Is discernment supposed to hurt? I realize it’s somewhat of a vague question but I don’t know that I can add much more to it right now.
I would imagine a range of emotions come with discerning, but it depends on the person.
Questions about discernment are best answered by a spiritual director.
Sometimes in the process of discernment, painful feelings can come up. Sometimes our greatest resistance can be the result of past wounds and not wanting to face up to painful emotions in order to heal. So, in discernment, you are called to heal first before you can decide on a vocation or commitment.
If there are no such issues then it might be the temptation to doubt or fear which is usually greatest when you are on the verge of a major decision. Once a decision is made, usually there is a sense of peace and joy.
As far as the actual process of discernment being painful, I would think that something may be amiss. Maybe you’re getting bad advice or pursuing a path before your ready or that you just aren’t meant for at all.