I suggest spending a few months or years making many predictions on Fatebook, and regularly re-evaluating your mistakes and brier score and calibration plot. This will not get you all the way, but when I tried this (in those days with predictionbook), I got much much better at figuring out what it felt like when I was bullshitting myself.
Then when I came to Berkeley and found people who wanted to bet on a bunch of stuff, I won a large number of those bets.
I appreciate that, betting on the market, but it requires that I study well to actualize my beliefs about the market. And if I bet on my own beliefs, my capabilities, expectations, and personal goals, to study myself?
Sorry, haha well i mean, on the racetrack of my life, I see horses of different breeds, trainers, and odds I could bet on: professional careers, relationships, personal projects, skills to develop. How can I bet better?
Some bets are very expensive, like the bet I made with myself that I could be a genius at probabilistic reasoning here at LessWrong, haha. And others just seem weird, like when I bet that eating a kilo of cheese would relax me and help me think better... (Well, it didn't. I could talk about other, weirder bets, but that one seems less likely to be canceled.) The point is, I left two expectations to analyze: one very difficult and one very easy.
Yeah, so you make probabilistic forecasts about events in the future, then you grade yourself later, and update based off what the results ended up being and how wrong or right you were.
If its expensive to test a forecast, prioritize those less until you have a better understanding of which experiments are more likely to be more valuable, and you have better prediction capabilities.
You need to have beliefs to test how well-calibrated your beliefs are. Studying is one way to form new beliefs. You could avoid that effort by just testing your existing beliefs.
Sometimes it's hard to define bets, especially if they're predictions about myself, right? Are you trying to make this type of bet?
You can try to make a prediction about what future you will think. For example, "in 2 years, I will think that working on project X was a good idea". If other people don't want to bet on those terms (since you can technically say whatever you want at the end), you can just write down predictions and then see whether your predictions in the past were correct.
You might object that now you don't have skin in the game, but I think you do, if you care about trying to win the game of writing down good predictions.
As I see it, most of the epistemic benefit of betting comes from:
A) Having any kind of check on nonsense whatsoever.
B) The fact it forces people with different opinions to talk and agree about something (even if it's just the form of their disagreement).
C) The way involving money requires people to operationalize exactly what they mean (incidentally revealing when they don't mean anything at all).
None of this requires betting large amounts of money; afaict, most bets in the rat community have been small & symbolic amounts relative to the bettors' annual income. So an easy way to 80/20 this would be to set yourself a modest monthly gambling budget (which doesn't roll over from one month to the next, and doesn't get winnings added back in), only use it for political/technological/economic/literary/etc questions (no slot machines & horse races, etc), and immediately stop gambling if you ever exceed it.
Then a valid response to your friend becomes "sorry, that's over my gambling budget, but I would bet 50 reais at 2:1 odds in your favor, and you get to brag about it if it turns out I'm wrong". (. . . and if you wouldn't have made that bet either, you'd have learned something important and not even have had to risk the money.)
I appreciate those points: more control, forcing agreements, and operating. But what if I bet on myself based on my own beliefs, my capabilities, expectations, and personal goals, to learn about myself?
Also, strong-upvoted for asking a good question. For a community that spends so much time thinking and talking about bets and prediction markets, we really haven't engaged with practicalities like "but what about people who [have | worry about] life-ruining gambling addictions?"
Let`s say in 2018, I was absolutely sure a candidate was going to win the election. I presented my arguments with great motivation, and a friend asked me if I would bet 500 reais on your expectations, so... I didn't want to risk my skin and he introduced me to the concept that a bet is a tax on nonsense.
Well, it seems that the more I see the risk of losing something important, the less lazy my mind seems to be.
When I'm about to calmly cross the street and someone honks in my face, I become an ninja at that moment. If I walk calmly and stumble, I pretend I'm a professional runner even though I'm wearing a tie and suit; the fear of falling. Risk activates me. But does that work for the nonsense I tell myself?
It seems like a good first step, but how can I avoid becoming a compulsive gambler? How to assess the risks when betting on what expectations to invest in? What would be better than asking key questions?