Ask HN: How do you condition yourself to be more critical

Two things:

1. For anything to succeed you need to have all the factors to be right and for anything to fail you just need one factor to be wrong (aka there are more chances of failure than success).

2. Analyse the failures, don't just get over it. Ask questions about the failure to learn about it so that the learning can help you in future.

Get over the idea of optimism and pessimism, these categories will never ever help you in any situation apart from social talks where people just feel proud/whatever of classifying them in these categories.

There's nothing wrong with being an optimist mate. You're much happier in life. You may want to look up Edward de Bono. He has some quite readable books on thinking.

Very interesting reading about this topic is in book Pragmatis by William James.

Its philosphy so its not easy reading for relax.

From critical thinking point of view, try to read something about rhetoric. If you know some approaches, try to get in practice and challenge some speakers.

Start with your friends and familly. But I have to warn you...you will not be favorite partner for discussions anymore :-) so don't overdo.

I'm a pessimist at heart. What if I had a stroke tonight? Slip in the bathroom, kill someone while driving to work. What if my girlfriend leaves me today. My mother could die tomorrow, my brother can get hurt while working. Optimists live happily through it all, depressed people close themselves in. Realists try to potect themselves by mentally doubling the estimates.

Before giving tips, how do you experience this frame of mind as a problem?

Question your assumptions.