I often have trouble with balancing a middle ground. When I have the boundary provided by professional distance I communicate well, and I’m fine with people that I’m very close to. But when there’s a middle ground I often falter.

I’m never sure how much to ask, how much to share. I have a lot of switches and not a lot of dials. I tend to view trust and openness as binary; complete or absent.

I know there’s a middle. I’m exploring it. Slowly, but nonetheless.

Would you rather be surprised by bad news, or know it was coming in advance?

Many people would instinctively say they’d rather have time to plan, but what if you couldn’t plan? If it were simply something that was going to happen, would you still rather know in advance, having to live with the dread?

Or is even dread something you can plan for?

Roll with the punches or be prepared?

I had to take a flight early this morning, leaving during a particularly busy time from a particularly busy airport.

I was approaching the escalator that went down towards the gate, and I saw a young boy, looked about 4, terrified of the machine that everyone else was hopping on so easily. He had his little Spider-man roller suitcase clutched tightly and was trembling and crying about the prospect of leaping onto a machine seemingly made (from his perspective) of perpetually-gnashing metal teeth.

His dad looked to be a guy my age, and was not impatient or unkind about this. He leaned down and said, “Okay, I know it looks pretty scary! But we can do it together, okay? Hold my hand, and on three we’ll jump together.” He counted three and they jumped, and the kid giggled at the stairs moving beneath his feet, but dad held him steady. “Ha ha, it moves pretty fast, huh?” he said cheerily, turning it into a fun ride instead of a scary danger.

I watched this moment happily and stepped onto the escalator behind them. They got to the bottom, and there was an older couple half-frantic waiting. They immediately seemed relieved when they saw the two, and profusely offered up their gratitude.

“Oh thank you thank you! It was so crowded and busy we hadn’t even noticed that he didn’t follow us down the escalator and then we couldn’t see where he was. We were starting to panic when we saw you coming down. Thank you so much for helping our grandson, it’s his first time ever flying.”

And this guy, who was not the kids’s dad, didn’t even know the kid, just said, “Oh, no problem. Have a good flight, little guy!” And the kid smiled and waved and dragged his little Spider-man roller suitcase with his grandparents off to their destination.

Humans are good. Humans are so good.

I once read an interesting “true crime” story about thieves that wanted to rob a particular hotel room. Apparently there was someone very wealthy staying in that room, with a large assortment of valuable things like jewelry, and the thieves wanted to get at it. This being a high-class hotel, the security was very good – all the doors were basically unbreakable and had all sorts of high-tech locking mechanisms and such. There was virtually no way to bypass these doors.

Except… to bypass them. Entirely.

The thieves just booked the adjacent room under a false name and cut through the drywall. Because that’s all it was: ordinary drywall, the same as would be between any two rooms that aren’t bank vaults.

I often see problems of this nature absolutely confound people. Even very smart people. Because society in general does a good job of herding us towards the doors. But if a particular door is incredibly secure – locked, bolted, sealed, onerous – then maybe look at going through the wall.

A classic example I see a lot in my line of work is submitting a job application. People are often nervous about everything from applicant tracking systems and keyword filters and hiring manager bias and competition and all those other barriers. But those are locks on the door. That machine is horrible – I’ve lived in it for years and years. Skip the door. Go through the wall, the window, the skylight.

That can mean a lot of things. In one instance an old client of mine just found out who the head of the department he wanted to work for was, recorded a video of himself making a pitch for the job, and then sent that video on a USB drive via FedEx direct to the manager at his desk. The manager had to sign for the package, which contained a USB drive and a hand-written letter from the applicant explaining why he sent it. The manager watched the video and hired the man the next day.

That’s going through the wall.

Imagine that you’re really, really good at jigsaw puzzles. You can do them quickly, efficiently, and you rarely if ever have difficulty finding the location of a piece.

Okay, now imagine I take a pretty difficult, thousand-piece puzzle and pick fifty of those pieces at random and give them to you. I don’t even show you the other 950 (heck, I don’t even tell you how many there are), nor the box or picture.

You can’t solve this puzzle. No matter how long you stare at those fifty pieces. No matter how you turn them and arrange them and consider them, you’ll never complete the jigsaw.

In this scenario, however, lots of people fail to realize why they can’t solve the puzzle. They do one of two things: Either they blame themselves and start thinking that maybe they aren’t so great at puzzles after all and they should just give up and never do a puzzle again, or they get mad and start blaming a cruel and unjust universe for delivering an unsolvable puzzle and they should just give up and never do a puzzle again.

