Be very careful with your assumptions about the complexity level of future tasks. Especially other people’s tasks.

Being able to accurately predict how simple or complex a task will be in advance is an incredible skill. It’s difficult to master and few people have it, though most think they do. The fact that most people think this skill is simple, when it isn’t, is actually about everything you need to tell you how complex this skill really is.

Many people overcompensate by just assuming everything will be ten times harder, take ten times longer, or cost ten times as much juice as they initially assume. That’s safer, but “safe” isn’t the goal. The goal is “accurate.”

This is a really helpful skill not only for your own time management, but because a huge percentage of our interactions with other people involves asking them for stuff. Accurately predicting the costs of the favors we ask and the tasks we assign goes a long way towards keeping those relationships healthy and getting the stuff you want.

A co-worker was looking for some ideas today on a project, and I offered an idea that I thought would be simple to implement and have a big impact. Unfortunately, the subject was pretty far out of my wheelhouse and my co-worker (very kindly!) informed me that implementing this idea would require entirely rebuilding our website. So, uhh… yeah.

Of course, there’s no bad ideas in brainstorming, so I definitely don’t regret offering up the suggestion (and in true brainstorming fashion, someone else took the idea, turned it into another idea, and off we went). But the point remains that you can think something will be very simple and it turns out that it’s wildly complicated.

The reverse can also be true. You might think something will be wildly complicated, but it turns out it was pretty low-cost. This is the heart of a lot of procrastination – you put off a task because you think it will cost a lot of juice, but if you had been accurately able to predict its simplicity, your negative emotions about it would have been lessened and it would have been done already.

I don’t necessarily have a magic method to get better at predicting something’s cost in juice, either for yourself or someone else. But I can give a few tips.

One, ask. Especially if other people are involved, ask them what they think the cost will be. Trust their answers as being honest, even if they also might be wrong. If you don’t like the answer, don’t disagree with it – find out what you can do to change it. If your mechanic tells you that your car will take 2 days and $1500 to fix, they’re probably right, but even if they aren’t, arguing won’t help. Instead, ask what you can do in the future to take better care of your car.

Two, be honest with yourself when you’re wrong. You took on a project thinking it would take a day, and it took two weeks. Our natural inclination is to punish ourselves for the wrong thing – we think that the fault lies in our work. If only I’d been smarter, or worked harder, etc. But the reality is that it was always a two-week project, and your flaw wasn’t in your work ethic or intelligence, just in your ability to predict that. Don’t be hard on yourself for the wrong thing. Go back and look at your initial prediction, and see which things you didn’t see then. Adjust your expectations in the future.

Three, try to make your predictions visible and recorded. Don’t give yourself or others tasks that don’t have a predicted cost in time, effort, juice, what have you. Call your shot publicly and be open to feedback. Don’t say “I’ll do this project for as long as it takes,” and then when it takes a month say “I always knew it was going to take a month.” That doesn’t improve your accuracy. Giving yourself a yardstick to actually measure against is a good way to be right about more stuff.

It’s a long journey, but it’s worth it. The ability to see into the future always is.

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Turn Up the Volume

A reader of my blog asked me today if I ever feel like something I’ve written isn’t good. Clearly I answered “No, I have 100% confidence in every single word of every single post; this blog will eventually displace Emerson and Shakespeare together in the annals of human wisdom.”

Hahaha haaaaaaaa. No way. I think 40% of what I write, at least, is hot trash.

But that’s okay! Because it used to be 80%. Plus, there’s a big benefit to committing to producing content every day – it doesn’t all have to be gold.

See, when you write a lot, you lessen the weight that any single piece has to carry as a representation of who you are. If one of my posts is less than stellar, that’s not going to make me a bad writer or not have anything worthwhile to say. If any one piece doesn’t appeal to you, there are hundreds of others if you’re interested.

That also means I can test ideas more freely. Because I don’t operate in a framework where every post has to be an absolute home run, I can feel free to speak my mind. Ideas strike me and I like to explore them. Exploring them is how I discover if they’re great or not, and this blog is my means of that exploration. That means naturally some of my thoughts will be incomplete or misguided or flat-out wrong.

And often not the ones I expect! Sometimes I start a post and genuinely expect that it won’t be very good, but I’m committed to writing anyway. And then that post will turn out to be one of the better ones. That’s happened more than once.

Being nervous about writing because you aren’t confident in it yet is looking at the skill in reverse. Practicing something is how you get good at it; you can’t get good before you practice. If you’re not good at something, do it all the time – turn up the volume.

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Pros & Dealbreakers

I think the traditional way we think about comparing “pros and cons” is wildly incorrect.

The traditional way is this: we make a list of pros and cons, and whichever list has more items becomes our yes/no decision. I see a LOT wrong with this strategy.

First, not all items are equal. Let’s say I’m putting down the pros and cons of robbing a convenience store. “Pros: 1.) Pretty easy. 2.) Pretty fast. 3.) Would get like 30 dollars. Cons: 1.) Will go to jail for 5 years.” Well, only one con versus 3 pros! Guess I should do it!

