Dealing with Disappointment: The conversational cheat sheet
- Michael Berkowitz
- Jul 9, 2025
- 4 min read
You know how heart-wrenching it is to watch your kids go through a disappointment.
They don’t have the maturity or awareness of the big picture to put a disappointment into perspective. So, what seems like a small issue to you can feel like the end of the world to them. If your son misses his favourite show or your daughter drops her soft serve ice cream on the sidewalk after just two licks, then I’m pretty sure you know what is coming next — tears and tantrums.
Fortunately, that “small” stuff is a piece of cake to deal with. All your kids need is some time to get over it (or a new ice cream). But there are also bigger disappointments that they might face — like a friend moving away, or losing the final game of the season, or not making it into the advanced class at school. Those sort of things are a bit tougher to get over because of their long-lasting effects.
When reality doesn’t match up to our expectations, that’s a recipe for disappointment. Most of life is beyond our control and disappointments are inevitable. It sucks, but it’s the truth.
Even if you could protect your kids from disappointment, would you want to? Not only will you be fighting a losing battle, but you’ll also be shielding them from learning critical coping skills. Those coping skills are a big deal. Without them, your kids are likely to fall apart at the smallest setback later on in their lives.
Whether a disappointment is ‘big’ or ‘small’, the coping mechanisms are the same. The Cognitive Behavioural Coaches at Captain Calm have developed an app packed full of these coping mechanisms.
But what we wanted to chat about today was how YOU can help your kids to deal with disappointments.
When kids face a disappointment, what they need most of all is your support to help them feel heard and guide them in assessing their feelings of disappointment.
If you always step in as the hero, then you’re setting up unrealistic expectations for the remainder of their lives. You need to let your kids experience their disappointments, or they will never learn how to deal with them.
So the next time your son or daughter comes to tell you about their latest disappointment, don’t let his/her trembling lower lip and sad eyes spur you into action mode. Instead, be the hero they need by being a sounding board and listening to their problems. Let him/her talk through what happened and how he/she is feeling, then urge him/her along a path to better deal with the disappointment.
Questions to help your kids to process a disappointment
- What is the worst part of it for you?
- Why do you think it happened?
- How long do you think this feeling will last?
- Is there anything you can do about it?
- Do you think it will happen again?
- Were you clear about what you wanted?
- Why did you want it to go differently?
- Is it something that you think was very likely to happen?
- How will you benefit from letting this go?
- Will this disappointment matter in six months time?
- Could you have done something differently?
- What can you do to help you move past this disappointment?
- Is there anything or anyone that can help you feel better?
Avoid saying
Now that you know what questions to ask, here are some things it’s best to avoid saying:
"You're acting like a baby."
A better response: "It's okay to feel disappointed. I'd be upset in this situation too."
Relating to your kids in this way lets them know that it's normal to feel upset, which will reduce the effect of disappointments over time.
"Let's do this instead."
A better response: "Do you have any ideas for what we can do instead?"
Asking the right questions to help your kids to come up with their own solution not only helps them feel better in the moment but also shows them that they can find ways to make a bad situation better on their own.
"It's not a big deal."
A better response: "I know this is hard for you."
Odds are the disappointment is a big deal to your child, and dismissing it as unimportant conveys that you don't know what matters to him/her.
Summing up
You’ll notice that you are not taking action on their behalf. Your goal should be to help them assess and deal with the disappointment in their own way.
Allowing them the space to solve their problems is really empowering, especially for kids.
Remember, you are trying to guide them to be realistic. Kids think everything is the end of the world and how they are feeling now will last forever. Remind them of difficult things that they have gone through already. Show them how much they have already grown and improved, and this is just another thing for them to grow from.
There’s an old parable of a man who goes walking in the woods and sees a butterfly trying to break free from its cocoon. Being a kind-hearted man, he unfolds his pocket knife and very delicately and gently cuts a slit in the cocoon so the butterfly can escape. And so it does. It wriggles out of the cocoon and then begins to flap its wings slowly. It lets go of the cocoon in an attempt to go skywards. But it can’t climb higher. Its wings beat very slowly, and it slowly flutters to the ground. And on the ground it stays for its short and unsatisfying life.
The man realises that by trying to help the butterfly, he doomed it. You see, butterfly’s wings gain the strength they need for flight by breaking out of the cocoon. They grow stronger through struggle, as we all do. They can only be released from their cocoon when they are ready to face the challenges of the outside world.
So please, when it comes to your kids, be the cocoon and not the well-intention human who doesn’t allow them to fly.
“It is impossible to live without failing at something unless you live so cautiously that you might as well not have lived at all — in which case, you fail by default.”
— J.K. Rowling
“Success is the ability to go from disappointment to disappointment without loss of enthusiasm.”
— Winston Churchill
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