It is a milestone that tugs at every parent’s heartstrings—the first day their little one wears a school uniform and steps into the world of learning.
For many, it is a cocktail of emotions: pride, excitement, anxiety, and even tears.
The moment is often immortalized in photos, capturing beaming smiles (and sometimes nervous glances).
Yet, behind the cheerful snapshots lie stories of parents quietly wondering, “Will they be okay? Will they make friends?”
This year, as toddlers across the country began their school journey, four parents opened up about the bittersweet experience of letting go and cheering their children on, one brave step at a time.
From emotional goodbyes to unexpected tantrums, their stories capture the highs and lows of this unforgettable milestone.
Francis
Francis Otieno, a financial accountant and first-time father, took time before settling for a school for his daughter, Aaliyah who is two and a half years old.
"Safety was my top priority. I wanted a school that would nurture my daughter's talents, especially in music and dance, while being close to our home for convenience."
After thorough research, testimonials, and even browsing local Facebook parenting groups, he found a school in Mirema that checked all the boxes. "Settling on this school felt like finding a second home for my daughter."
Preparing his daughter for school was a journey that began long before the first day.
"We started introducing her to the concept of school through children’ learning videos and educational shows on YouTube."
Gradually, he incorporated drawing books, pencils, and storytelling into her routine.
"We also talked about school being a beautiful place where she could learn, play, and make friends. This helped spark her curiosity," he shares. Pre-visits to the school further reinforced her confidence.
"By the time we told her she was about to go to school, she was already familiar with the idea."
Despite careful planning, Francis says he was overwhelmed by emotions on the big day.
"I thought I would feel nothing but happiness, but instead, I was flooded with mixed emotions."
Doubt crept in, had he made the right decision? Was she ready? But as he watched her confidently wave goodbye and join the other children, pride and excitement took over.
"Seeing her adapt so quickly reminded me not to overthink. Children often surprise us with their resilience."
Francis had braced himself for tears and tantrums but was pleasantly surprised by his daughter's cheerful demeanour.
"She was excited to see other children in their uniforms and happily waved us goodbye. It was a proud moment for me as a parent. She handled it better than I did!"
Like any parent, Francis had his share of concerns.
Francis grappled with the emotional aspect of letting go.
"Sometimes I work from home and the thought of not having her around during the day felt strange."
The first day of school ushered in significant changes to their household. "Everything from meal times to our daily schedule had to be restructured. Our nanny has been a blessing. She has taken on a lot to make sure Aaliyah transitions smoothly.”
Those first days were also coupled with communication challenges as Francis and his wife Jesca couldn’t quite tell if their daughter was enjoying school or not.
"Aaliyah wasn’t always able to express whether she was enjoying school or struggling with the changes. We encouraged her to talk about her day and also kept close contact with her teachers."
Francis believes that a strong partnership between home and school is key to a child’s success.
At home, he engages Aaliyah in creative activities such as drawing, reading, and singing to reinforce what she learns at school.
"We also review her school diary together, which helps us understand her progress and areas where she might need support."
They also teach her responsibility through simple tasks like taking her plates to the sink after meals.
"These small habits build independence and complement her school experience."
Nearly a month since their daughter joined the school, Francis says it has been a learning point, especially on preparation, patience, and perspective.
"I have learnt that children are more adaptable than we give them credit for."
Already, they have seen a positive impact of school in their daughter’s life. She has become more confident, expressive, and curious.
The experience has also deepened his appreciation for educators and the role they play in shaping young minds.
"Teachers are heroes. They create a welcoming environment that helps children feel safe and valued."
Ann, 30
For Ann Wangui, a 30-year-old corporate communications manager at the Coffee Research Institute, her daughter’s first day of school was a defining moment of her motherhood journey.
Ann says she approached this transition with heightened preparation, maternal instinct, and intentionality.
"Age was a key consideration and I wanted to ensure she wasn’t overwhelmed by starting too early or in a setting that didn’t align with her developmental needs. She is four years old."
The proximity of the school also played a crucial role.
"Choosing a school close to home was essential to avoid the fatigue of early mornings and long commutes at such a tender age."
Interestingly, Ann notes that her daughter’s fascination with learning came from observing her study.
"Seeing me with my books sparked her curiosity. She wanted to be like me, and so we would talk about it often. We talked about what she could expect in school like making friends, playing, and learning new things."
