How to Navigate Transitions and Endings in Life and Work
In the last quarter, Transitions by William Bridges has become one of my favorite books.
Not just for its insights on life transitions, but for how it makes sense of those chaotic periods — times when life feels directionless, or you quietly wonder if this might be a mid-life crisis moment.
One idea that’s really stuck with me is Bridges’ concept of the three phases of a transition: Endings, the Fallow Time, and Beginnings. I’ve started noticing these phases even in the smallest, everyday moments.
Take a recent scuba diving trip. It was my first time diving from a boat, and the instructor shared a tip I made sure to remember: “Even after surfacing and floating with your buoyancy jacket inflated, keep your mask on and regulator in your mouth while getting back on the boat.”
Being the ever-sincere student, I followed it to the letter. But on one of the dives, I noticed the more experienced divers weren’t doing it. It made me wonder what was going through their minds. Maybe they thought, “The jacket’s inflated — we’ll manage.” Maybe they felt lazy, or were still basking in the high of the dive, forgetting the dive technically isn’t over until you’re back on the boat.
That moment reminded me of a question from the book about how we relate to endings: When leaving a party, are you the one who slips out quietly, the one who lingers too long, or someone in between? The idea is that how we handle small endings might reflect how we approach bigger transitions.
I’m usually the one who quietly slips out — maybe saying goodbye to one or two people. Others stay till the very end, reluctant to leave, not wanting the gathering to end. Maybe they’d be the ones last to get back on the dive boat too.
It got me thinking: transitions are everywhere. Moving between meetings, shifting from one conversation to another at a gathering — even those small moments involve an ending, a fallow time, and a beginning.
And here’s where it hit closer to home.
At social gatherings, I often find myself mid-conversation when someone else joins in, or I spot someone across the room — and I switch focus without properly concluding the conversation. I used to chalk it up to distraction, but maybe it’s also about how I deal with endings.
Back to scuba for a second. Keeping your mask and regulator on is about safety. The dive isn’t over until you’re truly back on the boat. That clarity of process helps me stick to a proper ending. In a way, I felt good about that. When the steps are defined, I follow through on endings well.
But it also made me wonder: where else have I lost sight of the real end-point?
What have I been doing for so long that I’ve started shortcutting the endings?
One insight: when a coaching session runs over and I’m late for the next call, I don’t always close the first conversation properly. While the client may understand, I don’t feel good about it. I’d like to end better — even when I’m running late. Or at least reflect if I’m the one elongating the conversation unnecessarily.
So here’s a question for you:
What transitions in your daily life would you like to define more clearly — and end more intentionally?
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