Second, even if you were objective enough to only write exactly equally-weighted pros and cons, they don’t cancel each other out. Something could have lots of cons but still be something I want to do; those could be costs I’m willing to pay. Conversely, something could have lots of upsides but not be worth the price to me.

And lastly, something that has a lot of items in each column is probably not getting any clearer for you if you write them out. Because just listing a bunch of things doesn’t solve the hard choices that the first two problems present!

Let me propose an alternative method for you to use whenever you’d be tempted to use a pro/con format. I’ll call it “Pros & Dealbreakers.”

First, before you even start evaluating a potential course of action, list the top three things that would make you say “no,” no matter what potential upsides there might be. No matter what the “pros” are, for example, I won’t put my family’s well-being at risk. I won’t break my moral code. I won’t commit to spending more than $500 up front. There, those are my dealbreakers.

Next, set yourself a “pro” threshold – let’s go with 5 items. Start listing good reasons to do the thing; possible upsides, definite benefits, etc.

If you can get to 5, and The Thing doesn’t involve any of your dealbreakers, just do it.

5 good reasons is plenty to do a thing. Sure, you could probably come up with an equal number of potential bad outcomes if you wanted to, but so what? That’s another problem with the pro/con system – if you’re a pessimistic or risk-averse person in general, you can always come up with plenty of cons.

Life is full of potentially bad outcomes, but the worst one is never doing anything. If you can come up with 5 good reasons to do anything, do it.

Defined by the Negative

There’s no word for “not a murderer.” “Murderer” is the word we use to describe a person that kills others in cold blood, but we don’t have a word specifically for someone who doesn’t do that. That’s a good thing! Having a word for something generally means you need a word for that thing, and I like living in a world where we don’t have so few non-murderers that we need a specific word to differentiate them from everyone else.

The broader point is that you shouldn’t label or define yourself by what you don’t do. Take veganism, for example. I support anyone making ethically-driven choices along their own value lines. That part is fine. But if your moral system gives animals enough moral weight to be worthy of not being murdered, not murdering them isn’t really doing anything special. It’s the same as me not murdering humans. It’s literally the least I can do; it’s not praiseworthy by itself.

If you think lots of people are doing something that contributes to a problem, then not contributing to that problem isn’t good; it’s just neutral. You’d have to identify the problem itself and take active steps towards solving it in order to be doing “good.” In other words, good is defined by the positive action, not the negative space between actions.

If you’re not part of the solution, then (maybe) you’re part of the problem. But not being part of the problem doesn’t make you part of the solution. That’s it’s own thing.

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I’d like to talk about an unhealthy behavior pattern I often witness, and offer some advice on how to remove it.

Here’s the unhealthy pattern: I see people who have a decision coming up afraid of the information-gathering stage as if it represented a commitment.

Let me be more specific with some examples. Let’s say you need a new car, and you’re anxious about the decision. Buying a car is a reasonably “deep” decision for most people – it represents a decent amount of money, is a decision you have to live with for a reasonable amount of time, and has many factors. Being a little anxious about such a decision is perfectly natural. But what’s unhealthy is if you avoid test-driving a car because you’re anxious about the buying decision.

I see it all the time from many people. They don’t want to go to an open-house, an interview, a test-drive, or an informal first date – because they’re nervous about the ultimate decision. But those things aren’t the decision itself; they’re the pre-decision checklist. At that stage, you haven’t made a decision yet, you aren’t committed to anything, and you still can change direction at any point.

Here’s the advice: Don’t make any decisions in the pre-decision stage.

“I don’t want to test-drive an SUV because I heard they’re hard to handle.” That’s the point of a test-drive.

“I don’t want to go on this interview because I don’t think I’d like a job in finance.” That’s exactly why you should go, to find out.

“I don’t want to look at houses in the north side because I’m worried they might be too expensive.” It doesn’t cost you anything to read a price tag.

Gather information first. Write a report to yourself if you have to. Be comfortable with the powerful phrase: “I’m not ready to make that decision yet, because I don’t have enough information.” Have a plan to get the information you need, and then go.

But don’t be afraid of what you don’t know yet.


I heard someone say recently that the ability to follow instructions accurately is probably worth at least a few million dollars to you over the course of your lifetime. I think that could easily be true.

Tonight my oldest daughter and I followed a recipe from a cookbook. We went shopping together, with her doing all the math to convert package sizes to measurements the recipe called for (and doubling it, because we were feeding twice as many!), picking out the ingredients, and even suggesting creative alterations. But following the directions was the core.

Then we sat down and made it together. She directed and did most of the work. I never read the directions to her, though I occasionally asked her to repeat something if it seemed like she was off track.

The end result, I’m proud to say, was a huge success. The ability to convert information into results is a powerful one, and she’s got it.


No one is good. Some people are getting better. No one is smart. Some people are learning. No one is kind. But some people are trying, Ringo. They’re trying real hard.

