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.

People who are upset, depressed, sad, or filled with anxiety often unintentionally prevent themselves from being helped by performing a sort of bait-and-switch on themselves. It goes like this:

Sad Sam laments about his feelings to a friend, colleague, loved one, etc. That other person says “oh, you just need to get some sun/find a better job/sleep more/etc.” Some sort of generic but positive actionable advice. And Sad Sam says “That’s not it at all! I’m depressed, it’s not as simple as ‘get more sun,’ I have a real chemical/medical problem.” That’s a legitimate response, by the way! If someone truly has depression, they’re also sick to death of people in their life saying “just get more sun” and junk like that.

But! If Sad Sam laments about his feelings and the friend says, “well, it sounds like you have depression, maybe you should seek some sort of professional help and/or medication,” then Sad Sam is just as likely to say “I don’t have depression, my life is genuinely bad/rough/difficult/terrible!”

You see what happened? Whichever solution they’re presented with, they claim they have the opposite problem and it’s therefore unsolvable.

But that switch is false. First off, both things can be true – you can have a real medical condition that affects your mood, energy levels, thoughts and even actions, AND you can have a tough/difficult/crappy situation you’re living in. In fact, there’s probably a high correlation between those two things, so it’s not uncommon at all for one person to be experiencing both simultaneously.

But the “solution” to both is exactly the same, so switching the focus from one side to the other doesn’t work. The reaction to both is this: I work every day to get better or I give up and die.

That’s it. There’s nothing else.

If your external situation is crappy, you work to make it better or you give up and die. If your internal situation is crappy, you work to make it better or you give up and die.

What the actual methods are will vary from person to person. For an internal situation, possible improvements can come from medicine, therapy, spirituality, meditation, or Taylor Swift (seriously, listen to This Is Why We Can’t Have Nice Things and tell me you don’t feel at least a little bit better). For an external situation, possible improvements can come from physical exercise, getting a new job, moving out of a bad environment, or increasing your social activity. Lots of those things will have overlap into both situations – physical exercise both improves your mood and likely improves your situation in life for a variety of reasons.

But the point is, since the solution to both internal and external sadness is “put in the work or give up and die,” it’s a false defense to deflect from one to the other. If your car is both out of gas and has a flat tire, and someone says “oh, you have a flat tire, if you fix that your car will move,” it doesn’t really make sense to say “No, I’m out of gas – so my car will never drive again and it’s totally hopeless!” Look, the core advice is this: your car can drive again, but you have to fix a few things, regardless of which things they are.

So get to work. Or give up and die. But very, very preferably the former.

Sometimes, people you care about are stressed or upset or in pain, and that in turn makes you stressed or upset or in pain. You want to help. Reflexively, you might ask: “Is there anything I can do?”

Sometimes there is, but most of the time you don’t get a good answer to that question. Partially because there might not be anything you can do, but honestly that’s not really the problem. Often there’s a ton of stuff you could do, but you don’t know what it is.

Relying on the person who’s in pain to tell you what to do isn’t a great strategy. They’re in pain, they’re not ready to manage a project. They might feel guilty for asking for something specific, even if you’ve offered help in general. And they might just be too distraught to know what would even help.

In one of my past posts that I reference very often, I wrote about the important of doing literally anything when you’re stuck and don’t have a clear plan. In the context of that post, I was talking about helping yourself – but the advice applies well when helping others as well.

Small acts of kindness go a long way, and you can’t really do them incorrectly. They’re about expressing your sincere commitment to the other person’s well-being more than about fixing a specific problem. They’re about giving the other person a little momentum to get started.

Don’t worry if you don’t know exactly how to help. Just do anything, even a little thing. The little things go a long way.

There is a time to be wild and try crazy things, and a time to lean on tradition & habit. I think most people get those two situations exactly backwards.

When things are going very well for someone, they tend to coast. They don’t look too hard under the hood, and they don’t question things. Another entry in the “Johnny Loves Debunking Folksy Truisms” file is this one “If it ain’t broke, don’t fix it.” That’s terrible advice, and I’ll get to why in a minute.

Meanwhile, when things are going poorly and you’re in the red, people tend to panic. I’ve written before about why it’s so hard to do nothing even when “nothing” is the right call, and it’s still true. When the chips are down, people – for a wide variety of reasons – start wanting to mess with all the settings.

Let me explain why you should probably be doing exactly the opposite, and talk about why “if it ain’t broke, don’t fix it” is terrible advice.

There’s a fable about an old man with a leaky roof. When it’s raining, the water falls through a hole in his roof, necessitating him putting a pot on the floor to catch it. He can’t fix the hole then because it’s raining, of course. And then when it’s sunny out and he could fix it, he’s not troubled by it – because no water is coming in through his roof. So his shortsightedness means that he never mends the hole in his roof.

