thinking, communication, and personal philosophy
created 2026/04/09 modified 2026/09/19
Problem-solving
- Untools: a collection of thinking tools and frameworks to help you solve problems, make decisions, and understand systems — includes prompting questions to guide you to the best tool
- How to stop overthinking everything: deliberation is an admirable leadership quality, but there comes a point where helpful contemplation turns into overthinking — Melody Wilding, Harvard Business Review
- Sensitive strivers: high-achievers who process the world more deeply than others, with more active brain circuitry in areas related to mental processing — their minds take in more information and process it more complexly; often applauded for exploring angles and nuance, but more susceptible to stress and overwhelm
- Put aside perfectionism: ask — which decision will have the biggest positive impact on my top priorities? of all the people I could please or displease, which one or two do I least want to disappoint? what is one thing I could do today that would bring me closer to my goal? based on what I know right now, what's the best next step?
- Right-size the problem: write down which goals, priorities, or people will be impacted by a decision — differentiate between what's meaningful and what's not worth obsessing over; try the 10/10/10 test: how will you feel about this decision 10 weeks, 10 months, or 10 years from now?
- Leverage intuition: "thin-slicing" (rapid cognition) allows the brain to make wise decisions without overthinking — try a Day of Disinhibition (follow your intuition for 24 hours); each day, list 3–5 times you trusted your gut and whether the outcome was favorable
- Limit decision fatigue: make routines, build habits, eliminate unnecessary decisions
- Construct creative constraints: Parkinson's Law — work (and overthinking) expands to the time we give it; set constraints and accountability for when to make a choice
- Apart from making you think more, ambivalence can also make you think better — Psyche
Communication
- Weekly progress updates: every Friday, send your boss a short email (max 15 min) with three categories:
- The work you completed that week
- What you are working on, including any deadlines that may have shifted or obstacles encountered
- What you are waiting on — tasks completed but requiring sign-off or contributions from someone else
- How to ask useful questions — Josh Kaufman
- How to have a better argument:
- Make it easier for people to change their minds (give them reason that it's ok)
- Actually ask about their position
- Ask "What would make you change your mind?"
- People are sharing effective psychological tricks they use in everyday life: life hacks for communication — Michelle No, BuzzFeed
- Compliment people behind their backs to avoid drama
- Saying "You're right!" instead of "I know" makes you look less like an asshole and doesn't diminish something someone else may have just found out
- Turn around an annoying "why" with "I'm not sure, what do you think?"
- Instead of asking "Do you have any questions?" ask "What questions do you have?" — the first almost always results in silence, while the second helps people feel comfortable asking questions
- Listening to someone without giving advice or asking for more information usually gets you more info than pushing for it
- To de-escalate a situation, address someone at one or two emotional levels below where they are — being completely calm, reserved, and polite only pisses people off more
- Steps to dealing with a public mistake — Wikimedia
- Treasure your friends: they are more than ever the heart of happiness, of family and of love itself — Aeon
- Alternatives to "How are you?" — Kat Vellos
- How to talk to people — Mari Andrew
- The last sentence you say is the most important
- To people in despair, sometimes the best thing to say is: "I hate that you have to be so strong right now"
- In favor of more irregular verbs, in the style of "go, went, gone" — New York Times
- Defending against predatory listening: when someone starts a conversation just to criticize you, lean in and get them to explain their side — don't get caught in an argument
- On going a month without using exclamation points — WIRED
- Endless list of icebreakers
- I love stalking my friends via location-sharing, too — New York Times
Mindset
- There are two kinds of happy people: some of us strive for a virtuous life, others for a pleasant one — we could all use a better balance — Arthur Brooks, The Atlantic
- 1. Epicureanism (Epicurus): happiness depends on ataraxia (freedom from mental disturbance) and aponia (absence of physical pain) — "if it is scary or painful, work to avoid it"
- Four-part cure to banish negative thoughts: don't fear God; don't worry about death; what is good is easy to get (by lowering our expectations); what is terrible is easy to endure (by concentrating on pleasant things even amid suffering) — made easier when we surround ourselves with friendly people in a peaceful environment
- Promoted hedonia — in response to fear of death: "Death does not concern us, because as long as we exist, death is not here. And when it does come, we no longer exist."
- 2. Stoicism (Epictetus): happiness comes from finding life's purpose, accepting one's fate, and behaving morally regardless of personal cost — "grow a spine and do your duty"
- Approach = eudaimonia: life devoted to our greatest potential in service of our highest ideals; guided by naturalism, moralism — change what you can, accept what you can't
- Paradox of happiness: to attain it, forget about it; if we're lucky, happiness will come as we pursue our purpose
- Regularly ponder and confront death
- Balancing the two: each philosophy promotes different aspects of happiness — pleasure/enjoyment vs meaning/purpose; both are required
- Know thyself: when your mood is low, which set of aspects do you gravitate towards? PNAS survey to uncover hedonistic tendencies; UPenn questionnaire measuring eudaimonic tendencies
- Bolster what you lack: try to answer yes-yes — did this bring me enjoyment? did it also bring me meaning? did this make me feel afraid? did I learn something from this fear? did this serve my interests? did it serve the interest of others?
