A Love Letter to Good Will Hunting
October 27, 2026
This is a love letter to Good Will Hunting.
Going to school in Boston is one of the best experiences a person can have. You're surrounded by brilliant people in one of the densest college cities in the world, everyone running around like mice, learning, absorbing, and bouncing ideas off each other. I grew up watching a lot of movies, but rewatching Good Will Hunting while living in the city it's set in hit differently.
On the surface, it's a story about a janitor who happens to be a genius. Underneath, it's about love, and about how much it matters to be around friends who push you to be better than yourself. Chuckie does that for Will. In one of the film's best scenes, he tells his best friend that if he's still in the neighborhood working construction in twenty years, he'll kill him. It might be the most loving threat in movie history. The message is simple: you were gifted a brain, so you have to use it.
The movie is also about class. Skylar has a huge trust fund, and Will comes from nothing. Their relationship plays out like a textbook anxious-avoidant dynamic, with her moving toward him while he looks for a reason to run.
But the best part, for me, is how honestly it shows what real therapy does. Sean isn't a yes-man. He doesn't let Will hide behind his intelligence or get away with anything. He challenges him and partners with him to become a better version of himself. That's what real help looks like: someone who is on your side and still won't let you off the hook.
There's a lesson in Sean about who to learn from, too. Older people carry an immense amount of wisdom. And it's always better to talk to people who are where you are, or where you want to be, than to people whose lives you'd never want.
The working-class story runs underneath all of it. Will's friends bust their asses on brutal shifts, and the movie respects that while also being about the escape from poverty to something better. It also asks a harder question: if you got lucky enough to be born with a mind like Will's, what do you do with it? I think the answer is that you put your head down and use the gifts God gave you. If your gift is your brain, use it. If it's sports, movement, dancing, or singing, lean on that. Sean keeps pressing Will on the same question: he has all the agency in the world, so what does he actually want? That is so difficult for people to comprehend, including me.
I didn't land my first job offer by knowing exactly what I wanted. I was talking with a startup founder I'd met years earlier, and he asked me what I wanted out of life. I told him plainly: I want my life to be a series of projects that hopefully add up to something cool, I want a beautiful family, and I hope to die peacefully one day of natural causes. He said he loved it. Then he told me he'd be willing to put a few million dollars behind me and set up an entire division of his company for me to run. Holy shit.
I also found my own therapist, someone who helped me discover myself the way Sean helped Will.
My grandparents grew up under communism and worked with their hands, so college wasn't something they ever thought about. My parents came to the U.S. as first-generation immigrants and had to start over. They pursued higher education, but above all, they were hustlers. They built businesses, invested in properties, and worked tirelessly to give their kids opportunities they never had. They believed deeply in education and made our future a priority. This year, they celebrate 30 years of marriage. It wasn't always perfect, but they persevered, built a life together, and never stopped pushing forward. I admire them for everything they've accomplished, and I love them for it. Or, as I like to put it: "My parents are absolute badasses."
That's why Sean and Will's story lands so hard for me. It's beautiful to see something so powerful on screen and relate to it this much. If you're in your early twenties, it's a must-see. You're often your own worst enemy, and I believe everyone needs a therapist like Sean was to Will.