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The End of My Career

Just about twenty years ago, I got my first “real” job in IT (the first one worth keeping on my resume). I didn’t love IT, but it was fun enough – and I just happened to be very good at it. Plus, it paid significantly better than any other job I was “qualified” for at the time.

In 2001, I was at a job I enjoyed and appreciated immensely, but I saw the dot com bubble wearing thin and wanted to get myself to more stable ground. I was looking for a safe harbor where I could weather the storm of the inevitable market collapse, so I added yet another job to my seemingly endless string of jobs. I joined Citi for “just a few years” in April of 2001.

I was utterly jarred by the culture shock of going from my favorite job, helping to establish and lead one of the smallest companies I’d ever worked for, to an invisible role as a cog on an insignificant gear in the largest company I’d ever known. I felt completely lost. The only grounding rock I had to grasp onto was continually reassuring myself that it was a temporary job.

It turned out to be an ELEVEN AND A HALF YEAR LONG “temporary job” where I would work my way up to become (against all odds and everyone’s expectations – perhaps most of all, my own) a bank executive.

I was a Vice President at one of the largest financial institutions in the world. In fact, I was offered a big promotion to Senior Vice President when my boss asked me to be Citi’s global head of incident management in about 2009 or ‘10.

I declined my boss’s offer to play what would surely be a significantly impactful executive leadership role in Citi’s (sixty-four thousand employee) Operations & IT division. I declined because, despite my disposition to despise Citi, I did have them to thank for helping me to finally decide upon a career – about a year or two prior – and affording me the tools and training to pursue that career. While this SVP role would likely have launched me headlong into a highly successful (highly lucrative) career in incident management, that wasn’t the career I wanted.

Just about ten years ago, I decided I wanted to eventually be a “Director of Knowledge” – even though I’d never met anyone with that title. In fact, I’d never even heard of that role existing anywhere – but I decided it SHOULD exist, so I decided to make it my mission to convince someone, somewhere, to create such a role for me.

Every single professional decision I made from that point forward was with that astoundingly unlikely future role of Director of Knowledge as my North Star.

I learn quickly and well – and have always used that to play on my strengths to succeed. As a result, I’ve never really failed at anything. But this also meant I never really accomplished anything either – nothing truly meaningful, at least. I’ve never had to work terribly hard to achieve anything.

Throughout school, and in all the jobs I’d ever had up to this point (many dozens of jobs before starting in IT, and a few dozen more in the nearly fifteen years it took me to figure out what career I wanted) things came easy to me. I’d heard pretty much every schoolteacher I’ve ever had utter the exact same phrase to my mother: “Craig is exceptionally bright, but will never live up to his great potential if he doesn’t learn to apply himself.”

This would be my first real experience with this odd phenomenon of “ambition” I’d heard so much about. I had never set a truly challenging specific goal for myself, and applied myself with dedication to achieving something that was not only not a “sure thing” but was exceedingly unlikely.

In the ten years since I set this goal for myself, I’ve had six jobs across three companies. In that decade there have also been some tough decisions, rough paths, and challenging financial difficulties. Quite a few times over those years, I found myself wondering if it was a grave mistake for a high school dropout to turn down what would very likely be my only opportunity to land an extremely well-paid executive leadership role anywhere.

But, I don’t believe in regret – and I didn’t have the tools or wherewithal to start over – so I just kept pushing. I didn’t really see myself having any other valid options, because I put all my professional eggs into this one makeshift – rapidly becoming threadbare – basket. I was also unwilling to relinquish hope, however, because four of the five jobs I had taken since making this decision were roles that were created specifically for me, or reimagined to match my unique skills, experience and perspectives. I took it upon myself to entirely redefine the fifth. I had no idea if my efforts would pay off the way I’d hoped, but it certainly felt like I was doing something right.

At the beginning of February, I found a small (but stable and growing) company I can respect, who was looking to hire a “KCS Lead” to establish a new Knowledge Management practice in their Customer Success organization. The role, as written, was well below the stage I consider myself in my career, but I applied for it anyway. I didn’t apply because I wanted to take a step backward in my career – but because I wanted the opportunity to meet with the hiring manager.

I wanted to convince them they were wrong.

They have no Knowledge Management practices or infrastructure whatsoever in place yet. It’s a truly greenfield environment. They thought they wanted a “KCS Lead” to start them down the Knowledge Management path. I wanted to convince them what they really needed was a Director of Knowledge.

My first day in Zerto’s newly-established role of Director of Knowledge will be April 15th. (Well… The official title turned out to be “Director of Knowledge Management” but I can live with that – for now…)
My last day at Dell EMC will be April 12th.

This is it.

There is simply no “up” for me from here. This is, quite literally, the pinnacle of my career. This is the last job I plan on having in this field.

I expect this position to be extraordinarily challenging, but I expect it to be at least equally as rewarding.

I now have the first ever real professional accomplishment of my career. And I’m damned proud of that!
It’s also going to be my second-to-last career accomplishment – the next one being to bring my career to a graceful, painless end. I absolutely love the career I’ve crafted for myself in Knowledge Management – but it’s not my vocation. It’s time to decide what I want the next stage of my life to look like.

Do I want to retire from this job?
Do I want to start a brand-new career in an entirely different field?
Do I want to open that game and book bar – or finally launch the website I’ve been sitting on for the past twelve years? Finish the novel?
Do Liz and I want to set our sights on building that retirement Bed & Breakfast in Northern California?
Do I want to finally go to school? (I decided years ago I would only ever go to college if it were to study something that could NOT advance my career. I didn’t want the great cost, hard work and sacrifice of school to be for something so mundane, practical and spiritually devoid as “Professional Development” – rather something strictly for the joy of diving deeply into a subject I have a real, abiding, consuming passion for. If I do go to school, “Comparative Religion” would most likely be my focus.)

It may take another ten years yet to figure out what I do want next, but I feel (for the first time in over two decades) that I finally have the professional and financial stability to actually be able to do pretty much whatever I want next – and apply the limited, but adequate, resources I do have, toward achieving that goal. There is an incredibly powerful sense of freedom and opportunity in that. I feel as though I’ve been holding my breath for the past decade, and have finally been allowed to exhale a deep sigh of relief.

Now it’s time to start planning our first REAL vacation in many years. My family NEEDS some downtime in Northern California!

April 03, 2019, 04:56:53 am

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