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Looking around at the shelf behind me I see a dozen or two such books. I may still have some boxed up after my latest move (five years ago). Some date back to the 80s.
I don't think I've bought a new technical book since around 2010, but I have bought/acquired used ones. For instance, I have a COBOL book someone was giving away a few years back.
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I used to use my C++ Manuals as a doorstop
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Compared to my bookshelf, those are practically brand new. I still have books on (MS-)DOS internals and an old 8086/8088 programmers guide that details the entire instruction set.
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Last year I threw away books from that era covering similar topics. One I remember buying and then reading, and it went way over my head (I was in my early teens and had a hard time already understanding books written in English, let alone the subject matter). I went back to it years later, and (re-)discovered interrupt programming. Then it turned out for years to be one of my favorite books.
I also had about half a dozen OS/2 books - one with a foreword from Bill Gates.
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I remember running OS/2 2.x quite some time before Win95 released.
It was quite amazing to see true pre-emptive multitasking when all we really had was cooperative multitasking in the Windows 3 world.
Then Win95 released and OS/2 continued the issues of no driver development (your CD-ROM didn't work in OS/2 bec their weren't any drivers for it) and win95 killed OS/2 and OS/2 killed itself. 
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BryanFazekas wrote: I'd talk the next client into buying what I need for that contract.
I know a guy who does house renovations for a living. If there's an unusual tool he doesn't already have but needs for a job, he buys it and keeps it (or rents it for the duration needed if he knows he's never gonna use it ever again, or so rarely he can't justify the purchase). He doesn't make the customer buy it and then hand it over when the job's done. The customer has no need for the tool.
Things might be different in the software world; if you need a license to use some software, and the customer needs to run that software, this makes sense...but books? Even though you hand it to the customer after the job's done, you don't wipe out from your mind what you've learned from the book. You're the main beneficiary. And the customer (in all likelihood) also has no need for the book.
But, I've never done any contracting...maybe I'd change my mind if I was, or was working on stuff I have zero interest in after the job was done. Otherwise, I'd buy, and keep.
In any case...I did get rid (last year or so) of a big pile of books, maybe 5 feet high if I had stacked them all. Clearly some stuff I'll never use again. Although the hoarder archivist in me kinda regrets throwing away at least some of them. Some were brand new (clearly I got by without reading them...) I just never had a "proper" bookshelf and the books were just taking up place in a number of boxes on the floor of a closet. Otherwise I probably would've hung onto a few of them (some I was happy to be rid of).
What annoyed me the most is that I had checked with my local library to see if they'd take them, rather than sending them for recycling (which I know in some cases still end up in a landfill anyway). They wouldn't take anything older than 5 years. Yet these are the same people who are constantly complaining they're underfunded. They weren't junk, and I'm sure if I had bothered I might have found some buyers, even if only for historical value.
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dandy72 wrote: They wouldn't take anything older than 5 years. Yet these are the same people who are constantly complaining they're underfunded. They weren't junk, and I'm sure if I had bothered I might have found some buyers, even if only for historical value.
Err...except you just stated that some of them you had never read and that you would never use them again.
Libraries of course must either store books or dispose of them. Which costs money. You know the part where funding comes in.
And computing has impacted them as well. So they can easily track titles and genres which people do read and those that they don't. So they maximize the potential.
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jschell wrote: except you just stated that some of them you had never read and that you would never use them again.
Which doesn't make them valueless.
In that particular case I just wasn't the target audience. I just wanted to salvage this brand new set of 6 or 7 volumes, headed for the dumpster, still shrink-wrapped together. Very technical, very expensive, but I just never went in that direction.
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Old books are of two general types:
1. Programming-language specific
2. Language-agnostic like Algorithms, Maths, OS theory, etc.
Type 2 books are less likely to have expiry dates, IMHO.
(Of course, fiction, history, etc. books are of a different realm altogether).
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The Dragon book.
Since the newest one costs something like $150 I figure I will hang on to the older version if I want to look something up.
