Some introductory thoughts on the wisdom.

  • The items on offer here are based on my own experiences and sensibilities. They are each and all things that, above all, I have needed to learn.
  • None of these items is true for every person or for all times. In the event you ever find things that are true for every person or for all times, you may wish to start a religion.
  • None of these thoughts is offered with the intention of being unkind, exclusionary, hurtful, or existentially ugly. If any comes across that away, I sincerely apologize in advance.
  • Related: for any item here that strikes you as irrelevant or dumb or wrong or antithetical to your own experiences and sensibilities, please consider that it may not be, as we say, for you. The reader is encouraged to ignore or reject items that match any of these unsavory criteria.
  • These are things that I have believed to be true for myself at the time of composition. They are not immutable truths about The Universe, and I am open to changing my mind about any of them at any time.
  • If you believe that it is possible to grow without change, you are probably neither growing nor changing.
  • Bulleted lists are a useful way to collect items that are either unrelated or may not benefit from being puffed into actual fancy prose.
  • None of this should be interpreted as actual advice of any kind or for any purpose, and, thus, it is provided as-is.
  • You should not rely upon this document or its contents for any purpose without seeking legal, medical, mental, spiritual and/or directed career counseling.
  • No glass containers, coolers, or inflammable materials are permitted. No motorcycles after 3pm.

The Management


The Wisdom So Far

  • Sometimes, an email is just a way to say, “I love you.”
  • People think about you much less than you either hope or fear.
  • It’s often easier not to be terrible.
  • Whenever you’re not sure what to say, either say nothing, or ask a question.
  • Be sparing in how often you tell someone their negative feelings are wrong; it rarely helps a sad person to be told that they are also a liar.
  • Related: feelings are real.
  • Never organize anything you should discard.
  • As you cross the street, notice which car’s driver feels most likely to do something stupid or dangerous. Walk a little slower, turn your head, and make direct eye contact. Brains cannot help but notice faces, plus eye contact startles anyone into suddenly remembering they live amongst other actual people.
  • Related corollary: navigate an urban sidewalk by avoiding eye contact. Not because you’re anti-social, but because eyes tell you very little about where your fellow pedestrians are headed. Monitor feet and footsteps for imminent direction; unfix your gaze ~two head-heights above the crowd to detect emerging patterns.
  • If the thing you’re cooking doesn’t smell or sound like food yet, it’s probably not food yet.
  • Buy slightly larger shoes.
  • Say hello to every dog.
  • Always wave at children on trains.
  • Flirt with all elderly women.
  • Tip more.
  • Look for the chimneys.
  • Keep moving and get out of the way.
  • Never give advice to a pregnant person unless they specifically asked for it.
  • Never touch a pregnant person unless they specifically asked for it.
  • Never tell a pregnant person horror stories about childbirth unless they specifically asked for it.
  • Stop correcting people by immediately telling them what they “should have said.” You are not helping.
  • When you’re feeling awful and aren’t sure what to do, pretend you are the person you love the most, and give them your best advice.
  • If you see someone photographing a group, offer to take the photo for them so they can get in the picture. Please do not steal their camera.
  • Related: When you shoot a group photo, always take at least five shots from at least two angles. For the last couple photos, say: “Everybody say ‘BUTTS!’” You will instantly get many totally natural smiles, plus you just gave them a fun story.
  • In photography—as in life—always keep the light behind you.
  • Sometimes, a person will confess something embarrassing that obviously makes them feel really dumb and vulnerable. That is never the time to say “I told you so,” and it is rarely the best moment to offer advice that they never asked for. Just shut the fuck up and listen.
  • If you have a small household responsibility—no matter how lame or quotidian—just do it now and without being asked. If you think the trash may need to go out, do not “check” to see if the trash needs to go out. Just take out the fucking trash. And quit reminding everybody you took the trash out. This is not Vietnam, and you are not a forgotten hero.
  • Related: the greatest curse of the middle-aged American man is the persistent belief that he is inadequately appreciated.
  • Do not ask someone if they want a glass of water. Just bring them a glass of water. Everybody likes being given a glass of water.
  • Buy the nicest screwdrivers you can afford.
  • Every few months, take at least one panorama photo of your kid’s room. At least annually, secretly record your kid talking for at least ten minutes. I promise you’ll treasure both, and then you will curse yourself for not having done each way more often.
  • Most well-written characters have something they want—or something they think they want. The more fascinating characters also have something they don’t want you to know. The best ones also have something they’re not pulling off nearly as well as they think.
  • Related: These are each also true for real people.
  • Try always to store something in the first place you just looked for it. Not “where it’s pretty” or “where we used to keep it” or “where we have more room.” It goes where it goes—not where you think it goes.
  • Almost every task in life benefits from the addition of a nearby trash bag.
  • Just because you know something doesn’t mean everybody knows it. Every day, somebody’s born who’s never seen The Flintstones.
  • If an item is very precious or valuable to you, never set it down anyplace that you wouldn’t want it to be overnight.
  • Call people what they’d like to be called. And, don’t be a dick about it.
  • Constantly ask yourself: do I want to be right, or do I want to be happy?

