What is my goal in writing?

To be useful.

But useful to whom, and useful in what way?

To start, I’m writing to be useful to myself, in the sense that if I’m lucky, I have half of my life ahead of me still. What I’m trying to do in my writing is to codify the insights and stories that have been the most helpful to me in the first half of my life, so that I can remember them, carry them with me, and build upon them in the second. I want to record the ideas that have helped me find clarity amidst confusion, the ideas that have helped me overcome creative and personal obstacles, the ideas that have helped me be more loving and less fearful, more effective and less distracted, more fulfilled and less frustrated.

So these essays are a foundation I’m creating for my future self. They’re letters to the person who’s going to live the second part of my life.

But the challenges I face are not unique, and the things I want to get better at understanding and doing in my life are things that you might want to get better at too.

So I’m writing with the conviction that my words can be useful to you in some way – that some of my experiences, and some of the insights I’ve derived from those experiences, might inspire, inform, and assist.

That’s my starting point. Here’s what I’ve been writing:

Life is not a project
Life is full of so many projects that we might see life as one big umbrella project. But what’s at the other end?

Inner Luck
Any time we experience a metacognitive interrupt that allows us to escape our current thought and observe it from a distance, we are lucky and we should enjoy that luck.

On Fear
Fear creates a close-mindedness that makes us more likely to believe the idea that caused the fear in the first place, but if we know this is happening, we can change how we respond.

Self-compassion is hard and that’s not your fault!
Self-compassion is difficult to practice because it conflicts with virtues we hold dear, including responsibility, accountability, and ownership over our fate.

How to concentrate on a task you hate
Concentration is like balance in that it depends on constant recovery — to concentrate better, we can work on making recovery easier.

Don’t focus on the outcome, focus on the income
When a positive outcome is unlikely, we can still trust in a positive “income,” which is to say a positive inner return.

Sustainable Optimism
If optimism is the conviction that everything is going to work out as we hope, then it’s not sustainable. What is sustainable is the confidence that we can always find an “envaluing” perspective.

How to conquer negativity
Negativity enters our thoughts through the vector of our self-reports; we can conquer it just by giving a broader and more neutral answer to the question “What am I doing right now?”

Freedom of memory
To connect with our true selves, we need to give ourselves the opportunity to remember our best moments as snapshots in time that are not clouded by the memory of whatever disappointments might have come next.

The paradox of desire
We might see desire as a motivator that propels us toward fulfillment, but desire itself might train us to be unfulfilled.

The critic vs. the advocate
Whenever we play the role of a critic, we should ask “How much risk am I willing to take to create the possibility of being delighted?”

Don’t regret, reroute!
We can learn from a GPS’s ability to immediately reroute without harping on mistakes made in the past.

Advice for a flow junkie
To the extent that you love being “in flow” you might hate being “out of flow.” But it’s what we do when we’re “out of flow” that creates the foundation for flow to happen again.

On keeping gratitude
Gratitude is something we have to work at maintaining. To do this we need to be aware of forces like anger that take it away.

10 keys to finishing
My best advice on how to finish a project.

What is altruism and what should it be?
If a person does an altruistic deed because they believe altruism is in their own self-interest, is it still altruism?

Saved by intention
Identifying a timeless, universal intention before we begin a project can help us later understand how we have succeeded even if the details of the outcome did not match our high expectations.

Choosing Loss
Are there ever cases where we should choose a loss even without having a story that situates this loss as the pathway to some larger gain?

What I learned from my lowest moment
Moments in life are interconnected. Any situation provides an opportunity to practice our deepest values. Stop insisting on narratives that don’t serve you. If you got out of bed this morning, congratulations, you’re an optimist!

On receiving a compliment
A compliment can become a burden when we try to extract too much satisfaction from it. The hardest thing about receiving a compliment is letting it go.

On Setting Expectations
A detached and impartial perspective can protect us from disappointment, but when should we allow a bit of hope, a bit of faith back into our outlook?

How to be less frustrated by a Very Frustrating Thing
When we’re feeling upset, there’s often an “intensifying assumption” that makes our situation more troubling than it needs to be, and we can find relief in questioning that assumption.

Reconsidering Boredom
If boredom arises from monotony, from a lack of stimulation, from an unsatisfied craving for novelty, then why isn’t meditation the most boring thing in the world?

A radical mission of presence
What would it mean to choose “presence” as one’s mission in life?

Interruptible Meditation
Our thoughts interrupt us when we meditate. We practice gracefully handling those interruptions. If the interruption comes from outside our mind, like another person making noise in the room, we can practice the very same graceful response.

Why the feedback that reaches you does
The only feedback you’ll ever hear in your whole life is the feedback where someone had a CONTEXT in which to form it, they had a PATHWAY to convey it to you, and they had an INCENTIVE to go ahead and do that conveying. If you’re not hearing any response to your work, this “CPI” framework can help you understand why.

On getting what we want
Getting what we want creates new problems that make us forget that we got what we wanted. We have to find ways to remember that we did.

