Tackling that question has been driving me for the past couple of years. I answered this particular question on Quora and thought I'd bring it over here.
"How is the character going to do that? X is in his way."
"How is she going to fix this? Y is in her way."
"How is he going to get that? Z is in his way."
For the reader to care about the character there must be something important at stake. If the character doesn't succeed,
What bad thing will happen?
What failure will he need to live with?
What regret must she live with?
How will he have failed his promise to himself?
How will she have hurt another?
For a character to be compelling, they must show drive. (Which comes from having high stakes.) They need to be actively tackling obstacles that feel insurmountable. By actively I mean, when something blocks their way, either they're
Gathering information for a plan, or
Acting on their plan.
What you don't want is a character who wishes his obstacles would go away. Or resigns himself to suffering.
In your story your character is content in his life. He's just going along where life carries him. There's nothing driving him to move out of his comfort zone. There's nothing at stake in the choices he makes.
He faces annoyances (rain, no map), not obstacles. But he doesn't tackle them. He sighs. He groans. He complains. Then others sweep them away (his father, the lady at school).
But even if they hadn't been swept away, they're annoyances rather than obstacles because 1) there's nothing at stake and 2) they don't feel insurmountable.
Readers read to see how characters tackle problems.
They don't want to read about characters drifting along as obstacles get swept away. They want characters actively tackling obstacles.
The characters may be tackling them badly. They may head towards what they want or what they "should" want rather than what they really need (in order to be better people, to be happier.) They may be screwing up others' lives as they move towards what they believe they should go after.
Don't write what you love to write. Write what you love to read.
That's not a rule. Just a heads up. Obviously don't write what you don't love. But be aware that for some writers, it's very satisfying to write about characters being buffeted about by life. It's fun to explore their emotional reactions to what happens to them.
Unfortunately, no matter how satisfying that feels, it won't ever be a story. For a reader it will be like reading the diary of someone who is letting life happen to them. For the reader, once they set a story like that down there's no feeling of needing to pick it back up since there's no sense there's a success or failure at stake.
So how do you do that?
The best way is to pay attention to how writers create that in books and movies.
As you read and watch, ask yourself:
What does the character want?
What's in his way?
What's at stake? What will be lost if she doesn't get this?
How is the character actively tackling what's in their way?
What can make a story compelling is when a character has two desires. His issue is that going after one means he can't have the other. Often one desire is for his physical goal. The other desire is to maintain his belief or strength that's really his flaw.
Examples: In the first Indiana Jones movie, Indy wanted to go after the Ark alone. But Marion won't give him the staff piece unless she goes along. Indy is fiercely independent. (Which is his strength AND his flaw.) Taking her with him puts his independence is at stake. Turning down her offer lets the Ark fall into Nazi hands, and more personally importantly, lets his rival get the credit for finding it first. So he's faced with either giving up what's central to his character or giving up the satisfaction and glory of finding the Ark.
Later, near the end, Indy is faced with choosing between Marion's life and the Ark. One decision puts the life of the woman he loves at stake. The other puts the Ark into the Nazis' hands.
No random obstacles.
A well done story doesn't throw random obstacles at a character. The author designs the obstacles to uniquely challenge this character's weaknesses. Getting out of bed is no challenge. Unless you have no limbs. Taking on a partner is no challenge. Unless you're fiercely independent. Going it alone is no challenge. Unless you've always had family, friends or partners for support.
The reader doesn't just want to see the obstacles overcome. They want to know how this character will overcome obstacles that are insurmountable challenges to him. They want to see how he tackles it being who he is, with the skills he has (and lacks).
Obstacles reveal and challenge character.
At the beginning of the story, the wants and obstacles will often be more character revealing than tied into the big want that drives them through the middle of the story.
For instance, in the opening scene of Raiders of the Lost Ark, Indy is going after a golden statue not the Ark. He doesn't even know the Ark's been located yet. It establishes what his character wants from life, what he's willing to do to get it, that he's a loner, and that he has a rival. Not much later in the movie, it's established that the Ark may have been located. The movie sticks with that all the way through.
But at the beginning of the original Star Wars Luke wants to go to the Academy to learn to fly. Though it reveals he's a budding pilot, it has nothing to do with the bulk of the movie. Even after his aunt and uncle are killed, he's not going after the Death Star. His goal is small, just to deliver the plans to help the rebels. He really doesn't know what the plans are just that they're somehow important to the rebellion. It's not until half way through the movie that he's set on destroying the Death Star.
First draft isn't final draft.
While you observe how writers present wants, obstacles and stakes, there's one important thing to be aware of. You're looking at a final product. That writer's first draft likely didn't have that captivating first paragraph. It may not have had the big want the character pursues through the middle of the book. It may not have had the character's big flaw. The writer may have written for several chapters before they discovered what makes their character tick and what would be so compelling that they'd face their deepest darkest fears and put what they most value at stake to go after it.
So you don't need to have it all figured out before you write. Just, as you're writing, look for:
a flaw that keeps him comfortable doing things his way,
what he could desire so much he'd be willing to step way outside his comfort zone, and
something he won't want to live without that you can put at stake.