Neither is true. You just don’t have all the pieces. It has nothing to do with your abilities – how smart you are or how capable you might be. It also isn’t that life has dished out a particularly unfair dilemma in your direction. The problem is a simple one – you’re missing 950 pieces.

Where are they? Scattered around the city, the country, the world. You’re not solving a jigsaw puzzle – you’re solving a scavenger hunt.

That is an allegory for pretty much every problem you will ever face.

99% of problems can’t be solved by thinking about them. Thinking about things has a rapidly diminishing marginal return in terms of generating solutions. And that’s because thinking about things doesn’t generate new information; it just rearranges information you already have.

You need to do that… a little. When you have all the information, you need to assemble it correctly into the right action plan to solve your problem. But if you’ve been thinking about something for more than a few days and you’re stuck, then you don’t have all the information yet. You’re smart. If you had all the pieces, you could solve the puzzle. Ergo, if you can’t solve the puzzle, it’s because you don’t have all the pieces yet.

Go out and get new information. Go on the scavenger hunt, grab a few more pieces, and then think again for a little bit. You might not actually need all 1,000. This could be like Wheel of Fortune, where you can solve the puzzle before every letter is visible. But you can’t solve it if you only know 3 letters out of 100, and you don’t even know there’s a hundred total, and you can’t see the spaces between words.

No matter how long you think about it.

If I throw a heavy object at your head, you’ll duck or catch it or react in some way. You’ll do this even though you didn’t consciously decide to.

It was a reaction. An automatic response. Your brain runs these subroutines for you all day every day – you’d be dead in minutes if it didn’t. And while we should be thankful to our brains for this, we should be careful what we let slip into the grip of automation.

The Path of Least Resistance is a sincerely tempting one. But it leads to a dark place. Have you ever heard the phrase, “the road to Hell is paved with good intentions?”

Let me adjust.

“The road to Hell is paved with no intentions.”

When you coast, you end up somewhere significantly less than desirable.

My father had this habit of driving wildly sub-optimal routes when going from point A to point B. He’d pick me up from school, and instead of driving the mile or so to our house down the straight road that connected the two, he’d take a sharp left and we’d drive all over town before ending up home. When I asked him why he did that, he’d smirk and say “I make the rules.”

He’d take weird turns because the standard route offered him nothing new. He wouldn’t see anything he hadn’t seen before, or learn anything new, or meet anyone interesting. He’d get lost on purpose to teach himself how to find his way back instead, embracing what appeared to be a sub-optimal choice in the short term because of what it did for his life.

Taking a job at your uncle’s company right out of college because you don’t have to work hard to get it (or even work that hard once you’re in it) can seem like the best choice. It might pay you better than comparable jobs you’d have to work much harder for. It might seem absurd to opt out of that arrangement, in the same way that it seems absurd to take a meandering, 5-mile route from my middle school to my house when they’re actually less than a mile apart and on the same road.

But my father never, ever got lost. In the days well before GPS or even MapQuest, my father’s sense of direction was flawless and his sense of adventure unflappable.

Live an intentional life, even if it involves weird turns and odd routes. Choose to make choices, not to let them be made for you. Take the path of most resistance, to build in yourself the ability to fight resistance when you have no choice. You can do it. You make the rules.

There’s an old saying about what happens when you assume. You’ve probably heard it; it’s largely negative.

But here’s the thing – it’s impossible not to assume. You have to start with a base idea of what’s going on around you. You can’t walk into a restaurant and say, “Ah, a room of some kind! I don’t want to make any assumptions about what goes on here, so I’ll just walk up to the closest other human and ask them to explain the nature of this place to me.” In addition to seeming like a lunatic, this method would also just be painfully slow at gathering information.

No, it’s fine to make assumptions. If you walk into a restaurant, you can safely assume that someone there will direct you to a seat, take an order from you, deliver food that mostly matches your assumptions, and then charge you a price you assumed you’d pay.

Assumptions themselves aren’t dangerous; they’re necessary. It’s when we let them off the leash and allow them to take on a life of their own that they become dangerous.

Unfortunately, our brains aren’t great at separating out kinds of information, especially over the long term. It stores it all in generally the same place, and it doesn’t readily differentiate between “information with numerous backing sources and logical cohesion” and “stuff you made up.” So it’s really easy to get accidentally caught up in knowledge that you think you have. Then soon that knowledge gets used as the basis for something else, and before you know it you have a whole universe of false information.

You need to find a way to check your assumptions. Some people are naturally pretty good at this, but others aren’t – and it’s a vital skill to develop. It’s worth cultivating a healthy habit of asking yourself, “Do I know that for certain, or am I leaning too heavily on an assumption?” Check sources and keep track of what you only think to be true.

