Preheat oven to 375°F (190°C).
Slice a pocket into each chicken breast and gently pound to even thickness.
In a bowl, mix cream cheese, shredded cheese, garlic powder, salt, and pepper.
Stuff each chicken breast with the cheese mixture and asparagus spears.
Heat olive oil in an oven-safe skillet over medium heat and sear chicken on both sides until lightly golden.
Transfer skillet to the oven and bake for 18–22 minutes, until the chicken is cooked through.
Remove from oven and let rest for 5 minutes before serving.