Who’s Listening?

Whenever you have the opportunity to speak, the most valuable ten seconds you can possibly spend isn’t spent on collecting your own thoughts or deciding what phrasing you want to use. It’s the ten seconds spent taking a quick mental inventory of who can and will hear you.

You will save yourself enormous headache and heartache by knowing who’s listening when you speak (or who’s reading when you write). Sometimes you’ll realize the answer is “nobody,” and you’ll save yourself time. Other times you’ll note that there are far more people within literal or figurative earshot than just your narrow target. All of these things matter, and they matter far more than just what you were so keen to express.

Just as you should never fire a gun without knowing what’s downrange, you should never speak without getting an idea of who’s listening.

The Old Wisdom

Innovation is good. If we didn’t invent new things, whether actual “things” or new ways to do things, we’d be in unlit caves dying as soon as we’re born. It’s easy to recognize that innovation is good, and innovation means carving out the new ways, and so it’s thusly easy to trick ourselves into thinking “new ways” are always good.

That’s a bad, bad trick. There’s a thing called “survivor bias,” which is where you judge whether it’s a good idea to do something based solely on the examples of the people who were successful in doing it. Every zebra on the other side of the river is fat and happy, so we should try to cross the river, too! That line of thinking ignores that four out of five zebras get eaten by crocodiles on the way over.

When you see a successful new thing, what you don’t see are the 999 other new things competing in that same space to be the best new thing in that category, all of which were enormous flaming disasters. The one left behind displaces the old, solidified way of thinking and turns out to be better, so we think “duh, of course, new is always better.”

Here’s the about that old way, though. The people who have been using that old way for a long time can usually tell you a lot about why a particular new way won’t work. But people ignore the old timers, thinking of them as relics of an antiquated way of thinking. Because those fools are stuck thinking that there’s one old way and one new way, and those are the competing methods.

But that one old way beat out 999 others to become the old wisdom. And your new way is just one of a thousand competing to do the same. The old timers, if you stopped to ask, can tell you where to put your bets.


What a scary, negative word – “ultimatum!”

I don’t mean it’s scary to hear one. For most people, it’s far scarier to give one. No one wants to be the big meanie that breaks the final relationship by giving an unreasonable ultimatum.

But look at that sneaky word – “unreasonable.”

It’s not unreasonable to explain your circumstances. If I say, “hey, I can’t make the meeting on Friday because my kid has surgery, so we either have to reschedule the meeting or I’ll have to sit out,” that’s not an ultimatum. That’s just me telling you what’s up. You can change the meeting or not.

Sometimes you have to bend around another person, and sometimes another person has to bend around you. That’s just life, not a series of ultimatums. So don’t be afraid to tell someone what’s what.


Any sufficiently complex system can be gamed. Often, that should be your goal.

When I was in 7th grade, my math teacher told us on the first day how she was going to grade the class – what things counted for what percentage of our grade, etc. I studied that more intently than I studied any other piece of math in the entire class. I figured out that as long as I maintained a 90% average on tests and got a checkmark every day for class participation, I wouldn’t have to turn in a single homework assignment for the entire year and I’d still get an A for the class.

Sometime around halfway through the class, my teacher called me in for a one-on-one. She expressed concern that I simply hadn’t done any homework all year. Her exact words were “you’re barely getting an A.”

Most of the kids in the class who worked very diligently on the homework also had a 90% or better test score average and participated in class every day anyway, so they were gaining nothing from doing more work. Some number of kids scored low on the tests but diligently did the work; as a result, their test scores improved. That was good, but if their test scores hadn’t improved, the homework wouldn’t have helped them get a good grade. So it seemed to me like the system was working as intended: if you needed to do the homework, you should do it. If you didn’t need it (as evidenced by getting good grades on the tests anyway), then there shouldn’t be a penalty for not doing it.

It seemed to me, in other words, that my teacher had deliberately designed the system to work this way, and for some reason, no one else in the class had figured it out. Why else would she have told us how she graded at all?

It turns out I was very wrong about how the world worked. She told us which things were worth points not so that we would carefully balance our efforts, but so we’d do everything on the list.

That’s counter-productive nonsense, but it also turned out to be how most of the world operates.

Most of the world presents you with a system and then expects you to jump into the spirit of that system with both feet, regardless of whether you agree with the intent or whether you gain anything by doing so.

If someone puts a cage around you, they want you to stay in it. But if the bars are so widely spaced that you can walk through them, you should do so. You shouldn’t stay in a cage you can escape just because someone else wants you to.