My point is that no one is their ultimate self. We exist only as journeys. We don’t get a lot of time here; throw a handful of confetti in the air to celebrate your arrival and by the time it settles to the ground you’re gone. You have so little time to do anything, so contentment seems so out of place.

I don’t care which thing you do. Which thing you’re trying to improve or get better at. The beauty of the wide world is that there’s someone doing everything. And I can find something to talk about with you, some moment to share, no matter what it is – seeing people grow and strive and try and succeed is one of my favorite things. It’s certainly my favorite thing about being a parent; kids are doing this at light speed all the time.

But I find I have so little to talk about with people who are content. I’m certainly envious of them, in a way. I don’t think I have the capacity to be like that, even though it seems very nice. My entire means of communing with the world is trying to help people – I feel like I have nothing to offer to people who don’t need help. Once someone is successful, I seldom stick around to share the enjoyment of a job well done. I don’t really know what I’d do.

I think the most valuable connections we forge are the ones of shared trajectory. Of mutual help. That’s my incredibly selfish reason for trying to help people where I can – because seeing the best in another human is where I see the best in myself. There are probably all sorts of deep issues there with my need to feel needed or something like that, but I’m certainly not qualified to grapple with those.

But I’m trying, Ringo. I’m trying real hard.

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Happy to Help

I received three separate emails today, all of which were solely written with the purpose of thanking me for having helped them.

It’s me who should thank them. I sometimes wonder what I have within me to give to the world. I often worry that I can’t ever do enough to erase the weight of all the mistakes I’ve ever made; if any of us can. In our youths we burden others constantly, make their lives harder – intentionally or unintentionally. We incur a debt that we must repay with good deeds.

There’s really only one good deed you can do. Life throws many burdens at all people; lightening them, even a little, for another is the coin you use to pay down your balance.

If I helped, even a little, then I made a deposit against my own balance. For the opportunity to do so, I sincerely thank you.

Answer, Then Ask

Any time you want to ask someone a question, you should know the answer you’re looking for.

That doesn’t mean you know the content of that answer. That’s different. What I mean is that you need to know what you’re looking for. If you ask someone “Can you help me with this,” and they respond with “sure, how can I help,” then you sound like an awful dunce if you follow it up with “uhhh… I’m not sure.”

That’s not asking a question. That’s flailing for help.

Your questions, and the answers you’re looking for, should be as narrow as possible. First, because any time you ask a question you’re really both asking a favor and asking for their attention to even listen, and those are both big asks. But also because you actually want the help to be… well, helpful.

Give the person you’re asking all, but only, the information they need to help you. Catch them up with background if necessary, but don’t add anything that isn’t directly relevant unless they ask.

Sometimes you’re asking questions for reasons other than asking for new, helpful information. Sometimes you’re asking questions as part of an evaluation. I’ve lived inside the interview process in one way or another for some time, so I’m very familiar with this style, but it applies to any kind of evaluation, from first date questions to asking about a product you’re interested in buying.

A common mistake I see all the time is asking questions because they seem good, but not having any idea what kind of answer you’re looking for. Before you ask about a car’s fuel efficiency, ask yourself – do you have any idea what kind of answer you want? How to interpret the information you get? Before you ask a dumb interview question like “what kind of tree would you be,” make sure you have a framework to actually evaluate the responses (or, you know, don’t ask dumb questions).

Questions are good – you should ask many in your life. But ask them well; it’s a skill, like any other.

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Burn The Boats

There’s a story about Cortés and his campaign of conquest that I’d like to share. I’m not sharing it out of any endorsement of the action or anything, just because it’s a relevant story to what I want to talk about. Anyway, as the story goes, Cortés landed in Veracruz and wanted to start conquering, but the hearts of his men weren’t fully in it. After all, he wanted to commit them to a pretty extensive and dangerous campaign of bloodshed that totally wasn’t authorized, and he (rightly) feared that his men would retreat too early once the going got tough.

So once he landed and all his men were ashore, he burned the boats.

No turning back now!

In general, I think you should NOT emulate Cortés in like 99% of ways. But one important lesson you can draw here is that people with a fallback plan almost inevitably fall back on it.

If you want to accomplish something difficult, you have to remove any option to not accomplish it. You have to burn your own boats. Of course, unlike Cortés, you shouldn’t burn other people’s boats – only your own. But burn them you should!

When dealing with responsibilities, you should give yourself a safety net. It’s good to have savings, for example. It’s good to have health insurance. But if you’re trying to reach beyond your basic survival and really achieve something of your own volition, don’t give yourself the option to fail. Raise your own stakes. See what you’re really capable of.

Don’t like your job? Quit before you find a new one – you’ll be more motivated in your search. Don’t apply to a safety school. Climb that mountain without a harness. Okay, maybe not that last one. But if you did, I’d bet you’d be REALLY motivated to finish the climb!

Motivation isn’t everything. Ability counts. But motivation is what unlocks ability – without it, the ability languishes even if you have it. The fastest sprinters are chased by wolves.

Put a little more danger into your life, and see what happens.

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