Unpleasant rumors, bad plans, and even animosity between people can all come from unchecked assumptions that have run wild. Keep them as the theoretical concepts they were meant to be.

At the end of this week my oldest daughter and I are going on our first overnight camping trip together. I’m incredibly excited, and she is as well. Today, we went out and bought some gear for her so we can take a nice long hike while we’re out there.

She’s so funny. She was cracking jokes and making poses the whole time we were out, but she also had great insights and questions about the adventure ahead.

One of my favorite qualities in her is her utter readiness to do anything. She doesn’t think anything sounds “lame.” She wants fun, experiences, adventure – and she sees the potential for those things everywhere. She leans into whatever is in front of her, embracing the core concepts, asking questions, and learning as she goes.

She’s an interesting kid, but even more she’s an interested kid. She wants to know everything. One of my favorite activities with her is taking her many, MANY questions about the universe and guiding her through the process of finding out the answers on her own using the tools she has available. (Parenting tip: The “Calvin’s Dad” method works great here – if she asks a simple question, give her an absurd answer, and she’ll go find out for herself and not ask you again.)

My father once said to me: “If you’re gonna be dumb, be tough.” I think at the time I was probably crying about a self-inflicted injury, hence the statement, but there’s a much deeper wisdom there. We all have flaws. Working on improving them is a good thing, but not all of them can be improved substantially – some things are just part of who we are. So if that’s the case, you should develop counter-balancing traits.

If you’re gonna be dumb, it’s worthwhile to try to get smarter. But if you can’t get smarter, at least be durable enough to outlast your mistakes.

I am naturally a creature of extreme habit. It is almost never my idea to do anything outside of my normal routine. Without some outside influence, all of my days would look identical. But I don’t necessarily want that; despite my inclinations, I love adventure. I love the stories, the experiences, the life. But lacking the natural initiative to do those things, I instead cultivated a different trait – saying “yes” to stuff all the time.

It might not be my natural inclination to seek adventure. But when it comes knocking, I always answer.

I can smell adventure on people. From across the room I can tell that someone is going to turn out to be interesting. That they’ll be someone that brings more adventure into my life in one way or another.

Sometimes I work for those people. Sometimes I befriend them. Sometimes I get one mad at me, just to shake things up. But I like to know them.

My daughter is that, turned up to 11. I try to be like her. Ready to go.

Some things shouldn’t be done by people who want to do them.

There are some things in life that are burdens that need to be carried, even to the point where we greatly admire the people who carry them, but we should be wary of people who want to do them. I’m going to start with a really extreme (and uncomfortable!) example, but then pull it back into a more day-to-day examination of the concept.

There are people in the FBI who specialize in stopping the trafficking of child pornography. This is a good thing – I don’t feel like I have to take a strong stance here on “child porn is bad, mkay” but just in case. Now, an unfortunate reality of the capture and prosecution of people who traffic in that stuff is that someone on the law enforcement side has to look at it. Someone has to look through all the files on a criminal’s computer to see which are child pornography, or try to identify victims, or just evaluate for how many charges to bring against the person, etc. We can safely call that job a “burden.” It has to be done, but it’s not something a good person would look forward to.

Now, imagine you had a bright young FBI agent who was volunteering hard to get that job. It’s not impossible to imagine a scenario where their motivations are pure, but it’s pretty difficult. Like, that’s a really terrible and burdensome and soul-crushing job, and the kind of people who go beyond being willing to carry the burden for the rest of us and into being excited for the opportunity? If I met such a person, I would be extremely wary of them.

I knew a marine once who told me that he wanted to be a sniper, but they wouldn’t let him despite him having all of the proficiency and skill needed. I asked him why, and he said “I had a psych evaluation where I told them I really wanted to be a sniper.” That actually seems like sound policy to me.

Douglas Adams applied the philosophy to political leadership. To quote:

“The major problem—one of the major problems, for there are several—one of the many major problems with governing people is that of whom you get to do it; or rather of who manages to get people to let them do it to them.
To summarize: it is a well-known fact that those people who must want to rule people are, ipso facto, those least suited to do it.
To summarize the summary: anyone who is capable of getting themselves made President should on no account be allowed to do the job.”

(By the way, Douglas Adams was freakin’ brilliant.)

