Honesty is the first chapter of the book of wisdom.



— Thomas Jefferson

Deception is cancerous. The first mutation of a truth charts a path to colonize its host. One fib demands another, two lies need the proof of two more, until eventually even the most innocent half-truth metastasizes into a falsehood requiring surgery.

A lie is a deliberate attempt to fake the nature of reality. So a scientist who reaches a flawed conclusion through an error in her experimentation method may hint at incompetence, but she is not lying. But a guy who trades his own happiness for a fat paycheque and calls himself “successful”, must be charged with first-degree bullshit. His deception may succeed temporarily but he has not altered the facts, and the moral transaction is still charged to his account.

Why is faking the nature of reality bad? Because reality exists. No matter how hard you try to treat things differently than they really are, they still are. A job that drains your will to live is a job that drains your will to live. A girl who doesn’t respect you, doesn’t respect you.

When the disconnect with reality comes from a genuine error, the mistake is open to correction. The evidence of a fallacy shows up in the form of contradiction, and logic and reason can help stitch things back together. But intentional deceit makes the perpetrator a fugitive; sometimes physically, always intellectually. For whenever a liar’s evidence contradicts itself, he must flee further and further from the facts to maintain his sliding grip on sincerity.

The safe haven from the perils of denying what is, is radical honesty. To commit to radical honesty is to take an oath sworn directly on the face of existence. It’s a pledge — in your work, in your relationships, and to yourself — to see things exactly as they are, to the best of your ability. It acknowledges that almost all things are small things and that nothing is bigger than the truth.

Radical Honesty at Work

Few relationships will last longer, or have a larger effect on your day-to-day life, than the relationship between you and the value-producing activity that is your work. Applying radical honesty in your work means creating things that are of value to you personally.

Can each of us really do work that is of value to us personally? On what planet would we ever find someone to specialize in the manufacture of, say, toilet paper? Someone who would claim that such work is of value to him personally? You’d find that guy on the planet where ass-wiping technology doesn’t yet exist, where there’s a guy who’s sick of using his bare hands for the task, and where he is the only man alive annoyed enough to scratch this particular itch himself.

The things that are of value to you personally are entirely dependent on your environment and how you relate to it. For example, I couldn’t care less about growing my own food. There are lots of lots of people — “farmers” as they’re called — who already do this. And they’re willing, with the aid of an elaborate supply chain, to take my money in exchange for their food. If I didn’t have access to anyone who was willing to grow food, maintain livestock, and sell me either when I needed them, then I’d pretty quickly become interested in this problem. I value my own life and I need food to live.

What most frustrates you about the world? Almost every answer to that question is a business idea with your name written all over it. And when the work you do pays the bills both financially and spiritually, you have truly become your own boss.

Radical Honesty in Relationships

There’s a strong tie between your work and your relationships. Asking “What most frustrates you about the world?” is not only a means of identifying opportunities to create value in your life, it’s also a compass that directs you towards the people that will help make those dreams come true.

Radical honesty in relationships — whether platonic or intimate — requires self-respect. Self-respect is a seed planted by the standards you set: How do you treat people? How do you let them treat you?

Purpose is also paramount. In geek terms, your mission is like an Uninterruptible Power Supply, a primary source of energy and the motive power behind all the moving parts of your life. The relationships worth having are those with a voltage high enough to match your own, not those that cause a power failure.

Maintaining integrity in relationships means addressing problems that come up in real-time. Emotions are not chess pieces, and love is not a game of strategy. If you sense that something might be wrong, seek to identify and resolve the issue on the spot. If you’re constantly met with responses like the Solemn Downward Stare, followed by the Evening of Awkward Silence, and the Night Without Sex, then be warned: the game you’re playing isn’t worth winning.

Radical Self-Honesty

The hardest person to be honest with is yourself. Really, the only person you can be honest with is you. All delusion is ultimately self-delusion.

Radical self-honesty requires a matching dose of humility. Whatever score you give yourself in any category is almost surely inflated. If the currency by which we measure others is pounds, the currency by which we measure ourselves is yen. Some of these feelings of superior knowledge, skill, or judgement are no doubt justified. But many, if not most of them, aren’t. The moment you become conscious of this, your self-awareness expands. You begin to ask yourself more honest questions and give yourself more honest answers.

I find journalling to be an effective way to keep myself honest. I reach for my journal whenever I feel there’s an idea or milestone — good or bad — worth documenting. For example, I’ve got an overwhelming appetite for change. So when several months ago I started getting bored with my day-to-day routine, I made a journal entry about it. I even made a list of specific adjustments I wanted to make to shake things up. Looking at that list now, I’ve installed about 60% of those tweaks so far with more currently in progress.

How Honest Is Too Honest?

In the honesty business, there’s a fine line between radical and reckless.

Reckless honesty is the result of pushing the authenticity envelope so far that you shoot yourself in the foot. Radical honesty is having the balls to walk up to a girl and say “Hi” because you think she’s attractive and you want to find out more. Reckless honesty is walking up to the same girl and saying “Wow, you are absolutely gorgeous. There’s nothing I’d like to do more right now than to take you into the nearest bathroom, rip all your clothes off, and fuck you to God.”

Both approaches are, technically speaking, completely authentic. But one is obviously somewhat more productive. The border between radical and reckless must be patrolled by your intuition. Sometimes that line is obvious (like in the example above), but sometimes it’s not. As a general rule, accuracy is more important than precision.

If you have a habit of stopping short of saying what you really think, turning things around will take time. But there is no challenge more worth tackling. Authenticity accrues a compound interest, and even a few extra cents of veracity today could become a large down payment on your happiness tomorrow.