There are a few points in my professional career that I distinctly remember because in one way or another, something happened that triggered a change in my life. Periodically, I reflect on these crossroads of history to discover more about me. As you might have guessed, I’ve hit one upon one of those moments of reflection.

There was a point, say 10 years ago, where I did the typical thing and dwelled on “what would I have done differently.” Frankly, exploring that question really doesn’t matter — the important thing to explore is what have I learned and uncover more about myself.  It is through an understanding my actions, connections, and collaborations where I come to learn most about who I am and what I can do.

Now before you think I’m going all Zen and that a lengthy self-reflective writeup will soon follow, the reality is that what I uncover is for me and me alone (sounds a little like something out of the Matrix — “there is no spoon”). However, for those who may be curious, I’m happy to share the milestones that I often return to:

  • November 23, 1990: I was hired as a Macintosh technology consultant for Pertuit & Partners Communication Design in New Orleans; there I met my creative mentor, Hugh Ricks.
  • November 21, 1991: By mid-afternoon I figured out that the six-figure project I was assigned to manage just that morning was going to fail, and fail miserably.
  • January 1, 1992: I left my steady job to pursue a position at a multimedia startup that went bust within five months. At the end of that stint, I had to sell practically all of what I owned to survive.
  • November 16, 1992: I started my employment at the University of Chicago as a junior programmer specializing in computer graphics and multimedia. Shortly thereafter, I met three people who taught me quite a bit about research in higher education and how to appreciate it — Fausto CattaneoRobert Beck and Barbara Stafford.
  • February 12, 1998: I was offered the position of Director of Instructional Technology, which opened a whole new set of doors for me to learn about leadership through key interactions with my CIO, Greg Jackson, a number of provosts including Geoffrey Stone and Richard Saller, and people I met while doing IEEE standards development including Wayne Hodgins.
  • May 15, 2004: While in Paris, I needed to make a decision to stay at the University of Chicago or take another job somewhere else. I chose to stay at Chicago.
  • May 28, 2010: After stumbling across a job posting online and largely on a whim where the job “sounded like me,” I applied for a position at Blackboard. Three months later, I changed careers and started something new.

One can always learn from history; my suggestion is to reflect on yours. What points in your career changed you and what does that tell you about yourself?

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