You have to run training exercises. You can’t truly know if you’re prepared unless disaster strikes, so what you want to do is simulate small, controlled disasters.

In a way this is like a vaccination against catastrophe. You build up an immunity by exposing yourself to smaller incidents.

In the days before GPS, my father used to take my sister and me out for “Sunday Drives,” where he’d let us essentially pick left/right/straight at every intersection for as long as we wanted, with the goal of getting us totally lost, just so he could test his ability to navigate us back home. Of course we weren’t in any real danger, so it was a perfect “stress test” for his ability to navigate more emergent circumstances.

If you commute to work, try getting there one day without your car – use public transportation, a bicycle, even Uber. Be familiar with the alternatives, their costs, their timing. Know those things so that if your car breaks down one day, you’re not panicked. Leave your cell phone at home and go a whole day without it, just to see what problems you run into – and build backups (like contact lists, etc.) so that if you ever drop your phone in a sewer grate you’re not hopelessly lost.

Give yourself small disasters. Prepare for the big ones.

It is better to act on your convictions than to voice your opinions.

I recently read someone saying that it’s important to teach your children how to keep a few opinions to themselves, because there will be some views that society will punish them for having even if they aren’t incorrect. That might be true, but I think the lesson is backwards.

For the most part, I think the correct lesson is to, by default, voice none of your opinions. You’ll make plenty of exceptions (heck, I write a daily blog that’s pretty much just my opinions on stuff), but make those exceptions deliberate. Choose each opinion you want to share, and when to share it, carefully.

That isn’t the same as saying “don’t HAVE opinions.” Consider the world, chew it up in your brain, and form opinions great and small. Be open to changing them, but be prepared to act with conviction on the ones that you think are most correct and most beneficial. But that’s not the same as just spouting off all the time.

Working is greater than talking. If you have a view that you think improves the world, go work to make it happen. If you have an opinion about how to live a better life, live your life that way. That doesn’t mean you have to share everything you think with everyone.

I post at least one opinion a day on here, but believe me it pales in comparison to what I don’t share. I don’t have specific reasons not to share those other opinions – remember, my default is not to share. But I make it a point to make an exception a day, and I choose those exceptions based on which things I feel will provoke positive thought, encourage or help people, or even amuse and delight. I aim to bring value and raise the bar of discourse. If my opinion doesn’t seem to have at least the possibility of doing that, I don’t share it.

That doesn’t mean the views I don’t share are all dark and inflammatory or anything. It just might mean they’re not relevant. I have strong opinions on Mex-American Fusion Fast-Serve Restaurant Chains! You probably don’t care, and nor should you.

Be deliberate with your words; they carry more power that way. For all the other opinions you have, just build your own life out of them. If that life turns out well, people will ask.

Save your work.

Any time you work on anything, save it. If your work is already digital, save copies and organize them. If what you do is physical, document it in a digital way – take pictures, write about it, make a YouTube channel.

The point is to document. Keep a running file of your work. You know, blog if you like!

You are planting a gold mine.

The benefits are endless. Show people the real you, have deeper conversations, attract better attention, improve your work faster and more permanently.

If you spent a hundred hours painting a picture, you wouldn’t just throw it away after. You’d hang it up. Maybe you’d sell it, but even if you did I’d hope you’d take some quality high-resolution photos of it for yourself first.

Imagine you wanted the job of painting the Sistine Chapel’s ceiling. You’re one of the greatest painters of your time, but you’ve discarded everything you’ve ever painted. You have a great resume, though! Do you think you’ll get the job?

If you’re putting in the work to get better at something, plant these seeds. You’ll thank me later.

When I was about 6 or 7, my father took me and my cousin on a camping trip. He was a year younger than me, and this was his first such outing. For lunch on the first day, my father made us both peanut butter and jelly sandwiches.

My cousin said to my dad, “My mom cuts the crusts off for me.” My father gave a long side-eye at my cousin and said, “I’m not your mom.”

He made it clear – he couldn’t care less whether or not my cousin ate the crust, or even the entire sandwich. But he wasn’t making anything else, and he wasn’t going to cut the crusts off.

Faced with such adversity, my cousin got creative: he folded the sandwich in half and ate it from the middle, leaving behind a neat unbroken line of crust in the shape of a square with the inner sandwich devoured.

