Letting Go
Good Will Hunting is one of my all-time favorite movies. I could write an entire piece on the film and Robin Williams and I wouldn’t do the art its proper justice. For some reason, Good Will Hunting videos have been showing up on my YouTube homepage this past week and this one caught my attention. It’s one of the best scenes in the movie and the last conversation had between best friends Will and Chuckie (Matt Damon and Ben Affleck). Give it a watch:
Will is a blue collar kid that grew up in Boston his entire life. He has this amazing gift of intelligence, but grew up without the opportunity to exercise his gift in an academic setting. The movie revolves around his journey of opportunity, healing, and love. However, I don’t want to write about Will tonight. I want to write about Chuckie.
Will and Chuckie are having a smoke and beer break while working construction and catching up on life. Matt Damon’s character sees what’s in front of him. His hometown, his friend, how they grew up together, and how they’ll eventually raise their kids together and take them to Little League at the same field they played on. Ben Affleck delivers some resounding advice to his friend.
“Look, you're my best friend, so don't take this the wrong way. In twenty years, if you're still livin' here, comin' over to my house to watch the Patriots game, still workin' construction, I'll f***in' kill you.”
Damon tries to argue and bring up the same “inspirational” words he has heard from many others. Affleck isn’t having it. As he talks, I’m hanging on every word of Chuckie’s. Everyone needs a friend who will be blunt with them. Everybody needs someone who will help them see what they don’t see, whether it’s in themselves or in the world. He goes on:
“No, no, no. No, f*** you. You don't owe it to yourself. You owe it to me. 'Cause tomorrow, I'm gonna wake up and I'll be fifty. And I'll still be doin' this shit. And that's alright, that's fine. I mean, you're sitting on a winning lottery ticket and you're too much of a p**** to cash it in. And that's bullshit. 'Cause I'd do anything to f***in' have what you got, so would any of these f***in' guys. It'd be an insult to us if you're still here in twenty years. Hanging around here is a f***in' waste of your time.”
I mentioned in the first paragraph that this is the last conversation that these two friends have together (on screen at least). To be honest, I’ve lost more friends than I’ve kept in my life. And that’s totally fine! I don’t say that feeling sorry for myself or wishing any ill will towards them. I hope they are living their best lives. I really mean it. People move on. It can be hard, but people let go. Moving on and letting go are part of life. There’s not a single one of those friendships that I wish were still here because I know I’m the best I can be right now and I hope they feel the same about themselves. What is amazing to me is how Chuckie chooses to let go because he knows that is what’s best for his friend. He wants Will to use his intellectual gifts. He wants him to travel across the country to be with the woman he fell in love with. Chuckie is sticking around Boston and will continue to hang with the boys and drink beer while watching the Patriots. He’s content with that life for himself, but not for Will.
“I don't know that. Let me tell you what I do know; every day, I come by your house and I pick you up. And we go out, we have a few drinks, and a few laughs, and it's great. You know what the best part of my day is? It's for about ten seconds when I pull up to the curb to when I get to your door. 'Cause I think maybe I'll get up there and I'll knock on the door and you won't be there. No goodbye, no "see ya later", no nothin'. You just left. I don't know much, but I know that.”
At the end of the movie, Chuckie gets his wish.
The end of Good Will Hunting is not the end of tonight’s writing. Thinking about letting go took me to a song written by Jason Isbell. He and is wife, Amanda Shires, perform “Letting You Go” for their daughter. It is a beautiful song and, as a parent, this song touches all of the emotions. You love your kid with everything in you, but even that love comes with letting go. For my son to grow up to be the best person that he can be, I have to let go a little bit more each year. Watching your child walk for the first time is letting go of carrying them everywhere. Taking them to the first day of school is letting go and allowing them to learn from someone else and make friends. Someday letting go will mean letting them drive by themself for the first time and then moving off to college and maybe even getting married someday. Now, I’m early in my journey as a parent and there are a lot of great memories still to come, but I’m learning that this journey also comes with learning to let go. It’s a beautiful process even if it includes a few hard lessons along the way.
“Being your daddy comes natural
The roses just know how to grow
It's easy to see that you'll get where you're going
The hard part is letting you go
The hard part is letting you go”



I love your grasp of parenthood and the need to let go. Seeing your kids drive off is one of the hardest things in the world.
The unselfishness of Chuckie is quite admirable! To care about his best friend so much that he wants a better life for him than what he knows he himself will ever have, even though he will miss him and it will be hard to let him go! The song is very powerful and definitely speaks to me as a parent! Great article, Josh!