You should consider all rules as requests, and you should consider all the pros and cons of obeying. You should figure out what’s actually worth points (and how many) and what isn’t. And then you should make your own decisions. But understand the system you’re in first!

Immediate Physical Impact

When I was young, especially in my adolescence, the advice I received about my physical health was spectacularly bad. Not because it told me to do bad things (although let’s not talk about the Food Pyramid…), but because it was always presented as a long-term thing. “You need to make these healthy choices in order to live a long life or avoid heart disease in your fifties,” things like that. That’s not especially compelling to a 15-year-old, and so it often got ignored.

I wish I knew then what I know now, which is that the actual impact of healthy choices is that they make you feel immediately better.

Like, try this: drink a big glass of water, do ten pushups, and then relax for ten minutes in the sun. That’s a total of 15 minutes, tops. You will feel absolutely amazing all day.

The long-term impact is just a bonus.

Writers & Editors

I used to think that needing an editor was a sign that your writing was terrible. I viewed all edits as criticisms – harsh ones. If my writing was good, I wouldn’t need to change it. And if you were any good at writing, you’d be a writer instead of an editor!

Poppycock, of course. These are totally separate skills. Creative ideation and thoughtful execution are totally different in any context. But at the same time, there are some misconceptions – just like I had.

First, creative ideation isn’t better than thoughtful execution. People get that wrong all the time. It’s like saying the left wheels of a car are better than the right ones. Neither is better because you need both.

Second, these things aren’t always separate. Some people really can both write and edit their own writing. Some people can’t do either. Some people are 80/20, or 30/70. The myth that everyone is always exactly one of those things is fiction.

And lastly, there’s a pervasive myth that being good at one or the other correlates perfectly with enjoying one or the other, and also in turn correlates with all sorts of other personality traits. Creative writers love creative writing and are all artsy hippies, while all editors are nerdy accountants who love sharpening pencils.

Here’s really the only thing you really need to know: both are valuable, and if you’re primarily one of them you should value the other. Creative ideation and thoughtful execution combine to make great things, but they don’t substitute for each other. Find your mix.

The Fire Alarm

It isn’t your job to put out every fire you ever see. But you shouldn’t feel like you can’t pull the fire alarm.

When you see a fire, your first instinct is probably to either ring a bell or put it out, depending on the kind of person you are. Even if you’re a natural problem-solver, some fires will simply be out of your ability range, and you’ll alert the experts. But what would you do if the experts yelled at you?

What if they told you to put it out yourself, and stop bothering them? What if they blamed you for starting the fire? Well, you’d rapidly learn to stop pulling the fire alarm. Unless it was your problem directly, you’d at least hesitate next time, wouldn’t you?

We want people to alert us to problems. We want people to act as our early warning systems, but they won’t do that if we punish them for it. So if someone brings a problem to your attention that truly is your problem, don’t get upset with the messenger. They did you a favor.

And if you’re on the other side of that, remember – there will always be people who will appreciate you pulling the fire alarm for them. Those are the relationships to cultivate. They’ll do the same for you.


Why do we get distracted? I’m not talking about a sudden loud noise that makes you look up from your book. I’m talking about the longer, more enduring distractions – those that plague our days or even years.

What mechanism in our brains causes it? I want to work on a particular project – so why do other parts of my brain compete for control of the whole vessel? What disagreement do they have?

Some part of that mechanism must be something that was once helpful. Certainly, losing yourself in some delicious berries in the savannah may have made me vulnerable to tiger attack, and so different parts of my brain would have kept pulling my attention to my surroundings. If that’s the case, then is distraction no different than fear – a voice to be recognized and thanked, but ultimately unheeded?

That might be a paradigm to help me focus. It helps to not be afraid if you consider that the source of your fear isn’t the object of your fear, but rather your own brain. Likewise with anger – outside things can’t make you angry, they can only give you something to be angry about, but the choice is yours.

So perhaps distraction is no different! It’s my brain asking me to look at something else, not the thing itself. I can politely say, “Hey, thanks for keeping me alert for tigers and stuff, but I’m good. I’m gonna work on this for now.”

Perhaps you can, too!

How to Follow a Lead

When you’re learning about a new topic or engaging in the “scavenger hunt” that leads to new knowledge, you will never complete the journey in one step. You will have to iterate multiple times, moving closer to your goal in an often zig-zagging series of incomplete steps.

