This could be a good article (and I'd agree: start in discussion) with some more specific examples, and some way to quantify "intensity" in a useful way. I suspect you'll find that if you do so, you end up with something that looks like an expected value calculation from classical decision theory
Also, there's LOTS of things that you can rationally estimate with higher than 90% confidence.
My personal opinion is that this is the kind of thing that should be in discussion, not Main. Also, I recommend you standardize your font choice and size to fit with the other posts here.
Yes, one should vigorously enact risky, positive-expectation plans. I think that's clear to this audience.
How do you vigorously enact risky plans while acknowledging their uncertainty? This is psychologically much more difficult.
Things described around LW as productivity hacks will help. But the feeling of optimism and the acknowledgement of a risk are different things. I experience optimism as pleasant, motivating, and an aid to focus. It'd be awesome to feel optimistic about positive-EV risky plans, in general. Do you know ways to do this?
Actually, learning what 80% feels like is also important. For example, putting it in terms of "this talk will be a disaster at least once out of every five times I give it -- can I live with that?" might be useful.
On a scale of 1 to 100, how sure are you?
It's a good thing to ask yourself from time to time about intense beliefs, especially if you're having a disagreement with someone else smart.
Just putting a number on something is good. If you're in business, putting any number in the high 90's is dangerous and shouldn't happen too often.
Yet, you still have to aggressively and intensely pursue your plans.
You can be only 80% sure you're correct, and still intensely pursue a course of action.
Most people make a mistake: they only go intensely after things they have a very high certainty will work.
But this is backwards. It's absolutely right to say "I'm only 80% sure that going and making a great talk to this group will help develop my business," and to still aggressively pursue giving a great talk.
The same is true with having ridiculously exceptionally good service. You can say, "I'm only 60% sure that doing this is going to lead to more customer loyalty... this might just be a time sink and cost more than it returns. But let's kill it on it, and find it."
You don't need to be highly confident to intensely pursue something.
In fact, intensely pursuing not-certain things seems to be how the world develops.