How to Support a Child Going Through Transitions: Strategies for Separation Anxiety, Back-to-School, and Beyond - Happy as a Mother

How to Support a Child Going Through Transitions: Strategies for Separation Anxiety, Back-to-School, and Beyond

with Jess VanderWier, Founder of Our Mama Village


  • Why Transitions Are So Hard for Our Kids (And for Us)
  • Normal Anxiety About Transitions vs an Anxiety Disorder
  • Why We Need to Take Charge During Transitions
  • Special Ways to Remind Our Children of Our Bond
  • Things To Say To Prepare Our Children Before Transitions
  • How to Handle Transitions In the Moment

Transitions can be overwhelming for our children and for us. As moms, we want to know how to support a child going through transitions. We might experience our own anxiety, deal with mom guilt, or question whether they are capable of navigating big changes. 

But with the right strategies in place, we can guide our children, and ourselves, through times of change. Today, I’m joined by Jess VanderWier, founder of Our Mama Village to discuss how to support a child through the transition into school and separation anxiety. 

(This is the final episode of our 3-part back-to-school series. Don’t miss part one on kindergarten readiness with Susie Allison of Busy Toddler and part two on helping children cope with school anxiety with Dr. Becky Kennedy of Good Inside.)

The First Day of School Blues

Last year, my middle son started Junior Kindergarten. He is my neurodivergent son, and he sometimes needs more support during changes. I worked my best to prepare him for school, but he was still a bit nervous. 

He would ask me questions like…

What if I don’t make friends? 

What if the other kids don’t like me?

We decided that it would help if he took his lovey with him to school to leave in his backpack as a familiar comfort. 

As we walked up to the door, he had the lovey in his hand. He looked into the classroom, then looked up at me and said, “I’m okay, Mom,” and handed me the lovey before heading in. 

Part of my heart broke, seeing him so independent and big. But I was so happy to see his confidence and resilience. 

Transitions can be scary—both for our children and us—especially going to school or daycare for the first time. We wonder if our kids will be okay, if they will miss us, if we will miss out on too much, and if we’re making the right decision. 

Sometimes, like with my son, that transition is smoother than we anticipate. Other times, we all struggle through it. But when we prepare them and offer support, our children are able to navigate the transition, even when they are difficult. 

I was excited to welcome Jess back to the podcast to discuss how to help support our children through transitions. 

Why Transitions Are So Hard for Our Kids (And for Us)

Transitions can be anything from small shifts in the day, like bedtime, to starting something new or adjusting to a sibling. But no matter what the size of the transition, the difficulty comes down to the same root. 

Jess said that transitions are hard because they are seen as a threat to attachment. Attachment is the biggest need for a child, and if they think that something will distance them from their parent, they can perceive it as a threat. 

For example, children might worry about a new sibling or the transition into school because it feels like that attachment might suffer. 

Jess pointed out that the pandemic has increased attachment anxiety and separation anxiety for many kids. They have been home with their parents for longer periods of time and haven’t had many opportunities to practice separation. That can make the transition to school or daycare seem even more intimidating—both for our children and for us.  

We often experience our own anxiety around separation. We feel guilty for leaving our children for the first time and unsure about how they will handle the transition. It feels as if the distance might threaten the attachment. 

Jess said that as parents, we often see our anxiety about a transition and our children’s anxiety about it as connected—but breaking it into two pieces helps us manage it. We can work to regulate our own nervous systems and provide the support for our children that they need. 

Normal Anxiety About Transitions vs an Anxiety Disorder

When our children struggle with transitions or separation anxiety, one of the most helpful approaches is to think about what underlying questions and concerns they have. As we get curious about what is causing the anxiety, we can help support them through the change. 

For example, if our children worry about starting school, they might wonder if they are going to make friends or if they won’t fit in. We can assure them that other children are experiencing those same concerns and that we are confident that they can handle the situation. 

It’s important to remember that experiencing anxiety about a transition is not the same as having an anxiety disorder.

When children feel anxious about a transition we might see:

  • Clinginess
  • Restlessness
  • Crying when you leave them

Those are all very normal behaviours. But Jess said that it becomes more concerning if you are working to build new relationships with caregivers and the anxiety persists. If a child has been exposed to a new environment several times but still experience these behaviours a month or two in, it might require a closer look at what makes that separation continue. 

Different personalities and temperaments can factor into separation anxiety and how long it takes to adjust to a new transition. Sometimes children who are neurodivergent, highly sensitive, or even just more resistant to transitions have a more difficult time and might require more support. 

But the way we handle transitions can also ebb and flow. Children that normally handle bedtime transitions well might still experience a rough transition into school. Underlying factors such as sickness, new siblings, or tiredness can also impact them. 

Why We Need to Take Charge During Transitions

Rough transitions can be very dysregulating for us as parents. Seeing our children cry for us or have physical reactions, like kicking and screaming, can make it hard for us to cope. 

Sometimes, this leads us to question our choices and backpedal on boundaries we should hold. Boundaries do require a level of flexibility, but we should also hold boundaries even in the face of a child who is anxious. 

Jess said that when it comes to transitions or separation anxiety, children need an in-charge parent. When we let them take the lead, it’s too much responsibility for them. They need to be able to rely on boundaries to keep them safe and supported. When we do that, children can approach transitions with more confidence. 

