I believe we're conditioned from a pretty early age to be people pleasers, so getting out of people pleasing mode can be seriously challenging.
Utter your 1st word and it's like 'Oh, you're so clever, you're so wonderful', so you do it again. From crawling to walking, 'You're just so amazing. Good boy/girl!' You're parents, teachers and so on will openly tell you if they're pleased or not pleased with you. Key people in our life may tell us how we're 'failing' and how bad we should feel about it. Before you know it, you're trying to please everyone and then be left wondering 'How the heck did I get here to this point?' People pleasing can get pretty intense at times. You can find yourself lying just to please people.
As a 51yo gal, it actually took me more than 4 decades to get out of constant people pleasing mode. It was far from easy. In my younger years, I may have allowed someone to degrade me rather than upset them by speaking up. That's pretty messed up, hey. Allowing people to degrade us can get pretty depressing. Over time, I began to gain a natural sense of wonder, 'I wonder why that person has no filter. Why are they so degrading?' My basic sense of wonder progressed to, at times, wondering out loud at such a person, 'I can't help but wonder why you have no filter. Why are you so degrading?' I simply had to know why that person was so messed up :) Now, I warn you, it does tend to trigger a seriously arrogant person when you challenge them to wonder why they're so messed up :) The more arrogant, self righteous and closed minded they are, the more they're triggered. If you know anyone like this, you'll know what I'm talking about.
I must admit there are times where I'll wonder at a person just for personal amusement (only the nasty people). It's kinda like 'Let me trigger a feeling in you that you don't like'. Such people will have happily triggered feelings of worthlessness or depression in others. I know it all sounds a little arrogant but I get really fed up with horrible people, especially given what they do to sensitive people. I just love sensitive people, they're so beautiful.
I imagine you're sensitive enough to be able to sense how certain arrogant people will react to you questioning them. If this is a huge challenge, start with someone a little more low key to practice on (practice not being a people pleaser). See if you've predicted their reaction accurately.
Wonder is a great natural self esteem booster.