COLLEGE
Pay attention, class. One of the country's leading college planning experts is about to share the insider knowledge every parent wishes they had sooner.
Before a student ever submits an application, writes an essay, or steps onto a college campus for a tour, there's one question nearly every parent asks:
"Are we doing enough?"
The college admissions process has changed dramatically over the past two decades. Acceptance rates have become more competitive. Testing policies continue to evolve. Scholarship opportunities shift every year. Essays have become more personal, and students are expected to tell an authentic story about who they are, not simply list accomplishments.
For many families, it can feel overwhelming.
That's where Jenny Whittle, M.Ed., comes in.
Longtime local Education Expert and the founder of College Planners USA, Jenny has spent more than 20 years helping students and families navigate one of life's biggest milestones. A former guidance counselor, educator, and Director of Guidance, she was among the early pioneers of educational consulting, establishing College Planners USA in 2005 after completing specialized training through the Independent Educational Consultants Association at Johns Hopkins University.
Today, Jenny is recognized as one of the country's leading educational consultants. She and her team work with students nationwide, helping families build thoughtful high school plans, identify colleges that are the right academic, social, emotional, and financial fit, navigate scholarships and financial aid, develop admissions strategies, and craft authentic application essays. Her experience spans students of every learning style and background, from those pursuing highly selective colleges to those seeking the school where they will simply thrive.
The best part? Jenny doesn't believe college planning is about creating the "perfect" applicant.
She believes it's about helping students better understand themselves before asking them to decide where they want to spend the next four years of their lives.
For this month's Island 101, we asked Jenny to share the insider advice she gives families every day.
When should families start thinking about college?
One of the questions I hear most often is surprisingly simple:
"When should we start?"
My answer is always the same.
Whenever you're ready.
Yes, starting early gives students more time to explore interests, choose courses strategically, develop leadership, and discover what genuinely excites them. But I also work with many families who don't begin until junior, or even senior, year. There is no perfect timeline. The important thing is having a thoughtful plan once you're ready to begin.
What's the biggest misconception parents have today?
One of the biggest misconceptions I hear is that students need to fill every free moment with activities simply to impress colleges.
That's simply not true.
Admissions officers would much rather see a student who has invested deeply in a few meaningful interests than someone who has spent four years checking boxes. Authenticity matters. Curiosity matters. Character matters.
Has the admissions process really changed that much?
Absolutely.
Acceptance rates have become more competitive at many colleges. Testing policies continue to evolve. Scholarship opportunities change every year. Essays have become more personal, and students are expected to tell an authentic story about who they are, not simply list accomplishments.
The good news is that you don't have to navigate the process alone.
If you could give parents of younger students one piece of advice, what would it be?
Encourage your children to discover what they genuinely enjoy.
Whether that's music, athletics, theater, robotics, fishing, volunteering, entrepreneurship, or serving their community, authentic interests often become the stories that define a student's high school experience and, ultimately, their college applications.
What's one thing every parent wishes they had known sooner?
After working with hundreds of families over the years, there's one thing I hear again and again:
"I wish we had started asking questions sooner, not because we were behind, but because having a plan made the entire process so much less stressful."
The admissions landscape will continue to change. Acceptance rates will rise and fall. Essay prompts will evolve. Policies will be updated.
What won't change is the importance of helping students discover who they are, what matters to them, and where they will thrive.
After all, college planning isn't just about where a student goes next. It's about helping families approach one of life's biggest milestones with confidence, clarity, and hope.