The Good Stuff

What Adam Sandler's SNL tribute teaches us about cherishing the mess

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

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Earlier this week, SNL celebrated 50 years with a three-hour live special. No sooner had it aired than social media was flooded with clips, each urging: Stop what you’re doing and watch this one. No, this one. It’s worth your time.

In my particular corner of the internet, one clip made the rounds on heavy rotation: Adam Sandler, guitar in hand. Having grown up with The Hanukkah Song and Lunch Lady Land, and now as a parent stuck with his Elmo Song permanently lodged in my brain, I assumed we were in for another comedic anthem.

We weren’t. It was less Happy Gilmore and more Barry Egan.

Instead, Sandler delivered a brutally honest look behind the curtain at SNL. A love letter to the mess. The long nights, the flops, the sketches that never made it. Fifty years of chasing something great, only to wake up Sunday afternoon, stomach full of late-night pizza, wondering if you belong.

I kept waiting for the big laugh. The punchline that would make it all light and easy. It never came. Chuckles came and went but the audience never roared. You could feel them waiting and hear them listening closely — when can we erupt in laughter?

There would be no climatic crescendo of laughter but something better: a tribute to the struggle. The interns running errands at 2:30 AM (or was it Scorsese's kid?). The writers seeing Spielberg, not laughing at their sketch, then getting wasted at the afterparty convincing themselves — and anyone else in earshot — that Jaws was overrated. The moments where people stormed toward Lorne Michael’s office, ready to quit, only to chicken out and hand a knitted scarf for Lorne’s wife Alice instead. (I’m sure you’ve never punted on a difficult conversation at the last minute, replacing it with small talk and nervous laughter.)

And that's the point.

We tend to think of struggle as the cost of success. But the truth is, the struggle is what makes success meaningful. It's the late nights, the last-minute rewrites, the ideas you swear will be legendary — until they die at dress rehearsal. It's every creative endeavor, every job, every personal milestone. Not just the triumphs, but the moments you'd rather forget:

The middle of the night emails that felt urgent but read like gibberish the next morning. The meetings where the perfect response came to you in the elevator afterward — I wish I had been quick enough to think of this in the meeting. The work you poured your soul into that never made it to others. The impostor syndrome. The stress.

When we tell stories of success, we skip these parts. We act like everything made sense in hindsight. We prefer to package our journey into a neat story with a tidy bow. But Sandler's song reminded me — our lived story is better than the one we tell ourselves. The hard parts. The awkward parts. The failures that taught us. The tiny victories that only mattered to us.

And lest we forget your season is singular.

Like a Polaroid that can't be retaken, these moments only happen once. You can't reproduce the exact chemistry of that team, that challenge, that time in your life. The inside jokes that only make sense to those who were there. The silent nods of understanding when someone says "I don't think I can do this" because you thought the same thing yesterday. The collective exhale when you finally figure it out together.

These people become your crew — your Lorne and your cast. The ones who see you at your most uncertain and still believe in you. The ones who make the Sunday Scaries feel less scary and the late-night doubts less lonely. At your next startup, you'll work with other great teams, but there's something irreplaceable about the crew who was there when none of you knew what you were doing.

The beautiful irony is that these false starts become the best times of our lives. Not despite the struggle, but because of it. Because somewhere between the Sunday Scaries and the next-morning gulp of Pepto Bismol, we find out who we are and who has our back.

Growth isn't comfortable. Muscles tear before they rebuild. And every great career, every great project, is built on a foundation of self-doubt and persistence. Years ago, Gary Chou told me something I still think about weekly: growth requires two things: being pushed beyond your comfort zone, and having space to reflect on the mess. The push creates change; the reflection makes it stick.

So here's to the hard journey. The stomachaches. The moments where you almost quit but didn't. To the prototypes that died in user research and the ones that somehow made it to customers. To everyone who showed up, kept showing up, and found out what they were made of along the way.

Now go spend your next 5 minutes watching Sandler's tribute, and while you're at it — identify your Lorne and cast. Name the messy stuff that shaped you.

Because that's the good stuff. And it's always worth celebrating your season.