As children grow, so do their minds—full of richer, stronger ideas and firmer beliefs. You might start noticing:

• They clearly want to go skiing, but once they’re there, they want to back out.
• They can read English fluently, but if the sentence is too long, they shut down.
• They love playing in the pool, but freeze when it’s time for swimming lessons.

You think, “Wasn’t it easier before?” Back then, a few simple words like “We believe in you” or “Give it a try—it’s not that hard” could light a spark. But now?

• “We believe in you” is met with “I can’t.”
• “You’re amazing” turns into “I’m not.”
• “Just try” is countered with “It’s too hard.”

It’s frustrating. Encouragement used to work. Why not now?

The answer lies in understanding that the fear of difficulty often stems not from laziness, but from a mismatch between ability and goals—leading children to believe they’re bound to fail. And when kids fear failure, encouragement can sometimes backfire.

1. Why Encouragement Isn’t Always Enough

Many parents (myself included) feel disappointed or even wronged—after all, encouragement is better than pressure, right?

Yes—but only to a point.

While constant pushing can create anxiety and resistance, blind encouragement can be equally ineffective as challenges grow more complex. Encouragement acts like a temporary energy boost. It might help children over small humps, but it doesn’t equip them to scale mountains.

Worse still, encouragement can sometimes feel dismissive or add pressure, deepening the child’s frustration. Let’s look at some common traps:

“Don’t be afraid, it’s easy.”

This can feel invalidating. Adults often underestimate how difficult something feels for a child because we’ve already mastered it. This is what psychologists call the “curse of competence.”

It’s like the story of the pony trying to cross the river: the older cow says, “The water’s shallow!”—but the pony doesn’t yet have the experience to agree. The more we tell kids something is easy, the more they push back, feeling misunderstood and unseen.

“You can definitely learn this—don’t give up!”

This often comes from love and belief in our children. But kids may hear it differently:
“If I can’t do this, I’m letting you down.”

This fear of failure can lead to perfectionism, avoidance, or all-or-nothing thinking: “If I can’t do it perfectly, I’d rather not try at all.”

They begin to associate love and acceptance with success, not effort or growth.

“Just try—it’s not that bad.”

Sometimes, the problem isn’t emotional—it’s practical. The child doesn’t know how to solve the problem. Telling them to “just try” feels like telling them to walk through a locked door.

What they need isn’t cheerleading. It’s a coach. A guide. A teammate who’s in it with them, helping them break the problem down, not just yelling from the sidelines.

2. A Four-Step Path to Helping Children Face Challenges

a) Embrace Empathy—Start with Emotion

The foundation of any effective strategy is connection. Before problem-solving, join your child’s emotional space.

Say things like:

• “It’s normal to feel scared. I felt that way when I learned to swim, too.”
• “You’re right, it’s hard. I was afraid of math when I was younger.”

Validate feelings before addressing the facts. Help your child name their emotion: “I feel frustrated” or “I’m nervous” instead of “I just don’t want to do it.” Being seen calms the nervous system and opens the door to change.

b) Reshape Thinking—Help Build a Growth Mindset

Once emotions are acknowledged, help shift your child’s beliefs.

• Normalize failure: Talk about your own setbacks and what you learned from them.
• Reframe mistakes: “This isn’t failure—it’s feedback. What can we learn?”
• Recast ability as flexible: Swap “I can’t” with “I can’t yet.”

Praise effort, not talent:

• Instead of “You’re so smart,” say “You worked really hard on that.”
• Instead of “You did it perfectly,” say “You stuck with it—even when it got tricky.”

This builds resilience, not pressure.

c) Break It Down—Make the Task Doable

Children lose confidence when the goal feels too big. Your role? Become their scaffold. Help break tasks into steps and offer support until they can do it on their own.

For example:

• Instead of “Write a composition,” try:
  1. “Write one sentence about your favorite moment.”
  2. “Add a fun beginning.”
  3. “Describe a small detail with your senses.”

Each small success becomes a stepping stone to confidence.

d) Model, Support, Release

Sometimes words aren’t enough—actions speak louder.

• “I do, you watch”: Demonstrate problem-solving out loud.
• “You do, I help”: Let them try, but offer help as needed.
• “You do, I watch”: Step back and let them fly.

Turn abstract “ability” into visible strategies. Let your child see how to approach difficulty—and trust them to take over with time.

Final Thoughts: Turning Fear into Fuel

Fear of difficulty is natural—it’s our brain’s way of protecting us from failure. But our goal isn’t to eliminate fear; it’s to help children grow strong enough to move through it.

We’re not raising children who never fall. We’re raising children who get back up.

Take Jason, for example:

• He used to cry before ski lessons. But after a small demo and a few falls, he got up ten times in one trip. A stranger complimented his skating.
• He struggled with reading, so instead of pushing for a 90+ score, we walked through confusing sentences together—and he felt in control.
• He resisted swimming, not because of the water, but fear of being alone. Once we understood that, we stayed close—and now he’s happily diving in.

Children don’t resist effort. They resist overwhelm.

So let’s meet them with understanding, break goals into bite-sized steps, and model the courage we hope they’ll learn. In doing so, we help them press start on the game of life—and give them the confidence to keep playing.