1/25/25: The Writing is The Sabbatical
It seems most imagine what they would do on a sabbatical - should they ever have the nerve to take one.
Maybe an abnormally long vacation on a sun-dappled beach or a hike along white-capped mountains; possibly a trip to a foreign land for cultural immersion, or the time to read dozens of books, or the ability to exercise for three hours a day, or, of course, to spend quality time with kids, your spouse, your friends.
Sabbatical rationalization is obvious: a pause in the flow of work, a breather, an ability to clear one's head. To think. To refresh. To soften the sand of one's digital footprints.
For them, they aren't wrong.
But they are them. And them ain't me.
Blame is an inverted bastard of intent, and so my sabbatical finger pointing must begin here: Flipside's Friday CEO Notes.
For the past three years, every Friday, I've delivered a CEO note privately to Flipside. Like the wooden call of a cuckoo clock, 9 AM every Friday, you could set your watch by it. When these began they are likely what you'd imagine: a weekly update on company progress, a proclamation of our vision, shout outs to our team, financial updates and the like.
It didn't take long for this to feel plain to me, restrictive, like a corporate straight jacket. Like I was hiding my true self, wearing someone else's fancy tie and belt suspenders.
So I followed the feels and wrote what flowed naturally: Short stories and unique points of view; parables about Salmon and Squirrels or Rodent laws, maybe an occasional sex addict, a review of a strange wedding, instructions for switching hotel rooms and avoiding office colds; the art of giving a speech, or taking drugs, or moderate psychoanalysis of the arc of the human psyche. I was fortunate to have a captive audience in Flipside's team who - in the spirit of pleasing the boss - knew it in their best interest to read and humor me. These notes forced me to practice.
I was able to fail a lot, and succeed occasionally.
While I've always written - the college paper, articles in Inc. and Startup Grind, a published book here or there - I often wondered if I had a true voice.
And, well, three years of Flipside Friday CEO notes provided some direction. With no pressure, I realized my strength lay in essays over long form. That the voice in my head, with it's parenthetical and asides (you know, like this), or even the truly inner voice peeking through <scratches ear, wonders who really cares about all this> is reasonable to put on paper.
That I should observe more and preach less.
That I like semicolons; that sometimes I use them in weird spots.
And paragraph breaks for emphasis.
And colons: Blinking unexpectedly into existence like fireflies at dusk's arrival.
I also strengthened my resolve that the words would be there should I call for them. I've long ago surpassed my 10,000 hours, but the requirement to deliver a fistful of quality words ever week - words that were moderately readable - needed to be formalized.
After the first year or so, a motion took shape. I'd push out a draft on a Saturday or Sunday - 90-minutes or so, less than 30 if I was inspired - and then I'd edit like a hamster on Celcius all week, five-minutes here, 10-minutes there; refining, shaping, polishing; coiling and pinching raw clay into, well, what could be best described (maybe), if you were trying to get all literary or figurative, as a fruit bowl.
At the three-year mark, with north of 160 essays delivered, a revelation: I felt constricted. Don't get me wrong I've loved writing these pieces, but there seemed to be more behind them. It's as if I'd cracked open a door to the right dimension, but had yet to walk fully into the room to flip on the light, but instead stood self-consciously in the inky blackness, with my eyes adjusting, and only the silhouettes of shapes apparent.
The hill of Flipside's Friday CEO notes felt crested and some other writer's hill was beckoning. But what one, I didn't really have any idea.
And so, a Sabbatical. Mine arrived to certainly provide me respite from the daily grind of thirty years of leading companies but, also, to truly understand what words were cloaked in that darkened room. I yearned to know what notes were hiding there; I required the space to coddle them into existence. I feared it wouldn't be an easy task, like wooing a sheltered, anxious and slightly aggressive dog into your arms.
Over the years people have asked me how I know how to start companies. The answer seems to baffle most, and even me at times: It starts with a noise in my head that won't go away. Like the white static fuzz of a TV whose station that has gone off air, or the shrill a tea kettle whistle (this is where people look at me strangely, I know). The noise gets louder and louder until I do something about it.
<hang back a bit, Buddy. someone out there is about to call a doctor>
Well, that noise began to present itself in my writing. I've been doing my best to ignore it, to shoo it into the corner or to shake my head as if water had pooled in my ears. My day job is busy, but the noise cares little about that; it demands attention, it needs to be fed, it's been tugging at the cuff of my pants and looking up at me with hungry eyes and, well, it's starting to whimper.
I wondered if the noise would go away in the depths of Sabbatical free time; I wondered if I'd find myself just lazying around taking walks, maybe smoking weed, possibly playing Fortnite - and doing what everyone imagined I should be doing.
Instead, my Sabbatical has been like the uncorking of a bottle. Years of pent up ideas began spilling out. Drops turned into a flood of inspiration. Use whatever analogy you'd like, but what I found was with no distractions, I gravitated toward writing as often as possible (this piece is being edited in a car at 5:45 AM to give you an idea - and, no, I'm not driving).
Writing wasn't work. It isn't work. It is where I'm my most happiest, in between the words, inside the paragraph, foraging through the edits, letting the voice come out.
Countless people have reached out to offer an accolade on the flurry of published pieces over the last six weeks (I am so thankful for this, you have no idea), but just as many have asked me if I'm ever going to take the sabbatical I'd promised myself.
I think mostly I proved to myself what I required. I like to write. I love to write. I like to share what I've written. I want to do more of it, more often. I don't fear being the writer that finds insanity, lost in their own mind, drawing circles and patterns on the wall; inversely, I know there is a well of words and Writer's Block - arriving like a grim reaper on eight mares with flaming eyes - is an unlikely scenario.
"I thought you were sabbatical-ing, not Hunter S. Thompson-ing," offered my friend Gus.
The writing. That is the Sabbatical.
Not to them, not to many, but to me.
I've reflected and realized that was the point all along, even if I didn't know it at the time. With an impending return to leading Flipside, what I do with the writing now is at best a guess - both yours and mine.
But the room has started to brighten. The pup is out of its cage. The white noise is intensifying and I've learned a long time ago, when that happens, the best course of action is to listen to it.