"These conversations built her confidence and created excitement for the big day."
Like any parent, Ann says she experienced a mix of emotions on her daughter’s first day.
"I was excited to see her hit this important milestone, but at the same time, I was scared."
Her biggest fear? The unknown.
"Would the strangers treat her well? How would she adjust to new faces and routines?"
Watching her daughter bid her goodbye with a cheerful wave and an air of confidence, however, melted her worries.
"My baby was excited to join since her friends were already school-going children. She clapped for herself as the other pupils cheered her on for joining them. It was heart-warming and reassuring."
After the school drop, Anne returned with many thoughts in her mind.
"I was constantly on edge, checking the time and worrying about the school bus bringing her home safely."
Ann took a week off work just to make sure she was reachable in case of an emergency. Thankfully, the week went smoothly as her child fit right in.
"Seeing her enthusiasm to learn and interact with others made it all worth it."
The first day of school brought significant changes to Ann’s daily life.
"I now wake up earlier to prepare her snacks, and breakfast, and ensure she is ready on time for the bus pickup."
Mornings, however, have been challenging.
"It is tough waking her up. Seeing her struggle with sleep breaks my heart, but she has to adapt."
Pleading her to comply with the routine can be chaotic, but Ann views this as a necessary part of the transition.
"Mornings are a struggle, but the real challenge is doing homework together.”
Ann’s patience and creative problem-solving skills have been put to the test as she ensures her child finishes her assignments.
"We play educational games, watch cartoons that teach, and even play chess to sharpen her mind."
She also exposes her daughter to competitive environments.
"Being around children who are academically stronger or older pushes her to strive for excellence."
Ann has also been deliberate about building her daughter’s confidence through positive reinforcement.
"I encourage her to try her best and celebrate her small wins."
Ann is optimistic about her daughter’s future and excited to see her blossom in school.
"This journey has just begun, and I can’t wait to see how she grows academically and socially."
As a working mother, Ann acknowledges the delicate balance between her career and parenting. "It is not always easy, but moments like these remind me why I work so hard. I have learned that as parents, we can prepare and worry, but our children often surprise us with their strength and adaptability."
Her parting words of advice? "Celebrate the small victories, embrace the challenges, and trust the process. Your child is stronger than you think, and so are you."
Rosemary
Rosemary Kerubo, an IT expert and proud mother recalls her eagerness to send her daughter to school when she turned two.
However, she decided to wait until her daughter was two and a half, believing it would give her the maturity to engage with other children and adapt to a structured environment.
"The main reason I wanted her to start school was so she would not spend all her time at home watching TV and sleeping."
When selecting a school, Rosemary prioritised the quality of education.
"I got a private school with a small teacher-to-student ratio. I wanted her to be in a place where she could learn effectively and feel comfortable."
To prepare her for school, Rosemary began waking her child early on school days.
"I always told her that she would be waking up early and going to school every day. It is like she was tired of staying at home because it was never a struggle getting her to love school."
However, Rosemary found herself unprepared for the emotional toll of her child’s first day in school. "I cried. I won’t be embarrassed to say it—okay, maybe a little."
Separation anxiety hit hard, but Rosemary knew she had to mask her emotions. "I didn’t want her to cling to me or get upset."
Thankfully, her daughter’s first day exceeded expectations. "She was excited. She was ready to explore and had been looking forward to it for weeks."
The transition from home to school was seamless, a testament to the groundwork Rosemary had laid in preparing her child for this new chapter.
Unlike many parents who find their routines disrupted by their child’s school schedule, Rosemary experienced an unexpected benefit. "If anything, it has improved the dynamics at home."
With her daughter in school for most of the day, Rosemary says she has not employed a full-time nanny.
"I am now going home before she does, so I can help with her homework and wind down for the evening," she explains.
Her advice to other parents is simple: "Prepare your child emotionally and practically, but also prepare yourself. The first day of school is as much a milestone for parents as it is for the child."
Susan
For Susan Njambi and her husband, Stephenson Karugu, watching their children transition to school life has been a journey marked by learning, emotions, and pride. While their second-born child adjusted to school with remarkable ease, their first-born son’s experience was not as smooth.
"Our firstborn’s first day at school was all tears and tantrums,” Susan recalls. She used to work from home and the son got very attached to her.
"I had to reassure him that all was well. Despite trying his favourite treats and comforting him, he wouldn’t let go. I convinced the teacher to let me stay in class for 30 minutes to help him settle but he could not let go of my hand.”
