Hello, Goodbye
Last Call
The Late Show with Stephen Colbert signed off for good on Thursday night after eleven years and change. A final 80 minutes of everything that made it land for me — biting commentary smuggled inside punchlines sharp enough that you laughed first and thought second.
I watched the whole thing. Then I sat with a feeling I wasn't expecting.
Not sadness, exactly. Closer to regret.
Because once upon a time, I thought it would be fun to write for a late night show. Specifically, that one.
The idea started taking shape years ago when a comedy coach — known as The Joke Doctor — challenged me to write 10–20 jokes a day from any news headline. The exercise sounded daunting, but the technique was simple: isolate a few key words in the headline, do a little word association until themes and patterns appear, and the jokes almost write themselves in the form of mashups, reverses, and misdirections.
Almost.
That exercise is, more or less, how Sunday Setup got started. I picked headlines from weirdly funny stories because they were low-hanging fruit — the kind of stories that made me laugh out loud on first read — and built the rest of the newsletter around them. The setup was the doorway. The mindful takeaway was the room.
But the writer's room itself? The actual one, with actual late night writers, batting around actual jokes? That dream just sat there. Scary and exciting in roughly equal measure — until the scary part won by default.
I never sent a packet. Never really explored how it works. I Googled it once, but did nothing with the answer.
Colbert ran for eleven years. The door was open the whole time.
He wasn't everyone's cup of tea, but the idea of working with him was mine — and I let it steep too long to take a sip.
Watch the Closing Window
Something steeping too long doesn't tell you it's gone bitter. You find out when you taste it.
You keep meaning to ask someone to grab a coffee so you could pick their brain. They've been working the job you've imagined for yourself for a while, but they change companies, retire, or pass. Now the conversation is no longer available.
A job posting scares and excites you because it would be a stretch. You bookmark it. You draft a cover letter in your head. Then the deadline passes. The crazy thing is, no one except you ever knew you were considering it.
A product idea pops into your head one day and you workshop all the ways it could work. It remains in your head for two years, until someone else ships the same thing — and it lands. The frustrating part isn't that they thought of it. It's that you did, too.
Windows present themselves as permanent until they aren't.
Part of the problem is that closing windows don't announce themselves. Job postings don't ping you the day before they expire. Mentors don't send calendar invites for the conversation you should have had. Ideas don't come with shot clocks. The absence of a deadline is what makes the deadline arrive without warning.
We wait for a signal that's never coming — and then call it timing when it doesn't.
Question of the Week
What's been steeping that you haven't poured?
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