I think people get caught in traps around “informal” meetings or groups. You hear from someone in a professional context that they just want a quick, “casual” coffee or something like that, and suddenly you have no idea what that means.

When something is formal, it has – by definition – rules. And rules make things easy. They give you a set of things to do (or in some cases, tactically not do), which also means you know how to prepare.

Let me take the mystery out of an “informal” meeting for you – it also has rules. In fact, it has pretty much the same rules, but you don’t wear a tie.

Here are the “rules” – for any meeting:

  1. Before you go in, think about what you want to come out with. Don’t think about the meeting, think about the time after the meeting. How do you want your life to be different? If you don’t have a goal, then it’s just hanging out. That’s fine if that’s what you want, but it probably isn’t if you’re having an “informal coffee” with a potential new business relationship.
  2. Now that you know what you want (people very frequently skip this step, which is why none of the rest of this makes sense), write down three different ways to ask for it. Just ask directly, but three different ways. If a potential client wants to grab coffee, write things like “What do you need from your website development,” and “Tell me about your biggest challenge on website development right now,” etc. Those sound really similar. They are. You want to have options – you might ask all three with variations, or you might just want to have an idea of what you can use in an adaptable conversation.
  3. Ask those questions, write down the answers. Be polite. That’s about all you have to do during the meeting.
  4. Use the answers to follow up after the meeting. Take those answers and ask yourself “how does this new information get me closer to the thing I said I wanted?”

Don’t make this more complicated than it has to be. That’s how you get value out of every meeting – formal or not.

No Shadow Unturned

We so often hide the worst parts of us, shielding them from observation by others. But the worst parts of us are like mold. They thrive and grow in the darkness; they die in the light.

Our insecurities, our fears, our failures. These things will haunt us if we let them take up permanent residence in the dark recesses of our memory, forever protected from the hard light of public scrutiny. If we let them out, they diminish to nothing.

It’s the black mold itself that tells you that you should hide it, because it knows. But that darkness is a terrible advisor. Exile it into the sun, and leave no room for its growth.

Want Something

Think about a circle of people you interact with regularly. Your co-workers, perhaps. Maybe your extended family. Possibly the other people in your hobby group.

Without asking them, do you know what each and every one of those people truly wants, in their heart of hearts? What their deepest desires and ambitions are?

Probably not. So why assume they know yours?

The first step to getting what you ask for is to ask for it. The biggest reason people don’t give you what you want is they don’t know you want it. Speak up, tell them you want something. Ask them what they want, then work together.

Life is often easier than we make it.

Passion Beats Professionalism

When I was at the start of my career, a very common requirement in job ads was “no visible tattoos.” That’s an absolutely insane thing to imagine being on any job ad these days.

I talk to a lot of people who are worried about appearing “professional” to the world at large. There’s nothing wrong with that, by itself. The problem is that you have no idea what that means.

“Professional” is one of those extremely vague and variable adjectives that mean something totally different to everyone. It usually means, “looks, acts, and probably thinks very similarly to me.” Which is why it’s impossible for you to judge yourself as professional or not. You always look like you, but you can’t simultaneously look like everyone that you might want to work with.

Here’s the real deal about professionalism: it’s bullshit as a descriptor of demeanor. It can describe actions very well. Your actions are professional if they’re done with a level of dedication and seriousness that indicates respect for the outcome and those affected by it. A professional carpenter cares that the house he’s building doesn’t fall down and keeps the rain out, and builds accordingly. That carpenter may have tattoos, a Metallica tee shirt, and a mouth like a sailor. But if the house gets finished on time, under budget, and securely? He’s a damned fine professional.

That doesn’t mean everyone can curse a blue streak and be professional, of course. Notice that if you care about the outcomes and those affected by them, your language might matter! But it doesn’t automatically matter – and neither does your hair, your clothes, your skin, your taste in music, et cetera.

What people care about in your actions is professionalism. What people care about in your demeanor is passion.

When I size somebody up as someone I may or may not want to work with, I’ll draw conclusions about their professionalism by examining the outcome of their prior or current work. But if I’m going to draw conclusions about their demeanor, it’ll be whether or not they’re excited! Leaning forward in your chair and clearly being interested in the subject matter beats a three-piece suit or a Victorian communication style.

