Several years ago, I came across this blog post talking about how often we don't take obvious advice. A few instances of this spring right to mind. For example, my gym schedule was badly disrupted by Covid, and I never got back into it. I obviously should, but I haven't yet.
Relatively benign, but we can think of other cases where this is true. In David Whyte's The Three Marriages (a deeply soulful and philosophical book despite the fact it looks like self-help on the cover) has written about how hard it is to convince someone not to enter into a relationship, no matter how obvious it is that they shouldn't. Speaking from experience, he says that they're going to do it, and all the advice in the world won't turn them away. And certainly, we've all been advised to do something very obvious before starting an endeavour and then just... not done it.
But what really got me thinking was a friend that ran his job search strategy by me. He laid out what he was doing, and asked me what I thought. I've given plenty of people advice on this topic (why they come to me, a decidedly inexperienced person, I will never know) and it occurred to me that I had nothing to say for once. Because he was doing nothing that was obviously wrong.
Obvious and Wrong
Whether something is wrong is a function of reality. If you stick your hand in an electrical socket, that will be terrible for you. Whether it was obviously wrong depends entirely on whether you know what an electrical socket is.
What I've been thinking about is that your capabilities and intuitions around these two axes (obviousness and wrongness) move at very different speeds as you age. There are plenty of little tricks in various sports that might be the correct play at any given moment, were it not for the minor inconvenience of not being skilled enough to pull them off. That is, as I practice, I am decreasing the number of wrong options and increasing the number of right options. When I can't actually land any three-pointers, shooting three-pointers is always wrong. Increasing the amount of right in my decision space relative to the wrong in my decision space is slow.
However, I can very easily shift my intuitions around absolute blunders. I read Patrick McKenzie's post on salary negotiation and it has earned me around $60,000 over the past two years in one evening. That's insane. That is, there are now plenty of things that are obviously wrong to me in this domain. For example, I always had the ability to ask for more money, but it wasn't obvious to me to just... do it. Everyone I know who has ever done this in a salary negotiation seems to have gotten it eventually.
There's the endless field of startups that obviously built something no one wants to buy. It takes a few minutes of Googling to save you years of pain. Make sure someone wants to buy the damn thing before you make it. Easy. This has nothing to do with your ability to execute, but everything to do with your ability to learn from other people's mistakes, although you do have to execute something at some point.
When I received some guidance on why exactly we pretend things aren't bad at work, my entire perspective on how to be helpful to the organisation shifted instantly. I can't imagine how many years it took that guy to figure some of this stuff out, and he has the skill to navigate it more effectively than myself, but now entire categories of action are obviously wrong to me.
If you're learning adequately from people's mistakes or writing, it feels like slowly being constricted - or at least, I hope I'm learning adequately, and that's how I feel. Endless fields of possibility get shut down, and then I pry open a tiny bit through focused study when I actually get guidance on how to perform sales effectively, or how to operate a particular library, or how to have difficult conversations with people I love.
But there is something a little bit hackable here, which is you tend to get a lot of early gains out of first studying something in both domains. That is, when I started learning Python, my perspective on what is obvious and wrong shifted dramatically. A whole way to deal with problems had emerged (so manual work was both wrong and obviously wrong), and the same applies to basically every domain I've tried to actually learn from existing resources, from having better relationships to philosophy. I'm not weird enough to deploy some obsessive strategy of jumping into as many new fields as possible at this point in my life, but maybe I should be that weird, and maybe it's worth adjusting the dial in that direction just a tiny bit.
And finally, a small takeaway that my friend ultimately found comforting - if there's nothing obviously wrong, then he's doing the best that he can do. It's good that he checked, because sometimes it's obvious to someone else, who can make it obvious to you. And if something was obviously wrong, you actually have to stop doing it, which is sometimes inexplicably hard. But you know what, when he's kicking himself in a year because something was wrong, at least he'll know for sure that, at the time, he really checked that it wasn't obvious.