“It’s generally despicable moral values that drive remarkable people.”
This is why I pay attention to Penelope Trunk.
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I need to be challenged. I need someone to challenge me. I need someone to ask me tough questions. I’ve written this before, but I want to expand on it.
A lot of people in my life think or have thought that they’re asking me tough questions, but they’re actually lazy questions or selfish questions. Rather than being questions of me to challenge me to be honest, think clearly, and confront realities, the questions are actually:
- Ways of coping with their own failures through projection (i.e. they only think it’s a question for me, or maybe even an accusation aimed at me, but in fact I could be a houseplant or a watermelon; they’re really talking to or about themselves without realizing it).
- Ways of evanglizing or advocating for something (i.e. they think they’re asking me tough questions about myself, but in fact any answer that I provide is irrelevant because they have a particular destination in mind for me, and once again I could be a houseplant, in fact it would be better because then they could just pick me up and move me to where they’d like me to go).
- Ways of trying to pick my brain for some wisdom or insight they subconsciously imagine that I have (i.e. they think they’re asking me tough questions but in fact they’re hoping for my answers to their own tough questions and presuming that they’ll be better answers than their own answers).
I am in need of someone to ask me tough questions that are relevant to me in the interest of getting me to answer those questions for myself, either because they care about me or because I’m paying for the service.
Only it will have to be because they care about me because I can’t afford to pay for the service.
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I wonder if there are some people out there who don’t need to be asked tough questions and don’t need to be challenged in order to find clarity and success.
Certainly I’m not one of them.
I do believe that most everyone needs a good, regular mental and emotional ass-kicking that comes from a place of care and whose characteristics include directness and honesty. I think that most people descend into self-ignorance, denial, and escapism/lazy status-quoism without these.
But are there or might there be some people that have an internal self-insight mechanism? Wish I was one of them. I used to think I was, but that was just youthful naiveté.
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Best question-askers in my life so far:
- My dad. I wonder if I should impose on him for a good ass-kicking. The thing is, with him it has to arise organically. I think that if I asked for one directly, he’d have no clue what I was asking for, and might even be anxious and worried about the whole thing.
- My aunt—one of my dad’s sisters. I still remember a walk that I took on a golf course with her one day (the one and only time in my entire life when I set foot on a golf course). She was tough. Boy, was she tough—especially since it was one of the most painful periods in my life. But that’s what really good tough questioners are able to do—kick you while you’re down just hard enough that you get back up, because they know that you can, even if you’ve convinced yourself (in all your self-indulgent pathos) that you can’t. Boy was it good for me.
- Several professors. I wish I could say mentors, but the structural realities of my own academic life have always been such that I couldn’t afford mentorship. Because that would mean buying into the academic plan wholesale, and having the time and mental energy to become preoccupied with it. I was always the guy who couldn’t really afford to be there, so I couldn’t ever really take advantage of the context and make it worth my while. I went all the way to finishing a Ph.D. as the guy who couldn’t really afford to be there. I’m still the guy, in fact, who can’t afford to have been there. I had no business, given my economic background, playing a rich man’s game like academics. But I did. And there were three professors (none of them at Chicago, for those who are wondering) who were reasonably good at asking tough questions, though I sometimes think they could have been tougher. Probably they felt hamstrung due to academic culture these days and uncertainties about just how far they could push things before I ran to administration with a complaint about hurt feelings or something. After all, I never quite got to know any of them quite as well as I wish I had been able to—again, see the discussion on mentorship and economics several sentences ago.
So that’s it. It’s frankly not all that many. The older I get, the more it feels like a giant black hole in my life. I haven’t been pressed enough, haven’t been forced to grow enough, have been suck entirely too much on “self-reliance” and “self-insight.” Those are limited things.
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My ex-wife would laugh at this and say that it’s all bullshit because I don’t listen to anyone. She’s absolutely wrong on that point, though, always was.
I listen to people when they’re worth listening to. The people above have been very worth listening to. I continue to get the feeling that people like Penelope Trunk, despite the fact that I reference her in a totally different context (i.e. it’s not an interaction) is worth listening to.
The problem is that most people aren’t worth listening to, and most people don’t ask you questions honestly; they’re really doing something else when they ask them.
It’s true that some people don’t listen to anyone. But it’s also true that if you feel as though someone is not listening to you, you should ask yourself whether you’re saying anything worth listening to, or asking anything worth answering—or for which the askee’s answer will actually make a difference, either to you or to them.
A lot of people think that people aren’t listening to them when in fact people have already listened and realized that they heard every last thing that person was ever likely to say, encapsulated in the first five or ten words that came out of their mouth, and that it wasn’t actually all that useful or purposeful and so there was no point engaging with it any further.
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People who are worth listening to are few and far between. It pains me to say that because for years I held it as a taken-for-granted value that everyone was worth listening to. But it just ain’t so, ma.
That’s one of the sad truths of life in society.