Final Approach

How do you inspire others to challenge you?

My general demeanor is pretty confident. I don’t see much reason not to be – I might have plenty of self-doubt or hesitations, but those don’t provide me with any value if I express them, so I don’t. Even if you’re only 51% certain that a given course of action will be successful, once you’ve decided to act on it, you’d better act as if you were 100% certain.

One of my father’s great stories is about how he snuck into a concert without paying not by being stealthy or hopping a fence or anything like that. Rather, he found the employee entrance to the venue’s burger joint and burst in, loudly. He started shouting orders for people to flip those burgers faster, we’ve got hungry people waiting, those fries look done mister, go fill up the condiments! And then while everyone scrambled to obey his commands, he walked confidently out the front door into the crowd. Not only did he enter the concert, he probably raised production of the snack area by 10%.

The lesson that this story and so, so many others taught me is that with a truly insane level of outward confidence you can accomplish pretty much anything. You can will your desired place in the world into existence. The method works because the confidence becomes like armor – it keeps anyone from challenging you.

But sometimes you want to be challenged. Sometimes you need it.

See, the confident demeanor separates you from friend and foe alike. It keeps naysayers from dragging you down, but it naturally creates a sort of barrier between you and others. Even if your confidence is 100% friendly, and you never put anyone else down or give the impression that you’d use your powers for evil, it can dissuade people from approaching you.

“He’s so confident in his position, surely he won’t react well to someone disagreeing,” they might think. “Even if he isn’t argumentative or mean about it, he won’t budge. My opinions will fall on deaf ears. He might be great to lead people who don’t know what they’re doing, but I do know what I’m doing. In fact, I have information that would improve this process significantly, but there’s no way he’ll listen.”

That might be true or it might not be. But it’s 100% the signal you give if you act… well, if you act the way I do, let’s be honest.

I have thick skin, in a professional context. You could throw a pen at the back of my head, tell me to shut up, and erase my notes and start over, and as long as that was the level of discourse you’re comfortable receiving as well as dishing out, I’ll take no offense and in fact be thrilled at the bluntness. I mean, let’s solve problems, people! But other people have no way of knowing that. Egos can be fragile, and sometimes you challenge a confident person’s shtick and they lash out from wounded pride, resentful and vengeful. You’re probably right to be cautious.

But I don’t want that caution around me. My very presence can be silencing other voices, without a single conscious act on my part. I can welcome every single comment that comes my way, but still be discouraging them with the way I take over.

In the movie Pulp Fiction, there’s a scene where two of the main characters are in a real bind (to undersell the scene considerably), and they call in a specialist – Winston Wolf, who “solves problems.” He immediately takes over, giving curt orders and expecting immediate deference. When called on his bluntness, he explains that he’s there to handle a specific task and that time is a factor, so effectiveness in executing his expertise is more important than consideration of others’ feelings.

It’s a cool scene. And in a lot of high-pressure situations, I’m that guy. Calm under pressure, can act quickly and decisively, generally competent. What I’m absolutely terrible at is realizing that not every situation is like that. I’m not navigating an endless series of time-sensitive crises all the time, but I very much often act as if I am.

It’s not deliberate, and I’m definitely working on it.

But it’s not my strong suit.

What makes someone approachable? What signs about someone tell you: “this person won’t dismiss my thoughts and ideas, won’t be upset if they get challenged, won’t resent me for not following along?”

Another drawback of the Armor of Confidence is that I’ve never much had to consider how “approachable” someone is, because I’ll approach anyone. So I don’t really know what subtle signs one gives to assure other people that they are, in fact, not going to bite them.

Here’s what I’m trying to say: This goes on my Big List O’ Flaws. But that list isn’t carved on a stone tablet (I hope). It’s something to work on, and that work starts with reaching out. Like almost any problem in the world, you can’t solve it in your own head. If you had all the information required, it would already be solved. So this is my starting point for that research. I like my confidence, I like my, for lack of a better word, presence. It’s a trait that’s served me well. It’s armor against the world. But like armor, it needs to come off sometimes, and I’m trying to figure out when that is, and how to take it off.

Incentives at The DMV

In most actual businesses, “open until 4:30” means “we stop taking new business at 4:30, but we’ll serve everyone who was here before then, regardless of how long that takes.” Restaurants don’t always like it, but if they “close” at 11 they’ll seat you at 10:45.

There’s a good reason for this – those businesses have to care what you think. No matter what’s actually “fair,” the customer generally wins because the customer can – and will! – take their money elsewhere if they feel mistreated.

At the DMV, “open until 4:30” means “at 4:30 on the dot we go home, no matter when you got here, how long you’ve been in line, etc.”

