I’m an optimist about my abilities, not the universe. I don’t expect the universe (by which I simply mean “everything that isn’t me”) to dish out the fates I want – if anything, I expect the universe to throw nothing but curve balls. But I’m very optimistic about my ability to hit them, so I remain an optimist overall.

Sometimes people, when deciding on a course of action, fall victim to the fallacy of imagining their ideal preferred result of that action. Then they’ve tricked themselves; they find themselves answering “do I want that result” instead of “should I take this action,” and those are very different questions.

Be careful about assumptions you make about the universe. You can control what you do, but rarely the universe’s response. Be prepared for curve balls.

Don’t be the person who treats you the worst. Being overly self-indulgent isn’t good for you, but most people swing too hard in the other direction. No one will drive you like you’ll drive yourself, this is true – and good! But if you drove someone else as hard as you drove yourself, you’d also recognize that you had to reward that person for their efforts or the efforts would cease and they’d grow to resent you.

So don’t let that happen in your relationship with yourself. Work hard and stay diligent, but do something nice for yourself, too.

Sometimes, the ship has no captain. Sometimes it doesn’t even have a rudder. There’s a storm all about and nothing seems to make sense. You’re pretty sure this ship you’ve found yourself on isn’t going to reach its destination, at least not in one piece. In that situation, what should you do?

Well, the obvious answer is “abandon ship,” but just because it’s obvious doesn’t mean it’s correct. In fact, even in the situation I described, it still might be better to be on the rudderless, captainless ship than on no ship at all in the middle of the ocean.

Most of the time, you’re not going to literally be on a ship. But the analogy tracks for a lot of dysfunctional organizations. When you join a new company, team, school, or other organization, you join it with certain expectations of leadership. You expect your organization to be… well, organized. We picture a natural process of learning the ropes and acclimating to the new structure, then being able to contribute and produce valuable work thanks to that structure and the people in charge of it.

And then sometimes – maybe even often – what we get instead is chaos.

It’s a fact of life that not all organizations are run well. They don’t all have effective leaders. They aren’t all in periods of stability. Some of them are very much like rudderless, captainless ships. The people will create factions and cliques as they scramble to protect what they have – or even what they perceive to have. Some people are opportunists and want to turn that chaos into personal benefit at the cost of organizational harm. No one seems to be in charge, or at least you can’t be certain that who’s in charge today will be in charge tomorrow. It’s hard to do productive work because opinions around you all seem to differ on what “productive work” looks like – opinions that are guided primarily by those individuals’ own plans and schemes, and not what’s best for you.

In the best of times, you should always retain a healthy helping of agency over your own work, since outsourcing all decisions in your career is a great way to tank it. But when the chaos rises, you have to be even stronger. That doesn’t mean you should be like the vultures – opportunists who damage everything around them for short-term personal gain. You should strive for personal gain, yes. But in a way that helps those around you, for as long as they’ll accept it.

Remember: the ship will sink or it won’t. But for most people, the end result of their organization collapsing is the same as if they quit – they’ve lost their own position, and that’s it. If you join a company and it turns out that it’s a disaster, you can quit if you want. But until the paychecks stop cashing, it might be better to stay on and try to both provide and extract some value, the better to position yourself for the next stage.

So okay, practical advice time. You’ve joined an organization and it isn’t what it seemed. Chaos reigns. What should you do?

1. First, create boundaries. You’re going to want to avoid investing all of your time and energy into this new organization, because you need to have enough “you” left over in the week to plan your next steps, network, job hunt a little, etc. So first and foremost, make sure that you’re setting firm boundaries about availability, energy, and so on. Don’t work late, don’t take on extra projects, and definitely don’t let anyone pull you into their personal slice of the political pie.
2. Next, take an hour or so to get calm and ask yourself: “If this was a well-run organization, what would my job look like? What would I be doing to contribute, and what would success look like?” If you have trouble answering that, seek out assistance – network with other people in your position at other companies, or people who lead & manage that position. There are plenty of them, and networking with them is a great idea now, anyway. But stick with this exercise until you have a solid idea of what your role would look like if it was at a better org. Make it ideal – not just neutral. Don’t just picture an “okay” job, craft one you’d be really excited about.
3. Now, do that job. In the absence of anyone filling the void with actual certainty and saying “This is what you can do to contribute, be successful, and be recognized & rewarded,” just act as if someone handed you the role from Step 2. Whenever you don’t know something, make the best guess. Whenever you need approval for something, give it to yourself. Don’t wait for anyone to give you permission to do anything, because you won’t get it. Every day, do this job as if it were exactly what you were hired or recruited to do. But as you do it, pay special attention to Steps 4 and 5.
4. You’ve created the job you’ll do by default, but you aren’t going to die on any hills. The point of this is that 95% of the time, whatever you’re doing will be correct. But occasionally, someone will actually pop up and give you a real reason not to do something you’re doing. Occasionally, some vestige of real leadership will manifest and you’ll get actual feedback and direction. When that happens, be thrilled. Be extremely receptive, be grateful, and as quickly as you can pivot to include that new direction in your work. After all, that’s what you were hoping would happen in the first place! So don’t forget that some level of direction is what you’re seeking, even as you’re acting as if you’ll never get it.
5. You need to make at least 20% of your new job communicating about what you’re doing. This is a good idea anyway even in a well-functioning organization, but in this case, it’s serving two vital purposes: it’s building the value that you intend to take with you, and it’s covering your ass. In terms of building value – you want public visibility for the good work you’re doing because there’s no guarantee that it’s going to get used effectively once you hand it off. And there might not be anyone left to write you a letter or recommendation someday, so the more you communicate, the more your work becomes its own letter of recommendation for the future. And in terms of covering your ass – this should be obvious, but remember the vultures I mentioned earlier? Don’t give them anything. Don’t let them take credit for your work, don’t let them misconstrue your actions, and don’t let them drag you into their politicking. Stay in the sunlight, do everything publicly. Create email chains instead of phone calls, with multiple people on them. Do your work in publicly accessible file-sharing systems. Document frequently. Save things to your own computer. Stay above reproach by always keeping your door open, so to speak.