Things like investigating and prosecuting child pornography, being a sniper, or leading a nation are all terrible things to endure. They might need to be done (opinions may vary here), but they’re terrible for the soul of the individual doing them. In other words, they’re burdens. It can be noble to take on a burden, but when you’re eager to do it – not because you’re eager to spare others the burden, but because you’re actually eager to do something so damaging to the soul – it should give us pause.

And it might be a good reason not to let that person do that thing.

Now, I used some big, big examples to illustrate this concept. Heavy, heavy burdens. But there are lighter things that fit the general idea. Let’s look at rehab.

Drug and alcohol rehabilitation is tough. I know people personally that have gone through it. Every person is different – different in how intense the intervention has to be, how long they have to be “actively” in rehab, and so on. If two people sign up for a six-month rehab program on the same day, it’s totally possible for one of them to be in a good enough place to leave in two months, while the other might not actually be ready even after six.

But imagine that someone tells you, on day one, that they’d like to be done the program in two months instead of six. Even though you might know that it’s possible for some people to be capable of doing that, the very fact that the individual asks that on day one is a really strong indicator that it won’t be them. It shows that they’re not motivated to get better, they’re motivated to get through. Which in turn means you should probably put a note in that this person likely needs extra time, rather than less.

Why a person wants to do something matters, in other words. Sometimes the “alternative benefit” is obvious and just a matter of preference: when I was a teenager, I worked in a local convenience store. One of the jobs everyone hated was unpacking the big deliveries we’d get several times a week, because it meant you had to spend at least a few hours in the cooler unpacking all the drinks and stocking them onto the cooler shelves, and you had to do it by yourself so you couldn’t chat with your co-workers.

Here are some things I love: Listening to music, and being cold. If you’re unpacking the cooler you don’t have to interact with customers, so you’re allowed to wear headphones. And it’s freezing in there (obviously) even in the brutal summer months. So I always volunteered for that job. It was a win/win since most other people didn’t want to do it. I didn’t pretend that I was volunteering out of a sense of altruism, to save my co-workers from having to do it. I wanted to do it. But in this case, that’s okay – I was eager rather than burdened, but my eagerness wasn’t a harbinger of any other malicious intent.

Now, contrast this with the story of Kelly* (name changed). Another task everyone hated was counting out their cash drawers at the end of their shifts. We didn’t have a slick cash machine, so you had to count everything out by hand, enter it into a pretty archaic system, etc. Since it had to happen after your shift was officially over but took like 15 minutes, everyone actually ended up having to stay 15-20 minutes past their shift (torture to a teenager!), or much longer if more than one person clocked out at the same time (a frequent occurrence!), since there was only one archaic machine to enter your totals in. Kelly was JUST SO NICE and always told her shift-mates that they could go home and she’d stay behind and count everyone’s tills for them. Kids eager to run from work ignored the obvious red flags. Kelly was pocketing a lot of money from other people’s drawers (never her own), and she was very clever. Being off by $20 on your till was grounds for discipline, but letting someone else count your till was grounds for immediate termination. Kelly kept apologizing and saying it was an honest mistake until someone finally caught her counting multiple tills and just fired her for that.

Sometimes when someone volunteers for the burdensome job, there’s a bad motivator in there somewhere.

The point of all of this isn’t that you should be constantly suspicious of everything that everybody does. But you should seek to understand why people make the choices they do. Aligning people – including yourself – with circumstances where they’re motivated to do good deeds helps create a good world. Do it when you can.

Some things take a long time to pay off.

It’s worth remembering that on the days where it doesn’t seem like you’re moving the needle much. Today I finally saw a radical success in something that I’d been working on since last June, and it was great to see. Nine months isn’t that long, in the grand scheme of things – but the typical length for the kind of project that was is about six weeks, so it definitely felt like it dragged.

Which meant there were times I felt like throwing in the towel, but the long game is tricky. Sometimes it costs more to quit than to keep going.

Some projects (like this one) involve a lot of waiting. You sow the seeds and do the right things up front, and then see if they paid off down the line. You water them occasionally, but don’t have to involve yourself that much. So if you quit, you’re not really getting anything.

Quitting is a currency. You quit in order to buy something – you quit smoking to buy health and money, you quit a hobby to buy free time, you quit a bad job to buy happiness and freedom. But when a project isn’t really costing me much of those things, quitting doesn’t buy much of them back. That makes quitting a bad deal compared to hanging around and seeing if my long game pays off.

In general, this becomes a good (though unconventional) reason to front-load your work on any major project. If you do the majority of the work in the beginning, then quitting becomes a bad deal because it doesn’t buy you anything worthwhile. And then if, some time down the line, it pays off – you get to celebrate.

Cheers to that.