\u201cI want to go back to the Islands,\u201d my four-year old looked up with me with his blue eyes rimmed with golden flecks. He asked it with a hint of expectation, as if going to the Caribbean was as easy to pull off as a jaunt to the park.\r\nI brushed his golden locks off his forehead with my fingers, as I stumbled through an explanation of how special our sailing trip had been.\r\nWhen we spent a month on a sailboat, he\u2019d tell me, \u201cI want to go home.\u201d He missed hanging out with guys and would complain, \u201cThese girls are giving me a big, hard time.\u201d\r\nOnce when the boat got so heeled over that we stared at the sea passing within a few inches reach, he screamed, \u201cI don\u2019t want to drown.\u201d\r\nHearing his high-pitch scream undid me that afternoon. I worried I\u2019d pushed his comfort zone too far. Instead of exposing him to an incredible learning opportunity, I\u2019d terrified him.\r\nI wondered:\u00a0 Where does one draw the line when challenging their kid to get outside, pushing them to try new sports and new experiences? \r\nI asked myself whether a month was too long for my son to be out of his routine, how many hours was too long to sail each day. \r\nOne day I\u2019d think I\u2019d made a bad decision, and the next something on the boat sparked his interest. He\u2019d ask how the engine worked or poke his head in while we were doing the morning engine check, asking us about each part. My son asked how the boat turned and how the anchor held us in place.\r\nGetting comfortable on the boat wasn\u2019t immediate. One hour he\u2019d be full of questions and ideas, I could see the excitement in his eyes. The next he\u2019d be complaining that didn\u2019t want to go sailing. Later on he\u2019d pee off the side of the boat and I\u2019d see him shine with pride that he felt comfortable doing things on his own in a new environment.\r\nBy the end of the month, he\u2019d be the first to point out a surfacing turtle or a swooping pelican. He knew how to turn the engine on and off, and could even steer the dinghy on his own. At four, he could explain how the windlass worked to lower the anchor and what we needed to do in order to sail upwind. \r\nI glimpsed the person he\u2019d become. He would want to help out and get right in the mix, learning. He would have an easy relationship with his own skin and be most comfortable outside.\r\nIf I\u2019d balked when my son was the uncomfortable, he wouldn\u2019t have struggled, faced with opportunities to grow. The big leaps in his development sometimes happened suddenly, after days of struggling with his attitude. \r\nI realized that sometimes to know where the line is between what our kids can and can\u2019t take on requires that parents cross them. Boundaries aren\u2019t linear nor do they stay constant.