The Story of a Storied Career
"Midway upon the journey of our life I found myself within a forest dark, for the straightforward pathway had been lost." ~Dante's Inferno, Canto I
Whether you’ve stumbled across this post randomly or intentionally, maybe you found the easter egg url in the About Me section of my resume, or you’re my latest internet stalker, this is the story of a storied career. It’s how I got from there to here, and maybe the pretext for what’s next.
I hope you enjoy. ~G
Like most… okay, probably all… of my fellow project managers, in middle and high school my list of dream jobs wasn’t lawyer, doctor, the President, astronaut, Air Force pilot, or project manager.
I stumbled my way into a technology career after having gravitated toward medicine from the list mentioned above and spending 4 years earning a biology degree. Two weeks before graduation, and while starting to plan a summer-long, cross-country roadtrip to attend medical school, I went with a CS-major friend to a tech career fair and got offered a job on the spot (he didn’t, as I still occasionally get to tease).
We’ll zip through the rest of the ‘90s because, well… that’s pretty much how those of us in the Silicon Valley rolled back then. Early in the new millennium, within months of barely surviving Y2K, the dot-com bubble burst. I’d been in my second stretch as an IT Director, leading multiple teams within the IT umbrella: dev, help desk, and back office, most notably. Like so many of my colleagues, I suddenly found myself with some unplanned free time, and decided to take stock. No, I didn’t cash in my 401(k). I found myself in Dante’s forest dark, instead.
The first thing I realized was that any regret I’d had about the choices I’d made about my career after university were gone. I also knew that I had a passion and particular skill for how, who, and when, not so much what or why. Not that what and why aren’t also important, as I regularly assure my friends in product management. My final epiphany during that otherwise disappointing episode of stock-taking was that, in all the domains of technology I’d been exposed to, I loved the how of making software most. And, there was no close second.
With this enlightenment breathing new wind into my career sails, I spent what was my first real episode of funemployment leveling up my formal project management skills with various trainings and my trusty PMBOK (2nd edition!!) in hand. Along the way, I would also eventually take the opportunity to finally get a graduate degree more closely aligned with my career, but still not the MD my mother was pining for.
I spent the next decade-and-a-half honing my new craft in a variety of settings: a stint in government, a non-profit, back to Big Tech, then back again to government, and, between it all, start-ups… many, many start-ups.
I went from delivering features to products and then outcomes across lines of business. And, when engineering became the most productive function in the organization, I found the opportunity to support teams and efforts across the entire enterprise.
If they didn’t fold, as those many, many start-ups grew, I went from being the only project or program manager to coaching other project and program managers, then managing other project and program managers. From there, I began crafting processes and guiding managers of project managers and centralizing the function as a service within the enterprise. Lately, in addition to directing the project and program management practice (and building another PMO, my 3rd), I have taken on organizational strategy… in a way, guiding the C-suite.
I’ve helped build client-server applications, applications in web 1.0 and 2.0, and mobile apps. I’ve led teams building off-the-shelf consumer software, tools for devops, and everything in between, both front-end and back-end. I once even dusted off my waterfall chops and helped bring a hardware product to market.
I’ve led what was at the time the most expensive public works applications development effort in my state’s history, and I’ve facilitated changing the color of a button on a submit modal. I’ve led ERP and CRM implementations both in the cloud and in server closets. I’ve supported marketing GTMs and helped optimize the process of bringing consumer products to market in a DTC environment. And so much more.
I’ve led standalone projects, I’ve assembled multiple projects into programs, and projects and programs into portfolios. Along the way, I’ve dabbled in every flavor of how the teams and organizations I’ve supported have been willing to commit to, from waterfall to scrum to kanban and every derivative imaginable. I’ve even led the way designing and rolling out a bespoke product development lifecycle based on the principles of design thinking, lean, systems thinking, and… of course… Agile.
I was an early Agile adopter, and had the opportunity to be on the scene when the UK government was leading the way at scale. One of my last formal projects was a straight-up waterfall affair. Through it all, I’ve never become a purist… if I’ve learned anything in all this time its that every way of working has its place, and every place has its way way of working.
Looking back as I write this, it’s been a privilege to have had the opportunities I’ve had in my career, although this path isn’t what I dreamt way back when I thought anything and everything was just over the horizon... like that MD my mom will. not. let. go.
And, here we are on the verge of the post-Agile era and I no longer have much opportunity to roll up my sleeves and do day-to-day project management. What I do get to do is nurture future generations of amazing project and program management professionals, and, together, create new and innovative ways of working and elevating our craft.
And, that’s how I see what we do: craft. As the great Roseanne Cash said,
"Craft is the dovetailing of discipline and imagination, dedication and inspiration. When those spiral around each other and serious attention is given over to that alchemy, then one’s craft can be realized.”
These days, then, I’m an alchemist. That’s kind of like a doctor, right, Mom?