20 Questions 5 - Make your main character's obstacles more challenging

In stories, characters never change except in the face of adversity. And the conflict they face comes when what they want is blocked in some way. This is where setbacks, sacrifices, and (often) nasty surprises come in.

A sure way to improve your story is to tune up these obstacles so they demand the most of your main characters. Make them fierce. Make things go wrong. Don’t turn away from torturing your characters. To help you in this (sometimes painful) project, I offer 20 more questions for your story, these dealing with the obstacles the heroes and heroines must face.

1. Are all the obstacles expected by the genre and logline included?
2. Can you make the obstacles more challenging for your main character? 
3. Will readers have doubts about whether they can be overcome?
4. Are the consequences for failure or the required sacrifices as extreme as you can make them?
5. Do the obstacles escalate in difficulty each time they crop up in the story? Did you avoid plateauing or deescalation?
6. Is taking on an obstacle irreversible? Is there no way to go back? Must the hero or heroine go through or abandon the quest?
7. Are choices clear and reasonable? Have you avoided advancement of the plot by stupidity?
8. Does the main character have agency? Will it be impossible for the obstacle to be overcome without the choices and actions of the protagonist? Is deus ex machina avoided?
9. Do some of the choices for dealing with an obstacle represent dilemmas, where neither choice is desirable or without important costs?
10. Do all the obstacles upset YOU personally? Do you suffer along with your protagonist?
11. Are all the obstacles related to the goal? Do they make a difference? Are they of the right scale?
12. Does each obstacle advance the protagonist along his or her character arc, forcing change and growth?
13. Are the obstacles visceral? Can they be imagined and related to by readers?
14. Would at least some of the obstacles be insurmountable by the protagonist at the beginning of the story?
15. Do obstacles compromise the fulfillment of as many of the protagonist's needs (as reasonable), up and down Maslow’s hierarchy?
16. At one time or another, is the hero or heroine challenged in a variety of ways (e.g., physically, socially, intellectually, morally, psychologically)?
17. Are some of the solutions surprising while still being fair?
18. Do any obstacles threaten prized relationships?
19. Do obstacles challenge the protagonist’s self-image?
20. Do villains get more savvy and harsh with each obstacle they present? 

Without obstacles, a happy ending isn't earned (and a tragedy can fade to so what?).  By making the obstacles more daunting, the story inevitable becomes stronger, improving both the characters and the plot.