5 Regrets These Students Had from High School

crop pitiful black woman embracing knees on bed
Madeleine Karydes
Madeleine Karydes

Madeleine attended UC Berkeley and double-majored in English and Media Studies. She is now an integral part of the Empowerly team.

Given a year of massive change, it’s easy to look back and wish we could start over. “Hindsight is 20/20,” as the saying goes – a sentiment never more apt than now. And for you, the next generation of high school students, facing a major junction in your lives? I can only imagine that feeling is compounded. 

Wondering what can we do about it? I interviewed a range of thoughtful, reflective individuals to see what they wish they had known before leaving high school. 

“What I would tell my younger self is…”

  • Student: TK
  • State: California
  • HS Grad Year: 1986
  • College/Higher Ed: San Diego State University
  • Subject(s): English
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“What I would tell my younger self is to be more patient. Time becomes elastic the older you get and the smallest moments become some of the sweetest. No rushing necessary… [laugh] I sound ancient.”

“I would do my best to convince myself…”

  • Student: ZB
  • State: California
  • HS Grad Year: 2013
  • College/Higher Ed: University of California, Berkeley
  • Subject(s): Humanities, English
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“I would do my best to convince myself to approach interdisciplinary studies with a more open mind. At the time, it feels like a singular focus on your projected career path is the most likely to make you happy. In reality, all the old cliches about life never going as planned are spot on, and you’re likely to land in a field that’s not as straightforward as you imagine!”

“Although this isn’t completely academic…”

  • Student: AL
  • State: CA
  • HS Grad Year: 2013
  • College/Higher Ed: University of California, Berkeley
  • Subject(s): Humanities
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“Although this isn’t completely academic, I wish I had practiced more vulnerability in high school. I know that that is the LAST thing we all wanted to do as high schoolers, but I graduated with high levels of anxiety and very few friends because I didn’t feel able to confide in anyone or let them in. I wonder how my academic life might have felt more balanced, and how I might have learned more from teachers and my peers, if I had been comfortable asking questions and asking for help.”

“Would tell my younger self to…”

  • Student: AK
  • State: California
  • HS Grad Year: 1980
  • College/Higher Ed: Yes, some
  • Subject(s): Survival
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“I would tell my younger self to slow down and be yourself. Life moves at breakneck speed all by itself, no need to help it along. Reach beyond what you think is possible, and try the unachievable. You just might prove yourself wrong.”

“I am an eternal student…”

  • Student: EK
  • State: California
  • HS Grad Year: 2012
  • College/Higher Ed: University of California, San Diego; Reed College MALS Graduate Program

Subject(s): BA in General linguistics with minors in Theater and Literature; the MALS program is by default interdisciplinary, I’ve been focusing on language and literature courses.

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“I am an eternal student, wandering from school to school. I do wish I had a little bit more of a plan, because I have a tendency to just let the cards fall as they will, but so far that has served me really well. While I do not have a solid idea of my career path past Reed, but as previously mentioned, that’s pretty par for the course.”

“Wish I had taken some time…”

  • Student: Madeleine (author of this article; hello again!)
  • State: California
  • HS Grad Year: 2014
  • College/Higher Ed: University of California, Berkeley
  • Subject(s): Humanities
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“I wish I had taken some time to learn coding. True, I don’t know if I would have liked it, or been good at it, but I only realized that it was even an option after getting to college. I wish I’d explored different career paths and what skills I would need to hit the ground running.”


In all, I hope these small moments of wisdom help you find your way. I’m sure you don’t need me to tell you that it’s an uncertain time. And I can’t tell you that everything will be okay. In fact, we probably all have a few high school regrets, no matter how enthusiastic we are. What I am here to tell you is that you can always learn from your past missteps, and use those experiences as context for how you want to shape your future.

Thank you to each of the interviewees for sharing their knowledge and being open with their personal high school regrets, so that we may all continue to grow together. If you’ll allow me one final cliche, a rising tide lifts all boats; so let’s decide how we want our future to look.

Final thoughts

If you feel that extra guidance would help you follow your best future path, a college counselor is a great option to consider. If you’re looking for continued advice on how to make the most of your time and avoid high school regrets, reach out now!

Overall, I can say from personal experience that our counselor network is full of high-achieving, encouraging mentors who will push you forward. Empowerly will match you to a counselor that fits your goals and style to make sure you’re on the right track. In fact, the sooner you start, the more high school regrets you can head off from the beginning. Click the button below to talk to us about options today. 

Most of all: I believe in you.

Questions? Let us know!