When you try something new, don’t think of it as a matter of success / failure, but as success / learning to succeed.

use your honesty as a gift not as a weapon. Your honesty should benefit others.

A good sign that you are doing the kind of work you should be doing is that you enjoy the tedious parts that other people find tortuous.

Celebrating the success of others costs you nothing, and increases the happiness of everyone, including you.

To tell a good story, you must reveal a surprise; otherwise it is just a report.

a long horizon allows you to compound small advances into quite large achievements.

Often ideas are rejected because of the tone of voice they are wrapped in. Humility covers many blemishes.

When you are right, you are learning nothing.

Very small things accumulate until they define your larger life. Carefully choose your everyday things.

If you are impressed with someone’s work, you should tell them, but even better, tell their boss.

Humility is mostly about being very honest about how much you owe to luck.

You’re likely seen as a bright brain with a knack for solving problems, and what good are the liberal arts¹ and the humanities² in solving the world’s large, technically complex issues? You want your work to have impact and “matter” — something you know to require hard work, discipline, and things like “frameworks” and “mental models.” Tactical, practical, and efficient. But consider, for a second, your thinking. Where did your thoughts and beliefs come from? What about your conviction, your mission, your sense of purpose on this earth? These questions are why the liberal arts and the humanities, or subjects distinct from professional and technical subjects, exist.

The ecosystem that we inhabit as technologists was not built with humans in mind, it was built to run laps around other industries within the capitalist game, and it does this on the backs of the young people it exploits. In simpler terms: the status quo of technology was not designed to make you a happy, content, morally well-rounded young person. That, however, is precisely the purpose of examining the world through a liberal arts lens. Through this frame of view, we might think thoughts without action items, try opinions on for size, celebrate contradiction, and revel in the pursuit of understanding both each other and the world around us.

At their core, the liberal arts and the humanities serve as aggregated documentation on the human condition — the kind of documentation that is meant to be digested, discussed with others, and revisited from whichever angles serve you best along your journey.

It is difficult to advocate for the liberal arts by appealing to results or metrics. But our bias towards viewing these non-instrumental disciplines through a problem-solving lens is exactly why we need spaces that suggest other ways of seeing the world. While that lens grants impressive achievement, it might also leave you wondering why you were even chasing after the thing you achieved to begin with. Our goal is to show you that the problem-solving lens is one of many possible views you can have on the world. You can treat this view like a pair of glasses, one that ought to be regularly removed and replaced with a more reflective, contemplative, and critical lens.