Show professionalism in your work. Show passion in how you show up to it. And forget about any other bullshit.

Pyramid Scheme

It amazes me how often people try to build themselves up as a leader by building down from the sky, instead of up from the ground.

You can’t build a hundred-story skyscraper by starting with the top floor, suspending it from the moon with guidewires as you build the rest of the building down from there. But that’s often exactly what people try to do when they want to advance.

They want to be a leader more than they want to build anything worth leading.

Being a leader is actually really simple, though it’s also very hard. You just have to lead. You want to rise through the ranks at your organization? Train and mentor the people under you until they’re unstoppable. You want to be the CEO of a company? Start a small business and grow the heck out of it.

You can’t declare yourself CEO and then decide to build a business. You can’t get promoted and then worry about learning to train and mentor people. You can’t build the pyramid from the top block down.

No You Wouldn’t

I read a very sad story about a man who committed suicide. (Of course, all such stories are sad.) The man had gotten himself into some reasonably deep debt via gambling, something like $30,000, after losing his job. When faced with the prospect of having to explain to his wife and kids why they were going to lose their house and such, he couldn’t do it and he ended his life.

Naturally, the news story featured conversations with the man’s loved ones – notably, his wife and her parents. All of the quoted parties said that it was a “needless” tragedy, because $30,000 of debt seems like a such a small amount of money to end your own life over, and if he had just talked to them instead of doing what he did, they would have understood and loved him and found a way through it together.

I was very sad when reading this, for both the man and for everyone he left behind. But when I read those quotes, all I could think was: “No you wouldn’t.”

Of course, you’d say that when the shock hits you, but the reality isn’t anything like that. Sure, $30k seems like a small amount to kill yourself over, but it’s a lot to just ask someone for. And when someone’s still alive and asking, you don’t think you’re paying a paltry sum to save someone’s life – you think that your good-for-nothing son-in-law has gambled away his family’s future and is now begging for a handout. And if the man truly was radically honest? If he said, “I’ve got one end of the noose tied, but before I go through with it I wanted to make one last attempt to solve my problem another way, will you help me?” You’d think he was a manipulative jerk, basically using the threat of suicide as emotional blackmail.

Suicide is inherently unbelievable. If someone tells you that they’re planning to end their own life, your immediate thought is: “Well, if you’re telling me about it, you can’t really want to do it, you just want some measure of attention or something.” That’s exactly what happens in everyone’s head. And the best possible response is usually some sort of “crisis” intervention that takes you from the very edge and puts you like six inches back from the edge, doing a lot of damage to your life along the way, and then abandons you.

The road to ending your own life is a really, really long one. Imagine a long, maybe miles-long slope leading eventually to a cliff. Pretty much everything we do to prevent this – as individuals and as a society – is designed to try to put a net at the very end, to keep people from going over. But that’s it. We don’t talk about the slope at all.

I’m not saying we shouldn’t do things for crisis cases. But if you find someone standing on a bridge, pulling them back a few feet and then saying, “okay, all set,” isn’t doing enough.

You have to intervene way earlier than that. By the time someone is holding his own life in his hands, he’s doing it because all the other lines of communication were already cut. The parents and widow lamenting the fact that the man didn’t just talk to them? He knew how it would go. He knew he’d probably be facing a broken family, ostracization, hatred, scorn. It’s easy to say “we would have understood” when the man’s dead and you don’t have to face the unpleasant burden of actually understanding, loving someone through their mistakes, and finding a way forward.

The reality is that he already knew what would happen. He knew his lines of communication had been cut a long time ago.

Pulling someone off a ledge is dramatic and feels good and does nothing. Having a cup of coffee with a friend on a normal day as part of the tapestry that keeps them from feeling totally alone doesn’t feel heroic, but it saves more lives. It’s easier to stop that avalanche when it’s just a tiny snowball at the top of the slope.

Would you?

Time Lapse

Blink your eyes and things change. They change no matter what. You can’t fight it by observing. You think a watched pot never boils, but no matter how hard you stare, it will.

You can change the perception of time in your head, but you can’t change its flow. It’s your attention that lapses, not the world.

