The first day of preschool was tough. Not so much for our boy, but for my wife and me.

My immediate thought was, so this is where creativity comes to die. My wife and I spent three hours a day with him for the first week to help with the transitioning process.

During this time, I observed how other kids of varying developmental levels behaved. I saw kids having to wait their turn, listening to instruction, and trying to communicate with other 2.5-year-olds who weren’t good communicators.

As I thought about my negative reactions while soaking in the hot tub, I came to realize what I disliked about preschool was exactly what I disliked about work.

If you have a baby or toddler or are planning to have a baby, this post is for you. I’ve been running an interesting, real-life, real-time experiment on how hard it is to get ahead if you have below-average money and little status.

In 2017, we ended up applying to three preschools that accepted toddlers as early as two for the 2019/2020 school year. We then applied to five more preschools between SF and Honolulu that accepted toddlers after three for 2020/2021. We didn’t know what we were doing so we decided to play it safe.

Private schools are always stressing diversity and inclusion. Unfortunately, diversity and inclusion are theoretical goals made difficult to achieve because they are stymied by deep-rooted admission practices such as legacy admissions, bribery, and quid-pro-quo legal donations.

March 12, 2019 is a day I’ll never forget. Not only did the college admissions bribery scandal break that morning, we found out our boy got waitlisted by two preschools. Waitlisted is really just a euphemism for rejected.

The first preschool was a Mandarin immersion preschool I’ll call PooPoo about 20-25 minutes away. We had to go for an initial one hour tour, then a 30 minute parent interview with the admissions director who was hacking up a lung that day, and then a final play date interview along with 11 other kids and parents.

It was an arduous process that we found unappealing, especially given the commute. During our application process, the school canceled its 4-day a week part-time program in favor of only 5 full days a week. We found this to be too much for a 2.5 year old.

The school seemed like it was being run more like a business first, and a school second with its massive $1 million fund raising banner in the entrance and its decision to go 5 days a week in order to charge their full $31,240 a year in tuition.

Given these issues, we were not disappointed when PooPoo waitlisted our boy. We had already decided he wouldn’t attend. Spending $31,240 a year on tuition for a 2.5 year old felt extremely unnecessary. I speak Mandarin and we could use the money to live in Taiwan for a summer instead.

The second school we applied to I’ll call PeePee; it’s about a 15-18 minute drive away. We liked the school because it had a two day a week program that runs from 9:30am – 12:30pm for $8,500 a year. We thought this was a more appropriate transition for a young toddler first experiencing a school setting.

The only problem with the school is that it’s not very racially or socioeconomically diverse. Further, 11 of the 12 available spots for this upcoming preschool year for 2-3-year-olds were already preassigned for siblings. This ensured further homogeneity.

The Executive Director personally reached out over e-mail and told me that 80 people applied for the one open non-sibling position, which meant that they only had a 1.25% acceptance rate.

Given we had no connections to the school, don’t look like the majority of parents, don’t have any status since we didn’t tell them we run this site, didn’t donate any money, and learned the application numbers, we weren’t surprised about the rejection, just a little disappointed.

When my wife was pregnant in late 2016, a friend told me, “You need to apply to preschool within the first three months after he’s born.“

He had one kid in private elementary school and two kids in private middle school. He is also a centimillionaire. 

“Absurd!” I responded.

“Hey, it’s up to you buddy. Getting into preschool in San Francisco is harder than getting into Princeton. Don’t let your lack of preparedness hurt your son’s chances for a bright future.“

Damn it. Guilt sets in.

“Well since you put it that way. I guess I’ll get on it. Want to give us a recommendation when he goes in 2019 or 2020?“

“Of course I will,” my friend replied as we resumed our tennis match.

This post is an introduction into how daunting it is for families living in big cities to get their kids into preschool. It should also give some sense as to why there’s so much anxiety among parents and children early on.

As someone who has questioned the necessity of paying for private grade school tuition, yet who also wants the best for his son, this post serves as a type of mental penance for going through this process. I’ve spent the last seven years trying to escape the grind, but somehow, I’m always getting pulled back in. 

I also hope this post brings joy to families who live in lower cost areas of the country who don’t have to worry about hyper competition due to a lack of supply. Living in a big city has its perks, but helping your child get a quality education is not one of them.

It’s only until kindergarten where all families are eligible for a free public education.