When Saying Goodbye is Hard
Is your child crying at school drop-off or struggling with goodbyes? Here are some strategies for separation anxiety, goodbye rituals, and helping kids feel safe and connected when you leave.
Back to School series part 6: When Saying Goodbye is Hard
If saying goodbye is easy for your kids, share this with a friend who you know might need it!
This is the last of a Back to School series. We’ll link the other parts at the end!
Saying goodbye to our kids, at school or daycare drop off, or with a babysitter, can be one of the hardest parts of parenting. Tears, clinginess, and even panic are common. Many children struggle with separations.
In this post, I’ll share peaceful parenting strategies to make goodbyes easier, whether it’s at school, daycare, or home. We’ll look at what might be behind your child’s resistance, and then explore practical ways to help them feel more secure and confident when it’s time to say goodbye.
Before we jump into strategies, it’s important to ask: Why is my child having such a hard time saying goodbye?
Here are a few things to consider:
Is it the environment? Is the school or caregiver a good fit? Sometimes a mismatch can be the cause of distress.
How is your child after you leave? If they bounce back quickly and settle in, the issue is likely just the moment of separation. It can be normal for a child to have a few weeks of rough morning goodbyes. But if they stay upset all day, or the hard goodbyes last for a long time, it may be worth reevaluating the school, daycare, or caregiver.
Has there been enough transition time? If possible, a slower introduction to a new school or babysitter can help kids adjust. Go early to school and play at the playground if you can, or have some overlap with the caregiver.
Could it be separation anxiety? Some kids experience more than typical clinginess. If your child seems panicked or highly anxious, you may need specific strategies to help them manage their “worry brain.” More on that here.
Try switching up the drop-off
Sometimes one parent is simply easier to say goodbye to. When my middle son was two, he tearfully said once, “I like it better when Daddy drops me off.”
If you have flexibility, experiment with which parent (or caregiver) handles drop-off. Even small changes like this can make mornings run more smoothly.
Fill them up with connection before you say goodbye
Because kids struggle most with being away from the people they love most, it’s important to “fill their connection cup” before you leave.
Special time: Even a few minutes of one-on-one connection in the morning (snuggling, reading, playing) can make a big difference.
Laughter: Roughhousing or silly games help kids release tension and stress, making the actual goodbye less overwhelming.
Create a goodbye ritual
Kids love traditions and routines. A special goodbye ritual—like a unique handshake, “animal kisses,” or a short rhyme—can make goodbyes feel special and connecting.
For example, when my oldest son was in preschool, we invented a series of animal kisses (cat kiss, dog kiss, butterfly kiss, fish kiss) that we shared every morning before saying goodbye. That little ritual gave him comfort and consistency.
There are lots of ideas for goodbye rituals online!
Empathize
It’s tempting to dismiss a child’s sadness by saying, “You’ll be fine” or “You love school.” But that can make them dig in harder and feel alone. Instead, empathize:
“Of course you’ll miss me. I’ll miss you too” or “It’s hard to say goodbye when we love each other so much.”
My daughter had a hard time with goodbye for a very long time. I used to say, “It’s actually good that we miss each other. Wouldn’t it be terrible if we didn’t? It shows how much we love each other.”
Acknowledging their feelings doesn’t mean changing the plan—it just helps your child feel understood.
Bridge the separation
Instead of focusing on what your child will do while you’re gone (“You’ll have so much fun at recess!”), focus on when you’ll be together again. This technique, from Dr. Deborah MacNamara, is called ‘bridging’ the separation.
“When I get home tonight, I’ll give you a kiss goodnight, even if you’re already asleep” or “When I pick you up after school, we’ll go home and have a snack and play outside.”
Some other bridging ideas:
Put a picture of you or of you together in their backpack
Wear matching bracelets to remind them of your connection. I used to say, “Whenever you look at this bracelet, know I’ll be thinking of you!”
Reading books like The Kissing Hand, The Invisible String or Owl Babies
These bridges keep your connection palpable even when you are away from each other.
Don’t sneak away
It may feel easier to leave while your child is distracted, but sneaking away often makes things worse in the long run. It teaches kids that parents can disappear at any moment, which increases anxiety.
Always say goodbye—even if it’s hard. A quick, loving goodbye is better than a lingering or sneaky one.
Support after you leave
Whenever possible, make sure there’s someone your child can connect with after you leave—a teacher, a caregiver, or even a trusted friend. Having a “point person” to comfort them helps the transition go more smoothly.
Practice through play and stories
Separation games like peek-a-boo and hide-and-seek help children’s brains understand that separations are temporary—you always come back. Books, like Owl Babies, about separation and reunification can also reinforce the lesson.
You can also play games where YOU don’t want to leave them, or hug them and pretend your arms are broken and you’re stuck. Getting kids laughing about what makes them nervous (in this case, separation) helps them process their big feelings about the issue.
The hardest part: The Moment of Goodbye
The goodbye itself is often the most difficult part. To make it easier:
Normalize their worry: “Of course it’s hard to say goodbye.”
Teach them to talk back to their “worry brain”: “I won’t let you be the boss of me. I can handle this.”
In an interview with Lynn Lyons, anxiety expert, she explains ‘The Moment of Goodbye’ and how to make it easier for kids:
“I use my hands to make a little box and call it the moment of goodbye. That’s the key: it’s just a moment. We can normalize this for kids: “When we get to school, there’s going to be a moment of goodbye. It might feel big, and you might cry, and that’s okay. I’ll get through it and you’ll get through it.”
Keep goodbyes short, loving, and confident. Lingering often makes it harder for both of you.
Take care of yourself, too
It’s normal to feel upset when leaving your crying child. But remember: separations are necessary and build resilience. You’re teaching your child that they can handle hard feelings and that you always come back.
Reconnect after separation
When you reunite, prioritize reconnecting before jumping into the next task. Hug, laugh, play, or simply sit together.
Then, “tell the story” of what happened:
“It was so hard to say goodbye this morning. You were sad, but you did it. And I came back—just like I always do.”
This helps rewire your child’s brain, making future goodbyes easier.
Goodbyes might not be completely tear-free for a while, but with empathy, connection, rituals, and bridging strategies, you can help your child build resilience and confidence.
Saying goodbye is hard because love is strong. And with peaceful parenting tools, you can make separations smoother while staying connected and helping your child build resilience.
If you missed the rest of the series, links are at the bottom of this post!
xx Sarah and Corey
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