Since people would often rather complete a goal in a single (even very difficult) step than many smaller ones – especially if those smaller ones are uncertain in their efficacy – people have a tendency to be bad at recognizing this process for what it is. They get frustrated. And this leads to the inability to follow leads effectively.

For instance, let’s say you’ve moved to a new city, and you’re trying to find a new job in your line of work as a chef. Your new roommate says: “my sister is a hostess at an upscale restaurant downtown, you can go talk to her.” This is a lead.

What most people do with this lead is waste it. They go to the restaurant, sure. They talk to the roommate’s sister, sure. And they try to solve the problem in one single step by asking: “are you hiring chefs?” The roommate’s sister says sorry, they’re not right now. They say “okay, thanks anyway,” and then they go home. They go back to where they started, as if they hit a dead end. They keep looking, but they look from square one, asking people they know or looking in the want ads, etc.

Here’s how to follow a lead in an effective way!

  1. Recognize that all new information gives you a new starting point. Untether yourself from your starting position – the goal is always movement. There’s no such thing as a dead end, because all information is connected to more information.
  2. Adopt two personality traits during your search: Radical Honesty and Pleasant Gratitude. Be extremely candid about why you’re asking, give enough information for others to spark creative ways to help you, and be extremely grateful for every second of someone else’s time. Even if you’re not terribly creative yourself, this will often drive you along the path of knowledge. When the hostess says they’re not hiring, say: “Oh, thanks so much for letting me know! I’m new in town and I was a chef back where I’m from, so I’m looking for work again now that I’m here. I don’t really know the local restaurant scene like I did back home and don’t have many connections out here yet. It’s great to meet you!”
  3. Use your new starting point to find out anything you didn’t know before. You might think you’re looking for a specific piece of new information (like, “where is my next job”), but you don’t know enough yet to figure out which rock that information is under. So don’t be picky about rocks! And the best source of information is people. Ask who else to speak to, remembering the personality traits from #2. “Hey, before I go, do you think it would be okay to meet the chefs on your team? Like I said, I don’t know anyone at all out here and it would be great to have some connections.”
  4. Follow the other threads (that aren’t people) later. If you meet those chefs, ask each one where they worked before this. Ask them where they like to eat. Ask them anything. Many of those potential sources of new information won’t be people, but all sources of information are connected to people in some way. The restaurant where one of the chefs used to work isn’t a person you can question, but it has people that work there.
  5. Repeat & iterate. Go through it again. Look at all the new leads you’ve generated. There are no dead ends.

If you treat every question that doesn’t give you your ultimate answer as a failure, then you’ll forever be asking only the first question, over and over. You have to let your search develop down the path. Do that, and you’ll never run out of ideas.

The Space Between Minds

In your mind are truths. There are also many falsehoods and uncertainties, and you’ve got to sift out the truths in order to communicate them. This is an imperfect process.

Then, you have to convert those truths which you’ve found into words, written or spoken. Those words must carry the truth of your mind, but you won’t always know the right words or exactly how to put them together, nor be able to do so flawlessly. So this too is an imperfect process.

Then other people need to perceive those words. People’s perceptions are notoriously biased, applying filters to all information based on mood, heuristics, or even simple error. So the process of another person’s interpreting your words which carry your truths is (you guessed it) imperfect.

Then that person’s brain has to take that perception and find a place for it within their own mental model of the universe. Along the way, it may be bent or reshaped in any number of ways in order to fit in with the other truths (not to mention falsehoods and uncertainties) in their own mind. So converting your truth from their perception to their memory is of course very imperfect.

Lastly, in order for your attempt at communication to have been truly considered successful, the person receiving your truth must convert this new information into action – they must walk differently in the world based on what they’ve learned. The action they choose will be based on so many factors that your initial intent probably accounts for less than a percent of what they actually do; thus, this is as imperfect a process as you can imagine.

And yet, people get frustrated when they say something and the other person doesn’t immediately react perfectly.

Look at the journey your ideas must take! And when the other person doesn’t dance instantly like a puppet on the string of what we believe to be truth, we blame them. As if their actions had only one true purpose: to annoy us.

Look, you can’t build a bridge across a river by throwing bricks at the other side. It’s a process, and it’s a very difficult one. Respect it enough to improve it. Work diligently, work with a plan, and do not ever expect perfection – only improvement.

This is the truth of my mind. I wonder what it looks like by the time it reaches yours?