I’ve been working in the digital and outbound space for a little over four years now, and over that time I’ve noticed the same cycle repeat. Something works because it’s rare. Then it gets named and turned into a formula. That formula spreads, becomes oversaturated, and eventually people grow tired of it.
I remember a few years ago, after the dropshipping wave and into the SMMA and SaaS cycles, when Alex Hormozi’s $100M Offers book, which formulated offers, took off. Free audits, the thing that was popular in the home industry, entered the digital world. Giving things away for free became the move. Free audits, strategy calls, and work upfront. It genuinely felt like someone was putting their foot in the door and trying to be helpful.
Over time, that changed. “Free” no longer means free. It’s worse than the home industry because digital work has a low barrier of entry. When it becomes oversaturated, it turns into 40+ DMs/inboxes filled with the same messages daily, fatigue came out rather fast. Free offers started to imply an upsell, a follow-up sequence, and an expectation to show up and listen. Even before anything was said, the brain had already filled in the rest of the story. That implication alone created friction. What once lowered defenses started triggering them.
I think something similar is starting to happen in the outbound space. With AI doing research and tailoring at scale now the norm, the effort behind a highly personalized message is no longer obvious. When you receive one, it often doesn’t read as someone sitting down to write to you. It reads as step one in a sequence.
That’s the part I find interesting psychologically. Humans don’t respond to effort itself. They respond to what effort signals. Once a signal becomes cheap to produce, the interpretation changes. It’s easy to blame AI for this and say it’s no longer genuine, but this has been happening for decades. It’s much deeper than AI. When you turn a genuine human connection into a formula, it loses its meaning. I think this follows Goodhart’s Law: “When a measure becomes a target, it stops being a good measure.”
The point is, we humans don’t like not feeling special.
I don’t think personalization is dead, and I don’t think giving value was a mistake. It feels more like consistency doing what it always does. When enough people follow the same playbook for long enough, the market learns how to read it differently. And eventually, the opposite behavior starts to feel more human again.
It’s the same phenomenon we saw when ChatGPT was first introduced to students. Teachers thought their students were suddenly the next Einstein. I feel like in any industry that works with people, we’re always that student. We’re just asking for a chance to be recognized. Whatever tools we use and throw at the wall to see what sticks and get the attention, the underlying signal people respond to hasn’t changed. That is: there’s nothing more important than being genuine.
When a measure becomes a target, it stops being a good measure
-Goodhart’s Law
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-Jerson
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