My path:

Had computer and internet access at a young age. Learned DOS in elementary school playing 'Oregon Trail' on 5.25" floppies. Exposed to Lotus 123 in DOS. Played mahjong on OS/2. My first experience with copy protection was the "enter the X word on Y line on Z page" a la Commander Keen.
First touched the internet when 14.4kbps was a big deal. Played with File Manager on windows 3.11 like it was a toy. Fix errors in "MegaRace" install.
In middle school, discover IRC and fileservers. Get involved in Anime fansub scene, host fileserver around the same time that Cable Modems were first hitting the US east coast. Learn about video compression, encoding, fansubbing. Learn IRC script and create chatroom bots that respond to users. Learn FTP and FXP. Infect friends' PCs with Subseven like a true script kiddie. Get C&D letters from parents' ISP due to port scanning.
In high school, get CompTIA Network+ cert, A+ cert, MS Sysadmin Cert. Interstate 76 comes out for PC, learn what hexadecimal is. Around the same time, joined a guild on MPlayer for playing Mechwarrior 2. Learn HTML and CSS while creating a website on geocities/enchantedforest/cottage for the guild, learn what <table><tr><td> is. Create free website on angelfire for a friends. Learn how to embed a MIDI file. Learn what PHP include means. Learn JASC Paint Shop Pro. Learn how to Pirate JASC paint shop pro.
Go to college as CS major. Learn OOP in java. Touch SunOS and Emacs. (ed: i stand by my claim that emacs is not meant for humans). Enjoy programming, hate math. Halfway through college, switch to business major because I have a D in Calc 3 and dont want to blow up my GPA.
While finishing college, work as a Jr. Sysadmin consultant for a major ISP. Learn windows administration, learn core concepts of availability and scalability. Learn about backups. Active Directory, Exchange, IP telephony, DNS etc. Learn about corporate process and bureaucracy. Learn how to CYA.
Get job as IT manager for 5-person financial startup.
Get fired after 3 days.
Get job at Panera Bread bussing tables.
Get call from major ISP, quit panera after 2 days.
Get job for IT consulting company in a major metro area. Visit residential and corporate clients to act as IT department, doing break/fix, data recovery and small scale org planning. Appreciate the value of true IT knowledge in the marketplace.
Get job as Sysadmin at a media company. Use previous experience to deliver superior service to internal users. Build goodwill.
Around the same time, iPhone 4 is released, with retina display.
Become enamored with iPhone, recognize potential of the platform. Learn iOS dev with help from Stanford classes on iTunes U. Spend 2 months learning iOS, get comfortable working with it.
Decide to quit sysadmin job to study iOS full time.
Upon quitting, get offered the opportunity to transition to developer role at same company.
Accept opportunity, attend excellent iOS training course, begin transition to full-time dev role. Work on popular newsreader app. Gain experience and knowledge from dev mentor.
After 1.5 yrs, move on to smaller startup-y org for massive $ increase. First "real" programming gig since making transition from sysadmin. Overcome jitters, rewrite major application with great success. Read about electrical engineering, and Haskell. Consider what to do next...