Why aren’t I feeling that great?
If we start with the assumption that we’re not doing well, and then we look for reasons why, we can work ourselves into great distress. Questioning that assumption might be a better bet.

Depersonalizing the inability to meditate
If you’re frustrated that you can’t concentrate, try removing yourself from blame. Instead, blame the “Distractor” inside you. Now sit back and observe the Distractor.

All About Entropy
If you increase the disorder of something by a tiny bit, and you do this many hundreds of times over many years, and you take zero – precisely zero – steps to reverse this process, what do you get?

The Algorithm is a Mirror of the Mind
Not until the advent of social media has our attention been hijacked, dominated, extracted, and exploited so totally. Is there any good in this development? Anything to learn from it?

Resolution Blitz
We go through our lives imagining all the ways things could go wrong. Why not sometimes imagine a scenario in which everything goes right?

I need a vacation
If you find yourself wishing you could take a vacation, consider taking one immediately.

Social Anxiety and Mindfulness
Confronting the causes of social anxiety can do more for us than simply making us more comfortable in crowds – it can make us more whole as individuals.

Crappy Breaks
Many of the breaks we take are crappy: they don’t serve their purpose of providing rest and refreshment. Our breaks might be more stressful than the work we’re trying to do.

Stage Fright: Tip #1
To cure stage fright, stop thinking about your ability to perform. Focus on your ability to listen.

On caring what other people think of us
Why do we care so much about other what other people think? Because when we consider another person, when we remember what they are like, when we hold an image of them in our own mind, we are forced to model our relationship with them, and that includes what they think of us.

The Value Of Uncovering The Timeless Intentions Behind Our Everyday Actions
If we take the time to examine our everyday actions, we can connect them to timeless, universal goals. Doing this can help us appreciate our efforts and find the motivation to do more of what’s working. It can also reveal situations where our action works against the goal we are trying to pursue.

Overcoming The Three Obstacles To Fulfillment
We can experience a greater sense of fulfillment in life if we know how to respond to three kinds of obstacles: tunnel vision, scattering, and reactivity.

Reconsidering Background Noise
If we listen closely to background noise – the same noise that might otherwise annoy or distract us – it can set the stage for a musical note to sound incredibly wonderful.

Meditation and Stimulation
When we’re over-stimulated, we often go looking for even more stimulation – to relinquish it feels unbearable. But when we meditate, we’re detoxing from stimulation. We’re breaking an addiction. And that frees us from all of the detrimental consequences of seeking stimulation that we don’t actually need.

Meditation, Web Browsing, and Optimism
If you want to be happier, they say, you should look on the bright side. But if you want to be able to look on the bright side, you should practice habits that strengthen that ability, and break habits that weaken the ability. Meditation is a strengthening habit and web browsing is a weakening one – they are nearly perfect opposites.

How to enjoy meditation | How to feel better about mind-wandering during meditation | How to feel better about mind-wandering during meditation: Part II
Meditation is frustrating when we think about how often we’re getting distracted. But distractions are not everlasting. Each mental distraction is filled with many opportunities to recover. If we sit down for an hour and keep getting distracted by our thoughts, but if we keep feeling good when we notice and take an opportunity to recover, then our session fills up with small successes that can result in a kind of satisfaction or even pride.

Meditation is physical
It’s a mistake to think that meditation is all about the mind. When we meditate, we are choosing again and again to anchor our awareness in the sensory experience of inhaling and exhaling. We’re not simply calming our minds, we’re calming our minds by returning to our bodies.

On Breath
Life is several hundred million breaths. That’s what we get. If this breath-centric perspective casts life a simple thing – oversimple, a caricature – what still can we learn from that simplicity?

Are you lucky when you take a deep breath?
In the middle of a busy day, or simply in the middle of a busy series of thoughts, if you remember to stop and take a deep, calming breath, is there anything remarkable in what just happened? Are you lucky?

What could be more important than this?
It’s our stubborn sense of “what’s important” that makes meditation difficult. When we bring our attention to our breath, we find that other points of focus seem more compelling or more important. But are they really?

When deep breathing doesn’t work
Trying to breathe like a yogi when you’re agitated can feel inauthentic. Start by observing your breathing as it is, do that for a while, then make a small change.

When Meditation Feels Irresponsible
Meditation can challenge our sense of obligation to hold certain pressing or urgent matters in mind. When we disregard that obligation, we might feel like we’re being irresponsible, but that’s good.

On Stillness
Stillness is similar to vodka in that if we ever achieved pure stillness it would have no distinctive character. But we’re human, and as we progress toward stillness through meditation, there is usually some kind of “inflection” to the stillness we actually achieve. If one thing is missing in our lives, perhaps it’s positively inflected stillness – the kind of stillness that feels just a little bit good.

On Disappointment
Disappointment happens when we don’t get something we really need, but it also happens when we don’t get something we don’t need at all – something we didn’t even want until it was promised to us. When an inessential promise or an unforced expectation causes pain, there’s an easy way out.

