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A Therapist Explains How To Help Your Kid Navigate Mistakes & Challenges 

Lia Avellino, LCSW
Author:
May 11, 2026
Lia Avellino, LCSW
Parenting Writer
Parenthetical: how to teach kids lessons after challenges
Image by fizkes / istock
May 11, 2026

In mindbodygreen's parenting column, Parenthetical, mbg parenting contributor, psychotherapist, and writer Lia Avellino explores the dynamic, enriching, yet often complicated journey into parenthood. In today's installment, Avellino talks about helping your kid deal with challenges.

As humans we learn by experience; we learn about what not to do, by doing. We learn about what we want by experiencing what we don’t want. While this might sound reasonable, it can be very hard as a parent to witness our children experience sticky situations and not solve it for them, give them a short cut, or critique them for their way of handling it. 

Watching our kids face challenges is hard

When one of my kids told me she wasn’t in the mood to do her school work, I had to swallow teaching her a lesson about determination and ambition. When another one of my children told me she brought candy to school, even though her teacher told her not to, I had to sit with what response would allow her the space to consider the consequences without inserting my experience too soon.

This gets complicated as kids get older and the stakes become higher—we are balancing a desire to protect them with the knowing that there are some lessons they’re going to need to learn out in the world.

As a psychotherapist who works with caregivers, one of the ways I notice it being easy to lose connection in tricky moments (when our kids “mess” up) is trying to teach a lesson too soon. If our children aren’t in a place to learn, not only do they not receive the guidance, but they feel misunderstood. This leads them to lose access to us in a time they might really need us. 

Here are some considerations as you decide how to respond when your child is in a sticky situation.

1.

Have you connected before you redirected? 

Dan Siegel, M.D., psychiatrist and Executive Director of The Mindsight Institute, says “instead of command and demand, try connect and redirect.”

It can be very tempting when our children handle situations in ways we deem ineffective or do things that we see as wrong, to not launch into making a statement about their behavior. Sometimes we do this because we are protective of them and want them to learn a better way. And sometimes we do this because we look at their behavior as a reflection of us/our parenting.

Instead, ask yourself what you can do in that moment to stay connected to your own experience (noticing your fear, the heat in your body) and therefore them. In this case, we give ourselves space to regulate and can act as co-regulators, setting the nervous system tone for a productive and connected exploration of the negative behavior.

I remind myself that timing is essential here. Connecting to yourself, instead of focusing on them, might look like noticing the body-based signs of your anger or anxiety, and asking yourself what you might need to stay in yourself?

This may mean taking a minute to breathe in the bathroom; texting a friend you want to scream to release some of the internal pressure; or it might mean doing the “opposite action” that you are inclined to do (pull away or get outwardly angry) and instead getting down on your child’s level, holding hands or giving a hug.

This signals that even though you might not agree, you’re not disconnecting. 

2.

Did you get curious before you got judgmental? 

I believe that every negative behavior has a positive intention.

So, for example, if someone drinks more alcohol than serves them, it is also helping them with something else—like soothing, providing comfort in lonely moments, reducing anxiety.

Get curious about what your child’s “why” was—why did they steal, what is the reason they called their sister a name, what fear motivated them to cheat on the test.

Not only does this let them know that you care about their experience, but also that you are aware that they are good even if they did something “bad.” 

3.

Have you helped them build critical thinking skills? 

Helping children take a step outside of themselves and consider their behaviors helps them build introspection skills and relational self-awareness.

Ask questions like:

  • How do you think you’d feel if someone called you that name?
  • What might have happened if you got badly hurt?
  • Do you have any other ideas of what you could have done if you wanted something that was forbidden?

These can all provide new pathways for self-reflection and therefore an opportunity to do things differently next time.

Remember, if we over-function in problem solving over time it will enable our children to rely on outside validation rather than first ask themselves: “what’s the best way to handle this for me?”

4.

Remember the psychological concept of “natural consequences.” 

Natural consequences, unlike imposed consequences, are not governed by an authority figure that punishes, or revokes, but happens as a result of kids learning about what happens when they make certain choices.

If a child is unkind to another, and that person doesn’t want to play with them anymore, the child may learn the lesson by feeling lonely. If a child refuses to wear a jacket and then feels cold and uncomfortable, they may be more motivated to wear the jacket next time.

If they fail the test because they didn’t study, or get kicked off the team for not going to practice, these consequences might help them develop an intrinsic motivation for change, rather than extrinsic to please an adult. 

5.

Have you waited for the right moment for feedback? 

Sometimes our input is necessary, a lesson must be taught, or our child needs someone who has a developed pre-frontal cortex and risk management skills to step in.

But timing for this feedback is key—I often include it in a moment where we are engaged in something together, like a walk, while drawing a picture, playing with Play-Doh. For older children, you can ask when a good time would be, how they prefer to receive it (in writing or in a chat).

Teaching our kids that they can take in other perspectives and still make their own choices is a skill that will serve them in adult relationships. 

6.

Do you need to anticipate lessons and prepare them for the tough stuff?

Some lessons do need to be taught in advance for protection. The reality is, we live in a world with racism, bigotry, sexism, classism, and other systems of oppression that make certain bodies unsafe.

Consider if there are developmentally appropriate lessons that help your child understand when their bodies feel safe, when they can tell if someone is trustworthy, who they can contact if they are mistreated, or how they can set boundaries when their community isn’t honoring them. 

These lessons are living in the reality of what the world is, and not what you wish it was. It requires teaching about potential outside forces that are harmful before our children have to experience them, so they can feel more prepared if and when they do. 

The takeaway

Witnessing our kids make mistakes can be painful and scary. Getting clear on what is our work to feel about these mistakes, what is their work to experience in life, and when to teach versus when to listen is one of the trickiest parenting. Being compassionate with yourself and your kid as you navigate the learning process is both essential and one of the foundations of building a safe relationship.