My default personality is very risk averse. I do lots of things that look crazy to other people. Different knowledge base, different goals, basically.

I agree with the first point of setting a clear goal so you know what you are actually trying to accomplish.

Also, learn about statistics. Most folks make logical errors when they "bet." Flipping a coin, the odds are always about 50/50, no matter what the last flip or last ten flips were. But people tend to think "The last three were heads, so we are overdue for tails." Nope. It is still about 50/50 (with, I think, a slight skew towards heads).

Get the facts or hard data. Be very skeptical about data that comes from iffy sources or processes. Trying to decide on hazy info sucks so bad. Good info leads to better decisions. "Garbage in, garbage out."

Get a sounding board, preferably one who has different strengths and weaknesses from you, not a "yes man" and not someone biased in the same way you are. My oldest son is very opposite me in some important ways. When we both vome yo the,same conclusion from very different directions it tends to be a very sound decision.

Anyway, real work calls or I could possibly drone on.