Some Painful Questions We Ask Ourselves

discernment is good, discernment is hard

This post was written in collaboration with Cate Hall.

We are writing this because we have both screwed up a lot of things, and have been really screwed up. We’ve wasted years, destroyed relationships, had addiction issues, and so on. This has made us passionate about trying to live lives we can be proud of, to the extent possible. Part of this involves self-compassion and patience. But it also involves some degree of self-scrutiny. 

These are all questions that make us go “ow,” a little bit or a lot, based on either our current lives or some of our past foibles. They are not intended to drive us crazy, or anyone else. Self-loathing is not productive and typically doesn’t result in better behavior. But if you can’t see yourself accurately, you can’t change anything, or have any impetus to change: loving yourself isn’t incompatible with believing you’re capable of more.

These aren’t intended to be used all at once. Maybe explore one or two you find most relevant. 

1. Am I taking personal responsibility for the world, or am I waiting for someone else to tell me what to do?

Okay so like. On average, it might be bad for people to walk around thinking that they’re a Major Protagonist, capable of bending the world to their will. But you, reader, might be systematically underestimating your level of agency. Say that you would like the world to be a more compassionate place, or a place filled with more poetry, or modern nuclear reactors instead of coal plants. Is this a matter you’re investigating actively? Are you sure the best way to positively influence the world, as defined by you, will just kind of filter down to you? 

It probably won’t. Fortunately, both of us have found it shockingly easy to make things happen in the world if you simply decide to be the kind of person who does that. Deciding to be action-oriented, even in the face of uncertainty, is a superpower that is accessible to almost everyone. A willingness to simply say “I see this problem and I am going to take personal responsibility for doing something about it” is incredibly powerful. 

Experience often matters less than you think. You can achieve much by blundering into things and assuming they can be figured out. In one example, after Cate spent a few years wondering how she could help with EA causes, she started trying things. This led her to start believing she was a person who did things, and eventually, after doing some right things, and some wrong things, she co-founded a ~$100M pandemic medicine company with nothing on her resume that would obviously qualify her for that. 

2. Does this action bring me closer to or further from my idealized self?

In some way, your daily choices are a vote on your future self. Basically everything compounds. Why not compound towards the version of yourself you’d prefer?

Of course, you will never become an ideal version of yourself. And getting really obsessed with some precise vision of an idealized self might not be helpful: you might end up chasing an impossible fantasy that probably has something to do with your current hangups. (Sasha has lots of experience with this.) At the same time, if you have a nagging feeling that something you’re doing is making you worse or less interesting, it can be revealing to ask, “is the person who tends to do this the person I want to be?” At the very least it can get you to examine, for example, your use of fruitless tranquilizing dopamine pumps, your social conduct, and so on. 

This is less about being stuck in a frame of constant teleological self-observation, and more about paying some attention to designing your lifestyle with a view towards the far shore. This thing you do a lot of: does it take you closer, or further? 

3. If no one could see me doing this, would I still do it? 

It’s not like there’s anything monstrous about a little bit of signaling. Sometimes you have to do it, you have become inextricably entrapped in society by virtue of birth. But it’s worth examining how much of your lifestyle is based on, say, exuding an air of sophistication. Maybe not a lot, but maybe a lot, maybe a lot more than is required. Maybe a lot of your life is hanging on the mission of making yourself attractive to a large number of others. We’ve both found that “will people want to sleep with me” can be an insidiously pervasive thought behind much of life. 

Again, there’s nothing wrong with wanting to be attractive or, say, wanting to do the right thing in part because you will get credit for it (doing the right thing for the “wrong” reasons generally beats doing the wrong thing). But it’s gratifying to know what you actually care about for its own sake, rather than instrumentally. It helps guide you to things that will durably improve your self-respect, rather than making it so contingent on other people. Ultimately, we would hazard to guess that activities undertaken primarily for signaling value will feel unsatisfying, even when done successfully. And it’s easy to slip from “playing the human game to a reasonable extent” into “living a life of corrosive falseness for the ultimately unfulfilling approval of others,” and only you can spot where the line is.

Cate went through a long period of celibacy to see what she would be like with attractiveness taken off the table as a concern, and she found it immensely rewarding. Sasha realized that he didn’t care about most of what he was writing in the media and was largely pursuing his career to be impressive and attractive, so he stopped, and he has found this stoppage restful. 

4. If everyone could see me doing this, would I still do it?

And yet sometimes the opinions of others can be a reasonably good guide. Not for everything, obviously. But let’s say you have an uneasy feeling. You’re about to invoice someone for a job, and you’re thinking about exaggerating the number of hours you spent on it, thus charging an inflated price. It’s not like you’re committing fraud, you know, just rounding up, the way that most people probably do, right? And you were probably thinking about the project during lunches and driving to and from the office, or something. It’s normal, and no one will find out.

