A Path Not Taken

Occasionally, life nudges you to look over your shoulder, and wonder about what might have been.

I finished reading This Is How They Tell Me the World Ends, by Nicole Perlroth. It made me look back at a moment when the choices I made left clearly visible ripples in the pond.

In 2002 I was working for a startup that was running out of runway. I was asked to stick around and wrap things up, as much as they could be, but knew before long I’d be looking for “the next thing.” I started talking to companies in the Los Angeles area, and had a couple prospects.

I chatted with a company then called Overture, formerly known as GoTo.com, that pioneered the pay-for-placement search model. A few years later they would be acquired for billions-with-a-b dollars by Yahoo!, but I didn’t join them. So the story doesn’t go there.

One afternoon I headed out to UC Riverside, where I’d done my undergraduate degree, to say hi to some of the faculty I stayed in touch with, and have lunch. That conversation set the wheels in motion for me to return to UCR, work on a DARPA funded research project, and get my Masters degree. It also meant I got to kick the job hunt down the road by a couple years, which was fine with me. This was set against the backdrop of the “1st dot com bubble burst,” and while I was fortunate to have options, none of them were particularly compelling.

Over the next two years I met some fantastic folks, learned a bunch about topics that were new to me, taught a couple classes, got my first experience leading and mentoring people in an academic setting, publish a few papers, and even managed to build a system, write a thesis and defend it. Not bad, really.

For part of that time I’d been flying up to Seattle, at the invitation of a friend and repeat colleague to consult.

All good things come to an end, and I once again had to turn my attention to “the next thing.” Over a few months, I would interview with Amazon (didn’t join them, but that decision would turn out not to stick), was asked to turn my consulting role into a full time role in Seattle, and got connected through former colleagues to a little “cyber security” company called @Stake. I had worked at the same company as some of the principals before that ill-fated startup, and that was enough to get a phone interview, which turned into an on-site interview, and looked to be on track for an offer.

In 2004 the “cyber security” landscape was very different. Microsoft was investing heavily in improving security, catalyzed by Bill Gates’ annual memo in 2002. Break-ins at large companies that leaked sensitive data weren’t yet commonplace. The world hadn’t yet seen a nation-state weaponize software to attack physical infrastructure. That sort of plot was reserved for Tom Clancy novels, and bandied about by us tin-foil hat types. And Snowden hadn’t yet shown the tin foil hat types that there were threats in heaven and earth even they hadn’t dream’t of.

And in this “left-of-boom” moment I was seriously considering joining a software security firm. Helping customers defend their networks from bad guys and… well, who knows what else.

But that’s not what happened.

@Stake, it turned out, had started doing a bunch of work with Microsoft. Their offer was for me to move to Seattle and they expected a bunch of travel. I had two other offers to move to Seattle, and neither of them involved much travel, which seemed preferable when uprooting your spouse and moving to an unfamiliar place. When I said thanks-but-no-thanks to @Stake they didn’t push back on my summary of “moving plus heavy travel sounds like a great recipe for divorce.”

We did end up moving to Seattle. I turned the consulting gig into full time for a few years. I worked on music and media streaming, not keeping bad guys out of networks.

Perlroth’s book gave me a peak into the world I nearly joined. I’ve had a few brushes with that world over the course of my career. And there were moments in the book that resonated sharply.

Being on the defending side when a bad guy was actively trying to do things they shouldn’t. Working with a wicked smart group of colleagues to clean up a mess when defense succumbed to attack. Spending a few weeks in a windowless room, following the digital footsteps of a sneaky intruder to reconstruct a timeline of events. Finding digital fingerprints that led a colleague back to the intruders name, and address, and photograph. Sharing a look of shock when a coincidental power outage during an event made us all wonder if we were in well over our heads. Laughing when we realized that power outage had inadvertently neutered an otherwise persistent threat. Working closely with security professionals in private practice and in US federal law enforcement. Seeing the look of confusion when my wife said there was a call for me from the FBI one Sunday afternoon.

I’m not sure I’d call them “fun” times. But they were memorable.

At several points in the book, and while reading the closing chapter this morning, I found myself intensely curious about what might have been.

How life might have turned out had I made different choices.

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