“If it’s stupid, and it works, it ain’t stupid.”

Sometimes you want to care about technique, create sustainable methods, work towards efficiencies. But often, you just need to get the damned engine running. You just need to be airborne. Or, you just need to eat the sandwich.

My rule of thumb is that working on process is only a good idea if you’re in process. If you’re moving. You want every day that you aren’t perfect to still be a day where you moved forward and accomplished at least something. If you’re so concerned with methodology that you’re not making progress at all, you need to ignore methodology for a little bit and just get the ball rolling. Not only is iterating a hundred times easier when you have something to iterate, but you also don’t lose as much from small failures along the way.

Eat the sandwich, even if you have to eat it weird.

Most people have no idea how to negotiate. In fact, most people have no idea what negotiation even is.

If someone offers you a job at $50,000/year, and you say “I’ll do it for $60,000,” that’s not negotiating. That’s haggling. There’s a big difference.

Haggling is zero sum. Negotiating is win/win.

When you buy a cup of coffee, both you and the coffee shop owner win. You win because you wanted coffee more than you wanted $4, and the coffee shop owner wins because he wanted $4 more than he wanted the coffee. That’s how the world goes ’round, an endless series of win/win exchanges.

True negotiating is just finding the right bundle of those exchanges. Their initial offer might be $50,000 and you might want $60,000, but there’s something you can do that they want more than the extra $10k and you want less. And they might want you to work one Saturday per month and you value that less than the bump in title they’ll give you for it, and so on and so forth.

You want to watch real negotiations? Find a baseball card convention and watch the trades happen. Those people create trades with dozens of cards each, constantly moving pieces back and forth until they’re both happier with what they’re getting than what they’re giving up. It can be complex, but everyone wins.

That’s how you have to approach negotiations to be successful. There’s not just one single metric, there are a half a dozen or more things that both sides can get. You want to understand and respect what they want, just as you understand and respect that the coffee shop owner wants $4. You want them to get $4, because that’s how they stay in business and provide you with more coffee. In the same way, you want people who negotiate with you to get what they want, because then they’ll come back to the table with you again and again.

And every time you’ll get what you want, too.

I like to build kits. When I was a little kid, I would find any sort of container like a satchel, backpack, suitcase, etc. and then fill it with themed stuff. As a kid, this translated into old briefcases dedicated to Lego building (with organizers for different blocks and flat mats to build on), satchels for journaling and craft projects (marble notebooks, scissors, glue sticks, tape, stickers, vintage magazines, and markers) and even the now-infamous (among my family) “Pouch-o-Fun” which was just a fanny pack that contained various little dime store toys for fidgeting with on long boring car rides or in doctor’s office waiting rooms.

As an adult, I still build kits. For everything. I have a tool kit for around-the-house handyman stuff. I have a mobile office kit for when I work somewhere besides my house that contains every adapter, cord, and accessory I need to work in a truly remote capacity, including a mobile hot-spot. I have a kit for my shaving. A travel medicine kit with nothing that can’t go on a carry-on.

If I engage with any activity in a meaningful way, chances are I’ve built a kit for it. I tweak and shape them over time, optimizing for space and organization. The point of these kits is to make it easier to engage with the activity, and to make sure I don’t forget anything when I need to do so. Too many times when traveling for business did I realize I had a headache or an upset stomach or a stain on my only dress shirt or something like that, so I built out a kit of all of the remedies for those common troubles. Now when I fly, I just have to grab one thing and throw it in my bag, instead of trying to think each time, “Do I feel a headache coming on? What if this jacket gets a hole in it?”

I’m good at this. Building kits is a genuine talent of mine. “Everything You Need To Do X” in a well-organized container.

One thing that made me much, much better was when I realized the most essential component of any such kit: empty space.

I used to think that if a container wasn’t 100% filled to the brim with stuff, then I hadn’t truly optimized it as a kit. If it wasn’t full, after all, then either I could fit in more potentially useful stuff, or I could use a smaller container, and both seemed like upgrades to me. But one day I had brought my Lego kit (the aforementioned briefcase) to a fellow kid’s house to play, and the neighborhood friend was kind enough to gift me a few blocks I’d liked. And I had nowhere to put them. I carried them home in my pockets like a chump, because my Lego container was so efficiently packed that there wasn’t room for anything else, even a few bricks.

