I’ve coached kids who got into Harvard, Stanford and Princeton—3 things their parents regret the most

Over the last decade, I’ve worked with hundreds of high-achieving high schoolers on their way to selective institutions like Harvard, Princeton, and Stanford.

I’ve seen what the parents of my students have done to set their kids up for success, such as encouraging independence early on and respecting their interests. I also learned a lot from what they regret doing the most.

Here are three things those parents wish they had done differently:

Students should absolutely challenge themselves. But in competitive environments, it can be easy to go overboard. 

Every year, parents call me to ask if their junior should drop one of their many advanced placement (AP) courses. AP classes can easily add hundreds of hours of extra work to a student’s plate over the course of a school year.

After graduation, many students have told me that they took on so much out of fear that they wouldn’t be accepted into their top schools — not genuine interest in the coursework. Chronic stress has major long-term consequences for the developing brain, and sleep deprivation has been linked to mental health issues like anxiety, depression, and mood disorders. 

Ultimately, these kids thrive wherever they land. My best advice? Given the choice between a couple more AP courses and a couple more hours of sleep, choose the latter. 

By the time your child is 18, you will have spent 95% of the time you have with them. Life is too short to fight over homework. 

And if you’re always the one to make sure they get their work done, who will do that for them after they graduate? Not letting students take on that responsibility can ultimately undermine the development of essential executive functioning skills and independence. 

This type of fighting can affect your family dynamics, too. By the end of high school, parents’ relationships with their kids are often strained by external factors like homework, standardized tests, and the college application process.

Home should be an oasis where students can relax, unwind, and feel a sense of safety and belonging. As a parent, you should be a grounding force that your kids will continue to return to, even after they graduate. 

Becoming overly focused on any one college outcome is a recipe for failure. Getting too invested in a result that is only marginally within your control can yield stress and heartbreak.

In the end, many of my students and their parents frequently wonder why they were so fixated on a single school, whether or not there was an acceptance. 

If rejected, they’ll get excited about one of the places they got into instead. (The father of one of my former students told me that, in retrospect, their top pick would have been the absolute wrong choice.) If accepted, they may realize it was not worthy of their — and their family’s — unrelenting attention. 

One student who attended her top choice later said that she should have gone to her state college’s business school; all her friends there were learning the same concepts, while their parents were paying tens of thousands of dollars less in tuition.

You want to avoid creating unnecessary pressure during an already fraught period in your child’s life. School is hard enough. Additional burdens can risk lasting psychological harm as well as damage to your relationship with your kid. 

So often I hear parents question: “Why did I make such a big deal about that?” Start asking yourself that early on, before it’s too late. The stakes are too high not to. 

Theo Wolf is a writer and educator, with a focus on passion and purpose development in young adults. He is on the founding team of Spike Lab, a coaching program for high school students, and helped build Snowday, a free search engine for high school summer and extracurricular programs. Theo is a graduate of Cornell University and a mentor at Harvard University’s Lemann Program on Creativity and Entrepreneurship. 

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