At the organizational level, they have no reason to act differently. You have to use that service, and there are no competitors. No level of crappy service affects them in any way, so why change?

But even on a “trenches” level, I observe something interesting. When you come into a business at 5 minutes to close, the employees might stealthily roll their eyes, but they hustle. They want you out of there, so they can get out of there. 10 minutes to close at the DMV, they just stop working. They have no reason not to. They don’t have to clear out any queue before they can go home. They have no incentive, personal or organizational, to work hard.

Incentives matter, at every level. If you want a great life hack, figure out who’s incentivized to help you and seek them out. And figure out who has NO incentives to help you, and avoid them like the plague. Unless you’re forced, of course.

Who You Know

It’s virtually impossible that you don’t have a single person with a strong opinion of you.

There are people who are along for our journey in big ways for a long time – friends, loved ones, spouses, relatives. There are also many others who may have an intense relationship, but whose paths only cross ours for a short time. Co-workers, past loves, old bosses or clients.

We have a tendency to leave those behind without thought for how they’ll re-enter our lives, or if they ever will. We’re surprised when we run into an old friend or previous employer. But those people will leave a lasting impression for far longer than they’re directly interacting with you, and it’s good to not only be aware of that, but cultivate it.

Who do you know now that would likely remember you fondly? Have a good opinion of you? That person hasn’t been frozen in time since you last saw them – they’ve grown, developed, changed. They’ve gained wisdom and experience. If you liked each other then, imagine what you could do to improve each other’s lives now!

I like to imagine I’ve left good impressions on at least a few people who I haven’t seen in a long time. Every once in a while one of those people reaches out and it’s always a pleasant surprise. I’d like it to happen more, in fact.

Who could you reconnect with now? Who might you send a nice message to, thanking them for what they’ve done for you? This is a door that almost always contains something great behind it, yet we reach for so rarely.

And if you’re thinking to yourself that there are no such people – ask yourself why. Sow different seeds today, so that in a few years, you feel differently.

What To Say

My process for preparing for public speaking hasn’t changed much in 30 years.

First, I make sure I know what I’m talking about in general. It seems like lots of people skip this step, but I try not to end up in situations where I’m required to pontificate at length about topics of total ignorance for me. I truly enjoy speaking in front of groups, but I keep it to topics where my knowledge is both broad and deep.

Next, I bullet out my major points. Just to keep me on track, I make sure which core concepts I want to cover. If I want a reminder of a particular anecdote or analogy, I’ll jot one down, but usually I don’t write more than that in advance.

Then I’ll put down time blocks for each concept; how long to talk on each point before moving on.

Sometimes, right before a talk begins, I’ll get this small pang of anxiety – “What if my preparation was insufficient, and I’m not able to think of enough to say?”

I have this moment of anxiety despite the fact that this has never once happened to me in 30+ years.

The exact opposite problem is frequently the case. I have to check myself to make sure I don’t run over, ramble or digress. Despite the fact that this is something I almost always have to actively plan against, I have never once felt anxious about it the way I sometimes feel anxious about a problem that has literally never manifested.

I wonder why that is? Are my anxieties reflections not of what I think is likely to happen, but of what I haven’t prepared for?


Today’s going to be a bit of a departure from my normal routine. I saw something very interesting and I’ve been thinking about it pretty much non-stop, so I’m going to write my thoughts. I’ll warn you, I’m headed WAY out of my wheelhouse on this one, as you’ll see. But stepping out of your area of expertise is good on occasion, and I’m comfortable with being wrong or misguided as long as I’m thinking. So here we go.

First, the thing itself – a fantastic episode of Legal Eagle (as they mostly are):

If you don’t want to watch the whole thing, I’ll give you the basic spoilers. Back in the early ’70s, a couple owned a farmhouse in Iowa; a second home that was not where they lived. Because of its isolation, it kept getting burgled and the Brineys (the couple) were at their wits’ end. So Mr. Briney set up a shotgun trap in an upstairs bedroom where valuables were kept (this is in addition to countless locks, signs, etc.). The place gets robbed anyway by a guy named Katko, who gets his leg (mostly) blown off by the shotgun trap, and is in a cast/brace for two years. He serves time in prison for the breaking and entering, but then sues Briney because of the trap.

Spoiler: He wins. The Brineys had to pay not only his medical expenses, but also punitive damages equal to an additional 50% of the medical cost.

Now, here are my thoughts rattling around. I think the eventual outcome of this case was unjust, but not for what might seem like the obvious reasons. Basically, the reason the case was decided in the burglar’s favor was because it’s unreasonable to set up life-threatening booby traps in unoccupied homes. If there’s no inherent threat to life, it’s wrong to create a trap that could not only dis-proportionately punish guilty people, but also quite possibly injure or kill (relatively) innocent people, like perhaps kids just exploring an old farmhouse or something.