But what if everyone—your mom, the person you most admire, your current and future clients—knew you were the kind of person who, given the opportunity, would inflate your prices opportunistically? That might clarify things slightly. 

5. If I were choosing for an uncountable number of ‘me’s, would I choose this?

Envision yourself making the decision before you over and over again. If you find it repellent to try and imagine infinity, let’s say a million times. Would it be utterly intolerable? More or less okay? Would you be proud of it? Repeat with your day, your month, your life.

This isn’t necessarily an injunction to try and make a perfect choice. Fretting about the best choice to make for all eternity is a bad thing to do for all of eternity. More obviously this is a tool to really feel the pain of ugly compromises you don’t have to make, buried passions, confidences casually betrayed, wishes postponed forever, love unexpressed. Also more small-scale stuff, like, would you spend two hours on Twitter in a way that doesn’t make you happy if you knew that meant repeating those two hours one million times? It’s also a tool to feel the comparative relief of behaving in a way that you can stand behind, if only when examined by an audience of yourself.

6. Why would an insecure, status-seeking, fearful, vengeful person do this thing I’m doing?

It’s all well and good to try to act with the “right” intentions, like to genuinely seek to not take advantage of others. But motivated reasoning is really hard to see, and none of us have “pure” motives. We shouldn’t expect to, either; it’s not useful to expect that. Self-serving reasoning is one of those biases that doesn’t go away when you know it’s there. It’s not really even intentional—it just happens. 

But it’s easier for us to avoid behaving badly if we can see what the most potentially destructive of our ulterior motives are, or what the worst version of their exercise would be. It’s sometimes easier to spot this, and less painful, by examining it from a third-person perspective. Let’s say my current situation was engineered by a person with awful motives. What would those motives be? If this doesn’t result in anything interesting, you can turn the volume up by bringing it into the present moment: if you wanted to, how would you exploit this situation for personal gain? How could this situation be serving your less flattering psychological needs? 

Lately, Sasha has been getting some amount of attention for talking about his spiritual experiences. To this point, he’s reasonably sure that his utterances have been made from a place of genuine belief and conviction, rather than just a desire for attention. But it’s not like he minds the attention. And some version of him could lean into the attention-seeking, maximize it in an unprincipled way, and gain power for the purpose of personal exploitation, to the benefit of no one else. He should keep an eye on that possibility!

7. To what extent do I try to distract myself from direct exposure to the contents of my own mind?

Please note that this is not an implied argument against all distracting/benumbing activities. Distraction is a popular coping strategy, and not always bad. The question isn’t really whether you do it, it’s a question of whether you always do it. 

Many, many people go through the day from distraction to distraction, from TV to games to doomscrolling until sleep. Sometimes it can indicate that you’re scared of the contents of your mind. We’ve both spent a lot of time avoiding dealing with our shit in this time-honored fashion. Conversely, useful thoughts about important shit only really come when you make the space for them to bubble up. 

Accepting the possibility of boredom can also help us reattune ourselves in the face of an environment that tends towards hyperstimulation. After her drug addiction, Cate decided she would just be bored for a while—she took lots of long walks, sat staring at walls, and ate uninteresting food—so she could reaccustom herself to subtler pleasures, instead of the massive superstimulus of drugs. It worked.

8. Am I  avoiding information that I know might change my behavior?

In our experience, it’s possible to go around your life, for years, with obvious potential lessons lurking at the edge of the frame. You just don’t want to look. Like: maybe your dietary habits would change if you really looked at the effects of factory farming. Or: if you considered how you could be of service to others, whether close others or far others, you might change how you spend your time. Or maybe not! But are you willing to look? Are you sure you’d be able to justify your actions if you did?

The answer can be “no, thanks for asking.” Sasha, for example, is aware that he makes some dietary choices that he can’t really justify. We all do things we can’t justify! You’ve got to pick your battles, and you can’t be perfect. But it’s good to be honest about that rather than to justify yourself falsely. Seeing oneself clearly makes room for the possibility of change; delusion makes room only for further delusion. 

9. When engaging with new subject matter, am I motivated by a desire to understand it, or to have an opinion about it? 

Is Google primarily a tool for telling you that the world is more or less as you believe it is? How often do you take a position on an issue just by looking around and discerning what the “right” opinion to have is, then selectively learning the facts that justify that belief? Don’t feel too bad, this is probably most of what politics is. 

But do take a look! It’s fun! Notice what happens if you force yourself to examine how you know your opinions are right, to see whether the facts underlying the matter are known with enough granularity to actually justify the strength of your view.

We both used to talk about our political beliefs a lot. We have both realized that >90% of our public utterances in this domain were bullshit—not necessarily wrong, but made without reasonable justification, stuff said just to say stuff. We’re aware that probably a lot of what we say is still bullshit, but we’re working on it.