Backpedaling can create a cycle that is difficult to break out of. Jess used the example of a child asking for just one more book at bedtime, then continuing to push the boundary if we agree. It leads to more overtiredness and more difficulty going to sleep.

But if we hold space for their feelings, while still taking charge and setting boundaries, children can feel more secure and approach situations with more confidence. 

It’s hard to hold boundaries when our children are upset. But when we don’t, we often shut down the child’s emotional experience instead of providing the skills to navigate their feelings. 

We have to ask ourselves if the goal is the absence of a meltdown, or is it showing our children that they can navigate situations that are difficult?

Jess said it’s important to let children know that even when they are separated from us, there is another person that can be relied on for safety. If you can, show pictures of a caregiver or teacher and talk about them so children become familiar with them. 

Special Ways to Remind Our Children of Our Bond

There are many special ways we can remind our children that our attachment remains strong even when we are not present. 

Some parents make special bracelets together or draw a heart on their child’s hand, providing a visual reminder that Mom is thinking about them. 

Reading books like The Invisible String or The Kissing Hand can reinforce the idea that our children are safe even when they aren’t with us. 

We want to allow space for our children’s feelings, validate them, and ensure them that they can and will get through the transition. 

As we build trust and confidence that they are okay even when we aren’t there, we remind our children that our relationship doesn’t depend on being physically together all the time. 

Special goodbye routines can also help our children through the transition. Practice these ahead of time so your children feel prepared to say goodbye. 

Jess also said that making the reunion special helps remind our children that we are excited to see them, and that we are thinking about them even when we aren’t there. 

Sometimes, our children exhibit after-school restraint collapse, having more difficulty at the end of a transition rather than the beginning. But we can support our children in these feelings too, with predictable routines and connection. 

Things To Say To Prepare Our Children Before Transitions

In addition to the pecial reminders of our bond, we can also talk with our children to help them prepare for transitions and separation. 

One of the ways we can do that is by role-playing. If your child is worried about making friends, act out what it will be like when they meet someone new. If they are scared about the bus, act out the ride to school. Jess said it can feel silly to us, but children learn best with play. 

We can also use “I wonder” questions to help children begin to develop curiosity about their feelings. 

“I wonder why you think that way.” Or “I wonder what the other kids in class are feeling.” 

Another tool to prepare our children is storytelling. Stories are one of the most powerful tools we have to help prepare our kids for something new. Jess said there are three types of stories we can use to prepare for transitions:

Stories of Sameness: 

We can tell our children about a time that we felt the same way and how we got through it. Maybe we also had a difficult transition into school as a child, or in another new situation. 

“When I went to school, I was really nervous. I didn’t know if I would make any friends. But I got through it, even though it was hard. And I ended up loving school.” 

Stories of What is Going to Happen: 

You can also storytell about what will happen on the day of the transition. Either use your child as an example, or create a fictional character who is experiencing the same thing. 

“You are going to wake up and eat breakfast, then we’ll do our good-bye handshake and you’ll get on the bus to go to school. When you get there, your teacher will take you into class and you’ll start playing with your classmates…” 

Stories of Success: 

It’s also important to narrate what went well and celebrate the victories from the day. 

“You were nervous to go today. But you went right in and sat down. And you got through it even though it was hard!” 

All of these conversations will help our children gain confidence that they will be safe and secure, even when we’re not there. 

How to Handle Transitions In the Moment

After preparing our kids for the transition, we can also offer support in the moment by showing up as that in-charge parent they need and reminding them of what they can do. 

It’s important to keep our own anxiety in check and navigate our own feelings—just like I had to when I dropped my son off and he gave me his lovey. If I had let my anxiety take over in the moment, he might not have trusted himself to do that. 

Sometimes we underestimate our children’s ability to navigate these challenges, but they can handle more than we think—especially if we’ve prepared them. 

Trusting that they are capable is very important, both to keep ourselves calm and to reassure our children that they can navigate tricky situations. 

We might feel mom guilt start to rise, but we can remind ourselves that we don’t need to feel guilty—we can have solid attachment without being with our children at every moment. In fact, it’s healthy for them to develop attachment with other people.

Ultimately, it all comes down to trusting our attachment, trusting our children, and trusting ourselves to navigate the feelings that come with transitions. When we support our children in times of transition and allow them to work through change, we give them a beautiful gift. 

For more about helping your children prepare for school, catch the rest of our 3-part back-to-school series: part one on kindergarten readiness with Susie Allison of Busy Toddler and part two on school anxiety with Dr. Becky Kennedy of Good Inside. 

If you are working through your own anxiety or struggling with mom guilt, talking with a mom therapist can help. Book a free 15-minute consult through our Wellness Center today!

Jess VanderWier is a Registered Psychotherapist who helps families understand and respond to their child’s “big feelings” with gentleness, respect, and logic. Jess has a Master’s Degree in Counselling Psychology and has logged thousands of clinical hours supporting parents and their children. Through group presentations, and one-on-one clinical sessions Jess has helped thousands of parents restore peace in their homes and parent in a way that aligns with their values. 

As the founder of Our Mama Village, Jess uses her expertise to support parents through online courses personalized coaching, and free resources. Jess lives in the Niagara Region with her husband Scott and their three daughters, a 5-year-old, a 2-year-old, and a newborn.






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