How to Avoid the “What Were We Thinking?” College Regret
Can I confess something?
When it was my turn to pick a college, I may as well have closed my eyes, spun a globe, and pointed.
No tours, research, or big-picture thinking—just a quick checkmark on the “go to college” to-do list and a vague plan to figure it out later. Spoiler alert: it worked… kind of.
Here’s what I wish I’d known back then: picking a college isn’t just about landing somewhere with classrooms and textbooks. It’s about choosing a place that opens doors to a future your teen hasn’t even dreamed of yet.
Why Strategy Changes Everything
Take my story: I ended up at the University of Maryland—a massive state school (30K undergrads, even back then!) with killer programs in engineering and economics.
My major? Graphic design…😆
Did I make it work? You bet! I found my place in a tiny program in the corner of a big campus that allowed me to dabble in everything from architecture drafting to history (and even economics for fun—don’t judge).
But here’s the kicker: I didn’t even know art schools existed!
I also had no idea how much the right college—one that aligned more with me—could have changed my trajectory.
Don’t get me wrong. My college experience was fine. But it could have been extraordinary.
What’s Changed About College Choices?
Back in the day, most of us now-parents applied to 1 to 3 schools. Now, the number is often around 12 to 15.
Just yesterday, I chatted with a parent who had applied to 12. Laughing, I told her she was a 🦄 and she agreed. Clearly, she was way ahead of her time!
But more applications don’t equal better results. Without a deeply considered plan, all those applications and essays just add unnecessary stress and busywork, not to mention cost. (Each application is an average of $65—which can add up fast.)
Picture grad-school applicant, Kaylee (not her real name). She put all her chips on her dream school—which had only 12 seats—assuming she'd land one. When it didn’t pan out, her “backup” schools felt like afterthoughts. Now, she’s working with me, considering a gap year in order to regroup, and we've got a clear roadmap to make her dream a reality.
That’s what happens when college is treated like a lottery instead of a strategy.
How to Build a College List That Actually Works
Here’s what I tell families to help them go from “What are we even doing?” to “This feels right!”:
1. Sneak in some college visits.
Headed to a family reunion or soccer tournament? Swing by a campus. Anymore, most have “DIY walking tours” online to help you get around. A quick walk-through can reveal a lot: “This place feels magical,” or “Wow, this is definitely not it.” More data points early in the process can help a family find great-fit schools more quickly.
2. Rankings? Meh.
Sure, big-name schools sound impressive, but what does your teen actually want? A 300-person lecture or smaller discussion classes? Flexibility to explore majors or a specialized track? The “best” school is the one that fits them not the one a media outlet has ranked on data that might not even matter to your student.
3. Think opportunities, not just academics.
Does your teen love theater and science? Find a school where they can perform in plays without majoring in drama. Into tech? Look for places with internships that scream “hire me” on a resume. The right school connects the dots between passions and possibilities.
4. Plan for the curveballs.
Fun fact: most teens will change their major. (Some of them multiple times—ask me how I know.) The key? Pick a school where switching gears midway through (or even before they move into their freshman dorm) doesn’t mean starting from scratch.
Don’t Wait Until You’re Scrambling
The clock moves faster than you think. I’ve seen families assume they’ve got time, especially with their oldest, only to find themselves panicking as deadlines creep in.
Meanwhile, younger siblings tagging along on those early college visits? They’re soaking it all up. By the time it’s their turn, they’re confident pros who know what feels right.
Start early. Explore now. Your future self will thank you.
It’s so Worth the Effort
This process isn’t just about finding a school—it’s about finding a launchpad. The right college can shape who your teen becomes: their confidence, their opportunities, and their next steps.
When you approach it thoughtfully and strategically, the results can be magic—for them and for you.
Making College Planning Feel Doable (and Even Fun!)
Right now is the perfect time to start.
If you’ve got a sophomore or a junior, this is your moment. Planning ahead now gives you the time and space to be truly strategic—so when deadlines start rolling in, you’re ready (and not scrambling).
Sure, while AI tools can be helpful (… don’t forget to grab my AI college research guide at the end 👇), nothing beats real expertise. With over a decade’s experience in college admissions (and a background as a strategist for a multi-million dollar company!), I’ve helped countless families connect the dots in ways they might not have considered.
I love this stuff. I live for this stuff. And I can help you think beyond the obvious—whether it’s spotting a unique talent that’s worth exploring, lining up the right schools that align with your student’s strengths, or identifying the perfect internship opportunities for later down the line.
It all starts with a plan. Let’s make one for your teen. 🚀
With love, strategy, and big dreams,
Christy
👋 Hi, if we haven't met yet, I'm Christy. I help students craft standout essays so they can submit their best possible applications with confidence.
Wanna chat? www.calendly.com/easiercollegeessays/30min
