“Lives are lived in parallel and perpendicular, fathomed nonlinearly, figured not in the straight graphs of “biography” but in many-sided, many-splendored diagrams. Lives interweave with other lives, and out of the tapestry arise hints at answers to questions that raze to the bone of life: What are the building blocks of character, of contentment, of lasting achievement? How does a person come into self-possession and sovereignty of mind against the tide of convention and unreasoning collectivism? Does genius suffice for happiness, does distinction, does love? Two Nobel Prizes don’t seem to recompense the melancholy radiating from every photograph of the woman in the black laboratory dress. Is success a guarantee of fulfillment, or merely a promise as precarious as a marital vow? How, in this blink of existence bookended by nothingness, do we attain completeness of being?”

— from the opening chapter of “Figuring” by Maria Popova

I’ve been following Alain de Botton and his wonderful School of Life content for years. When I saw that they were hosting one of their weekend conferences in San Francisco, I signed up immediately.

The conference — best described as philosophical self-help programming focused on emotional intelligence — took place over Friday afternoon, Saturday, and Sunday morning. It was mostly Alain de Botton himself lecturing charismatically from on stage, interspersed with short video clips, pair-up exercises with someone sitting near you, and line-up-at-the-mic exercises where one person in the audience spoke to the full of audience of 500.

The pervasive word of the weekend was pessimism. None of us is normal. A degree of loneliness is the norm. No one can fully understand anyone else. So walk through life, Alain said, with a kind of “cheerful despair.” Of all the topics covered, from self-knowledge to meaning, from work to sex, the topic that received the most airtime was romance and relationships. Love is the source of our deepest happiness and our deepest despair. Pessimism pervaded all discussion of romance at the event.

There’s an obvious alignment between Buddhism and the School of Life. Life is suffering. Life is unsatisfactoriness. The inevitability of death was remarked upon as frequently at this conference as at a Buddhist meditation retreat.

For the most part, I was in violent agreement with the ideas Alain laid out, and utterly captivated by the breadth of topics explored. Where I part ways intellectually, I think, is the School of Life’s intensive focus on psychotherapy, particularly as understood by childhood experiences. Many of the frames they use involve analyzing your parents. Childhood experiences matter, of course, though I’d submit not as much as psychoanalysts would have you think. Even then, there are a range of childhood influences beyond strictly parental.

One of the most poignant exercises of the weekend involved this prompt: “On a piece of paper, write down something rather personal and vulnerable that you are longing, in a way, to share with someone, if only they were trustworthy and kind.” People wrote down sometimes stunning confessionals. And then the confessionals were read aloud on stage anonymously.

One of the most difficult exercises was to pair up with a person sitting next to you in the audience — a complete stranger — and describe your sexual fantasies. Yes, your uncensored sexual fantasies.

One of the most amusing exercises involved writing down a long-held life dream you’ve maintained — perhaps to achieve a certain kind of change in the world, finally marry a soulmate, accomplish a professional goal — and then throw the piece of paper containing the dream in an oversized trash can that had been rolled on-stage. Relinquish your dreams!

Other nuggets I wrote down in my notebook:

