Getting Old(er)

When I first started my professional career, it was hard to envision what it would be like to have a life-long career in tech. For starters, the software industry was primarily dominated by Gen Xers like myself, and I would rarely encounter anyone more than a decade older than me. This situation was exasperated further by the Dot-com boom , which enabled many engineers with good timing (and a lot of luck) to retire early. Hordes of Microsoft millionaires in their thirties were cashing out and leaving just as I was starting1. Thus, I never thought I would last as long as I have. I figured I would work in the industry for a few years and then either start my own business or return to school and teach. After more than two decades, I suppose it is about time to admit I was wrong.

One of the aspects of aging that I have found fascinating is the need to refresh the cultural stories we tell within organizations so that they stay relevant. At Microsoft, I used to always tell new hires that one of the things that made Microsoft successful was its cultural value to "Not make the same mistakes as IBM." When I told this story, I would usually need to explain a bit about how IBM was so focused on how much money they were making in mainframe computing and that they failed to see Apple as a threat until it was too late. IBM's rush to catch up meant that they had to build the original PC from off-the-shelf parts – which enabled competitors like Eagle, Columbia, Hyperion, and (eventually) Compaq to ship compatible computers and take over the market. BillG instilled a core value at Microsoft that if there was going to be a product to cannibalize market share for a Microsoft product – it should be another Microsoft product.??

I love this story – and the lessons learned from it. But it is complete gibberish to someone who has only ever known IBM as a consulting company that built the Jeopardy! playing robot (and even that reference is going to be lost on many readers). So, I switched to telling a story about how Microsoft Word completely re-invented itself as a WYSIWYG editor built on Windows instead of MS-DOS – leaving WordPerfect in the dust. But, this story aged quickly too. When I told it, I would get a lot of blank stares and have to spend a lot of time trying to explain what a text editor was to employees that had only ever known computers with graphical interfaces.

I used to take great delight in telling folks that I used to work in Netscape building one that housed Marc Andreessen's infamous hot tub (that I wouldn't touch with a ten-foot pole). But the story loses a lot when I need to explain what Netscape was. Similarly, it is hard to explain the impact of Bill Gates' Internet Title Wave memo (which signalled Microsoft's (late) embrace of the Internet) or Ray Ozzie's Dawn of a New Day email (which kick-started Microsoft's move to cloud computing) to new hires that have always lived in a world with the Internet and Cloud Computing. The stories we tell need to evolve to stay relevant.

This year, most of our new college hires were born in the years after I graduated college. That is a bit of a scary thought (for me, at least). But the cool thing about working in our industry is there are always new stories to tell. I started this series of Flegg's Follies articles a year ago. I wasn't sure how much I would have to say (or if anyone would care), but thus far, it has been a positive experience. It has not made me wildly famous, but I have found it to be a great way to share ideas and keep in touch with folks I have worked with over the years. Going forward, I will likely switch to a biweekly schedule to balance my family responsibilities better. But as long as you keep reading, I will keep writing.??

Be Happy!

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Footnotes:

1. There were some real perks to starting at Microsoft during this era. Microsoft had an internal newsletter called MicroNews that had a classifieds section. It was awesome. Many Microsoft Millionaires were getting married and liquidating their "bachelor-life" assets like boats, motorcycles, gaming rigs, and more that could be picked up for pennies on the dollar.

Please note that the opinions stated here are my own, not those of my company.