UNITED STATES – When my wife and I took our seven-year-old son to climb a more than 270m-tall piece of rock near our home in Colorado, it seemed like a good idea at the time.

We had done a climb of more than 180m the previous year and he had loved it.

This one, called the “Standard Route”, up the Third Flatiron in Boulder, was marginally tougher – shaped like a steep, rocky slide that is attached to a skyscraper.

Yes, he told my wife the night before, and again that morning, that he was too scared to do it. She worried that we were pushing him, but I insisted we go ahead. And the kid seemed confident once we all got to the foot of the route.

Alas, it did not go well. The angle was a little too steep and the whole thing took about two hours longer than I had planned. A cloud of bugs at the top was almost intolerable and the rappel off the back involved an uncomfortable mess of limbs and ropes pinning my son against the rock.

“This is the worst day of my life,” he screamed at one particularly hard moment.

It was not our first daddy-inspired mishap and I cannot see it being our last. I was raised to believe that challenging a child is a good thing – my father always called it “building character”.

But where is the line between being scarred for life and sufficiently scuffed up to build resilience? It is a choice parents weigh every day – when to cuddle them if they scrape their knee, and when to give a dose of hardship so that they become tough enough to take on the road ahead.

To get clarity on how or where I may have gone wrong, I asked a few experts for advice.

What is resilience and what builds it

Resilience is a popular term in modern psychology that, put simply, refers to the ability to recover and move on from adverse events, failure or change.

“We don’t call it ‘character’ anymore,” said Dr Jelena Kecmanovic, director of Arlington/DC Behavior Therapy Institute. “We call it the ability to tolerate distress, the ability to tolerate uncertainty.”

Studies suggest that resilience in kids is associated with things such as empathy, coping skills and problem-solving, though this research is often done on children in extreme circumstances and may not apply to everybody.

Still, many experts are starting to see building resilience as an effective way to prevent youth anxiety and depression.

“I think a lot of kids are really cautious – maybe overcautious – today,” said Professor Kathy Hirsh-Pasek, a developmental psychologist at Temple University, an expert in play and author of Becoming Brilliant: What Science Tells Us About Raising Successful Children.

“We live in a society that tells us consistently that if we don’t do well, we are failures.”

One solution, say experts, is to encourage risk-taking and failure, with a few guardrails around physical and emotional safety. For instance, it is important that children have a loving and supportive foundation before they go out and take risks that build resilience. And they need to know that they will be loved even if they fail.

Find the difficulty sweet spot

“Challenges” are challenging only if they are hard. Child psychologists often talk about the “zone of proximal development” – the area between what a child can do without any help and what he or she cannot do, even with help.

“You set the bar where he has to reach to grab it, but not beyond his reach,” said Dr Ken Ginsburg, founder of the Center for Parent and Teen Communication at Children’s Hospital of Philadelphia and author of Congrats – You’re Having A Teen!. “If you set the bar above where he can reasonably reach it, he will feel like a failure. And more significantly, like he failed you.”

How do you find the bar? He recommends asking your child: “What do you think you can handle? What do you think you can handle with me by your side?”

Let their interests guide you

The best way to build resilience is doing something you are motivated to do, no matter your age. For parents, that means listening carefully to what excites your kid as opposed to forcing him or her to do what gets you excited.

“Your adventure might not be his adventure,” Dr Ginsburg said.

Do not always give them an out

Many people remember hating the first few days of summer camp, hunkered down in a musty cabin, so homesick they wanted to cry. But a few days of tie-dyeing and canoeing later, Prof Hirsh-Pasek said, it became a treasured childhood experience.

Sometimes, parents just have to lay down the law and force children to break out of their comfort zone, she added.

“If you don’t persevere through something that’s a little bit hard, sometimes you never get the benefits,” she said.

Fear of a rock climb is fine, fear of communication is not

My little misadventure with my son had some healthy elements, Dr Ginsburg said: being outdoors, getting my boy to stretch his abilities past what he thinks he can do and celebrating his accomplishment.

But one thing gave him pause.

“What I wouldn’t love is if your son felt as if he couldn’t say it was more than he could comfortably stretch into,” he warned. Or that “he had to fit into a box of presumed masculinity as defined by his father”.

Now that the ordeal is over, he is proud of what he did – he still brags about it, and smiles in the car when the mountain comes into view.

In the end, I cannot see myself changing my parenting strategy that much. If my son has one truly empowering experience for every debacle, I would count that as a success.

But it is crucial that I show (and tell) him that no matter what he does, he will not lose my love and respect. And, as he gets older, I need to ensure our adventures are challenges he wants to conquer as much as I do. My kid loves the water, so maybe next time we’ll try a nice day of kayaking instead. NYTIMES