When this year’s 5- and 6-year-olds wave good-bye to their families and walk through the door to kindergarten – as early as next week at local parochial schools and on Sept. 2 at District 65 public schools – the little people clutching the crayons might not be the ones reaching for the Kleenex.

“I told my boss I needed to be in Chicago, not traveling [on the first day of school], because I needed my day to cry,” says Cheryl Miller, who with her husband, will walk Max, their firstborn, to St. Athanasius School next Thursday.

“I’m sure I’ll be crying,” says Rebecca Finklestein, imagining saying good-bye to her oldest child, Joshua, at Washington School. Rachel Omundson, too, expects to tear up when she watches her son, Patrick, enter St. A’s.

Kindergarten is an emotional change – and a leap of faith — for many parents. Joshua Finklestein is enrolled at his neighborhood school because his mom, a product of the District 65 and 202 systems, says she is “very pro-public-schools.”

Still, she explains, while she “paid for and chose his preschool,” for kindergarten she says she feels she is “giving Joshua up to the School District, trusting that the teachers Washington chose will nurture and support him in the same way I would.”

While acknowledging a certain sadness, each mom is quick to accentuate the positives of her child’s transition. “It’s exciting more than sad,” says Ms. Miller. “Every year it’s more fun [with Max].”

Beth Tucker, mother of Lincolnwood-bound Gwen, calls it a “double-edged sword: You want more time for yourself but will miss having her around.”

“It’s a big adjustment when your child is not around as much. You don’t have the easy, daily time together,” says Anne Viner, whose Brooke will join an older sister at Willard. “But it’s good. Brooke is excited to be at the big school and be with her sister and learn to read,” she says.

“He’ll be okay; it’s a healthy trend,” Ms. Omundson says, preparing herself for “a nostalgic moment” the first day.

Beyond the sentiments of leave-taking, a child’s starting kindergarten has practical ramifications for the whole household. Often the shift necessitates a restructuring. “I’m nervous,” Ms. Miller says. “We both work, and [kindergarten] means a change of schedule. Kindergarten starts later [than preschool]. It means a whole new routine.”

Max Miller started daycare when he was 11 weeks old. His day there began at 7:30 a.m.; St. A’s, which starts at 8:45, does not open until 8:30. So Max’s parents will take turns going to work late, and one day a week Max will go to a friend’s house before school.

For Ms. Omundson, the 8:45 bell at St. A’s means the opposite – an earlier start than for two-and-a-half-hour preschool. “It will be a challenge to get everyone [Patrick, a preschooler and an infant] ready in time to leave for kindergarten by 8,” she says.

In District 65, school starting time has been a contentious issue for working parents. With all District elementary schools beginning at 9 a.m. this year (some previously began earlier), many families will need before-school daycare.

For Beth Tucker, stay-at-home mother of kindergartner Gwen, Lincolnwood School’s change to 9:00 from the 8:20 a.m. of previous years poses a different, if less serious, problem: Gwen’s brother “will be late to preschool every day – it starts at the same time,” she says.

Ms. Viner says she is lucky to “have options” for work hours. While she previously engaged a nanny for Brooke during her three-day work week, she is considering working five shorter days now, in order be home in time to pick up both girls from school.

For kindergartners themselves the length of the school day can be the biggest hurdle. While some, like Max, are accustomed to full-day daycare, many new kindergartners will spend their first whole day in school this fall. “I’m worried about how exhausted Joshua will be at the end of the day,” says Ms. Finklestein.

Ms. Omundson says “being away from home all day” will be a big change for Patrick after half-day preschool. But, she says, “He’ll be okay. It’ll be a healthy tired.”

And although experience tells Ms. Viner to “expect Brooke to be a little wiped out,” she says, “she’s full of energy. And there is a rest time with mats.”

Preparations for kindergarten vary. Parents say St. A’s advises not heightening children’s anxiety by making too much of it. Max Miller got a letter with his teacher’s picture – and chose to put it on the refrigerator, says his mom. She and her husband took advantage of an online offer and ordered school supplies to be shipped directly to his classroom.

Rachel Omundson has been taking Patrick by St. A’s and arranging play dates with new classmates. They will shop for supplies soon, she says, and “we’ll let him choose and cross off items as we find them.” He is excited about having different subjects, she says, but she and his dad are “trying not to over-prepare him…so we have just said he’ll be going to a different place this year.”

Brooke Viner already has her backpack and lunch bag and will be going to Willard for popsicles and ice cream – and to drop off supplies – on Aug. 27. Joshua Finklestein and his mom have been attending Friday picnics on the Washington playground this summer along with other incoming kindergartners.

Beth Tucker says Gwen’s nursery school suggested that parents tell stories about their own kindergarten experience, including feelings like nervousness. For her summer birthday Gwen received a book Ms. Tucker has found helpful to calm jitters. “Wemberly Worried,” by Kevin Henkes, tells the story of a mouse who is very anxious about kindergarten.

Many families have begun to make plans for the opening day of school. Brooke will be picking out a first-day outfit (“It won’t be fancy,” Brooke prompts her mom). Her dad will stay home from work so the family can walk to school together and do something special – ice cream or a dinner out – at the end of the day.

Everyone plans to snap photos. And in the Omundson household Patrick’s father will be carrying on a tradition. “My husband’s father made French toast on the first day of school and then walked the kids to school,” says Ms. Omundson. Patrick’s dad will do the same.