  • Every project is a triangle made of time, money, and quality; shortening the length of one side necessarily lengthens one or—more often—both of the other sides.
  • Less well known is that we each tend to blow it hardest in estimating the sides of the triangle we least understand or respect.
  • Kindly note that the grave existential truth of the Project Management Triangle is non-negotiable. People hate this. Which is normal.
  • If the person with whom you are negotiating finds it difficult to provide a decisive budget estimate for their project, ask them to try and situate it between two orders of magnitude. As in, “How many zeroes are we talking about here?” Quickly discovering that your ballpark figures are 2 to 6 zeroes apart can save you both a lot of time and frustration.
  • Related: if the client’s estimate for any given aspect of the project feels poorly thought out, mentally double the estimated budget for money and time. At the end of all estimations, add at least another 20% to the time and budget. You’re gonna need it, and, boy, are you ever going to earn it.
  • Related: have you leavened your estimate of the project with your hunches about the credibility of the client? Have you accounted for human foibles and flakiness in your estimate?
  • When estimating the time it will take to do anything involving a child, add at least ten minutes per child. Make that 30 minutes for kids under five or over twelve.
  • Always have a twelve-pack of Diet Coke and a good quantity of unflavored fizzy water. A lot of people love one (or both), and most of the people who do drink a lot of it.
  • Whoever wants the meeting most usually holds the least power.
  • Archive any email that’s older than 30 days. If it kills you to archive a given email, immediately turn it into a task, and then archive it.
  • Most team culture comes out of a combination of what is tolerated and what is rewarded. If you legit want your culture to improve, change what you reward and rethink what you will tolerate.
  • Any Slack is only as good as the guy who always has the latest post. (And, it’s nearly always a guy.)
  • Avoid any children’s movie whose theatrical trailer includes more than one fart or butt joke. That’s their idea of the best parts of the movie.
  • If you don’t remember what an app does, you can probably delete it.
  • If you don’t remember what a cable does, you can almost definitely discard it.
  • The earlier a kid is around books often (and in any way), the earlier and easier their life of reading will go.
  • Any time you locate a piece of digital information you were hunting for, tag it something like, “#OutboardBrain.” Chances are you’ll want to find it again, and chances are you’ll definitely forget it again.
  • Avoid vegetarian dishes that struggle to recreate a recipe that’s typically based on meat.
  • In any large retail store, choose the line that’s mostly young people who are by themselves.
  • Always make all the bacon.
  • Never try to bribe someone unless the amount you’re offering them feels ludicrously high.
  • If you really want a glass of water at a restaurant, always order that first. As you do this, look the server in the eyes and nod.
  • You’ll probably need to listen to at least three episodes of a podcast before you will know if you could really love it.
  • If you want an honest opinion, ask for the second superlative. For example, if you want a thoughtful answer about someone’s job, ask them their second-least-favorite thing about it.
  • Avoid any food whose name has been altered for legal reasons.

