Wondering how you're traveling. Hoping you're discovering some positive differences here and there.
With that second guessing aspect of self, it's typically programed into us. I believe it's not a natural part of who we are, therefor it takes a bit of practice and perseverance in ridding our self of it. Still can't completely shake the habit myself.
I find one of the best ways to get rid of the second guessing which, in turn, goes toward boosting self-esteem is through the statement 'That's questionable' or 'That's questionable behaviour'. For example, when your dad announced 'You know any kids that do this too themselves? So stupid, they're just trying to get attention'. Who the heck says this sort of thing? That's questionable, such a statement. Don't leave yourself thinking 'I feel stupid'. Would it make more sense for your dad to have said 'You know any kids that do this to themselves? So concerning, they really need attention, care and understanding'. Would this have been the statement of a more thoughtful person? If you'd have made this comment, wouldn't that make you a thoughtful person? Through 'That's questionable', you can reach the conclusion, in this case, you're far more thoughtful than your dad.
Reading a room is pretty similar. You can walk in, suss everyone out and be led to think 'That's questionable (behaviour)' from certain people. At a party, you might notice one person looks pretty down. You might go to them with a smile and say 'Hi, how you going. Enjoying the party?' You might become the person they open up to. Another person might be drunk, acting as the centre of attention. You may think 'That's questionable behaviour'. You observe them for a while as someone comes up to you and says 'She's always drunk, every party I go to'. This may lead you to naturally think 'She can't be happy without alcohol'. While others judge her for being an attention seeking drunk, you may be more sensitive to the idea that she cannot feel happy without alcohol. This may lead you to have compassion for her. Before you know it, you've read the room better than anyone else could, all through the intuitive thought 'That's questionable'.
Wondering if you're questioning yourself more than you're questioning others. Should you be questioning others more, their comments and behaviours? Tell you what, when you start questioning the questionable behaviours of others, the 'sane' people actually start to appear pretty crazy in their ways.