Let’s take that and extrapolate on the lesson of it. Of course, the old man was half right – fixing your roof in the rain is a pretty terrible idea. Not only is it much harder, but the risk is also way higher – not just your personal risk of injury, but the risk that you’ll actually make the problem worse! One wrong move and a small hole could become a man-sized one and suddenly one small pot on the floor isn’t going to cut it as a stop-gap solution. No, during the rainstorm the correct move is just to hunker down – put the pot on the floor and ride it out.

We all recognize that in the story, the mistake of the old man wasn’t not fixing the roof in the rain, but rather, not fixing it in the sun. When the day is sunny, you can do anything! Lower risk, more available resources (such as good natural lighting to see by), and less chance of a big mistake doing anything to create immediate disaster. Even if you did put a bigger hole in your roof during your repair attempt, your living quarters would still be dry and you’d still have time to fix your mistake.

That’s a great analogy! When you’re in lean times, either as a business or an individual, you have to rely on the tried-and-true things to get you through that patch. Don’t try to think your way out – work your way out. Put in the time doing the most reliable things you know how to do until you’re in the black.

But when you are in the black? Try anything! With extra resources and a low risk point, that’s the time to try out new things, make riskier investments, etc.

I can’t tell you how many people I’ve heard say, “Oh man, I just got laid off from my job, so I think I’m going to go back to college and get another degree.” Those same people wouldn’t have taken a $50 online course for a relevant skill when they were employed, but now that they’re in a bad way they want to drop a thousand times that number (and several years) on something they aren’t sure about?

When your back is to the wall, work. When you’ve got a good amount of runway, that’s the time to get wild. Don’t reverse them. If it’s broke, fix it just enough to get it working again. If it ain’t broke, build ten new versions of it, so you have them when the first one breaks.

Someone can be wrong about something without their incorrect belief being unjustified.

Information is rarely perfect, and lots of signals can be misinterpreted. Even assuming charitable, intelligent observers, those observers can still get an incomplete picture.

If you wear a yellow shirt only two days in your entire life, and some by some coincidence you interact with a particular bank teller only on exactly those two days, the bank teller might have the impression that you frequently wear yellow shirts. They’re wrong, but they’re not unjustified. (Sure, they might be savvy enough to know that two data points isn’t enough for such speculation – but few honestly think this way intuitively.)

Now imagine that you see the bank teller on a third day, only this day you’re wearing your trademark red shirt that you always wear because you love it, and you only wore that yellow shirt those two days because your red one was being mended. Bank teller sees you and offers a friendly hello, and then maybe makes a comment like “Where’s your famous yellow shirt today?”

Now imagine you got mad. How dare this person! You’re not some yellow-shirt-wearing person! You’re a tried-and-true RED-shirt-wearing person! Everyone knows that! You don’t ever think of yourself as a yellow-shirt person. How could anyone think that?! Oh, you’re so mad and frustrated and upset!

Look, you might take it as an insult to be associated with yellow shirts. You might really want to be known as a red shirt person. And you might even BE a red shirt person – the bank teller was wrong. But that doesn’t mean they weren’t justified in their assumption.

You shouldn’t be mad. Instead, you should reflect: “What made this bank teller think that I, noted red-shirted person, was a yellow-shirt?” And if you’re smart, you’ll realize the limits of other people’s information about you compared to your own self-perception.

Someone can be wrong about you, but that doesn’t mean they were wrong about the information they received.

Okay, so obviously yellow and red shirts here are metaphors. Stand-ins for, honestly, whatever you want them to be. If you’re one thing, and someone else thinks you’re something else, don’t get mad. Reflect on why they think that. Even if it’s not true, you have to take ownership of that information. They think that for a reason. If the person is intelligent and charitable, they might even think it for a very good reason, so you shouldn’t just brush it off.

That’s something a yellow-shirt would do.

Some people are just naturally very negative. They hear an idea and immediately jump to a reason why it won’t work. “Why don’t you apply for that job,” you ask. “Oh, I’ll never get it, they want someone with blah blah blah,” they respond. These kinds of people aren’t evaluating risk versus reward, they’re just reflexively reversing whatever idea is presented to them.

This habit, once you let it take hold, is very hard to overcome. If your first instinct is that something will fail, chances are good that you’re far too risk averse and you’re missing a lot of areas where you could positively impact your life with small changes in effort. That can eat away your life, but once it’s there, that poison is hard to cure.

So what if you just turned it to your advantage? If your first instinct is to reject ideas, why not give yourself bad ideas to reject? Push the needle hard in the other direction, and let your instinctual rejection cause it to bounce back into the positive.

“Hey, you should throw out your exercise equipment. Just put it on the curb,” I’d say to you. Maybe without even realizing it, you’d say “No way, that equipment is useful, I’m going to work out right now.”

You’re a pessimist? Fine. Be a pessimist about pessimism. Assume you’ll fail at failure. If tricking your mind is what it takes to get started and begin to work the poison out of your system, I certainly won’t hold it against you. Whatever it takes to make that first spark.