How to Teach Kids to Handle Failure | Embracing Enough

My 10-year-old daughter didn't make the travel softball team. And that's okay. Here's why I believe disappointment is one of the most important lessons we can teach our kids.

Nov 14, 2026

How to Teach Kids to Handle Failure: Let Them Try, Let Them Fail

My 10-year-old daughter, Valentina, recently tried out for a 12U travel softball team.
She didn't make it.
And I'm glad she tried.
It was a big leap for her. She was competing against older girls, some with considerably more experience. She was stepping outside her comfort zone, meeting new people, and seeing what softball looked like at another level.
She wasn't nervous. She went out there, competed, and gave it her best shot.
When we got the news that she hadn't made the team, she took it surprisingly well.
"Well, it just wasn't meant to be," she said.
"That's a great healthy attitude, sweetie," I told her. "And we'll just continue working and developing and growing."
And that was pretty much it.
No tears. No blaming the coaches. No great family crisis.
She had tried something difficult, and it hadn't worked out.
As far as I'm concerned, that's an important part of growing up.
Kids Need to Experience Disappointment
I believe kids need to experience disappointment.
They need to hear no. They need to lose games, miss opportunities, and occasionally discover that someone else is better than they are.
Not because I enjoy seeing my children disappointed. Of course I don't.
But because disappointment is part of life, and learning how to handle it is a skill.
As parents, we naturally want to protect our children. We want them to be happy, successful, and confident. But I don't believe we accomplish that by removing every obstacle from their path.
I've written about this in my broader philosophy of raising independent kids. I believe our responsibility is to prepare our children for the world, not protect them from it.
That means allowing them to take risks, experience setbacks, and figure out what to do next.
When Valentina didn't make the softball team, I didn't see a problem that needed fixing.
I saw an opportunity for her to grow.
My Son Wasn't Always the Kid Who Got Picked
My son Gio had a similar experience growing up in youth baseball.
He wasn't always the kid who got picked. In fact, he was often overlooked.
He started behind some of the other players, and I felt like he never really got a fair opportunity to show what he could become.
Eventually, we made the difficult decision to leave his travel baseball team and find a different environment where he could develop. I wrote about that experience in Why We Left the Travel Team.
But changing teams wasn't what made him a better player.
The work did.
He practiced. He learned. He made mistakes. He kept showing up.
Today, he's one of the strongest players on his 13U travel baseball team.
And I think about that journey whenever one of my kids faces rejection.
Where they are today doesn't determine where they'll be tomorrow.
But they have to be willing to keep working.
Don't Teach Your Kids to Blame Someone Else
I remember watching a Little League game where a kid struck out looking.
As he walked back to the dugout, his mother called out, "That's okay, sweetie. It's the umpire's fault for the strike zone."
I remember thinking, what a missed opportunity.
Maybe the umpire had a terrible strike zone. But the kid could have protected the plate, adjusted his approach, or swung at a close pitch with two strikes.
Instead, he was being taught that someone else was responsible for his failure.
I'm not suggesting we criticize kids when they make mistakes. We should encourage them and help them learn.
But when we blame someone else, we take away their opportunity to grow.
I'd much rather my kids walk away asking, "What could I have done differently?" than believing someone else is responsible for everything that goes wrong.
How to Teach Kids to Handle Failure: Four Things Parents Can Do
I don't want my children growing up believing that failure is something to fear.
I want them to understand that failure is a normal part of learning anything worthwhile.
Here are four things I try to practice as a parent.
1. Encourage Them to Try Things They Might Fail At
I want my kids trying out for teams, auditioning, competing, and challenging themselves.
Even when the odds aren't necessarily in their favor.
Especially then.
There's value in walking into an unfamiliar environment, meeting new people, and measuring yourself against a higher level of competition.
Valentina learned something about herself simply by showing up for that tryout.
And I want her to keep doing it.
2. Praise the Courage to Try, Not Just the Outcome
It's easy to celebrate when your child hits a home run, wins a championship, or makes the team.
But what about when they don't?
I'm proud of Valentina for putting herself out there.
She didn't need to make the roster for the experience to be worthwhile.
I want my kids to understand that their willingness to try difficult things matters just as much as the results.
3. Don't Rescue Them From Every Disappointment
When your child gets rejected, it's tempting to explain away the outcome.
Maybe the coaches didn't recognize their talent. Maybe the tryout wasn't fair. Maybe they deserved another chance.
Sometimes those things might even be true.
But immediately searching for someone to blame takes away an opportunity to learn.
Let your kids feel disappointed. Listen to them. Help them understand what happened.
And then help them move forward.
4. Turn Failure Into a Plan
This is where failure becomes useful.
What didn't work?
What could we improve?
What can we do differently next time?
For Valentina, that means continuing to develop her softball skills, gaining experience, and preparing for future opportunities.
It doesn't mean she needs to become obsessed with making that particular team.
It means she has another reason to keep growing.
Failure alone doesn't make you better. What you learn from it, and what you do afterward, does.
Let Your Kids See You Fail, Too
I also make a point of sharing my own failures with my kids.
Running a business gives me plenty of opportunities. Sometimes I make the wrong decision, miss a goal, or work hard at something that doesn't turn out the way I hoped.
I talk to Gio and Valentina about those moments, what I've learned, and what I plan to do differently.
I want them to see that I'm human, too. I'm facing many of the same obstacles they are, just in different circumstances.
Failure doesn't stop when you become an adult. Neither does learning.
And sometimes the best way to teach your kids how to handle disappointment is to show them how you're handling your own.
Keep Trying Out
Think about actors, stand-up comedians, musicians, or professional athletes who eventually become successful.
How many times did they fail along the way?
Comedians bomb in front of audiences. Musicians get rejected at auditions. Athletes get cut from teams or passed over by coaches.
And yet they keep going.
They believe in their ability to improve, even when the results aren't there yet. They understand that failure isn't necessarily evidence they can't succeed. It's part of the process of getting there.
That's what I want my kids to internalize.
Failure is as natural as breathing. The sun comes up every morning. Sometimes things work out, and sometimes they don't. That's life.
The important thing is what you do next.
Valentina didn't make the softball team. But she showed up, competed against older girls, met new people, and gave it her best shot. When the answer was no, she accepted it.
And we'll keep working. Keep learning. Keep growing.
I don't need my kids to believe they'll succeed at everything they try. I want them to believe they can keep getting better, even when they fail.
The goal isn't to raise kids who always make the team. It's to raise kids who never stop trying out.

“Know what’s enough. Build what matters.”