I do not disagree with that. While I believe that you have the right to defend your property, I also believe in the limitations set out above – the likelihood of harming an innocent third party being the main one. I mean heck, the place could have caught on fire and a firefighter could have been in there and gotten shot in the face; that’s bad. All sorts of bad outcomes could happen there.

That’s not why I think the outcome was unjust. The reason I think the outcome was unjust is because Katko should not be the recipient of any money.

The central argument used to win the case is that “booby traps are bad,” and so you should be punished for using them. Sure. But that punishment should be a criminal matter, not a civil one. If Briney owed a debt, it should be to society, not the burglar.

Think about it. Katko paid for his crime by serving time and paying a fine. But he didn’t pay the fine to Briney, even though it was Briney who was robbed. And he did his time in jail, not in service to the Brineys. But then he got paid for burglarizing the house (well in excess of the money he would have gotten from the stolen goods!), and that seems on the face to be a miscarriage of justice.

Katko was injured during an attempt to wrong Briney; both legally and morally. If Briney had been forced to pay a fine or even serve some time himself, I don’t think I’d have further complaint. But Katko deserved no recompense; his fate was the result of his own actions, and those actions were unjust. That’s the essential combo – a firefighter who got shot would also have been harmed “because of his own actions,” but those actions would not have been unjust.

Was Katko’s “punishment” in excess of his crimes? Certainly. Breaking & entering doesn’t deserve a lifetime crippling injury. And Mr. Briney was guilty of that. Even had the judgement been simply medical costs to make Katko whole, I might not think ill of the decision. But $10,000 in punitive damages to the man who was injured while robbing your home is clearly a miscarriage.

Or at least, I think so! I’m about as far from a legal scholar as you can get, wandering far, far afield of my normal thinkin’ grounds. But that’s fun – even more so because I’m not emotionally invested in this line of thinking, and thus am wide open to counter-arguments, other thoughts, fun debates, and the like. Have a different opinion – or even a fun other thing I should watch? Let me know!

Owls & Alligators

A grade or so ago, my daughter was given a little quiz at school. She was shown a piece of paper with pictures of four animals, and told to determine which one was not like the others. The animals were an eagle, a pigeon, an owl, and an alligator.

My daughter, I kid you not, said the owl. Why? Because it was the only one that’s nocturnal.

Lesson One: My kid is amazing.

Lesson Two: Nothing is actually the same as anything else; I could find a reason to choose any one of the four. A pigeon is the only seed-eater. An eagle is the only one that’s a patriotic symbol. Those kinds of questions, and their assumed answers, tell us to look for the obvious; to take the easy path. “Alligator” is the answer that requires the least thinking. That quiz also tries to tell us that things that are mostly the same should be categorized together.

Look, I get that I’m over-analyzing this. I get that the real point of the quiz is just to teach kindergartners that there’s a difference between birds and reptiles. But honestly, I don’t think that’s nearly as important of a lesson as teaching them that we can find differences – and therefore similarities – in anything.

That lesson has far wider-reaching applications. Honestly, I’d rather my daughter grow up not knowing the difference between bird and reptile as categories than have her thinking that just because three things look the same, they belong together – and the thing that looks different doesn’t.

I think a better version of this kind of quiz would be to just show four random pictures of anything, and tell kids to come up with things that they have in common. Look for connections. Look for reasons to draw threads from one piece of information to another. Reasons to group, rather than out-group.

Most importantly, I like that style because there isn’t an inherent “expected” answer. That might be the most important lesson of all – that knowledge and insight don’t have to stay in a box.

Go, Ready, Set

You’re never ready for anything. That doesn’t matter. “Ready” is an illusion. You can’t perfectly predict the future, unexpected things happen, and the marginal unit of preparation decreases in value fast.

I suggest aiming for, conservatively, 75% readiness on any serious task, and 50% on any non-vital one. Those numbers are made-up and therefore meaningless, but here’s what I’m getting at: When you’re preparing to do something – look for a new job, buy a house, have a baby – just focus on being generally competent and adaptable and not on a checklist of impossible goals.

Go first, then you’ll get more ready as you iterate. An hour of doing will give you more readiness for the next hour than a week of planning would have given you.

Think about what you’re planning for right now. What things are on the horizon that you’re still in the preparation or even decision-making phase for? What are you “thinking about” doing, or perhaps even hoping for?

Just do that thing. Badly, but today. Then better tomorrow.