Whenever you plan to ride your horse outside, practice groundwork in that environment before getting in the saddle. While doing groundwork in the arena is certainly beneficial, taking your horse from an environment that he’s used to (like the arena) to riding him outside is putting him at an unfair advantage. He may have been using the thinking side of his brain in the arena, but as soon as you take him outside the first time, he’ll likely be reactive and curious about his surroundings rather than focused on you.
When you first practice groundwork with your horse outside of the arena, expect him to be more energetic and pull on the halter and lead rope or mecate a little bit. With a wide open space to move in, the reactive side of your horse’s brain will kick in and the foundation you built in the arena will be put to the test. Just remember that the more you move his feet forwards, backwards, left and right and always reward the slightest try, the sooner he’ll use the thinking side of his brain and relax.