The School of Life Conference

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.

What’s the Reward for Uncovering Truth?

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.


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.

New Essay: Happy Ambition

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!

New Essay on Pros and Cons of Wealth

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!

The Pros and Cons of Being an Insider vs. Outsider

A striking section of Elizabeth Warren’s memoir is about advice she says Larry Summers once offered her:

After dinner, “Larry leaned back in his chair and offered me some advice,” Ms. Warren writes. “I had a choice. I could be an insider or I could be an outsider. Outsiders can say whatever they want. But people on the inside don’t listen to them. Insiders, however, get lots of access and a chance to push their ideas. People — powerful people — listen to what they have to say. But insiders also understand one unbreakable rule: They don’t criticize other insiders.

This gets at one reason why powerful people tend to become less intellectually honest as they accumulate power: they begin protecting fellow insiders instead of speaking truth.

At various points of my life, in various contexts, I’ve been an outsider and I’ve been an insider. As an outsider, I relish the opportunity to think independently and speak my mind. But as Summers suggests, my outsider status relegates me to the margins of the “conversation.” As an insider, I tend to feel muzzled — i.e. countless blog posts drafted and then deleted. But I have the most impact on the world when I’m on the inside of a power structure, exerting influence.

Tradeoffs, tradeoffs.

The Dangers of Empathy

Photograph: Samantha Stock

Paul Bloom makes a persuasive argument in the Boston Review about the dangers of empathy as a guide for making moral decisions. He begins definitionally: there is a difference between what is sometimes called “cognitive empathy,” the capacity to understand the thoughts and emotions of others, and “emotional empathy,” the capacity to feel what others feel. He’s referring to emotional empathy.

Everyone seems to think empathy is an unabashedly good thing. Bloom says no.

First, “Strong inclination toward empathy comes with [individual] costs.”

Individuals scoring high in unmitigated communion report asymmetrical relationships, where they support others but don’t get support themselves. They also are more prone to suffer depression and anxiety. Working from a different literature on “pathological altruism,” Barbara Oakley notes in Cold-Blooded Kindness (2011), “It’s surprising how many diseases and syndromes commonly seen in women seem to be related to women’s generally stronger empathy for and focus on others.”

Moreover, an individual who’s less empathetic may be a better professional in certain contexts. Bloom writes that in one-on-one interactions with doctors, we seek them to be cool, calm, and collected — not necessarily empathetic.

More broadly, empathy distorts wise policy making and philanthropy. Some think apathy makes us better altruists:

“the empathy-altruism hypothesis” is when you empathize with others, you are more likely to help them. In general, empathy serves to dissolve the boundaries between one person and another; it is a force against selfishness and indifference.

It is easy to see, then, how empathy can be a moral good, and it has many champions. Obama talks frequently about empathy; witness his recent claim, after his first meeting with Pope Francis, that “it’s the lack of empathy that makes it very easy for us to plunge into wars. It’s the lack of empathy that allows us to ignore the homeless on the streets.”

And yet:

Empathy is biased; we are more prone to feel empathy for attractive people and for those who look like us or share our ethnic or national background. And empathy is narrow; it connects us to particular individuals, real or imagined, but is insensitive to numerical differences and statistical data. As Mother Teresa put it, “If I look at the mass I will never act. If I look at the one, I will.” Laboratory studies find that we really do care more about the one than about the mass, so long as we have personal information about the one.

In light of these features, our public decisions will be fairer and more moral once we put empathy aside. Our policies are improved when we appreciate that a hundred deaths are worse than one, even if we know the name of the one, and when we acknowledge that the life of someone in a faraway country is worth as much as the life a neighbor, even if our emotions pull us in a different direction. Without empathy, we are better able to grasp the importance of vaccinating children and responding to climate change. These acts impose costs on real people in the here and now for the sake of abstract future benefits, so tackling them may require overriding empathetic responses that favor the comfort and well being of individuals today. We can rethink humanitarian aid and the criminal justice system, choosing to draw on a reasoned, even counter-empathetic, analysis of moral obligation and likely consequences.

The best way to think about empathy, says Bloom, is how we think about anger: we don’t want none of it (anger protects us and can spur positive moral action) but we don’t want too much of it (we want anger to be subservient to our rational mind). He says: “If we were all constituted in this way, if we could all put anger in its place, ours would be a kinder and better world. That is how we should think about empathy too.”

There are various responses to the essay by people like Peter Singer, Sam Harris, and others, at the same link above.

(Hat tip: Tyler Cowen)

“Don’t Compare Yourself to Others” – The Envy Problem

“Don’t compare yourself to others.”

It’s common advice. When you compare yourself to others, you are “comparing your insides to someone else’s outsides.” When you compare yourself to others, you’re more likely to become motivated by extrinsic, shallow reasons (fame/status/wealth) than intrinsic, sustainable reasons (meaning/purpose). When you compare yourself to others, you kill your joy.

