• by Steven Rosenbaum , Featured Contributor, December 22, 2025

Every year it starts the same way.

You open your inbox in early December, and the first holiday email lands before your day has even begun. It is cheerful in theory, aggressive in practice, and oddly confident that one more subject line will finally work. By mid-month, it is everywhere.

Holiday spam is not new. What’s new is how little effort it now takes to make it worse. AI has removed almost every natural brake that used to slow bad communication down. There was a time when sending an annoying email required someone to actually write it. Now it requires a prompt, a list, and very little judgment. The friction is gone, and so is most of the restraint.

AI is exceptionally good at producing volume. It can generate dozens of subject lines in seconds, rewrite the same pitch in multiple tones, and personalize each one just enough to feel vaguely uncanny. What it cannot do is care whether the message should exist in the first place.

That is how we ended up with fake intimacy at scale. “Steve, I’ve been thinking about you this holiday season.” No, you haven’t. A system assembled a sentence that resembles warmth because it has seen millions like it. The shape is right. The feeling is not.

Urgency has also been automated. “Last chance.” “Final reminder.” “Ending tonight.” When everything is urgent, nothing is. AI does not understand that diminishing returns exist. It just knows which words spike open rates, so it keeps using them until they collapse under their own weight.

Then there is calendar guilt. “We know this is a busy time of year, but…” That line is everywhere because models have learned it lowers resistance. It acknowledges your stress while actively adding to it. Naming the problem does not excuse contributing to it.

AI has even industrialized the holiday pun. “Sleigh your goals.” “Yule love this.” “Unwrap massive savings.” These are not jokes so much as outputs. Puns are easy for machines. Taste still isn’t.

More unsettling is how AI enables emotional pressure at scale. References to exhaustion, uncertainty, or collective strain, followed immediately by a pitch. The system is not being cruel. It is being efficient. The result still feels wrong because it collapses empathy into a tactic.

Nonprofits are not exempt. December fundraising emails now arrive perfectly formatted, relentlessly urgent, and endlessly varied. AI makes it easier to sound desperate without stopping to ask whether desperation is the right tone. Caring about a mission does not automatically justify how you communicate about it.

And then there is the most insidious category of all: the email that pretends it is not automated. “Just checking in.” “Circling back.” “Bumping this to the top.” AI is very good at mimicking casual human follow-up. It is not good at knowing when that mimicry crosses into something deceptive.

The problem is not AI itself. The problem is what happens when speed replaces judgment. When sending becomes frictionless, someone still has to decide whether a message deserves to be sent. Too often, that step gets skipped. People are not tired of email. They are tired of being flooded with messages that were never really meant for them.

The best holiday emails still stand out for the same reasons they always have. They are brief. They are clear. They sound like a person made a choice to send them. And sometimes, they do not ask for anything at all. AI can help write those messages. But only if someone is willing to slow it down, edit it, and take responsibility for the result.

Before you hit send, ask yourself one question: Is this making my communication better, or just easier? If it is only easier, maybe skip it. In December, restraint might be the most human signal you can send.

One important thing, so this does not get twisted. I love real notes. I love actual holiday cards. I love thoughtful emails that sound like a human sat down and decided to write to me. And yes, I donate. Every year.

This year alone, I’ve supported WFUV, WNYC, WBGO. ByKids, De La Salle Academy, and other organizations I genuinely care about. Their work matters. When they reach out in a real way, I’m glad they did.

So this is not a rant against asking. It is a plea for how you ask. By all means, reach out. Share what you are building. Tell people why it matters. Make the case. Just do not hand the whole thing over to a system designed to maximize output instead of judgment.

A real note feels different because it is different. You can tell when someone chose their words, chose their moment, and chose you. So please, send the holiday card. Write the email. Ask for the donation. Just skip the AI spam.

In December especially, attention is finite. Respect it, and people will show up.