If you follow that action plan, it won’t fix the organization. But it won’t damage it either – and while you’re there, you’ll actually be contributing to both the org and your own development. In the best-case scenario, the organization gets the leadership it needs, and that leadership has plenty of evidence that you’ve been an awesome team player even during chaotic times. In the worst-case scenario, the organization tanks anyway, but you’ve still got a body of valuable work you’ve contributed and your own personal time wasn’t wasted. You’ll be able to show your next leader what you were capable of as if you were working in a well-functioning organization all along.

There’s a fun little group activity I’ve seen used in a lot of settings. I used to think it was dumb and bad, but I’ve come around on it significantly, and I’ll explain why.

Here’s the exercise: at everyone’s seat is a face-down piece of paper. The facilitator will tell everyone to flip over the paper and then follow the directions on it. The paper will have a big list of directions, maybe 30 or so, and they’ll all be silly things like “stand up and clap three times” and “loudly proclaim your favorite color so the room can hear,” etc. The facilitator also (crucially) has to put a narrow time limit on it, something like: “You’ll only have three minutes total to complete all directions. Do as many as you can. Aaaand… go!”

But here’s the gimmick: The list is structured a certain way and has some specific instructions for numbers one, two, and thirty. Here’s what the list looks like:

What do you think happens? If you guessed “a bunch of people make fools of themselves,” you’re right!

A number of people in every group will basically ignore number 2 and will just start following the silly directions in numbers 3 through 29. They’ll see the big list and the time limit and just start rushing through, shouting to the room and spinning around and all that stuff.

Meanwhile, there will also be a certain number of people who scan the page like they should, see number 30, and smile smugly as their peers botch it. By the end, you’ll have made some people feel very smart and some people feel very foolish.

I used to hate this – I’d been a part of it several times in several different contexts (which of course, ruins it – if the trick works at all, it only works once) and I always felt like it was poorly used. As an arrogant young man, I thought, “If they’re not immediately firing everyone who messed this up, what’s the point? Those people just showed that they’re idiots.”

Now, I realize differently.

Being able to follow directions, especially complex directions in a time-pressured situation, is a skill. It’s a very valuable skill, but it’s not the only marker of intelligence. And because it’s a difficult skill, most people don’t naturally have it – they have to learn it.

This exercise really helped to hit home how important that skill is – and shattered the assumption that people were automatically good at it. If you messed that up, you were embarrassed but not harmed. That’s a good position to create the humility needed for learning.

One of the biggest lessons I’ve learned as I’ve aged is that almost every ability I thought was just “basic intelligence” was, in fact, a highly specific skill that I happened to possess and therefore I arrogantly judged people who didn’t. That doesn’t mean those skills aren’t very helpful and worth learning! It just means you shouldn’t judge someone for not having them yet.

The corollary, of course, is that there are plenty of those kinds of skills that I don’t possess. It keeps me humble and looking for them. Hopefully, you’ll do the same.

My middle child is in first grade. Tonight, she was doing some math homework in front of me; specifically, she was finding “number partners” that add up to 10. The first four questions have one side of the partnership filled in – 9, 8, 7, 6 – and she’s supposed to write the other part. She correctly writes 1, 2, 3, 4. Then the last question has both sides blank, leaving her to put in both of the “number partners.”

Without hesitation, she writes “10” and “0.”

The lesson I learned: no matter how sure you are of the right answer to something, someone can still surprise you – they can come up with something totally different than what you came up with, and still be right.

