#187 Authenticity Wins: How Intentionality Led Jack Goldstein to UPenn

Flourish Coaching

Aug 12, 2025

In this episode, Lisa and Jack discuss:

How authenticity influences a student’s journey through high school and college admissions
Making intentional academic and extracurricular choices instead of chasing prestige
Personal growth through adversity and how it can translate into advocacy and leadership
Using entrepreneurship to solve real-world problems in the college admissions process

Key Takeaways:

Crafting a college application around a meaningful personal narrative—especially one rooted in overcoming adversity—can create a clear and compelling through-line that ties together academics, extracurriculars, and long-term interests.
Prioritizing activities that genuinely excite you, rather than selecting them to impress others, leads to more fulfilling experiences and naturally stronger, more authentic application materials.
Letting go of lower-impact commitments, even those you once valued, can open up time and energy to go deeper into areas where your skills, passions, and long-term potential align most powerfully.
Seeking out immersive experiences, such as internships or independent projects, helps translate personal interests into tangible accomplishments while also shaping a clearer vision for future academic and career decisions.

“If you love what you’re doing, you won’t get tired. If you love what you’re doing, you’re going to be excited to wake up every day the next morning.” – Jack Goldstein

About Jack Goldstein:

Jack Goldstein is from Portland, Oregon, and is heading to the University of Pennsylvania in the fall to commence his pursuits down the pre-law track. He is also the co-founder of Quadzio, a startup that will change the way the college tour process takes place. Passionate about advocacy and student empowerment, Jack aims to bridge gaps in access and authenticity within higher education. His work is driven by a belief that meaningful connections and lived experience should shape how students choose where to learn.

Episode References:

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