Ambition, Regret, and College Applications: The Conversation I Wish I’d Had 30 Years Ago

What colleges did you apply to in high school? Did you apply to colleges at all? Do you regret those decisions now? And what would you do differently if you could do it over again?

Those are the questions I would have liked to have asked my future middle-aged self when I was a teenager. And I suspect Kelly Olson wishes she had, too.

When Kelly was in high school, she took all the college entrance exams that might be necessary: the PSAT, SAT, and ACT. And she did very well. So well, in fact, that she was named a National Merit Finalist. Her scores put her in the top one-half of 1 percent of all college-bound high school seniors in the country.

As a result, she probably could have gotten into any school she applied to, likely on scholarship. She just didn’t fully realize it at the time.

And since her family wasn’t overly wealthy, she didn’t want to burden her parents with Ivy League debt. So when it got right down to the application process, she only applied to one: Hendrix College — the same hometown college where her father worked as a professor.

After all, Hendrix was a private liberal arts college that attracted top high school graduates from several neighboring states. And since her father worked there, she could attend tuition-free. It was an excellent choice by any standard. And it had always been assumed she’d go there. So why apply anywhere else?

Even after successfully completing graduate school at William & Mary in Virginia and many years in the working world, she’s confident the education she got at Hendrix was top notch and allowed her to be competitive with any of her peers. But when asked thirty years later what her biggest regrets in life are, the first one she mentions is not applying to other schools.

Notice she didn’t say not attending another school. She said not applying. The reason was this:

Don’t get me wrong,” she says. “I loved my Hendrix experience. But I’ve always wondered what my life would have been like if I had applied to Ivy League schools, for example. Why didn’t I at least apply? I might have been offered scholarships, and then I could have made a more informed choice.”

Kelly might have still chosen Hendrix at the end of the day. But if she had set higher or at least broader goals for her college application process, she wouldn’t suffer that lingering doubt thirty years later.

Kelly and I have a lot in common: we grew up in the same neighborhood, went to the same small-town high school, both only applied to Hendrix College in undergrad, both thoroughly enjoyed and appreciated that undergrad experience, yet both regret, 30 years later, not having considered any other option.

My reasons for that choice were different than Kelly’s, but the result was the same. Like Kelly, two years after graduating from Hendrix, I finally satisfied my ambition by applying to and gaining admission to a master’s program at an Ivy League school. That helped me get into the career path I wanted. But it took me an extra four years to get there than if I’d tried sooner.

Whether you think all this talk about hometown versus fancy east coast schools is a meaningful conversation or nothing more than academic snobbery is irrelevant. What matters is whether your kids will think it would have been a meaningful conversation when looking back thirty years from now. And since you can’t know that, it’s a conversation I’d encourage you to have with them, so that they’re not suffering that thirty-year lingering doubt Kelly and I harbor.

Encourage them to apply to their dream school they think they have no chance of getting into. Or tell them why you think college is a waste of time and money. But have the conversation either way. What you should take away from these stories is that teenagers (like Kelly and I) can be unaware of the limitless possibilities for their future. They need somebody — somebody like you — to talk to them and to ask them those questions they’ll wish they could have asked their middle-aged selves thirty years earlier.

As with all of these stories, I encourage you to share this with your kids, and then have a discussion about it. Here are some questions to get you started.

  1. What do you think it would feel like to regret something for thirty years?
  2. Do you think you’re more likely in life to regret things you did and wish you hadn’t? Or things you didn’t do and wish you had?
  3. How do you think Kelly would have felt if she had applied and been accepted to an Ivy League school but decided to attend Hendrix anyway?
  4. What regrets do you have so far in your life? Is it too late to do something about them?
  5. If you could get into and afford any college in the world, which one would it be, and why?

Source: Parenting with a Story: Real-life Lessons in Character for Parents and Children to Share, by Paul Smith.

PAS square profile Paul Smith is one of the world’s leading experts on business storytelling. He’s a keynote speaker, storytelling coach, and bestselling author of the books Lead with a StoryParenting with a Story, and Sell with a Story.

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Comments

  1. Gina Null says:

    This is probably one of my biggest regrets as well. My high school guidance counselor was not helpful as far as applying to college and I didn’t know that my test scores were high enough to earn a good scholarship, which would have saved my parents a good bit of money. I went to the local hometown university and did well and this hasn’t hampered my career in Nursing, but I think part of the college experience is the people you meet and the contacts you make. I’ll always wonder what might have been if the circumstances were different.

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