But here’s a constant: each year you learn more about yourself. You see yourself in different environments, different styles of living, different communities and friend circles which reward slightly different things. You get to see yourself bend to the world around you as you evolve from one stage of life to another.

I’m convinced each of us has certain fundamental dispositions, whether they’re contained in our genes or attachment styles or Enneagram types. But we’re also prone to making up stories about ourselves, stories that we wish were true. Time is the best antidote to all our attempts at self-deception: it’s easy to lie to yourself for a day, but a lot harder to lie to yourself for a decade.

I think a lot of folks feel like you should be doing these certain things like writing the great American novel or reading the 100 Greatest Movies of All-Time when in actuality these are achievements that have no real guarantee of happiness. Unless you are truly enjoying those journeys, there is no reason to set upon them.

I don't think there is anything wrong with having hopes and dreams, but I do feel that maybe we allow those things to be excuses for not living a content life. I also think at times we hold onto old dreams that no longer serve us, instead of focusing on something new and more applicable to your current situation.

adulthood wasn't full of Ferraris and mansions, and I found out rather quickly that I wasn't going to save anyone, because I was struggling to save myself.

Non-okayness is the opposite. I’ve described it elsewhere as being “mildly disgruntled all the time.” You’re frustrated with life and with yourself. You feel like there is something wrong with you, although it’s a different problem in each moment: you’re too soft, you’re too rough, you’re too social, you’re too alone. You constantly feel like you’re in the wrong place and you “should have” done something else to avoid this situation.

I distinctly remember one of my first days back in New York after my retreat. I was on PTO so I had the day to myself, and I didn’t have much of an agenda. Usually this is enough to put me on edge: I like maximizing productive use of my time, so I make detailed schedules and todo lists. If I spend an entire day off doing “nothing”, I’ll feel really bad and frustrated with myself at the end of it.

This day, post-retreat, was not like any day I had experienced before. It felt like literally anything could happen and things would be perfectly fine. I do some work? Great. I don’t do any work? Great. I felt like I could just sit there and stare at the brick walls of my apartment all day. I felt such unbridled affection for my roommates and friends. I started reading Stephen Batchelor’s Buddhism Without Beliefs, and felt moved by every paragraph. I could read for a whole hour without the slightest urge to use my phone. And even when bad things happened—one night I was hurt by something my friend did, another night someone at a bar yelled at me—I would feel upset, and then I’d move on, and it wouldn’t spiral into an endless internal echo of “I should’ve done this, I should be that, I should do that.”

One of the things about okayness is that it entails a lot of presence, and the more your sense of presence deteriorates, the less aware you are of the fact that it’s deteriorating.

entering stable okayness is a non-voluntary inner movement. There are many outer, voluntary moves you can do to make it more likely that the inner, non-voluntary move occurs, but none of them will reliably trigger the inner move. Being in a state of non-okayness is like having an internal knot in your mind, and the harder you try to untie the knot—the more you clench and tug on it—the tighter the knot becomes.

The things that tend to nudge me towards okayness are: retreats, quiet time to myself, long walks, reading, and looking at beautiful things. The things that nudge me away from okayness are: consuming a lot of social media, socializing a ton, having a lot of deadlines. This doesn’t mean that those things are strictly bad and to be avoided at all costs. It’s just about working through your own relationship to these things — trying to figure out what it is about these things that uproots yourself sense of okayness, and address that.

One of the trickiest aspects of the inner knot is this: each time it gets tied again, it’s in an ever-so-slightly different shape, requiring a different move to untie it.

The shift that has been working for me most recently is to recognize that okayness just isn’t something I can reliably produce. And repeatedly asking myself, what is the truth of this moment, rather than trying to figure out how I can get to some other state, or some past memory or object of blame, that has nothing to do with what is going on right now.All these things are little nudges to help make it more likely that you get to okayness.

Okayness is when you feel fundamentally at ease with reality and with yourself. You feel like you are enough: there is nothing fundamentally deficient about you. You move through life with grace and fluidity. When bad things happen, negative emotions arise, and you just feel them, and then they pass, and none of that detracts from the fundamental beauty of your experience. Life feels inherently meaningful, you’re perfectly content with how things are, while also naturally gliding towards the things you want

To have that sense of one's intrinsic worth which, for better or for worse, constitutes self-respect, is potentially to have everything: the ability to discriminate, to love and to remain indifferent. To lack it is to be locked within oneself, paradoxically incapable of either love or indifference. If we do not respect ourselves, we are on the one hand forced to despise those who have so few resources as to consort with us, so little perception as to remain blind to our fatal weaknesses. On the other, we are peculiarly in thrall to everyone we see, curiously determined to live out—since our self-image is untenable—their false notions of us.

At the mercy of those we can not but hold in contempt, we play rôles doomed to failure before they are begun, each defeat generating fresh despair at the necessity of divining and meeting the next demand made upon us.

It is the phenomenon sometimes called alienation from self. In its advanced stages, we no longer answer the telephone, because someone might want something; that we could say no without drowning in self-reproach is an idea alien to this game.

Every encounter demands too much, tears the nerves, drains the will, and the spectre of something as small as an unanswered letter arouses such disproportionate guilt that one's sanity becomes an object of speculation among one's acquaintances.

To assign unanswered letters their proper weight, to free us from the expectations of others, to give us back to ourselves—there lies the great, the singular power of self-respect. Without it, one eventually discovers the final turn of the screw: one runs away to find oneself, and finds no one at home.

I had not been elected to Phi Beta Kappa. This failure could scarcely have been more predictable or less ambiguous (I simply did not have the grades), but I was unnerved by it; I had somehow thought myself a kind of academic Raskolnikov, curiously exempt from the cause-effect relationships that hampered others.

In brief, people with self-respect exhibit a certain toughness, a kind of moral nerve; they display what was once called character, a quality which, although approved in the abstract, sometimes loses ground to other, more instantly negotiable virtues. The measure of its slipping prestige is that one tends to think of it only in connection with homely children and with United States senators who have been defeated, preferably in the primary, for re-election. Nonetheless, character—the willingness to accept responsibility for one's own life—is the source from which self-respect springs.

Robert Pirsig’s definition of Static and Dynamic Quality:Our language is an imperfect instrument created by ancient and ignorant men. It’s an animistic language that invites us to talk about stability and constants, about similarities and normal and kinds, about magical transformations, quick cures, simple problems, and final solutions. Yet the world we try to symbolize with this language is a world of process, change, differences, dimensions, functions, relationships, growths, interactions, developing, learning, coping, complexity. And the mismatch of our ever-changing world and our relatively static language forms is part of our problem.

Words can only approximate Quality, but never fully encompass it. A static thing can never fully capture a dynamic thing.

We create problems for ourselves by using static language (e.g. judgements) to capture a reality that is dynamic & ever changing — by mixing observations and evaluations.

The caveat to keeping your identity small is when you want to identify as a positive trait – “I’m a kind person” – so that you’re forced to live up to it, especially when this is an unchanging desire.

Gatekeepers could see themselves not only as talent hunters for their own organization, but also as managers of society’s collective supply of ambition. We could demand that they consider it a responsibility to waste as little of their applicants’ ambition as possible. That they strive to redirect and allocate that ambition wherever it is most needed.

In practice, there isn’t any single solution. Rejection is a facet of life, and everybody needs to figure out their own strategies to cope with it. The most I can offer is that it’s better when you’re aware of how it works. It isn’t enough to know, on an abstract level, that rejection is typically random and impersonal — but it helps.