The Ivy League Challenge

The Ivy League Challenge Everyone deserves to reach their potential and the college admissions process shouldn't hold you back

If you’ve been considering The Ivy League Challenge, the March cohort is your last chance to finish before summer and us...
03/20/2026

If you’ve been considering The Ivy League Challenge, the March cohort is your last chance to finish before summer and use those months strategically instead of just “staying busy.”

The next cohort will be next school year (late August).

When students complete the Challenge before summer, they head into break with:
- Clear direction
- A meaningful impact project
- A plan to build a story that stands out for admissions and scholarships

To kick off the March cohort, I’m running a 2-day workshop:
“Hacking College Admissions.”
It’s the best way to see how the program works and decide if it’s right for your family.

Register for the Hacking College Admissions workshop at tilc.to/admissions.

Most ambitious students are doing a lot between 8th and 11th grade:Honor classesClubsLeadershipVolunteeringTest prepFrom...
03/10/2026

Most ambitious students are doing a lot between 8th and 11th grade:

Honor classes
Clubs
Leadership
Volunteering
Test prep

From the outside, it looks great.

But when it’s finally time to apply, many discover that all of that effort didn’t naturally turn into a truly compelling story for selective colleges or competitive scholarships.

It’s not usually an effort problem.

It’s an alignment problem.

I’m hosting a live online workshop where we’ll fix that.

Together with a current Yale student who works as a paid Yale admissions ambassador, we’ll:

Analyze real supplemental essays from students admitted to Yale and other selective schools

Use a simple 3-tier framework to see which stories are “fine” vs truly top-tier

Connect each essay back to the activities and choices those students made in 8th–11th grade

If you want to know whether your current path is leading to a strong application (and what to adjust if not), join us.

📅 Date: March 15
⏰ Time: 8 PM EST
🎯 For: Students in grades 8–11 + parents
💰 Cost: $197 per family (free for current Ivy League Challenge families, but you still need to register)

Registration at tilc.to/supplemental.

I’ve seen top students get rejected — and others with the same stats get admitted.The difference isn’t luck.It’s strateg...
01/13/2026

I’ve seen top students get rejected — and others with the same stats get admitted.

The difference isn’t luck.
It’s strategy.

Join my FREE Hacking College Admissions Workshop and learn how admissions actually works.

📅 Jan 14–15 | 8 PM EST
👨‍👩‍👧 Parents & teens encouraged to attend together

👉 Save your seat and join us live. Register now- tilc.to/janworkshop

Parents and teens often fall into the “impressiveness trap”--padding resumes with activities that anyone could do, hopin...
10/17/2025

Parents and teens often fall into the “impressiveness trap”--padding resumes with activities that anyone could do, hoping it will look good.

Admissions officers aren’t impressed by quantity. They’re excited by alignment: activities tied to values, initiative, and real impact.

I’ll be unpacking this in my free October workshop →tilc.to/activity

Building Your Activities List: What Stands Out (and What Doesn’t)

The biggest lie in college admissions is that only the most impressive kids get in. I’ve seen teens with simple but imp...
10/14/2025

The biggest lie in college admissions is that only the most impressive kids get in.

I’ve seen teens with simple but impactful activities stand out--even at the most selective schools.

Trying to be “the most impressive” isn't just exhausting, it will probably backfire. Instead, let's focus on being authentic, consistent, and impactful.

That’s what I’ll be teaching in my free October workshop: Building Your Activities List: What Stands Out (and What Doesn’t)
📅: October 21, 2025 8PM EST
🔗 RSVP here: tilc.to/activity

🚨 Just published in Business Insider!Too many students are chasing the wrong things when it comes to Ivy League admissio...
09/24/2025

🚨 Just published in Business Insider!

Too many students are chasing the wrong things when it comes to Ivy League admissions — and it's costing them more than they realize.

I charge $25,000 to coach students through the process… but what I teach surprises most families.

It’s not about joining more clubs or cramming for higher test scores.

It’s about discovering your core values, and making a real impact on the world now, not someday.

In this article, I share the real reason why students get in… and why so many don’t.

👀 Read the full article here:
https://www.businessinsider.com/harvard-college-admissions-expert-how-to-get-into-ivy-league-2025-9 (link also in the comments)

Let me know what resonates most with you in the comments 👇

Address

Boston, MA

Website

Alerts

Be the first to know and let us send you an email when The Ivy League Challenge posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The School

Send a message to The Ivy League Challenge:

Shortcuts

Share

Category