Here are two tricks that occasionally help me when I'm trying to make a decision. By understanding my real motivations better, I can choose with better intentions.
Factoring out fear, a.k.a. the light switch test. Sometimes the fear of going through with something can cloud your judgment of whether it's worth doing at all. Should you start that really hard conversation? Ask for that favor from someone you look up to? Imagine that's it's as easy as flicking a light switch — you flip it, and then it's done, over. The switch is right there in front of you. Do you do it? If so, beware rationalization telling you otherwise.
Factoring out social knowledge. Which job would you want if no one could know your job? Where would you travel if you couldn't tell anyone about it? Who would you date if no one could know who you were dating? Not your friends, or family, or anyone you met. This works two ways: you'd get no respect for the prestigious job, nor any judgment for the unprestigious one. Would that affect your choice? Thinking from this angle can help you identify what you want for yourself, versus what's on show for others.
Of course, fear can tell you something, and social judgment is real and consequential — I'm not saying to ignore them. But you might end up happier if you can figure out what's what.