In response to Steve's Scripting/Sysadmin Meme and Richard's call out ... I've answered the questions, but I'm not going to tag anyone else.
How old were you when you started programming?
I was 12. I think my very first program calculated factorials
What was your first machine?
The School had a Digital PDP 8/f. You had to toggle switches on the front panel to start it up, and if you got it wrong you had to reload the OS and BASIC interpreter from Paper tape. Not surprisingly they moved onto Commodore PETs. We had a Sinclair Spectrum at home but it wasn't mine. The first computer that I could call my own was an RM Nimbus of some kind when I started work there.
What was the first real script you wrote?
Script rather than program... probably something in the Job Control language used by the Cray-1 I was allowed to borrow when I was a student in 1986/7
What scripting languages have you used?
What was your first professional sysadmin gig?
Depending on your definition of Sysadmin, fixing a stack of code for an Actuary when I was still at school, most of that was Microsoft Basic on the Apple II, but later it became Lotus Macros and DOS batch files.
If you knew then what you know now, would you have started in IT?
Sorry, but I think that's a daft question. Given my time again I'd have married my wife earlier than I did, had kids earlier than we did and joined Microsoft earlier than I did. But you make your decisions with the information you have at the time and live with them. If I'd known how tough some things were going to be (e.g. running a small Microsoft partner for 5 years), I would have looked for something easier and missed out on a lot.
If there is one thing you learned along the way that you would tell new sysadmins, what would it be?
Remember why you're there. IT should get help get business task done quicker, more reliably, more easily and with less drudgery. If you find you're hindering these things rather than helping them.... get out.
What’s the most fun you’ve ever had scripting?
It's like solving a sudoku or crossword or some other Puzzle more than it is like climbing a mountain. You might look back and say what is the greatest Peak you climbed, but the greatest puzzle you ever solved ??? Recently I wrote some Powershell to match my underwater photos to the information in my Scuba Dive log, and use it to set the title in the EXIF data in the picture. I was jolly pleased with that, but like doing the Christmas giant crossword it will fade.