How can I bet on my values and goals to get better—and faster—information?

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Published on August 29, 2025 6:33 PM GMTEvery goal I set in my life I see as a bet, an investment. I bet time, energy, and resources on the belief that it will lead to something valuable. I try not to leave it to chance. I try to pick my bets based on what helps me the most, on what gives me information about myself as fast as possible.In 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.Some bets are very costly—like my case of studying probabilistic reasoning here on LessWrong, haha. And some just seem weird, like when I bet that eating a kilo of cheese would make me wiser. (Well, it didn’t, but it gave me great material for this post).So, would you like to help me? How can I bet on my values and goals to get more—and faster—information? I’ve developed a specific framework to evaluate these “bets.” [Link to acclimatization]Here’s what I’ve been thinking:What’s my track record with this type of horse? Tough one—my memory is too biased to keep a reliable history, but maybe I can build an app that logs my key moments. [more in this link] What are the real odds? Hard to know. I’d need a whole battery of questions to assess my resources. Maybe that could help? [more in this link] What’s my competitive advantage? Even harder—if I don’t really understand my own variables, which are already a universe to study, how can I compare my universe with someone else’s? What’s the real cost of the bet? Maybe with key questions and specific comparisons to myself I can get an idea, as I suggest here. [more in this link] Why do I really want to bet on this horse? Same as above—I’d need a database of personal insights, which I could start building with this framework. [more in this link] What are the signals that I should pull out my bet? What indicators will show me I’m off track? At what point would it be smart to cut my losses? How will I know if I need to change my strategy? What does victory look like? In life it’s rarely just yes/no. I’d need a framework to see levels of victory, like evaluating my peaks and lows of motivation and satisfaction. [more in this link] Am I diversifying my bets? Am I putting all my resources into a single goal? Do I have a balanced portfolio of short-, medium-, and long-term goals? Do I have enough resources to diversify well—or am I spreading myself too thin? And what happens if this bet doesn’t pay off? I feel there’s something in common between goals and horse racing: not all my bets will be winners. But if I improve my questions, my odds increase dramatically—and at least I won’t end up burying myself in cheese for nothing.These questions grew out of my work with therapeutic humor in tough contexts. [more in this link] I’ve worked with more than 200 incarcerated people using humor as therapy, and I want to apply some of what I learned there to improve myself. I mean—if I can help rapists, why not apply it to me and others too? (Okay, dark example, I know). [I will publich mys insides here]Discuss