Other characters reinforce these obstacles or help him overcome them. All characters have emotional triggers and cause explosions by pulling other people’s emotional triggers.
This is where you can utilize their core traits (introversion/extraversion, intuition/sensing, feeling/thinking, perception/judging) for or against them. If they are introverted, make them go public. If they are an on the fly guy, make them have to come up with a plan and stick with it. If they don't, the plan goes to hell and creates further conflict. If they hate being in the limelight, shine it on them. If they struggle with commitment, give them no choice.
You can make this a crippling phobia (though a lot of these have been overused). You can make it more subtle, but equally effective if they overcome an unreasonable fear to solve a problem.
We covered the sixteen currencies in earlier posts. It is hard to encourage someone by promising them something they don't want or threatening to take away something they don't care about.
Tapping Your Character's Currency
Character Currency in Action
In SBB II, I talk about ways to bend and twist your character's personality. You can use those emotional wounds and neuroses to create intense conflict at the scene and overall story levels.
Your characters don't live in a vacuum. There are societal rules, family rules, or organizational rules that they have internalized. Some characters break rules easier than others.
Make it hard.
For more about how to craft characters, pick up a copy of Story Building Blocks II: Crafting Believable Conflict, available in paperback and E-book and Story Building Blocks: Build A Cast Workbook, available in paperback and E-book.