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I was born and raised in Miami, Florida. Growing up as a student here, I remember the pressure to be everything to everyone: the honor roll student, the volunteer lead, the club president. We are told that if we check every box, the gates of the Ivy League will swing open.
It’s a lie. And in 2025, it is a dangerous one.
Today, I am writing from the campus of Harvard Business School, where I am completing my MBA. Before this, I managed global HR operations at Google. Looking back at my path—from a high school theatre kid in Miami, to an Economics degree at the University of Chicago, and then to Big Tech—I realize I didn’t get here by being “well-rounded.”
The “Well-Rounded” Trap
For decades, parents have been sold a “check-the-box” playbook. The goal was to appear as competent in all things as possible. But the data shows this strategy is now obsolete. Since 2020, applications via Common App have surged by over 40%. This flood of “well-rounded” applicants has crashed acceptance rates at schools like Harvard to roughly 3.4%.
Admissions officers are drowning in applications from students who are “pretty good” at everything. To build a diverse class, they don’t want 2,000 well-rounded generalists; they want 2,000 “spiky” specialists who are exceptionally passionate and visionary about one thing, not everything. When everyone is shouting, the only voice heard is the one with a distinct pitch.
Worse, this pressure to be perfect across the board is breaking our kids. The CDC’s latest Youth Risk Behavior Survey reports that 40% of high schoolers feel persistently sad or hopeless. We are burning them out on a strategy that no longer works.
The Solution: The “Young Executive”
Over the last eight years, serving as a mentor for the Hispanic Scholarship Fund, I have guided dozens of the nation’s brightest, most ambitious students. Through this work, I realized that the students who win are not students in the traditional sense.
They are Young Executives.
They possess the vision of a CEO, the strategic execution of a COO, and the resource management of a CFO. They have a unique skillset and a drive that they lean into, rather than trying to flatten themselves out to fit a generic mold.
This is the methodology I used to navigate my own career, and it is the missing link for Miami families. Today, as a career and life consultant, I ask my students: “What would you do with your life if you had all the resources?” I push them to remove the constraint of scarcity and lean into what happens when they self-actualize.
It is incredible to see how much these students open up when they stop blindly following a carrot through the forest, and instead look around and decide to start carving their own path. Rather than vaguely aiming for “college” (Point B), they identify a life and career vision (Point C) and reverse-engineer their admission.
This is the Young Executive mindset: to execute on a passion with the discipline of a business leader. If your child loves sports, don’t just put them on the JV team. Ask them what metrics and biomarkers influence player success. If they love art, don’t just enroll them in AP Art History. Have them design a go-to-market strategy for a local gallery.
The Path Forward
We need to permit our students to stop doing everything so they can be great at something. Miami has the talent. We just need to update the playbook. Let’s stop raising tired generalists and start raising Young Executives who are ready to lead.
Austin J. Regalado is a Miami-Dade County native and attended high school at New World School of the Arts. He graduated Magna Cum Laude from the University of Chicago with an Economics degree and is currently an MBA Candidate at Harvard Business School (Class of 2026). Austin is the founder of Young Executives Advisory, providing career and life consulting for select families and students dedicated to becoming Young Executives. To apply for a consultation, email him at aregalado@mba2026.hbs.edu
