I went back into the Matrix
#managing_yourself I took the red pill, then I took the blue pill again
When I was early in my career, I often hoped that leaders would shed some light into the real reasons they make career transitions. For the most part, the fancier your title the more opaque the real reasons are. I want to help change that.
It's been nearly a year since I last wrote here, mainly because I had to confront the realities of how my expectations of what my life would be after I left the conventional working world didn't meet my expectations.
For many people, the idea of not having a conventional boss to report to and the freedom to experiment with what your life could be is an oasis. It certainly was for me, and I had worked my whole life to achieve that.
As a leader, what people don't tell you when you stop working or even outright retire (which was never a thought in my mind) is that you lose something valuable that transcends having a job or a fancy title: its purpose.
So when I found myself back in the desert of the real, the titles and the artificial sense of authority and responsibility went away. I was left alone with my keyboard and the freelancers I hired to make something, in hindsight, anything that people would be willing to use.
At Post-PC Labs, we did build and launch things, but we never got very far. However, this isn't a post about that (there will be a future series on my lessons learned).
The lack of results that met my expectations started to wear me down because, deep down, it felt like until we had built something people would use, I didn't have a “why.”
My journey back to the Matrix probably began in earnest in 2021 since it wa1s then that my floundering began to eat at me enough for me to explore consulting on the "side" as an option.
That year, I was fortunate enough to have landed a role as an associate partner at AKF Partners. People often describe AKF as the company start-ups called when they had severe problems; they were the ghostbusters of technology, and it was awesome to be associated with them.
In my brief time at AKF, I felt not unlike Luke Skywalker training in Dagobah - I learned a few tricks on my own up to that point but when confronted with the diaspora of different companies and the varied ways different environments work, I once again became a beginner.
The feeling of being back in the management training gym every day was refreshing for a while. I didn't always agree with the solutions or the philosophies that AKF espoused, but I always felt that those differences were welcome and that there were seemingly endless co-creation possibilities and an openness and willingness to evolve there.
But as the months wore on, I grew tired of talking about what people could do and instead yearned to be part of the work. So I tried to look for an interim role through AKF, and it was there that I found myself working with an old friend, Jeannie Yang, as her chief of staff at SmartNews. There, the work was intense, but I found it to be a blast because it reminded me of a time when I was back in the Matrix.
In fact, it was not unlike all of the other times, when I was doing the work with people I liked, mentoring people when they needed it, and working on something that was meaningful.
So when I had this epiphany, I decided it was time to go back for a while. I still have a few years left in my career, perhaps even a decade if I am lucky. I've been off the grid for years, but I never stopped doing the work, and in many ways - the executive I was when I left Upwork is far more versatile than the executive I am today. I can still make a difference in the working world, especially when so many people are miserable at work.
In preparation for my return, I decided that two conditions were necessary (but not sufficient) as I narrowed down opportunities:
An opportunity to lead product and engineering reporting to the CEO. For many years, I've been part of and witness to complex dynamics between functionally structured product and engineering organizations. If I wanted to create career-making, memorable experiences for my teams - I yearned for the opportunity to manage both. I also wanted to do this for myself because, for so many years, I didn't dare to say I wanted to be the CEO. So if I am giving up entrepreneurship life, I need to position myself along the path of becoming a professional CEO. I feel compelled to say this out loud for everyone like me who had to work for everything and passed up for some things because they were too afraid to ask and all too often settled for a title that didn’t match their contributions watching less skilled people take credit.
A domain I know. At this point in my career, I realize I don't have the luxury of learning on the job. If I return to the Matrix, I need to know the space, and I need to have mastery of the job so that I can go in like Neo, guns blazing.
After a brief search, much shorter than I expected, on December 27th of 2021, I chose to join Recharge, which fulfills both conditions. I also liked Oisin and Mike a lot as people, so that helps.
Upon my return to the Matrix, I posted on LinkedIn that Mnemosyne was the name I gave my Recharge laptop. Quirky reference aside, I don't think anyone knew why I chose that name.
As it turns out, the chronicles of Neo were also revisited the week I started at Recharge in 2021: The Matrix Resurrections. The 4th movie details Neo's time back in the Matrix after a hiatus. The ship he traveled in upon his return was the Mnemosyne.
You see, when you start a new executive role, it is almost certain that there are expectations that are no doubt unreasonable. Every CEO or senior executive will wax poetic as if you are the "one." It turns out that even in the Matrix, there were seven (two of them unstable) other Neos before the Neo of the movie came to pass. These fancy jobs have giant expectations and a short leash, but with each Neo that passes, they build on the works of the other.
I can't address my time at Recharge here further than I already have, but I want to acknowledge that I am back and it’s been fun!
Neo says this better, "I don't know the future. I didn't come here to tell you how this is going to end. I came here to tell you how it's going to begin."
For those unfamiliar, the Matrix was a film series about a man who discovered that the world he lived in, was a simulation and that the real world was very different, with ostensibly more worrying matters. As much as all of us take our jobs and careers seriously, I suspect many of us realize there are more important things in life than just work and career and it should not be something that represents an all-consuming world. I also think the analogy is apt in a different sense - the working world is often times, literally, another world, that is very different than how we see our real selves.