Indeed, Leo Babuta says, “One of the biggest reasons we’re not content with ourselves and our lives is that we compare ourselves to other people.” He analogizes the issue to running in the park and seeing someone run past you. It’d be silly, Babuta says, to conclude, “Gosh, he’s a faster runner than me, and therefore better than me!” You have no idea how far he’s running, where he is in his particular run, what training plan he’s on, etc. Better to just focus on your own run. Learn about yourself as you run. Focus on your journey.

But it’s more complicated than this. You can benefit when you compare yourself to someone else. For example, what if the person who runs past you in the park sports a running technique that’s superior to your own and that you could adopt with success? What if the person running faster wears a certain kind of shoes that you could buy for yourself? What if his training plan offers valuable insight that you might incorporate into your own training plan?

When you compare yourself to others, you might be inspired to run faster in life. Better yet, you can get ideas for how to run faster. The best way to achieve expertise in anything is to study the masters, deconstruct their techniques (by comparing your techniques to their own), and consider adopting their best practices into your own routine.

I believe what people really mean when they say “Don’t compare yourself to others” is “Don’t let yourself get consumed by envy. Be the best version of yourself, not someone else.” It’s the second order effect of comparing yourself to someone else that’s the dangerous thing. Thus, the advice would be better stated: “Don’t let yourself get consumed by envy.”

Envy sucks. It really does cause unhappiness. It’s important to remember, though, that you don’t feel envy when Bill Gates has a big success. He’s so different from you and me. You also don’t feel envy as much when someone achieves great success in a wildly different life pursuit. So when do you feel envy? You feel envy when someone who is roughly the same age/location/life stage/life situation as you achieves something similar to your goal in your field of choice.

Hence, the dilemma: how do you learn from successful people without being consumed by envy for what they have?

Here’s a perhaps radical approach.

First, study the lessons from successful peers in adjacent fields. If you’re a development director at a non-profit, study the career of and compare yourself to a director of finance at a fast-growing startup. If you’re a young doctor, study the career of a peer at a biotech company.

Second, study the lessons of people in your direct line of work but who are way, way ahead of you. Compare yourself to him or her. If you’re a software entrepreneur, study Bill Gates’ life and career. Or anyone else who’s 10-15 years ahead of you. Learn, learn, learn by comparing, comparing, comparing to a party elder. Read biographies.

Third, if you find yourself nevertheless obsessing over your direct peers fighting in the ring next to you — and, because we’re wired to obsess with where we rank in our tribe, it’s a hard instinct to suppress — then create a tribe of one. Forge a life so idiosyncratic that it’d be silly to compare yourself head-on to someone else. Take the path less traveled. Adopt a unique life philosophy. Do something crazy.

If you do something common, you have lots of direct comparisons. If you go to law school and become a young attorney, there’ll be thousands of people right next to you, neck and neck in the race of life, and their success will almost certainly trigger biting jealousy. They are like you in every way…except they succeeded.

Do something uncommon, and it’s hard to make the case — in your own mind, anyways — that it’s an apples-to-apples comparison. When you compare yourself to someone who by strict demographics may be a peer — by age, race, location, etc. — you have a narrative in your head that’s envy-repellent: “I can’t compare myself to him. I spent two years in my 20’s surfing in Costa Rica while he climbed the corporate totem pole.” Or: “Unlike many, I’ve chosen a flexible work schedule so I can play with my kids and husband on the weekends. This comes with tradeoffs. No one else at my company has arranged their schedule in this way. ”

Bottom Line: Comparing yourself to others is a great way to learn. Just make sure you compare yourself to people who are sufficiently different or sufficiently ahead of you so that your drive to soar will come from genuine inspiration instead of envy. That takes imagination. Better yet, carve a life so unique that there won’t be reasonable direct comparison points. Then you can freely stitch together whatever you learn from others into a life that’s all your own. That takes courage.

Happiness vs. Meaning, Continued

I re-wrote my post last week on meaning vs. happiness in a more succinct form for LinkedIn. Pasted below. Also, here’s Chris Yeh’s rebuttal post.

The things that make you happy (low stress, good health, sex) are not the same things that make your life seem meaningful (sacrifice, service, goals). Compare the effect that staying at a luxury hotel has on you (happy!) versus the feeling of training really hard for a marathon and completing it (satisfying and meaningful!).

Adam Alter, in this recent online New Yorker piece about whether the poor have more meaningful lives than the rich, noted that if happiness was all that mattered, people wouldn’t do ultramarathons or Tough Mudder events: “Some of the most rewarding life experiences are popular because they favor meaningful hardship over simple pleasure.”

According to the research, if you ask someone who’s crazy busy, sleep deprived, and anxious about the future about whether he’s happy, he might well answer no. But if you ask him to zoom out and reflect on his broader life satisfaction and ask whether he thinks he’s living a meaningful life, there’s a better chance he’ll answer yes. Especially if his busyness and stress and sacrifice is serving some greater good (or what he perceives as the greater good). That’s because having goals, sacrificing for the future, and being part of something bigger than oneself all lead to a sense of meaning.

What does this mean when thinking about your career?

