How do you know it’s time to let go?: Life Hacks by Charles Assisi

Exiting a job or relationship, stepping away from something that mattered a whole lot – I’m starting to see there is a way to do it right, for the right reasons
“Because it is time,” he said, on the phone, about his decision to step down.
He and I had first met on a flight to the US over 25 years ago. He looked like a serious, no-nonsense kind of person. We got talking. We hit it off, and stayed connected over the years.
While I hopped around, he stayed wedded to one organisation. He nurtured it, turned it into even more of a powerhouse than it was. I watched in awe as he built it into the kind of place where people aspire to work.
That is why, when he announced it was time for him to step down, no one could believe it; myself included. The way I see it, the mid-50s is the age to stay, consolidate, cash in on the decades of toil that finally let a person operate a machine that size without flinching. He is, by any measure, at the top of his game.
I have watched from a distance as this man has worked 18-hour days, for weeks on end. Taken a day off, then done it again. Over and over. For decades.
To those on the outside, it appears as if he woke up one day and decided it was time to leave. But what most people don’t know is that he did the unglamorous thing: he separated intention from theatre. It wasn’t a decision made overnight. A successor was in place; he had waited it out for some years until the successor was ready to take on the job. While everyone had assumed he was building his legacy, he had also quietly been working to ease himself out of the picture.
“Why now?” I ask, hunting for the crisis I assume he’s hiding. If I don’t do it now, I’ll never do it, he says. The dream of disappearing somewhere quiet will stay a dream.
The question that won’t leave me now is this: How does anyone know whether they’re leaving because it’s genuinely time, or because they’re afraid of discovering what will happen if they stay? “It is time” is also what a person tells themselves when what they really mean is “I have become ordinary at the thing I used to be exceptional at, and I would rather leave the stage than let anyone watch that happen in slow motion.”
There is no external test that tells the two states of mind apart.
We’ve built a moral vocabulary that treats staying as its own reward, and leaving as the opposite. We say things like “never give up” and “till death do us part”, but we have no vocabulary for virtuously stopping.
The entrepreneur who didn’t give up gets the biopic. The person who says “I love this but I don’t want to do it anymore” gets suspicion. Why should leaving something before it becomes unbearable require an explanation?
The reverse is true as well. Some people leave too early. Some mistake a bad quarter for a bad decade; a difficult spell for a dead relationship; a plateau for a ceiling… and go looking for a fresh start. My friend’s 20 years of unfaltering, exhaustive excellence are the reason I believe him. “It is time” makes perfect sense.
I don’t think the lesson here is: learn to leave. The challenge, harder to ace, is learning to tell the difference between leaving because something has reached a conclusion, and leaving because one has grown impatient with how one operates within a challenge.
I admit I don’t know how assess my own life reliably on these parameters. I continue to hold on to some relationships that I know are past their expiry date. The heart calls it loyalty. The mind doesn’t know it may just be fear in loyalty’s clothing.
What I keep coming back to isn’t whether my friend made the right call. It’s that he made it with a sense of certainty that came from within.
I’d like to think I will someday be brave enough to do the same. I fear, however, that we may not all be built that way. More’s the pity.
(Charles Assisi is co-founder of Founding Fuel. He can be reached on assisi@foundingfuel.com. The views expressed are personal)

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