2008: A personal retrospective

Guinness Draught bottle... a modern day masterpieceAh, the final day of the year. While many of you are partying the night away, I’m sitting at the computer, pondering what happened in 2008, thinking about what’s going to happen in 2009… and, as is often fitting of an evening after the house is finally quiet, enjoying the greatest invention of the modern era: the Guinness Draught bottle.

Back to reality. What were my personal highlights—and lowlights—of 2008? In no particular order…

  1. Leaving a full-time job to go back to work for myself — for the third time in ten years.
    Granted, the actual change happened in early December 2007, when I left a job with the New York Yankees to go back to being an independent consultant. Most people are amazed that someone would do such a thing, but I’ve made a bit of a history being just that person. Alas, my indy career didn’t last…
  2. Getting a full-time job and ending my days as an independent consultant — for the third time in eight years.
    It wasn’t an easy decision, but ultimately, there were a number of factors. What were those factors? In no particular order…

    1. I realized something about myself: My greatest value is not as an independent. As good as I may be as a technologist, solutions provider, consultant, developer, manager, adviser, whatever, my most notable successes have always been when I worked for someone else. Perhaps that’s because the stakes were always higher for me when I worked for the man. Perhaps it’s because I incorporate differently as a full-timer than as an independent. Either way, I realized I have to go where I am most effective: full-time labor for someone else.
    2. I burnt myself out by trying to be Superman — an ultra-involved father and a self-employed man just don’t mix. Too many very late nights doing work, then getting up too early. I was burning myself out. I’m too old for this (I turned 38 this year).
    3. The economy slowed, my clients tightened, and I found an incredible full-time opportunity at a great company: Business Intelligence Associates. In one month they have exceeded my expectations. I hope that in time they realize what my true potential is and give me as many opportunities to make an impact. Why don’t they know my true potential? Because I’ve masked it by making a major career blunder…
  3. Realizing the biggest career mistake I ever made was made nearly four years ago.
    Four years ago I had a very good job at a law firm, Kramer Levin. I reported directly to the CTO, had a great team of guys working for me, was responsible for nearly every business-critical system, and was doing an incredible job. Why did I leave? There’s lots of reasons, and they all made sense at the time… but looking back, leaving this job (I left to become — you guessed it — an independent consultant) set the stage for a nearly four-year stretch where I sabotaged my career. Four years ago I was well-positioned to be a senior technology manager (if not a small-company CTO) in four years. Instead, today, I am trying to re-establish my resume to get back to where I was four years ago. If I knew then what I know today, I’d make a different decision, but it’s water under the bridge at this point. Career damage control is a major 2009 objective.

Reading this, you probably are thinking, “How many times does this guy change jobs?” The answer: 14 times since 1992 (totaling 15 jobs). In chronological order:

(1) Sears, (2) Music Pen, (3) Sears (again), (4) independent music instructor, (5) World of Science, (6) Visiting Nurse Association, (7) Square One, (8) Merrill Lynch (as independent consultant), (9) some company name I can’t remember, (10) Merrill Lynch (as a full-timer), (11) Kramer Levin, (12) independent consultant, (13) New York Yankees, (14) independent consultant, (15) Business Intelligence Associates.

Spilled milk. It happens...Needless to say, I’ve very acclimated to change, and I’m very good at not crying over spilled milk.

Back on track… What am I looking forward to in 2009, which starts in 60 minutes?

  • A new addition to the family. My second child, another girl, is coming into my family in February. An infant, combined with a 3-year old, should keep me from sleeping, not that I sleep very well anyway.
  • A reinvigorated career. As outlined above, I’ve finally learned from some mistakes, and I’ve got a great job with a great company. That’s a lot to be optimistic about.
  • Something new to blog about. I got an idea, which will require some intense record-keeping next year, but I think it’ll be an enlightening project to share with people. (Hint: See that new “Taxes” category at the top of the page?)
  • Being older and wiser. When I was young, I thought experience meant nothing, that it was all about smarts and hard work. Now that I’m older, I know it is all about smarts and hard work — it’s just that experience is a huge part of intelligence. “He who doesn’t learn from his past is guaranteed to repeat his mistakes,” to paraphrase a famous quote. Fortunately, I’ve always had a fair degree of objective self-reflection. I just need to be more vigilant listening to it. 😉

Well, 53 minutes to go, and my Guinness is starting to get room temperature… I’ll leave you to your party, and wish you a HAPPY, HEALTHY, AND PROSPEROUS NEW YEAR!