The Cost of Imagination
Imagination isn’t free. We have to bring something to the process of imagination to get something out of it. But we’re not always aware of how much energy our imagination demands and how much energy we’re actually supplying. When we use our imagination without sufficiently powering it, we might be disappointed and confused by what it shows us.

Three Life Lessons From Investing
By investing in the stock market and observing our emotions over time, we can learn three things about life. Reward comes from taking risks. A short-term risk, taken repeatedly over time, might result in a negligible long-term risk, but a near-certain gain. Our safest-seeming option might actually be the most risky.

The Fourth Lesson From Investing
In investing and in life, we can acquire wisdom and practice it successfully over many years, but we shouldn’t assume that a long and solid track record makes us immune to unexpected panic. We’ll always need the help of another person – an advisor – to keep us grounded in those moments that might take us by surprise and make us question everything we’ve assumed.

Gainful Dualities
To fall prey to “dualistic thinking” is to see the world in terms of opposites like good versus bad, or true versus false, or happy versus sad, in a way that makes us blind to subtlety, ambiguity, and complexity. But is it always bad to categorize reality according to a binary framework, or does the badness come from the particular categories we use? If we shake up our categories and use the same kind of dualistic thinking with these new categories, might we learn something useful?

5 Questions To Improve Any Situation
To improve any situation, we should start by noticing our view of it, then identifying the consequences of our holding that view, and finally adjusting our view in a way that allows for the consequences we actually want.

What is procrastination?
Procrastination is pain avoidance. But the way to confront pain is not to scold ourselves for being weak. Bravery is what we need, and that’s more than pain-tolerance, it’s positivity.

When To Rest And When To Keep Going
After a setback, the best thing you can do is rest and try again later. Unless it’s one of those setbacks where you should immediately jump back into action. The challenge is knowing the difference.

The Connection Framework
The purpose of life is connection: connecting with one’s inner self, connecting with other people, and connecting with the infinite or the divine.

Trivial versus Deep
It’s natural to want to spend our time on things that are substantial, meaningful, or deep, while minimizing our time on what’s insignificant or trivial. But labeling a task as trivial prevents us from taking pride in our work, and stops us from seeing how the task may be deep in its own way.

10 Reasons To Quit Our Phones
You’ll never believe #7.

The Peril Of Pairwise Comparison
We try to ascertain our preferences by pitting the options side by side and rapidly comparing them. But that only tells us how the options interact in an artificial competitive setting. It doesn’t always tell us which one we really like the best.

Practicing Finding Meaning
Building muscle is something we know we have to work at, but thinking positively is something we expect ourselves – and others – to be able to accomplish just by once deciding to do it. Instead, we should think of the ability to find positive meaning in situations as a creative skill that we develop through practice.

The Virtue Of Not Looking For Meaning
It’s often said that when we endure a hardship, we can heal by searching for positive meaning in what we’ve been through. But as much as it can be a virtue to look for meaning in an experience, painful or otherwise, there are times when it’s a greater virtue to not look for meaning, to know when to refrain from that search, to know when to move on. In the context of meditation, while we might typically observe our thoughts, still perceiving them as meaningful although we don’t engage them, we can also try to ignore them altogether as noise, listening instead for the sound of our breathing against the background of that noise, in the same way we would listen to a conversation partner in a crowded room.

What if I valued health above all else?
Should health come before achievement, or achievement before health? If you put health in second place, it’s easy to believe you’re already doing enough towards it. That’s an argument for putting it first.

A trick for being in the moment by choosing what to look forward to
When we look forward to an arbitrary reward that we’ll get after completing a strenuous activity, the reward draws our attention away from the present moment. Instead, we should look forward to a positive future experience that can only derive from our being present right now.

Declutter like an investor
Want to fail at decluttering? Simply refuse to make any decision that exposes you to the risk of regret.

Old Beer Labels
What happens when a person no longer wants or needs a gift that was lovingly prepared for them by their earlier self?

On Being Overtired
Children are known to throw tantrums when they’re overtired. As exhausted adults we’re still throwing these tantrums for the same reasons, but the tantrums are better disguised. There’s great value in knowing when it’s “past our bedtime.”

The Value Of Mode Awareness
Oftentimes we already possess the skills we’re looking to gain. What we lack is an awareness of when we’re applying those skills, and when we’re forgetting them.

On Being Reckless To Escape Fear
Fear often comes with a conviction that to turn our attention away from a perceived threat would be reckless, foolish, or irresponsible. To free ourselves from fear, we need to become more comfortable with the feeling of recklessness.

On Balancing Foresight With Presence
Our ability to imagine the future is both a great strength and a great vulnerability. It makes planning possible, but it opens the door to worry. When we try to escape the trap of worry, we must struggle against a prevailing bias for future-mindedness over presence. Thinking ahead is supposed to be the way to get a leg up in the world, whereas appreciating the here-and-now is an invisible choice whose benefits are known only to the self. What’s missing from our mental arsenal is the idea of “ignoring the future” as a deliberate, respectable technique that we should employ – from time to time – in the interest of health.

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