Coaching myself on being more careless

I've been training myself to make all sorts of investment decisions over the years. Some don't involve money at all, only meat and time. Some are calculated, some are intuited. In 2012 I was mainly concerned that I would be afraid to lose money, so I torched $25,000 very slowly over about three months, just to coach myself to be intentionally careless. Then in 2015 I wrote off about $15,000, and committed my life to a business, which ended up lasting 5.5 years. In 2023 I find myself worried about my work, but after some reflection, I think it is more a matter of fear of being wrong ( epistemologically ) than fear of losing money. So I have to practice being wrong more carelessly. That is something I should look forward to doing more in 2024 ... taking higher risks of judgment, and writing off the consequences immediately, before the outcomes are known. That should help me to improve my focus on work.