In Free as in Freedom (2.0) it reads (PDF, page 98):

In many ways, the Symbolics war offered the rite of passage toward which Stallman had been careening ever since joining the AI Lab staff a decade before.

I didn’t know "careening", so I looked it up in a translation dictionary and found two translations that seem to be mutually exclusive quite different:

  • to careen ~ to stagger/lurch/totter
  • to careen ~ to race

What does it mean in this example sentence? Was Stallman determined/single-minded ("towards which Stallman had been racing …"), or was he not so focussed ("towards which Stallman had been staggering …")?

Is the meaning here obvious? If so, why?

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    I believe "to rush headlong or carelessly" is the best fit, according to thefreedictionary.com/careen. To me, it's not that obvious. (I needed to read a few paragraphs above that quote.) By the way, you can think of the verb careen as to rush recklessly too. That works for me. – Damkerng T. Dec 3 '13 at 16:19
  • @DamkerngT. Your comment is a good answer! I encourage you to post it. – Tyler James Young Dec 3 '13 at 17:46
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    The first meaning (which I think is perhaps not adequately glossed by "stagger") is a figurative extension of the original meaning of careen. It gained the second meaning later through confusion with the verb career ("to move rapidly"). The two meanings have merged somewhat, so that these days it commonly means "to move rapidly, probably out of control, while lurching from side to side". It doesn't always have that combined meaning, though. – snailplane Dec 3 '13 at 18:52

The core meaning of careen is a motion that is accompanied by sideways oscillations. It doesn't intrinsically imply that the motion is fast or slow. An object or person may be careening because it is hampered in its movements, for example a ship on a rough sea or a drunk person who cannot walk straight, and thus it is moving slowly. Conversely, it may be careening because it is moving so fast that it has difficulty controlling its motion, for example a car going too fast on a windy road or a sled racing downhill. Although a careening motion is not plain, straight sailing, it is nonetheless motion in a well-defined general direction. (Contrast, for example, with wandering or meandering, which imply that the trajectory is very far from being straight and may not have a goal at all.)

Here, I understand the metaphorical use of careen to imply that Stallman's life until that event had given hints of what would happen later, that the event was not unexpected, but that he hadn't had that event as a fixed goal in mind. Stallman hadn't been aiming for it, but in hindsight, it was a predictable outcome. The motion was careening because while it did eventually reach an identifiable point without major deviations, it was not specifically headed for this point.

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I believe "to rush headlong or carelessly" is the best fit. (ref)

Is the meaning here obvious? To me, it's not that obvious. (At first, I couldn't even decide which sense it should mean in the context, because it seems to mean both to lurch or swerve, and to rush carelessly.) I needed to read a few paragraphs above that quote. Fortunately, I can find the chapter at O'Reilly.

Although I didn't read the entire chapter, another page at Wikipedia seems to indicate so. Considering amount of his works during the AI Lab at MIT, it seems like he was, at that time, really working recklessly. (According to the sections: "Early years: MIT," and "Background: events leading to GNU".)

NOTE: Even after reading it, it seems to me that the word careen still conveys both senses, but I think it emphasizes more on the rushing.

By the way, I think of the verb careen in this sense as to rush recklessly. It works for me.

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  • (Good idea re. more context. I added the direct PDF link to my question. The O'Reilly edition you linked is the original publication without comments by Stallman, but the relevant parts for this question should be the same.) – unor Dec 3 '13 at 19:12

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