It took a few more incidents like that for me to really learn the lesson, but the point is that a good kit needs some room for adjustments “in the field,” whatever that happens to mean for a particular use. When we go camping, my daughter and I always pack a few extra empty bags or other containers – for me, it’s usually for trash and for her it’s usually for cool rocks she finds, but there are a million other uses.

The most useful kind of bucket is an empty one. If it’s filled with water, you have water – and water is good! But you can’t do anything else with that bucket. An empty bucket, on the other hand, can do a million things, including carrying water if you find it.

Here’s the broader lesson: leave room in whatever you’re doing. Room to pick up cool rocks, room to accept gifted Legos, or room to adjust and change and bend as you need to. If you work a 40-hour week, don’t pack it so tightly that there isn’t 15 minutes to accept an impromptu meeting with someone that could be very beneficial. If you have a lot of hobbies, don’t over-schedule yourself to the point where you can’t just grab dinner with a friend.

It’s very good to be organized. But don’t make the mistake of organizing away all your margins. Leave a few for good measure.

In every person’s life, there needs to be an Ultimate Virtue. A foundation of aspiration that exists at the end of every chain of motivation.

You find your foundation by asking yourself the deeper why behind every action. Do you work hard? Assuming the answer is “yes,” then there are only three possible reasons why you do so:

1. Working hard for the sake of working hard is your Ultimate Virtue. You derive no deeper reward from it and it serves no further end; your personal philosophy is that hard work is the end-all be-all to a fulfilling life. I don’t think many people are in this category, but it’s certainly possible.
2. You have a chain of motivation that runs deeper than the work itself, and ends somewhere else at your Ultimate Virtue. For instance, you might work hard in order to get money, and you get money in order to put it into savings for your kids, because you believe that providing as big a head start as possible for one’s children is the Ultimate Virtue. Or you could work hard because you want the status of your job, because you want to leverage that into an even higher-status job, and so on and so on until you command vast legions because you believe power over society is the Ultimate Virtue. Or one of a million others – but you have a foundational motivation that lies far underneath your daily toil.
3. You don’t know; you’re an automaton who isn’t happy and isn’t getting any happier; you have no fulfillment and you work hard mostly because that’s the channel that society’s institutions mostly funnel you towards if you don’t have any other aspirations. You default.

Personally, I respect the position of a drug addict more than the position of #3. Why? Because in a certain sense, a drug addict’s position is understandable. Imagine this was your Ultimate Virtue: “All life is temporary and meaningless, and the only worthwhile thing you can get out of it is pleasure in the moment; maximizing your happiness in the next 10 seconds is my foundational aspiration.” If that was what you truly believed, doing a ton of drugs would make sense. But the person in #3 doesn’t even have that.

Why do anything? You can’t just stumble through life on default, taking the path of least resistance and then dying and hoping it all works out. If you don’t believe that life has greater possibilities than that, then why not just live a life of drug-fueled hedonism and die young? The number of people who seem to believe “life is miserable, so I’d better make mine last as long as possible” is staggering.

I think the meaning of life is simple: pick a thing you truly believe in, and then act as if you truly believed in it. If you align these things, your life may get much more difficult, but at least it will be worth the difficulty. I’d rather do a lot of work for a lot of gain than do a little bit of work for nothing.

You may have a thousand chains on you, and in a lifetime of struggle, you may do no more than loosen one or two of them. The struggle is worth it. One breath you earn is of more merit than a hundred thousand that are handed to you, even if it’s your last.

Sometimes I write posts that end up being a point of reference for me often in the future. And sometimes, as with this post, I’m writing it specifically because I know I’ll want that reference in the future.

This is going to be a post I’ll show to anyone who wants to ask me for advice. If people frequently ask you for advice, feel free to copy this post and use it yourself!

The reason I want these things in an evergreen format is many of the questions I’ll put below can seem a little off-putting or even insulting if you think I’m asking them of specifically you and you alone, but are perfectly reasonable if you know that they’re just the baseline questions I always ask. So I’m putting them here in advance so I can prove that’s the case!