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Over the last several years I have thinned my herd of technical books quite a bit. Here at work I have about 18 inches of shelf. At home it's about half a dozen volumes, a couple of college textbooks from 40 years ago plus some 'work' technical stuff.
I recently dumped a couple boxes of technical books I had stored at home. MS-DOS references, internals, and undocumented stuff. I used a lot of this back in the 90's at work.
Software Zen: delete this;
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They are great for target practice.
My in-laws would shoot various guns on Thanksgiving day -- mostly we shot clay pigeons (20 gauge and 12 gauge) but they would also haul out other guns - .44 handgun, other various rifles etc.
But often they would say, "well, let's just shoot at that twig down there about 30 yards"
It was terribly un-fun that way.
I started taking my old tech books and place 4 or 5 in front of each other.
That was a blast (literally) as you could track the bullet through the pages of the book. So cool!
Great Science
I remember they were shooting a hollow point out of the .44 pistol and the bullet hole was perfectly round on entry and halfway through an 800 page tech book but then somehwere around page 400 or so the bullet mis-formed and ripped a huge hole through the rest of the book.
So, use your old tech books for target practice.
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Side note, bales of hay don't work so well for practice with a bow and arrow. The bale will start falling apart... 
Jeremy Falcon
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Somehow this conjured up a mental image of some dumb action movie where the good guy dives behind a bale of hay for protection...
Something Weird Al would do anyway. 
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It's a shame I threw out all of the mechanical engineering textbooks from college. Even though I was a computer engineering major, I still had to take statics, dynamics, strength of materials, thermodynamics, and electromagnetics. They made up about 15% of the credit hours for my degree and have been utterly useless.
Those books would have made profoundly satisfying targets.
Software Zen: delete this;
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I bought very few books. The "treasured" ones are from a very long time ago; 6502 programming, manuals for UK101 etc. A bigger problem for me, now acting as several inches of loft insulation, are user manuals and course materials that I wrote, for various software vendors. Can't chuck them as probably the only copies still in existence! 😂
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Hello Derek how are you ?
In a closed society where everybody's guilty, the only crime is getting caught. In a world of thieves, the only final sin is stupidity. - Hunter S Thompson - RIP
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I'm fine thanks. Haven't visited CP for a while, need to catch up... Change of routine. Good to see the CCC is back - an incentive to get going by 9am!
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BryanFazekas wrote: Is there any value in books this old? WordPress is probably 12 yo and it's the youngest. ASP and XML are circa 2000, and C is circa 1990.
Yes, for historical purposes. But, not in physical format. You never know when you'll need it. Yes it's outdated tech, but for studying history it's nice to get context. Unless you know for certain you'll never, ever use that tech again.
If there are eBook versions, get those and recycle the paper version if you don't want to lug it around. It'll be searchable too. If there aren't any eBook versions, consider making an eBook out of them. There are machines that'll take care of the grunt work for you. You can use a book scanning service.
Sometimes, just sometimes, you want info that's out of print. Like when MSDN dumped all their Win32 info after .NET came out.
Jeremy Falcon
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Jeremy Falcon wrote: Like when MSDN dumped all their Win32 info after .NET came out.
MS published all of that in some "MSDN Library Archive" set, that came in two big blue CD binders. I made a point of keeping that one. This is not quite it, but very similar.
(actually I just found my copy of the disc that had the cover at the link above).
I remember also making a point of keeping the very first MSDN disc set. Grand total of 14 CDs, if I'm not mistaken. Then it quickly ballooned to hundreds of discs.
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I donate all my old books to my local city library branch. They even have a drive-by deposit box. What they do with them is part of their job. I have actual seen some of my old books on their shelves inside the public part of the main library.
"A little time, a little trouble, your better day"
Badfinger
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You could donate them to your local community theatre (if you have one) as props.
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I had forgotten about Smalltalk, heard of it many years ago but, like others, didn't do anything with it.
Downloaded Squeak, already have a germ of an app that I might try.
A home without books is a body without soul. Marcus Tullius Cicero
PartsBin an Electronics Part Organizer - Release Version 1.4.0 (Many new features) JaxCoder.com
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