I wanna be a digital cowboy

Funny how round numbers and periods of introspection seem to arrive together. I turned 40 a couple of weeks back, and (I hope to God) I’m coming to the tail end of a rather brutal period of self-reflection and, peripherally, some thinking about the work we do – no surprise when that work takes up so many of our available hours.

The thinking: I’ve been doing the IT/technology thing (or things closely related to it) for almost twenty years. To give you some time-line context, I thought I was at the top of the programmer heap when I got an IBM PC AT with a (huge!) 30MB hard drive to build Dbase III applications.

On the upside, I’ve had what I think is a relatively successful career in a very cool business.

I’ve piloted DB2 and relational databases at a big oil company (man, my tables were so well normalized that I’d have to write eight-table SQL joins to get anything out of the machine – my queries would eat up everything an IBM 3080 had and then dim the lights in the building. An early lesson learned here: the need for an effective balance between technical purity and pragmatism.

I’ve built client/server applications that displaced many a green screen 3278 terminal, and I helped build the first intranet for a big company, using a Web crawler to pull information overnight on emerging energy technologies (at one time, just knowing how to work tags and hyperlinks made you some kind of a Web genius), and I’ve been able to turn my hand to planning and leading some really big and interesting projects.

All of which has allowed me the chance to travel, to see places (mostly big cities, of course) I otherwise wouldn’t, to work on projects and for organizations that I wouldn’t have imagined when I was twenty.

God bless the IT business and the changes it went through in the ’80s and ’90s and where it’s taken me.

Of course, many blessings live only a hair’s breadth from a curse, and I’ve come to see that my previously un-hesitatingly enthusiastic belief in what I do for a living has cost me a lot.

Yes, there is a downside to this hard-charging business, Virginia: at the tender age of 40, I still find myself a wage slave, overly fond of good hotels and decent wine, hauling my keister across the continent and back at all hours and on any day, weekend or not, at the whim of my clients. And why not? After all, they’re paying the (sometimes significant) bills for my time.

In my darkest (and most arrogant) moments, nursing my second scotch and water on a long haul back across the country on a late Friday evening, I think of myself, in the consulting role, as something of an apologist for a bunch of corporate weenies with half as much talent as I have. Probably not true in most cases, but the fantasy of it is one that I hold on to when I’m thinking about giving up the whole damn thing.

Taking the good with the bad, twenty years of experience, and an eye to the possible, I think I’ve figured out what I really want to do when I grow up: I wanna be a digital cowboy.

This whole idea started when I met a real one on a plane three or four years ago on a stopover in Salt Lake City. Picture me in my uncomfortable suit (client meeting to get to), settling into the business-class seat I’d managed to scrounge through a clever cobbling together of upgrades and negotiations with the airline. Then this guy sits down beside me, in jeans, cowboy boots, and a casual (but obviously not inexpensive) jacket, and he opens up the coolest Mac portable I’d ever seen.

Seems that this guy worked from home most of the time, home up in the mountains around Alberta where he could “easily stay in touch with [his] clients, but still ski whenever [he] wants to.” He appeared to travel comfortably and well, but “never more than once a week, and never for more than a couple of days at a time.” Hmmm….

He and some other folks I met during my travels made me rethink some of my choices…but more about that next issue.

Hanley is an IS professional in Calgary. He can be reached at [email protected].

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