  • Sometimes, people ask you how you’re doing when they’re especially concerned about how they’re doing.
  • Stay focused on the outcome, not your original strategy. Viz.: if you’re looking for a USB cable, don’t fixate on finding a specific box that might contain a specific USB cable. Just find a goddamned cable.
  • Related: when you get stuck and frustrated about how to solve a problem, stop, take a breath, and ask yourself, “What am I actually trying to accomplish here?” Because, that’s the outcome on the other side of a new and less ambiguous strategy.
  • Before you freak out about how you are feeling right now, ask yourself how much (or how little) you’re having of sleep, food, sex, water, exercise, alcohol, drugs, sunshine, human touch, family time, and probably some other stuff I don’t know of but you definitely will.
  • Whenever you need to carry two seemingly identical things (like, drinks or toothbrushes or what have you), always—and only—ever carry the one that’s yours in your right hand. When you pick up the two items, always mutter aloud to yourself, “I’m always right.” Because, now, you are always right.
  • After you’ve had two alcoholic beverages, begin alternating with equal amounts of water. If you have more than five drinks, change that ratio to two-to one in favor of water.
  • Dinner parties and most large group meals are not really about eating. They’re mostly about easy socializing. So, if you get weird when you’re hungry, eat before you arrive. It’ll make everyone’s evening more easy and more social.

  • Sometimes in life, even though it’s not your fault, it’s still your problem.
    (thanks, Marco Arment).
  • Being on time for things is a sign of character and respect. Adults who are pathologically late for things are unconsciously telling the world that other people’s time is worthless to them.
  • To clean out a junky drawer, remove the contents and put it in a box. Only when you’ve used one of the items in the box twice is it allowed to live in the drawer again. After a month, pitch or donate the remaining contents—or move the precious or useful stuff to deeper storage. But, yeah, you should probably just pitch it.
  • Never argue on the internet. No one will remember whether you won or lost the argument; they’ll just remember that you are the sort of person who argues on the internet.
  • Whatever your problem is, remember that before you can get better, you have to stop getting worse. Try first to stop getting worse.
  • Don’t let people tell you whether, when, or how to season your food. It’s your body.
  • Just in general: never explain food. Yes, I see the provided sauce. And, no, I do not need a webinar on how it should be deployed.
  • Whenever someone demands you change who you are, it’s useful to ask yourself what they stand to gain from you agreeing to become someone else.
  • To an anxious person, it often feels like the only way to achieve relaxed certainty is to keep seeking new information. But, remember that the more you know, the more you’ll realize you don’t know. And, then, you’ll usually just find yourself fretting about getting more and more information, et cetera. Incline yourself towards getting out of the information centrifuge.
  • Everybody grieves differently. You’re not the mourning police, and no one benefits from you telling them they’re being sad wrong.
  • “Experience” is rarely the verb you’re looking for. Reword your sentence with a more clear and muscular focus on what actually happened—and who or what caused it to happen. So, maybe don’t say “I am experiencing technical difficulties” if you really mean “I broke the internet.” You’re not fooling anyone.
  • Related. Please don’t say “impact” (v.) if you just mean “affect” (v.). It makes you sound like a lame PowerPoint about dentistry.
  • Few journalists get to choose the headline for their piece. So, whenever the clickbait of a terrible, search-engine-optimized headline belies an actually-good article, consider getting mad at the editor. Not the writer.

