One of the most dangerous, and therefore regrettable, books floating around in the various design-related industries is John Maeda’s Laws of Simplicity. The book is actually great, but in the category of “Learn it in 120 Pages” and “x Rules to Success” books, this is probably the one that creates the most dangerous reflexes. By fetishizing simplicity, we’ve turned it into a weasel word. The success of nearly everything can be attributed to simplicity. Anyone in a meeting can say “let’s make it more simple” and have it pass as useful, insightful, or designery. The trickiest reflex, though, is achieving simplicity by cutting — cutting words, cutting features, cutting links or buttons, and, eventually reducing the overall quality and enticement of the product or experience.
What’s interesting, though, is that Maeda actually tries to prevent this and other reflexes. In the book, Maeda offers a simplicity acronym: S/H/E standing for Shrink, Hide, and Embody. Three paths to simplicity, but only one of them actually suggests cutting. The others suggest design — balancing, trading off, managing form, function, levels of attention, lines of sight and cognition. They suggest it in a way that pulls you into interesting design ideas like paced layering, and which remind us that people use things more than once and that you win when the things actually get better over time (ie, discovering a new feature, finding your own shortcuts, optimizing and customizing, anticipating how it feels.)
In his TED talk, Maeda takes people in a direction that is much more productive. At 2:30 into the talk he points out that simplicity isn’t really what we crave and proves it nicely with pictures of a sunset. The simplest sunset is a 41% grey one:

It’s nice, but not that exciting, not what you want to sit on the deck and watch for an hour. Instead, this is what we love:

Nothing simple about that one but it’s what we <3. Why? Complex thing are interesting, they have crunch, they engage many parts of the brain emotionally and intellectually, they fascinate as they change over time even if they remain static, like a piece of recorded music. (This is familiar territory for fans of Steven Johnson's Everything Bad is Good for You which has great demonstrations of how we have, over the years, come to demand more complex material and plotlines and characters in TV.)
So what are we getting at? Is there a way out of the pendulum swing of shrinking and adding and shrinking and adding?
One answer was inspired by a passage I read in Mark Frauenfelder’s Made by Hand where he talk about the process of seeking “complexity out of chaos”. It’s a nice phrase in that it highlights differences between chaos, complication, complicatedness, and complexity. Complication is something no one would ever seek — in fact, it’s a much better word to contrast with simplicity. But saying people crave complexity is a little risky — complexity, as a word, doesn’t connote something virtuous. But richness does. People seek things that are rich — things that go somewhere, are worth revisiting (re-reading, re-listening, re-watching, re-thinking in your head, re-ferencing in conversation, making into a metaphor or analogy), things that yield nuance, depth, and new truths and emotions on longer, sustained watching — like a song that builds to a part you love, or the build-up to a great line in a movie.
So you could look at the goal like this:

People want the richness that comes from exploring complex things, but want to avoid complication. So it’s tempting to do this:

Make simplicity out of richness! But that takes design too far — simplifying richness puts a narrowing word too close to the expansive. I would argue that it’s better to think of simplicity as an interface to richness:

This puts you in a place of thinking about designer-y things like affordance, pace, multiple use, conceptual portability (if you’re writing), clear prose, rich metaphor in simple language, use of symbols.
Create richness out of complexity, provide simplicity as an interface to it. Don’t be simple.