To make it (a little) less nerve-racking, your best strategy is to spend as much time as possible charging alongside your kid, so you both become confident in their abilities, then give them increasing amounts of independence.
"Letting them go in incremental steps can help make the consequences of messing up smaller, too," says Eugene Buchanan, author of Outdoor Parents, Outdoor Kids. While skiing, Buchanan would let his child hit one run alone while he and his wife took another, then they'd all meet up at the chairlift. Each time everything went well, the leash grew a little longer, until skiing a whole morning solo became no big deal. "Doing it like that isn't just good for kids," he says. "Parents also need to learn to let go."
There's no magic formula for deciding when your child is ready to go it alone, but a key indicator is when they start voicing what they're not ready to handle. "It's a sign of maturity, knowing when to say, 'That's too dangerous,'" says Kristy Sturges, co-owner of Otter Bar Kayak School.
Ultimately, proffers big-wave surfer Laird Hamilton, whose daughter Reece, now nine, has recently taken a liking to cliff jumping, raising adventurous children is a bit like being forged into a sword. "Your kids heat you up, beat you with a hammer, then stick you in a bucket of cold water, over and over again," he says. "Eventually, you get tempered."
See more: Outside's best writers share their thoughts on fatherhood and nature-bonding with Dad.