  • You are not obligated to have a strong opinion about everything. Get fewer opinions about way fewer things, and then strive always to interrogate the basis of your strongest opinions. This is very difficult, so be grateful if you’ve found fewer strong opinions to interrogate.
  • Priorities are like arms. If you think you have more than a couple, you’re either lying or crazy.
  • If you’re struggling to understand someone’s behavior or motivation, understand that it’s usually because of money, fear, or both.
  • If you have cool stickers, use them. Put them on things. Be carelessly joyful about using your stickers. If you die with a collection of dozens of cool stickers that you never used, you did it wrong.
  • Whenever you meet someone new, ask them what they’re most excited about right now. Everyone interesting is excited about something right now, and they’d probably love to tell you about it.
  • Related. When you meet a child, ask them if they would share the coolest thing that’s happened to them this week. You can also ask them about their favorite food. Kids love food and have many thoughts about it.
  • Whenever you’re considering escalating any relationship, ask yourself whether you’d be okay with getting ten times more of them. In other words, consider whether a lot more of “how they are” is a thing you really want to pursue.
  • Take a walk in a place that has lots of leaves and grass and other natural, irregular patterns. It stimulates dopamine, plus you should probably be walking more anyway.
  • Related. This is why the carpeting in casinos and hotels has such whackadoo patterns. They’re squirting your brain parts with free happy juice. From a scientific standpoint.
  • Once you’re seated, always order a large pepperoni pizza for the table.

  • Treat every person you encounter as though they are having a way worse day than you.
  • Related: ask yourself how you might become the least annoying stranger that a given person met today. If you became the subject of a private anecdote, how great would you feel about hearing it?
  • If you’re not sure what you want, it’s almost definitely more sleep.
  • Your kids are not little versions of you; they are little versions of themselves. So, don’t be sad or alarmed whenever they are becoming something different from you. Because, they will become lots of things that are different from you, and that’s arguably the whole point. It is inarguably a thing that you need to cheerfully celebrate and support.

  • If you have trouble keeping up with washing dishes, cutlery, or cooking stuff, you probably have too much of them.
  • Be mindful about giving gifts. A gift you give with any expectation is a burden, and people rarely enjoy being given a burden.
  • In thinking about optimizing how you work, try to distinguish between the parts of your job that are necessarily difficult versus the parts that are harder than they actually need to be. The former is the reason that you get the big bucks, and the latter is the reason why you may often feel like the bucks should be bigger.
  • Be gracious when someone points out a dumb error you made. Especially when it comes from someone whom you respect. They’re doing it because they like you, and because they pay attention to stuff that you do.
  • Related: To bad faith actors, you may wish to say something like, “You might just be right” or, “Yeah, life sure is pretty complicated.” Answers to bad faith can and should be extremely personal.
  • Use shoe trees. It’ll make you feel like a fancy duchess, plus it’ll make your shoes last a lot longer.
  • Bring along an extra pen that you like.
  • Buy supplies before you need them and gadgets after you need them.
  • Three is two, two is one, and one is none.
  • Related: change the toilet paper before the roll runs out. There is no reward for using the last slice, and, also, you are not seven.
  • Always have fresh lemons around.
  • Write down the travel items that you forgot to pack while you’re still traveling. You’ll never remember them once you’re back home.
  • Order more appetizers and fewer daily specials.
  • If you want something in life, consider just asking for it. Your friends, clients, and romantic partners are probably not mind-readers.
  • Related: if you want a sex thing that you think is a little weird—and your partner is a healthy adult—just tell them. They probably want a weird sex thing too, and if you could just give a special thing to each other, how cool would that be?
  • Be circumspect about which strangers are allowed to alter your mood.
  • Change the soap in your shower way more often.
  • Listen to a record you liked when you were fifteen.
  • Take more photos and videos that include the faces of people you love in them.
  • Write at least a paragraph a day. Of something.
  • Throw out all shitty scissors.
  • Bring in your neighbor’s trash cans.
  • Talk to your pets, and remind them they’re not so bad—considering.
  • Close the door behind you.
  • Except: Always hold the door.
  • Say “thank you.” And mean it.

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