FIt didn’t help that Susan too was experiencing separation anxiety.
“It was a sad day because I had not been separated from my baby for that long."
After a week of sitting with him in class each morning, he grew comfortable enough to embrace the school routine.
"Evening pickups became the highlight of my day. He would come running and hug me tightly."
For both their children, the decision to start school was based on careful observation of their development. They looked for signs of readiness, such as their ability to follow simple instructions, carry out tasks like washing hands and putting away toys, and being potty trained.
"When we saw these signs, we knew our children were ready for a structured learning environment," Susan explains.
Choosing the right school was a careful process for the couple.
"We considered whether the school had a strong academic foundation, extracurricular activities and whether it was in a safe neighbourhood," Stephenson says.
Their second-born daughter, however, exceeded their expectations on her first day in school.
"She was so eager to start school that she woke up earlier than usual on the big day. At one point, she became angry because she was ready to go to class and show off her learning materials to the teacher and felt we were running late," Susan laughs.
How to navigate your child’s first day of school
Vallaria Bioreri Gisemba, a seasoned early childhood educator from Moi Educational Centre encourages parents to prepare their young ones for school.
"Show them short clips about school or read picture books that depict school life to make the concept familiar and exciting," she advises.
Building independence is equally essential.
"Teach your child how to use the toilet properly, tidy up their toys, or put on a coat," she adds.
Incorporating these activities into playful routines can make them less daunting.
For instance, turning the morning routine into a game can also motivate children to get ready with enthusiasm.
Jean Sigey, an English teacher at Kericho Day Secondary School emphasizes the importance of emotional preparation. "Children need to know they can trust their teacher. Reassure them that their teacher is there to listen and help," she says.
Common Challenges
"Some children, especially those raised in isolated or indoor environments, struggle to mingle with others. Especially those raised in urban areas where most of the time they are left with caregivers," Vallaria says.
"Sometimes, they may feel irritated or unwilling to even share toys." For children with delayed speech or anxiety, unfamiliar settings can be overwhelming.
Educators play an important role in addressing these challenges. "Patience is key. By being friendly, offering hugs, and using motivational tools like stickers or healthy snacks, teachers can help children feel secure and accepted," Vallaria says.
How long does it take for children to settle into school life?
"It varies. Some children adapt immediately, while others take up to a week or even more," Vallaria adds.
A smooth transition often depends on the educator’s approach and parental involvement.
Sigey notes that creating a routine at home can help children adapt more quickly.
"Children thrive on structure, and aligning home routines with school expectations makes the adjustment smoother," she says.
Separation anxiety is also a common challenge for both children and parents.
"Hugging the child, reassuring them that they’ll be reunited soon, and maintaining a positive tone are effective strategies," Vallaria says.
She also suggests involving other children to cheer up those feeling anxious.
"Positive reinforcement works wonders. Encourage children with kind words, smiles, and small rewards like stickers or extra playtime. These gestures make them feel valued and supported," Sigey adds.
The Parent's Role in a Smooth Transition
"Children are mirrors of their parents and if a parent shows excitement and confidence about school, the child will likely feel the same," says Sigey.
Conversely, negative attitudes toward school or teachers can cause the child to develop resistance.
Sigey emphasised the importance of parental involvement.
"Visiting the school, meeting the teacher, and showing genuine interest in your child’s education creates a sense of security and support," she says.
Caution to parents
Parents often experience a mix of emotions on the first day of school. "Stay calm and composed because your child picks up on your energy. If you are anxious, they will sense it."
Handling conflicts with teachers is another area where parents need to tread carefully.
"Avoid confrontations in front of your child. Instead, calmly address your concerns with the teacher or escalate them to the school administration if necessary," Vallaria warns.
Sigey encourages parents to accept the transition as a natural and necessary part of their child’s growth.
"Focus on the bigger picture: your child’s development and future."
Effective communication between parents and teachers is crucial for a child’s success.
"Thanks to technology, parents and teachers can now stay connected through platforms like WhatsApp," Vallaria notes.
"Agree on a communication schedule to discuss your child’s progress without disrupting the teacher’s day."
Sigey emphasizes the importance of in-person meetings.
"A quick visit to the school to discuss your child’s needs or achievements fosters trust and collaboration. Always create some time for that as a parent," she says.