I went through a really tough time about a year ago.  My buddy Ryan thought at the time I was having a mid life crisis.  He was probably right, but the problem was just as likely that I was moving out of my comfort zone of “doing” and into an area I was less comfortable with of “managing”.

At the time I had tons of experience the “how’s”, but not nearly as much experience with the “why’s”.

As I roll towards the big milestone of 40, I’m looking back and reflecting on my life.  This isn’t where I thought I’d be when I was 20, I thought I’d be either Michael Bay or Kevin Smith by now, but fate moved me in a different direction.

Now I’m a web guy, I’m in IT (I NEVER thought I’d be in an IT department).  I’m a Manager (capital M), telling rather than doing.  I’m a leader (lower case “l”), who rallies and motivates people.  I’m an entrepreneur, I started Canada’s Online Comics Superstore All New Comics (plug), opened and closed HeadsDown Internet Design, and I’m a partner in New Ninjas Inc..

Over the last year or two I’ve been compiling a massive post of what I like to call “What I’ve Learned So Far”.  This is a list of things that I’ve taken away from each job I’ve had, and stuff that has shaped me into the person I am today.

Netstar / TSN / TSN.ca (January 1997 – January 2000)

Pressure is good for the soul

I always hear people upset that dates are arbitrarily made.  I believe in deadlines and dates.  Trade Deadline is March 3rd.  The Draft is July 6th.  The Olympics are February 12th.  You cannot miss those deadlines.  That kind of pressure inspires you to work your hardest.

Get things done

We just did stuff.  We said we’d do it.  We worked together.  We got it done.  One of my favourite memories is of a micro-site that the sales guys had sold for Honda Power Tools.  Two of us built a 12 page site in 6 hours one night, from design and concept through populating content.

Get things right

Bloggers think that it’s most important to get it first, at TSN it was hammered into my head a billion times that it’s most important to get it right first.  In three years nobody will remember who broke that trade story, but they will remember when you got it wrong.

Be able to scale

When I arrived at TSN we had one single web box, it was even called Webbox.  It was an old Sun server, pretty tiny really, and it just served up our website…out of our building (right behind the security guys).  By the time I left (the first time), we had 14 custom Dell Opteron servers and we were serving up about five times the traffic we had in 1997.

Learn something new

I came into TSN knowing CSS and HTML,and that was it.  I learned how to program a batch job, how to create shell scripts, how to use UNIX.  I taught myself how video encoding worked, and became our best encoder of video, constantly tweaking and improving our video encoding and our ability to stream.  Meanwhile I spent time in the video editing booth, doing SportsDesk and Soccer Saturday shows, and some time in the graphics department learning how to use their sweet $50k O2 machines that built the graphics packages. I learned about business plans and business cases. In those three years at TSN I did a masters’ degree worth of learning, and got paid for the privilege.

Don’t be afraid of change

As we were rebuilding our website, going from an all flat HTML site to one that included things like “Server Side Includes”, and a “content management system”, Joe, our Tech Guy decided we should move to this funky new “ASP” platform by Microsoft.  I got on board and started building pages as quickly as I could.

Activate (January 2000- January 2001)

Work Hard

I only worked at Activate for a year, but I put in about two year’s worth of time there.  I did so much stuff that was cutting edge and at the far limits of what I was capable of.  I templated most of my work so that I could do more custom development, and took on anything they threw at me.  Sure I was crusty as all hell most days because of the never-ending torrent of work…but I was doing a LOT of good stuff.

Don’t be an idiot with your money

When I arrived at Activate, its parent company had a $4billion war chest.  I watched as they squandered millions of dollars on the most ridiculous of things.  Saw them burn through cash at an alarming rate, and witnessed stupidity like company events for twelve people that cost in the tens of thousands of dollars.  All while we weren’t making enough money to cover our base costs.

A good network is the most important thing you will ever build

When I was laid off at Activate, I sent out an email to all of my contacts.  Five minutes later I got a call asking if I wanted to meet for lunch.  Over lunch I had a job offer.  The next day I started my new job at Alliance Atlantis.

Up Next: Alliance Atlantis, Centennial College, Bell Globe Media, All New Comics, Info-Tech, and New Ninjas Inc.