There is something sneaky people can do: they can extract a bunch of resources from a lot of people, and make it so that no one tries to stop them. They can do it in broad daylight. How?

Simple: you just don’t take more from any one person than the cost to that person of caring enough to stop you.

Think about it like this: Imagine I stole, through electronic hacking of bank accounts, one dollar from every person in America. For me personally, that would be a tremendous boon! I’d get hundreds of millions of dollars; surely more than the cost of doing the hacking. But each individual person would only have lost a dollar – many people wouldn’t even notice their bank account changing by a figure so little, and few others would care to put in any effort to get it back. In fact, it would be irrational to try to get it back. You’d spend more than a dollar’s worth of effort before you’d even begun to make progress.

Now of course, there are some flaws in this plan. For one, it’s illegal – which means there are systems of people who are paid to care about it beyond their own lost dollar. The nature of a legal system is that even if it cost double to catch and persecute me what I’d actually stolen, they’d still do it – because they have to. The whole system depends on people’s faith that they will.

But this sort of thing isn’t always illegal.

Imagine a slightly different scenario: imagine that the bank takes one dollar out of every account they manage. Tens of millions of dollars. Then, imagine they immediately apologize and let everyone know they did it – that it was a “software error” and you can get your dollar back by simply clicking a link that will be sent to your email tomorrow and filling out the form it takes you to, verifying your prior account balance and new account balance in order to confirm the incorrect transfer had taken place.

How many people do you think wouldn’t do it? (For reference, here’s a fun little fact: billions of dollars in tax return money go unclaimed every year.)

A huge number of people would just never click that link. The bank would get a huge amount of basically free money. So why don’t they do this?

A few reasons. One, reputation does matter. You can get away with that once, but twice starts to look really fishy and people will just start using banks that don’t do that stuff. And there are government agencies that investigate this sort of thing to see if it really was a software error or if you’re pulling a fast one. But even in a one-time event that was a genuine error, there’s another factor: enterprising individuals can consolidate the care. These are usually called “class action lawsuits,” and they happen in exactly these situations. A law firm will realize that there’s millions of dollars worth of “caring” somewhere, but it’s spread across so many people that none of them will act. So these people will take it upon themselves to act on everyone’s behalf, trying to get anyone who might have been involved to agree with as little effort as possible. That’s why you may have gotten an email in the past saying something like “Did you shop at X store any time over this three-year period? Click this button and you might get some money!” And then there’s nothing else required. Their goal is to keep the effort you have to put in to join the bandwagon under the limit of how much you care about what happened, so you’ll actually do it.

Okay, where am I going with this?

Well, people playing this game – trying to distribute what they take across many people and concentrating it into the hands of a few so that no one cares enough to object – is the source of a lot of ills, both to society at large and to you personally. For example, a huge percentage of the taxes you pay go to things you’d rather not pay for, but each individual one of those things might only be raising your tax bill by a few cents. As a result, you object – but not enough to do anything. So whoever gets your tax money is raking it in, but they’re mostly playing this game. And the only people who do object are the opponents in that same game – not people who want you to get your money back, but people who think they should get it, and think that they can get it if they concentrate enough caring toward their side.

In large companies, sometimes you have to do something dumb and obtrusive, but not so dumb and obtrusive that you’re willing to quit over it. And you have to do that dumb, obtrusive thing because someone managed to get themselves into position as Head of The Dumb, Obtrusive thing and it’s a sweet gig for them, even though it harms everyone else. They get so much benefit that they’re heavily incentivized to keep convincing the senior leadership to invest in it (in fact, that might be the majority of their time), and no other employee suffers enough individually to waste time trying to fight it.

No matter where you go, people just call this “the cost of doing business” and move on – either because they’re rationally bored by it, or because they’re the perpetrators and they want you to be rationally bored by it.

What’s the point of me pointing out a problem to you that I’ve also just described as requiring you to act irrationally – against your own interests – to solve?

Well, here’s my advice. Sometimes – not all the time, but on occasion – be irrational. Make a stand over a dollar or over ten minutes. Spend a hundred bucks and ten hours to win it back, out of spite. Out of rebellion. Because you’re a human, because you have a soul, and because sometimes you should just pick a fight – just to remind people that you can. That you can’t always be predicted. That you won’t always hand over that dollar or minute or whatever they’re asking for. Sometimes you’d rather burn it all than see it go into the hands of the people who play this game.

Let the people who want to steal one piece of candy out of every dish be just a little afraid that a few of them might be poisoned.

Don’t do it always – that way lies madness and ruin. But every once in a while. Every once in a while, make the cost of doing business dealing with you.

Sometimes, everything is fine – but an inch in any direction is a thousand-foot fall. You’re fine as long as nothing changes. This is an illusion; you’re not fine at all.

