If, as my mother taught me, the road to hell is paved with good intentions, from what fictional materials must the journey not taken be made?
Not too many years ago, I learned that confidential data belonging to a client involved in what some had labeled the intellectual property lawsuit of the century had been found on a criminal server on the dark web. When I approached the person responsible for protecting that data, suggesting we meet with the folks whose tip I was acting on, I received a startling rebuke.
“What makes you think I want to know anything about that? With the guarantees we made to our client, can you imagine the fallout if what you’re suggesting turns out to be true? I’m gonna wait this one out—and pretend we never spoke.”
And as he did speak, a mighty tide receded, irreversibly, into time’s black hole.
Lyn Manuel Miranda’s Hamilton suggests we might only ever get one shot in life. Paul McCartney’s Magic Christian taunts that if I want it, I should come and get it and then sends out the tide:
But I better hurry ’cause it may not last.
In a day when so much depends upon not a little red wagon but a swift boat, Shakespeare’s Brutus advises of a tide in our affairs that, taken at the flood, leads on to fortune.
Omitted, all the voyage of our life is bound in shallows and in miseries.
The tide rolls in, and time rolls out.
The most regrettable career mistake I ever made was not acting decisively when a tiny ripple of water called a message broker rolled my way that, when it finally crested, fully formed what the wave we now know as the Dot-com Era. Caught flat-footed as its water splashed around my ankles, instead of high stepping out to sea, I stood stiff as a post, the wet sand seeping beneath my heals my toes until anchored in place when my might have been ship came in all I managed was to stare dumbly and wonder how something so titanic had got so close to shore.
I had been evaluating two business solutions competing for millions of investment dollars from their parent company. Following a protracted bake-off between a highly successful product team with a storied track record and an unpedigreed proof-of-concept with an uncertain future, it was on me to designate winner-take-all funding for the most promising of the two. When the day came for my big reveal, every shark in the tank fully expected the proven winner to carry the day—again. Imagine their shock and awe when I stood to deliver my counter-intuitive recommendation that the time had come to cut loose the baggage of the past and go all in on the future. To be fair, half my age ago, my mealy-mouthed equivocation was not what anyone might have mistaken for confidence.
“I suggest we hedge our bets for the moment and continue to fund both programs,” I began. “This will trigger the transfer of earnings from the diminishing Cash Cow to accelerate the growth of the up-and-coming Star,” I did not muster the spine to further mumble.
Before the room began to roil, my boss leaped to his feet and frog-marched/ear-pulled/practically booted me into the hallway.
“What could you be possibly thinking? We have a fleet of cadillacs in there and you want to strip their hubcaps so that a couple of kids without a license can ride down a hill in their little red wagon?”
That was not all he said, but this post will not attempt to answer his question. Instead, it poses a new one.
When’s your tide, and will you be ready to take it when the water reaches your knees?
In Beauty for Ashes, a personal post from earlier this year, I recount the most regrettable moment of my youth. After a spring melt, I crossed into my neighbor’s yard, rake in hand and tail between my ten-year-old legs, to resume a fall leaf job I had abandoned before the winter snow.
“That’s not the way it works, Son,” explained my kind but wise patron as he reached for the rake on the verge of delivering a timeless lesson ahead of anything I would later learn from Miranda, McCartney, Shakespeare, and Chaucer himself, whose Clerk preceded them all when declaring that Time and tide [and unraked leaves] wait for no man.
“Certain things can only be done at certain times,” he said warmly. “After that, it’s just too late.”
When we miss our boats—and we sometimes will—too often, the best we can hope for is whatever ego-assuaging, self-rationalization we manage to conjure against our knowing better. Earlier this month, I came across a spot of revisionist science in the New York Times about what to do when leaves decide to clutter the lawn without our permission. Let them stay where they lay while going the way of all nature, Remy Tumin’s Why You Don’t Need to Rake Leaves advises.
My soggy-leafed neighbor who, in a backstory only Dickens could have drafted, happened to be the father of one of the principals on the upstart side of the multi-million dollar bake-off I recounted above. Though he has gone the way of all nature, what difference will Tumin’s post facto rationalization and exonerations of its ilk make to his composting lawn, my compromised character or the conscience of everyone in that room whose spin they would of fortune’s wheel was bound in shallows and in miseries?
I’ll tell you. About as much difference as when, after they formed their own company whose message brokering software was on the verge of single-handedly enabling the coming of the dot-com era by storm, I came clean to my neighbor’s son and his co-founder about how ashamed I had been of letting them down that day. They had been gracious enough to ask me to write their marketing copy even though I had, to my way of thinking, sold them up the river or whatever the appropriate water-based analogy might have been at the time. When I told them my analysis had clearly favored their offering, just not the message I managed to mis-broker in the prevailing winds, they instinctively laughed in my face.
“Are you kidding? Scott, If we had got the piddly funding you had on offer that day we would never have dared break away to take our shot!”
When’s your tide? And how will you exploit it?
This post is from a series of “Declarations on Being and Becoming,” originally written as part of a LinkedIn Newsletter called Say the Change. You can access the entire series here.