• “I’m a little broken” should be the first words on a first date with someone. “Hello, my name is… And I’m suffering because…”
• Let’s all strive for “sane insanity.”
• There’s no such thing as overthinking; only thinking badly.
• Kierkegaard quote, which could be the modern Stoic manifesto: “If you marry, you will regret it; if you do not marry, you will also regret it; if you marry or if you do not marry, you will regret both; whether you marry or you do not marry, you will regret both. Laugh at the world’s follies, you will regret it; weep over them, you will also regret it; if you laugh at the world’s follies or if you weep over them, you will regret both; whether you laugh at the world’s follies or you weep over them, you will regret both. Believe a girl, you will regret it; if you do not believe her, you will also regret it; if you believe a girl or you do not believe her, you will regret both; whether you believe a girl or you do not believe her, you will regret both. If you hang yourself, you will regret it; if you do not hang yourself, you will regret it; if you hang yourself or you do not hang yourself, you will regret both; whether you hang yourself or you do not hang yourself, you will regret both. This, gentlemen, is the sum of all practical wisdom.”
• Manic cheeriness is an ill of modern society.
• Many people’s #1 problem is they are too hard on themselves.
• Think through the worst case scenarios
• When lusting after someone new from afar, stare into their eyes, and think about all the ways s/he could annoy you over time.
• Good sex involves decadance, roughness, immediacy, vulgarity. Good relationships involve respect, responsibility, patience.
• Tip on humor to lessen the fights with your partner. Exaggerate the annoying tendency of your partner to make him/her laugh. For example, if your wife is obsessed with cleaning, try to out-clean her to such an extreme degree that she can’t help but laugh at your newfound obsession. If your husband is always panicked about getting to the airport early, pack your suitcase and propose leaving for airport the night before the flight–just to be safe. Make him laugh.
• True love is the forgiveness of weakness; not the admiration of strength.
• Interview question at job: In what particular ways are you crazy?
• Hang a sign at the office that says, “No one who works here is entirely normal.”
• Over-obedient adults are more problematic than under-obedient ones.
• What are you most afraid of? Who are you afraid of letting down?
• Frustration + Surprise = Anger. Frustration + Expectation = Sadness.
• When you encounter a local frustration, instead of maintaining “local pessimism” around whatever happened try enveloping your feeling into a kind of “global pessimism.” For example, if your kid spills rice all over the floor, the local pessimist would say: “My kid isn’t neat.” The global pessimist would say, “Children are lifelong punishment for a few moments of sentimentality.”
• As a child you cry when angry or wronged. As an adult you often cry at tender moments or when encountering profound beauty.
• To have a meaningful life, become skilled at cultivating meaningful moments. Hardship can be meaningful when it’s a byproduct of your search for something meaningful.

Thank you, Alain, for all you do. And thank you to the School of Life for being a fount of ideas and inspiration.

A friend emailed me the below excerpt from Mark Nepo’s The Book of Awakening. The closer we get to the core of all being, the more synonymous the effort and its reward.

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So often we anticipate a reward for the uncovering of truth. For effort, we expect money and recognition. For sacrifice and kindness, we secretly expect acceptance and love. For honesty, we expect justice. Yet as we all know the life of experience unfolds with a logic all its own. And very often, effort is seen, and kindness is embraced, and the risk of truth is held as the foundation of how humans relate. However, the reward for breathing is not applause but air, and the reward for climbing is not a promotion but new sight, and the reward for kindness is not being seen as kind, but the electricity of giving that keeps us alive.

It seems the closer we get to the core of all being, the more synonymous the effort and its reward. Who could have guessed? The reward for uncovering the truth is the experience of honest being. The reward for understanding is the peace of knowing. The reward for loving is being the carrier of love. It all becomes elusively simple. The river’s sole purpose is to carry water, and as the force of the water deepens and widens the riverbed, the river fulfills its purpose more. Likewise, the riverbed of the heart is worn open over time to carry what is living.

All this tells us that no amount of thinking can eliminate the wonder and pain of living. No wall or avoidance or denial – no cause or excuse – can keep the rawness of life from running through us. While this may at times seem devastating, it is actually reassuring, because while the impermanence of life, if fixed on, can be terrifying, leaving us preoccupied with death, the very same impermanence, if allowed its infinite frame, can soothe us with the understanding that even the deepest pain will pass.

I just published a new essay on my web site titled Happy Ambition: Striving for Success, Avoiding Status Cocaine, and Prioritizing Happiness. In some sense it’s a follow up to my previous essay on wealth. It also covers some new ground.

These ideas came together over many months, and while they’re still a work in progress, I’m happy to share them now…in part to benefit from additional feedback!

I just published a new essay on my personal web site titled The Godilocks Theory of Being Rich. It’s about the pros and cons of being “super rich” as I’ve observed it second hand, along with some other comments on the connection between wealth and happiness. Any and all feedback, as ever, is welcome!