While this may seem like a silly exercise, it actually has a long and storied tradition inside of hacker communities.  There are a number of well known “guides” that have circulated the halls of old Usenet and dusty Jargon files from many years back with contributions from such luminaries as Bruce Parens, Eric S. Raymond, and Larry Wall.  Basically I am going to offer a stupidly basic outline of what I would like to have learned, in the order I would like to have learned it in, to have developed my skill-set (or lack thereof) in the quickest fashion possible.

*One caveat is that I have changed this list 8 times in the last 3 weeks (which is why it has taken so long to post) and added another step just minutes before posting again.  My point is that I will probably continue making updates for a while and I would encourage anyone comments or suggestions on how it can be improved.

• Step 1: Start by visiting/read these websites, mailing lists, & newsgroups.. everyday!  ArsTechnica,  Phrack, SecList, Schneier on Security, OWASP, ITSecurity, cDc, and the LiquidMatrix Blog.  For extra credit read everything you can handle from the SANS Reading Room.  If you don’t understand what you are reading, Google it!
• Step 2: Build your own computer.  Check out the ArsTechnica System Guide to make sure you have compatible hardware that will actually be cost effective and then purchase the parts at PriceWatch (be sure to check the vendor ratings before you buy.)  Yes, you could actually buy a system “kit” from someplace like NewEgg but the value of this exercise is in learning the hows and whys of each component.
• Step 3: Install a Unix style OS on your newly built system… and/or every other system you can get your hands on.  I recommend either Fedora or Ubuntu to start with as they are the easiest to begin using but in reality any *nix style will work (i.e. FreeBSD, Linux mint, OpenSuse, OpenSolaris, etc.)  No hacker I know lives in Windows (well… unless they are gaming.)  Linux OSes provide access to a system on a level you simply will NEVER get on Windows.  This is partly because of the power of the Unix system model and partly because hackers develop for hackers on Linux/Unix.  After you install your new OS, use it, everyday, as your primary OS.
• Step 4: Make your own website… from scratch.  Go get a $6.00/month HostMonster account, decide on a domain name, learn FTP, setup an email account, and start making a website!  It is a cheep way to get some direct experience doing many of the most common web task.  Finally, got get a copy of the Lama, Pythonista, or Rails Tutorial and go through the ENTIRE tutorial thus creating your first dynamic website content.
• Step 5: Continue building your library.  Nobody can know everything there is to know about technology.  Having quick access to information that you have (at the very least) read before is a HUGE help.  Additionally, going through the programming and hacking literature will give you the best hands-on experience necessary to take the next steps.  You should own/have read as many of these as possible:
• Programming:  CC2,  SICP, the Camel, Design Patterns, Refactoring, K&R, the Dragon Book, The Little Schemer, and if your are really brave the “Art of Computer Programming.”
• IS Management: Peopleware and MMM.
• Networking: Computer Networking, Computer Networks, Unix Network Programming, and Hacking.
• Hacking: The Basics of Hacking and Penetration Testing, The Art of Intrusion, and Hacking (again.)
• Hacker Culture: The Hacker Crackdown, The Hacker Handbook, the updated Jargon File, Open Sources, Underground, and Stealing the Network.
• Others:  If you have any specific technology interests (say Cisco switches or MS SQL Server) find the appropriate user forums for those groups and ask their users which books are MUST reads.  One good technology book is better than 10 mediocre books.
• Step 6: Download the Linux From Scratch book and build your very own custom operating system from source code.  You will more about how operating systems work 99.9% of IT professionals do.  Doing your own OS build will change the way you see systems and how to protect them.  The results of a LFS build is not the system itself (you will probably go back to using Fedora shortly after finishing) but that you will NEVER go back to be just a technology user…

KDE

A big room somewhere in Europe with lots of chrome and glass and a great big whiteboard in the front with lots of tiny, neat writing on it. There are about 50 desks, each with headphones and pristine workstations, also with a lot of chrome and glass. The faint sound of classical music permeates the room, accompanying the clicky-click of 50 programmers typing or quietly talking in one of the appropriately assigned meeting areas. (Which of course consist of elegant contemporary white pine coffee tables surrounded by contemporary white pine and fine leather meeting chairs.) Coffee, tea, mineral water and fruit juices are available in the break area.

At the end of the day, *everyone* checks in their code and the project leader does a “make” just to make sure it all compiles cleanly, but it’s mostly only done from tradition anymore since it always compiles cleanly and works flawlessly. When all milestones have been met, and everything has been QA’d, (usually within a day or two of the roadmap that was written up 18 months previous) a new KDE release is packaged up and released to the mirror sites with the appropriate 24-hour delay for distribution before being announced.