Pay attention to the things worth paying attention to, and let time flow when it needs to. Close your eyes. It’s okay to let some things slide past you. You need the rest.


If you want to spoof or lampoon something, you have to understand it perfectly. Understanding it perfectly also comes with the ability to make such a stunning homage to it that often the two intertwine.

Star Trek, as a franchise, has a lot of movies. The best Star Trek movie is a movie called Galaxy Quest, which isn’t a Star Trek movie. It’s a parody of Star Trek movies, but it’s done with such incredible conviction, respect, and heart that it absolutely became a pure example of the genre.

Within a given genre, creators need to constantly reinvent. They need, specifically, to vary their entries; to depart from the norm. They have to do that to stay relevant, or else their works become lost as “just another” example of the same old thing. But those deviations don’t always hit, and each one dilutes the pool of what that genre represents.

Then you get the satirist. The person who is lampooning an entire genre all at once. When Weird Al Yankovic parodies an entire group or even musical genre instead of just one specific song, the result is almost always the best example in the category. Terry Pratchett wrote better fantasy epics than virtually every fantasy author.

Because in order to parody an entire category of something, you not only need to understand what makes that category what it is to begin with, but you also have to strike directly at the heart. You can’t parody the outer edges; you have to go for the core experience. And on top of all that, you have to be charming – mean parodies are just bullying. Charming works that blend parody and homage thus become some of the absolute best examples.

All this is to say – if you really want to understand something, go look at why the parodies of that thing work. Galaxy Quest is a great movie even if you’ve never seen Star Trek, but it’s wonderful if you’re a Trekkie. And if you can see why, you can appreciate Star Trek even more than before.

Not every genre of every creative endeavor has its own Galaxy Quest. But even if it doesn’t, you can follow the patterns. Look for the pure, the things so iconic that you can lampoon them easily. Follow comedy. It helps you understand, and appreciate.

Will, Want, Get

Wanting something takes more effort than getting it. Hemming and hawing over a decision doesn’t get you closer to making it.

When you think you might want something, immediately start working towards it. The work will help sharpen your decision. You’ll either decide that yes, you do want it – and then great, you’re closer! Or you’ll decide you don’t, and oh no you made extra money or whatever.

So much of how to think better is just to do it less. Thinking is its own worst enemy if you waste its power on every little detail, draining its strength with minutiae. Stop forcing your amazing brain to manage all these little details that are beneath it. Put that stuff on auto-pilot.

Chores and details shouldn’t be the domain of the will. They should be outsourced. Write stuff down, keep a calendar. Put your habits in there and stop thinking about them. Don’t constantly battle yourself. Leave your brain the room to work with the good stuff.

Furniture Sliders

Imagine you move into a new house. You get your furniture into the correct rooms, and then you break out the hammer and nails. You nail down all your furniture, locking it into place in the first configuration you chose. Without great effort and perhaps even some damage, the configuration can’t change.

Seems silly, doesn’t it? Even if you’re perfectly happy with how your furniture is arranged (and why wouldn’t you be – you picked it!), you recognize that it might not always be so. It’s not even that you might change your mind, it’s that you might change your situation. You might get new furniture that’s a slightly different size and shape. You might get additional things, or no longer need something you now have. You might move again – or someone new might move in with you. In any case, you recognize that things may change in ways you can’t predict now.

One of the best small purchases I ever made were these little furniture slider things – basically small felt pads you put on the bottom of furniture to make it easier to move around without compromising stability. They’re great.

The configuration of the furniture in your place is a system. That system serves a purpose, but it also needs to retain some flexibility. All systems do. Otherwise, we have to entirely scrap them when even the slightest thing changes. But we forget to install “furniture sliders” on so many of our systems. We forget to build, in advance, the ways to make future change easy.

We save things as PDFs and email them to colleagues instead of sending them a link to a shared Google doc that we can continue to modify. We build an org chart for an exact headcount but don’t incorporate procedures for bringing on or losing team members. Stuff like that.

Any time you’re building a system that you intend to use for more than a month, especially if your timeline for using that system is “indefinitely,” make sure you put some sliders on it. Don’t nail it to the floor.