For the first time since the fall of 1978, I do not have a full-time job.
I have transitioned into what I describe as “semi-retirement.” Was gonna do this in 2022, but my wife had other ideas. For the past two years, I have managed “external affairs” for the Manhattan Chamber. Essentially, a lobbyist and fixer.
It’s been a white-collar career, working in the private sector, public sector and in deep-pocketed philanthropic systems, where, owing at least partially to the depth of the pockets, the notion of accountability never seemed to be a priority.
Toiled in the cubicle, the newsroom, the c-suite, the broadcast studio, the Statehouse, the corner office and from home in my jammies. Deejay, journalist, TV news anchor, spin doctor, and system strategist. Along the way, I’ve had a host of side hustles, some of which I intend to keep. I have written a couple of books, and a third one is framed up, at least in my imagination. This column is a side hustle.
Some of the most valuable advice came early, from one of my first mentors. “Develop an edge without being the smartest guy in the room.” In politics and government, I worked alongside scapegoats and fall guys (girls, too) and very quickly developed the vital skills needed not to become one.
At roughly the midpoint of my career, I discovered there is no such thing as a dysfunctional organization, that every system is perfectly aligned to achieve the results it gets. After that sunk in, I developed new skills and positioned myself as a change agent. Who wants to be a status quo agent? If those atop the org chart also fancy themselves change agents, you’re in. Otherwise, you’re just tilting at windmills.
A large chunk of my career success stemmed from managing perceptions and I came to believe what we think is “real” is limited by our own perception, which often falls short of general reality. Then new data supersedes the old understanding of things. Kant or Buddha might call that enlightenment. It’s a process. It never ends.
In industries notorious for giving people the boot, I was never fired, downsized or otherwise shown the door. I also count myself fortunate to have succeeded in this career completely unencumbered by a college degree, so I’ll cop to being a bit of an outlier.
In the boardroom, I have seen the knives come out, the question called, and Caesar stabbed. But I have also witnessed consensus emerge from meticulous cultivation. Oh, and lest you believe “executive sessions” are confidential, don’t kid yourself. Someone always leaks. Another lesson: If you want to keep a secret, don’t tell anyone.
My old man was a high school physics teacher and placed a lot of stock in the steady paycheck. To him, job security was self-worth. A generation deep into the 21st century, I have come to believe the centrality of work and career to our sense of self and identity is damaging old and young alike.
In my most recent job, carrying the water for a special interest group (men, women and families who comprise the Manhattan business community) would frequently smack right up against my journalistic instincts. Very often, I would encounter a situation or circumstance ripe for an opinion column, but would not cross that line, based on allegiance to the system and loyalty to its volunteer leaders. Day job v. side hustle. I am now free from that self-imposed ethical restraint.
The last few years, I would sometimes find myself thinking, “…but what if you are… the smartest guy in the room?” That seems like a dangerous data point.
As I approach this new life phase, I feel the need to expand my bandwidth for creativity. Though the 40-hour work week is now behind me, I won’t cease working altogether. In fact, I’ll be a bit more “visible” than ever, as the career comes full circle. That’s called a spoiler alert.
Stay tuned, as we say in the business.
Comments