KDE developers are generally between the ages of 16 and 25, like art made of lines and squares and the colors white and black. When/if they finally stop taking government subsidies and get around to getting “real jobs,” most of their salary will be taken in taxes so the socialist government can subsidize the care and feeding of the next generation of KDE developers, just like it did for them. A high percentage of KDE developers, during their mandatory 5 years of government military service, crack from their years of cultural dullness and flee Europe to become terrorists for the sheer joy to be found in killing random strangers for no discernible reason.

GNOME

An abandoned warehouse in San Francisco, kitted up as for a rave, electronica playing at 15db louder than “my ears are bleeding and I’m developing an aneurism” volumes and the windows all painted over black so that the strobe and spotlights and lasers can be seen better. Computers, mainly made of whatever stuff has been exchanged for crack or scavenged from dumpsters behind dot-bombs, are scattered around on whatever furniture is available, which also consists of whatever stuff has been exchanged for crack or scavenged from dumpsters behind dot-bombs. There’s no break area, but you may be able to bum a beer (or more likely something harder) off of one of the developers hanging around, and they will probably be too jacked up on X, coke, acid, heroin, ether or all of the above to notice that you’ve taken anything.

Development strategies are generally determined by whatever light show happens to be going on at the moment, when one of the developers will leap up and scream “I WANT IT TO LOOK JUST LIKE THAT” and then straight-arm his laptop against the wall in an hallucinogenic frenzy before vomiting copiously, passing out and falling face-down in the middle of the dance floor. There’s no whiteboard, so developers diagram things out in the puddles of spilt beer, urine and vomit on the floor.

At the end of the day – whenever that is since an equal number of programmers will be passed out at any given time – or really whenever someone happens to think of it (which is rarely), someone might type “make” on some machine somewhere, with mixed results. Generally nothing happens, so he/she shrugs his/her shoulders and wanders off to look for someone who might have more pink/black-striped pills. Once in a great while, generally in the unpleasant time between the come-down from the last thing they took and before whatever it was they took just now comes on fully, someone will tar up a bunch of random files and post it on a website someplace it as the next GNOME release, usually with a reference to some kind of monkey.

GNOME developers rarely live past 25 and prefer “alternative” art – generally stuff made of feces that’s “too edgy” for most people to “understand” or “like.” Core GNOME developers are heavy Ketamine users. The bodies of GNOME developers can often be found in dumpsters or floating face-down in any sufficiently large body of water.

Copyright 2002, Derek Glidden.

Even if I knew that tomorrow the world would go to pieces, I would still plant my apple tree.
-Martin Luther

While checking one of my WordPress sites I noticed an update for one of my favorite plug-ins, The Events Calendar.  Everything was broken after the update so I when to the support site to get things running.  Long story short, I got the site working again based on the support recommendations they had but regardless, some functionality was still missing.  The reason for this was related to a huge shift in the underlying focus of the WordPress post design.

the issue you state about other plugins integrating has more to do with WordPress being in a period of flux between having everything be either posts or in its own table and authors fully adopting custom post types. The core WordPress team is placing a heavy emphasis on CPTs and most major plugin authors are moving over… As more and more plugins make the move, the integration you want to see will return in a much more powerful and controlled manner.
–Shane Pearlman

The Events Calendar has converted over to a new design method called Custom Post Types (CPT) whereby individual modules can define their own post “types” instead of adding functionality to default post type already available in WordPress.

This drew my attention because the new version of The Event Calendar provides a “Professional” version, with more functionality, that can be purchased. I haven’t actually seen much software in the WordPress universe that followed this model (and I don’t believe The Event Calendar did until this new update occurred.)

My concerns were confirmed with some web searching:

Custom post types aren’t really meant for that use […] Custom post types are great for things that are more or less catalogued: products (in an e-commerce site), listings for a real estate site, etc. For regular content creation as described [by Chris], you can already do [that] by using custom taxonomies and/or stylesheets to make post templates.

Some part of the WordPress team has been pushing these these CPT’s and it looks like they have been doing it primarily to capitalize on the success of a Free Software program. I suspect that most developers who are interested in focusing on this kind of feature set are probably not Free Software developers but are, instead, quasi-open source developers running Macs who would be making iPhone apps if they knew something more useful than PHP.

This kind of monetizing has become massively popular with the success of Apple’s App Store and Google’s Market. A significant number of developers who have built very popular software stacks on top of Open Source applications are looking for ways to turn that work into cash flow, and I don’t blame them. That said…

…I really don’t like something about it. Maybe it is because I left a “free” blog application because it stopped being free (I learned a valuable lesson between Free Software and free software and I still have a bad taste in my mouth about it.) Maybe it is because I have actually contributed work to a number of WordPress plug-ins and would NOT have done so if I had known my efforts were going to help someone else make money. Maybe it is because the new version of The Events Calendar actually broke a lot of functionality in the name of changing their platform model to a for-profit design and now I have to use an unsupported version of the software until I find another or I write one myself.

Whatever the reason, Open Source software is loosing something of itself if this is actually the intent of their focus, and we are all the less because of it.