Okay, preliminary stuff out of the way. If I sent you this link, it’s because you asked to have some sort of meeting or conversation with me about some topic and want my input. If that’s the case, here’s the first thing you need to know: I don’t actually want to give you advice. I’m responding to a request and I’m happy to help, but this is me helping you. I wouldn’t stick my nose in your business if you didn’t ask, believe me – so don’t take anything as a personal insult.

The second thing I want you to know is that while I’m a generally pretty competent guy who has been around the block, I’m not some sort of universal expert or even particularly smart. It’s worth making sure that you actually want my input. Be skeptical! Confidence can be easily mistaken for expertise, and even with me you should be careful who you listen to.

Okay, assuming I haven’t chased you away from the idea of asking for my input about stuff, let’s get down to the things I’m likely going to ask in 99% of situations.

1. After you’ve described an unpleasant or sticky situation, let’s examine the following idea: what would you do if you were literally the only human in the scenario who was capable of change? What would you do differently?
2. List at least two ways in which you are the architect of the current situation. Unless a meteor fell from space onto your house, you had SOME input in getting here. I don’t want this to be accusatory – rather, I want to equip you with the insight to not have a bad situation repeat.
3. What advice would you give to someone who was in a nearly identical situation, except they didn’t have any financial worries at all? How about if their situation was identical but they didn’t care about other peoples’ feelings? What if they had the same situation except they were invincible, immune from bodily harm? (Creating these “what ifs” can help isolate the real problem in a complicated situation.)
4. What solutions have you already thought of and dismissed, or tried and failed? If the answer is “none,” then we’re not having the conversation we should be having.
5. Lastly – do you want my advice? I know that seems like a weird question to ask this late in the game, but the reality is that a lot of people think they want advice and what they really want is to be listened to. And if that’s the case, I’m genuinely happy to do it – I’m a friendly ear whenever you need it, and not all problems need solutions; some just need friendship.

There’s a theme around these questions: personal responsibility. I’m a big believer in it, for one. But also it’s just a practical concern – I can’t really impact any of the other people in your story, so we have to focus on the brain in front of us, and that’s yours. You can see how some of those questions might feel a bit confrontational if I asked them right after you told me about an unpleasant problem you’re facing; they might feel like I’m exclusively putting “blame” on you or something. But it’s not that at all – it’s just that you’re the one I can empower.

Anything you do frequently, you should take the time to improve and make more efficient. If you spend a lot of time at a desk, it’s worth optimizing that desk for your comfort and efficiency. Similarly, I spend a lot of time advising (it’s my literal job, for one, but also the structures of my life and relationships just tend to run that way), so I want to make the process as efficient and effective as possible.

If you’re a parent, a manager, a leader of any kind, the go-to person in your social circles or family for practical advice, or any kind person who hears they phrase “hey, can I pick your brain about something” more than a few times per week, this same methodology can be very helpful for you as well. My goal is to give advice sparingly and thoughtfully, and to be considerate in my approach – if that helps you as well, then I am doubly glad.

It’s good to do weird stuff. Take strange jobs or assignments, visit unusual places or events, interact with oddball people. It’s good to do this because it expands your Weirdness Radius.

What’s your “Weirdness Radius?” It’s the distance from your normal baseline life out to the weirdest thing you’ve ever done. That radius defines a circle, whose area is defined as “things you’re pretty confident you can handle.”

Note that the trick here is that it doesn’t matter which direction the weirdness was in – the circle expands equally in all directions and therefore encompasses new things that might have nothing to do with the experience that led to the expansion in the first place.

When I was a teenager, I once took a nine-hour road trip to see this absolute lunatic named Gene Ray speak at MIT about his crackpot theory “Time Cube” (warning: if you go down that rabbit hole prepare to lose several hours of your life). It was a wild experience. If you asked if I learned anything directly from the lecture, the answer was obviously “no.” But indirectly? I learned a ton. I learned how mainstream thinkers treat outsiders. I learned about how obscure things can go “viral” before such a term existed. But more than all that, I just learned how to interact with and not be intimidated by a weird experience. At time, The Great Time Cube Road Trip defined my “Weirdness Radius,” and anything less weird than that, regardless of whether or not it had anything to do with crackpot mathematical theories or road trips, wouldn’t phase me at all.

The more weird stuff you do, the more resilient you become to life’s unexpected twists and turns. If you’ve eaten hormigas culonas in Colombia, you’re probably not freaked out by a spider in your kitchen.