I generally agree that hindsight is 2020, and its hard to tell who's wise vs just throwing darts.

However, not all types of prognostications are created equal. A big part of identifying trends and devising strategies is being able to sort out what's worth getting on top of, just watching, or dismissing outright. Same for journalism.

This article was a typical counter-hype pageview driver pounded out for a deadline. The writers job was to make a plausible-sounding story for the opposite side.

Its the plausible-sounding story part thats tripping people up here. Here's what he did:
* He says everyone is going gaga over it
* He gives a bunch of reasons why they'll have a tough time in the market
* He cites a random analyst
* He muses his personal take on its market feasibility and makes a strawman argument about it being a 'defensive product' that he summarily knocks down
* He concludes, decisively, that nothing is going to change

We've all read this article. Its like the 5 paragraph essay from grade school. And like the 5 paragraph essay, it can be graded for how much it makes sense.

Just on cursory view, he clearly hasn't done his homework on Apple or consumer trends. Namely, he doesn't address the success factors and relevant details of the iPod.

1. He cites price as an issue (but the iPod was almost the same price, anchoring high end value before dropping in price to get mass market scale).

2. He mentions people really excited about the iPhone but later muses he doesn't know who its targeted at (how does he think Apple sells things? tech specs?).

3. He suggests the playing field is level against competing models (ignoring the demonstrated ecosystem power of iTunes, the fact that no ecosystem exists in phones, and of course, ignoring the holyshit demo that showed iPhone's superior usability).

4. He says at the end an outside player may come provide competition but they'd have to bring some new tech or different user experience (ignoring the decades of R&D groundwork and IP portfolio that Apple laid for the iPhone, all the way back to tech demos in the 80s and the Newton in the 90s).

In other words, he's probably dodging the issue or doesn't know anything. This quote is great:

"Likewise, who is it pitched at? The price and the e-mail features make it look like a business product. But Apple is a consumer company."

He's grappling aloud with a square peg in a round hole of his own making. Like the rest of the article, nowhere in there is the author demonstrating an ability to imagine something that does not exist today - the basic skill required to understand the history of technology.

To a reader without any industry knowledge, at the very least the context of what type of article this is (a counter-hype story), the logical inconsistencies within the arguments, and the complete lack of imagination would raise a flag about how valid this piece is.

To a reader with industry knowledge, they'd see points 1-4 not covered and think this guy shouldn't have his job.

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Now to your example, I don't think these are the same type of prediction.

That the iPhone would be a general market success was an easy prediction, because the playbook and success of the iPod was right there, and it was easy to see that phones were going to be like the iPhone once it was shown, because it was that much better.

The Fuji vs Kodak is a hard prediction, because those companies are having their core business models threatened by an external change looming over them. The change here isn't about the success or failure of a product, it's about whether companies can manage a transformation. Transformations are hard and messy, and hard to predict.

I see the 'its hard to predict the future' argument as more than a little bit similar to "correlation is not causation" that seems to pop up here occasionally. Yes, correlation is not causation, but it can imply it, depending on the circumstances, measurements, R^2, etc. Similarly, the conditions for a future prediction depend on what information we have, what the context is of change, what we're trying to predict, etc.

The only thing I think where the iPhone prediction was difficult was just how crazy a success it was. But whether it was going to be a general success or general failure? For anyone who knew a bit about the iPod, that should have been answered the moment they saw the demo.

EDIT: All this said, I definitely agree with the important lesson to balance short/long term and not try to over-predict the future, especially when it comes to the path individuals are on. I think thats what you were getting at at the end. Wisdom of this kind is important in this (young) community.