- Build a happiness portfolio: include faith, family, friendship, and work in which you earn success and serve others — all four require full presence (Epicurean) and hard work/strong commitments (Stoic)
- 1. Epicureanism (Epicurus): happiness depends on ataraxia (freedom from mental disturbance) and aponia (absence of physical pain) — "if it is scary or painful, work to avoid it"
- Take on the role of a productive skeptic (link needed)
- Don't take things at face value; don't make things personal; be optimistic
- Be genuinely curious
- Look inward at your own assumptions: for any argument you want to make, ask yourself 1) Where did this come from? 2) Is it really true?
- If you notice yourself feeling strongly about something, take it as a trigger to stop and think — "Assuming that how we feel is an accurate representation of reality is one of the BIGGEST misplaced assumptions we make."
- Don't be a martyr (work can't be all courageous acts); choose your battles wisely
- "With multiple immediate crises to manage, make sure that part of the team stays focused on the long term agenda or the short term will absorb everyone." — Jack Lew, former White House Chief of Staff
- In defense of thinking: we cannot make sense of ourselves or the world without putting in the mental cycles necessary to wrestle frenetic information into useful forms — thinking is not just another healthy habit to add to a list, but a way of life; one that's become even more radical in an increasingly shallow world — Cal Newport, Study Hacks Blog
- How civilization broke our brains: imagine the 21st-century worker accessing two modes of thinking — productivity mind (time- and results-optimizing, proving industriousness to the world) and leisure mind (allowing us to watch a movie or finish a glass of wine without considering our reputation). On Sunday evenings, a psychological tug-of-war between them plays out — Derek Thompson, The Atlantic
- 10 reasons not to change
- An exploration of morality: includes an explanation of Derek Parfit's Reasons and Persons, many trolley-paradox scenarios to support and refute theories of self-interest and altruism, and why it's okay for us to care for some people more than others — Dynomight
- The secret to finding more joy in less time: not all moments are created equal — plan intentionally for the highlights — Ingrid Fetell Lee, The Aesthetics of Joy
- The 20-5-3 rule for spending time in nature
- Face it, you're a crazy person: when you fully unpack any job, you'll discover something astounding — only a crazy person should do it — Experimental History
- Be a specialist in your work and a generalist in your leisure: reframing recreation as continuously broadening experience, rather than turning every hobby into an overwhelming, extreme version of itself
- 100 little ideas that explain the world, by Morgan Housel — favorites: Base-Rate Neglect (assuming the success rate of everyone who's done what you're about to try doesn't apply to you), Apophenia (perceiving correlations between unrelated things because the mind can only handle tiny sample sizes), Hanlon's Razor ("never attribute to malice that which can be adequately explained by stupidity")
- Musings by Adam Mastroianni on the thought patterns that keep us stuck in hard times — "I'm waiting for the biggest jackpot of all: the spontaneous remission of all my problems without any effort required on my part." — Experimental History
- Related: when trying harder isn't the best idea
- Also relatable: the experience of depression
- On the emotional attachment to the million internet tabs you have open — New York Times
- Hanif Abdurraqib on the connection between laziness and discipline, and how he overcomes their inherent opposition: "I cannot stay in bed, because I would much rather be in pursuit of some revelation that might arrive to me in the process of doing this work."
- A slick trick to get around procrastination on writing a first draft
- Why you should pretend every time may be the last time
- You don't have to build a habit — just do it once
- You can't hoard life: "experiences are for having, not for hoarding... there is no little pocket situated outside of life to which you could take life's provisions and squirrel them away." This hit me hard.
- How random are you, really? Something I genuinely struggle with, especially when doing art — it's so hard to make or draw a truly random pattern
- Why kids make the best philosophers — The Atlantic (and more on this — Emily Oster)
- A compelling argument against the current system of applications, and some alternatives that sound sorta crazy at first but are growing on me pretty quickly
- This newsletter, "In Defense of Debate," resonated with me — I so often automatically dismiss free speech advocates by virtue of their viewpoint, but Jill Filipovic makes a solid argument as to the value of continuing to defend our basic rights
- Words of wisdom — Mari Andrew
Related
- Subtract — Leidy Klotz
- On Kindness — Adam Phillips & Barbara Taylor
- The Scout Mindset — Julia Galef
- The Biggest Bluff — Maria Konnikova
- Turn Towards the Dark: Fear, Courage, and Surrender — Hala Alyan
- Good Reasons for Bad Feelings — Randolph Nesse
- Chatter — Ethan Kross
- Think Again — Adam Grant
- In Love with the World — Yongey Mingyur Rinpoche
- The Motivation Code — Todd Henry
- How to Change Your Mind — Michael Pollan
- Weird — Olga Khazan
- High Conflict — Amanda Ripley