In my final weeks as a student in the College, I approached the Campus Director and said I wanted to run an experiment and do a full security audit on the campus network and asked for her approval and confidentiality. She agreed and I hacked the network, ultimatly prodicing a 40 page audit document that not only hilighted the challenges, but also the solutions. This random act of kindness (I didn't charge the college for the work), led to them asking me to come in and give a lecture on security about 6 months after I graduated.
Between the tutoring, the taking on ownership and producing a comprehensive security audit and lecturing for the college, I was their first call when their programming instructor gave her notice about a year after graduating. They wanted me to come teach for them. I would be the secondary Programmer/Analyst Instructor (they had another one), but only for about 6 months, until the other Instructor acknowledged that I had a better understanding of the courses and the content, making me the lead instructor. The CDI model was interesting and insane at the same time. Initially you had to be able to answer any question in any of the 52 course modules at any moment in time, so you really needed to know your stuff and keep on top of all the course changes. They eventually shifted to a cohort model and only had students starting every few months (which made the cohorts more like classes that stuck together) but in the early days, it was pretty bonkers.
One of the challenges I had was the way the college tracked the students and their grades, because it was a self directed program, students were all over the place and it was a challenge to track them. So I did what most developers would do, I rolled my own basic student tracking system (built in Excel). I used VBA under the covers to automatically generate a new students tracking worksheet with all the correct dates, average their grades and produce the monthly reports, and set up bi-weekly, 1:1 meetings with every student to help keep a finger on the pules of my students and learn more about them.
In my second year, I was put in charge of the Y2K efforts to ensure the college would survive (it did, but I did intentionally leave one system un-patched just to watch it fail (it did)). Next was taking on the duties of the ONA and ensuring the network servers were kept up to date and healthy on top of my regular duties. Then they had me teaching some of the Networking courses as well as the Programming courses. When I caught wind that the campus was considering leaving a unfilled position, well, unfilled, becasue I was able to cover both, I had a sit down with the director about salary and responsibilities and risk. Ultamatly, I gave them 6 weeks notice and jumped over to the Toronto School of Business to teach e-commerce & web design part time.