1. There are certain career paths that seem to lead people to neither feel happy nor create meaning. Stereotypical lawyers and bankers fall into this camp. There’s the obvious stress that reduces happiness; you make money but don’t have time to spend it; and all the while, there’s no sense of broader aspiration or sacrifice for something bigger.

2. There are certain career paths that don’t offer much day-to-day happiness but do promise meaning. A classic example is working at an NGO or non-profit in a tough place in the world (rural Africa, for example). Many tech entrepreneurs also have low happiness, high meaning. The tech entrepreneurs I know who are striving for big world-changing outcomes are not actually happy most days. But the long term change they believe they’re enacting, and the personal legacy that it might create, adds a sense of meaning. That makes the journey worth doing from their perspective.

3. Finally there are career paths that offer happiness but not meaning. An easy, low stress job — like being a highly paid social media analyst at a large company — is going to have you feeling good day-to-day, but won’t leave you feeling purposeful.

If you had to pick whether to prioritize happiness or meaning, my advice would be: choose a career that’s meaningful, but weave in happiness habits as much as possible. By “happiness habits” I mean the small tactical things — like keeping a gratitude journal — that’s proven to lift your mood day-to-day.

Another approach would be to embrace the fact that life is long, people evolve, and that you ought to emphasize different values at different times. For example, perhaps there are stages in life when you want to consciously focus on meaning and stages when you focus on happiness. Early on in your life you seek meaning with audacious career goals and sacrifice and travel; later in life you optimize for day-to-day happiness with a lower-stress, family-oriented job.

Do you buy the difference between happiness and meaning? If so, which do you optimize for you in your career and in your life?

Life is Not a Highlight Reel

The economist Tyler Cowen once told me a test for whether a couple can be happy in a relationship is whether they can go to a drug store together with a shopping list, pick out the right items, pay, and leave the store, without once getting in an argument. His point, as I understood it, was that when you’re in a relationship you need to get through the day to day trivia and tedium of life — such as picking up extra toilet paper at a Rite Aid — with a kind of communal contentment.

A romantic relationship is not about the “highlights” you see on Instagram or Facebook of international trips or fancy dinner parties. Those things are nice but necessarily infrequent. Most of the time is downtime, and if you can’t love the downtime, you’ve got a problem. As Kramer in Seinfeld once famously mocked, conversation with a spouse tends to be repeated discussion of very ordinary days.

Relationships, like life in general, consist mostly of ordinary moments, not extraordinary ones.

In David Foster Wallace’s commencement speech at Kenyon, he notes that our day-to-day lives are full of tedium. For example, suppose after you work you need to pick up some food: “You will go to the supermarket. At the supermarket you will get a cart. The cart will have three functional wheels, and one wheel that spins out all curvy in a weird direction. That wheel – and thus the cart – will drive you mad. If you let it.”

Wallace’s point: How we choose to respond to things like the supermarket cart that can’t roll straight, and the million other daily hassles, in part defines who we are.

The minimum response, I think, is to simply tolerate the trivia, in some Zen kind of way. Accept the trivia for what it is and don’t get too depressed by it. Simple, but not at all easy.

The more ambitious response, as articulated by various sages over the years, is to aspire to find sacredness in, and have compassion towards, the ordinariness around us. Even if said ordinariness seems maddening or utterly banal on the surface. As Abraham Maslow put in: “…the sacred is in the ordinary…it is to be found in one’s daily life, in one’s neighbors, friends, and family, in one’s own backyard.”

Indeed, some of the happiest people I know find joy in the smallest of pleasures and find amusement in what are usually inconsequential inconveniences.

And to Tyler’s point, some of the happiest couples I know are at their best when it’s just the two of them on the couch looking at YouTube videos on their iPad, or taking their dog for a walk together.

So, as I’ve come to see it, the reality is this: For the most part, life is one damn mundane thing after another.

The choice that determines sanity is whether you let the little things drive you bonkers, or worse yet let the little things foment existential angst — or whether instead you can find a way to tolerate it all peacefully.

The choice that determines higher wisdom or enlightenment is whether you can learn toappreciate the little experiences — most of them trivial, indeed — as the precious, joyous stuff.

As the writer Dani Shapiro has noted, if you wait for the special, the extreme, the extraordinary to happen — you may just miss your life.

If You’re Hot and Smart You Can’t Be…

Many years ago, when I was writing my first spec for a software product, an engineer told me: Your software can be good, fast, or cheap. Pick two.

It crystallized the idea of tradeoffs very powerfully in my brain.

Ever since, I’ve noticed the “pick two out of three” rule applies in a broad set of contexts. Tradeoffs abound when traits are inversely correlated or simply rare in combination.

Here are some other examples some friends and I came up with. Pick two out of three.

  • Products generally: easy to use, secure, private
  • Your significant other: hot, smart, emotionally stable
  • Vacations: exotic, relaxing, cheap
  • Non-fiction: original, entertaining, short
  • Meals made at home: tasty, nutritious, easy to make/cleanup
  • Shoes: comfortable, durable, stylish

And as I learned in compiling this list:

  • Blog posts: honest, politically correct, concise