You can try to build a bridge to a safer location while carefully balancing on one foot. But sometimes, the smarter thing to do is just jump. Embrace the disaster, get it over with, and climb back up to a better spot.

No matter what anyone says, it’s definitely possible to change the past. It’s just that without a considerable amount of effort, those changes are usually for the worse.

Consider: You’ve just had a lovely meal at a great restaurant. You go to sleep that evening quite satisfied with your day. The next morning, you catch a news story about how the head chef at that restaurant was arrested for doing something untoward to the food before serving it to guests. You feel sick to your stomach, maybe even vomiting. Your previous evening is ruined, despite it happening in the past.

Sure, the actual events didn’t change. But your past changed considerably. And that’s what matters – after all, ‘the past’ is just a concept anyway. It doesn’t actually exist anywhere but in your own mind, as context for your current life. That’s why, under normal circumstances, “don’t try to change the past” is good advice. There’s nothing to change, so it’s just wasted effort.

But if you view the past this way, suddenly you realize that you can change it. You can’t change the events, but you can change the context and the framing – and thus change your present. You can’t undo a prior disaster, but by reframing it instead as a moment of growth and learning that gave you new wisdom, suddenly you’ve changed the only version of ‘the past’ that matters – the one in your mind.

It can be hard to leave. There’s a strong inclination to linger; to keep one foot in the old country. But it’s hard to move forward without both of your feet.

Sometimes, it’s just best to hit the road and not look back.

I’m going to be geekier than usual today and talk a little bit about board games. Well, that’s not what I’m really going to be talking about, but that’s where we’re going to start.

I’m a hobbyist board gamer, which means I own more games than most people will ever play. (It’s a whole thing if you don’t believe me.) There’s a common issue that lots of people in this hobby face, which is the realization that how many board games you own doesn’t necessarily correlate to how many board games you play.

See, buying a board game is easy. Assembling several adult friends into a common physical space for a few hours is much harder. In the best of circumstances, for many adults (especially ones like me with jobs, kids, etc.) it isn’t going to happen more than a few times a month. What often happens is that people in this hobby go through a period where they’re really more collectors of games than players of them. They get a game that they think seems neat, but some part of their subconscious is imagining that what’s actually in that box is three friends with a free evening.

At some point, if you’re honest with yourself, you just admit that many of the games you so eagerly purchased just aren’t ever going to get played. (The insider term for this is the “shelf of shame.”) When you have limited time and bandwidth, you often want to play the games that give you the most joy. The core of your collection becomes more important, and the peripherals less so.

Okay, so where am I going with this?

Well, all things take up some kind of “space” not only in your home, but in your life. You might think that a board game you’ve already bought doesn’t really demand much from you, so why bother selling it or giving it away just because there’s a 99% chance you won’t play it? But that’s not really the way human brains work. Everything in your life takes some emotional energy to maintain. Some more than others, but everything. I moved a massive collection of books across three different relocations before I got sick of carrying all those boxes and realized that in three different pack/unpack cycles, I hadn’t opened the vast majority of those books. Owning them was costing me something. I felt emotionally burdened – even guilted – by them. I didn’t want to re-read them (I’d already read them!); I wanted people to know I had read them.

I didn’t want books; I wanted erudite friends who would discuss the topics within. That was burdensome. So I gave them away – and you know what, giving them away started more conversations about those topics than having them on my shelf ever did.

You only have room in your life, your calendar, your home, your brain, and your heart for so many things. You have a limited amount of emotional connection to spread across everything in your life. And sometimes you will find yourself spending that limited energy on things that are not cycling it back to you in a healthy way.

You might think it doesn’t hurt you to keep a collection of movies you never watch, books you never read, a bike you don’t ride, people you consider friends but who never call, or an unrequited love that you never talk about. But those are all manifestations of the same thing: you pouring out energy into a void.

When I take my favorite game off the shelf and play it with some of my close friends or my children, I put it back in a few hours feeling very satisfied. I put energy into that game in the form of thinking about it idly on occasion or in the form of being excited for the next play, but it gives me energy back in the form of great evenings and experiences with people I care about. That’s a good relationship. That’s an energy cycle that maintains itself and renews me.

This same measurement applies to literally everything in your life. Nothing in your life gets a free ride – every person, place, and thing is a relationship that you’re maintaining with some amount of your limited emotional energy. If that relationship isn’t giving you energy back, then it’s just a parasite. It’s killing you, and it isn’t even trying.

Make room in your life for those relationships that make room for you. The friend who calls deserves your friendship. The book that gives you joy to read for the 8th time deserves to stay on your shelf. And the game that gives you regular evenings of enjoyment deserves to stay in your collection.

But the rest? Don’t leave those things trailing behind you, tethered by unwarranted hope until they become weights that keep you from moving towards the actual joys in your life. You don’t have room for it.