That may be one of the strange things about transitions: we often don’t recognize them while they’re happening. We tend to think of a transition as an event.

The resignation. The new job. The move. The launch. The reorganization. The first day. The last day. Those are easy to put on a calendar.

But I’m increasingly convinced that the actual transition usually starts much earlier. Something stops fitting quite the way it used to. The questions change. Your energy shifts. You begin imagining something different before you have any idea what “different” actually looks like.

Maybe it’s the space where A no longer quite fits and B hasn’t fully arrived.

I recently made a pretty major professional transition myself, stepping away from an organization I founded and led for many years to build something new with Way Ahead. It's been exciting, challenging, uncomfortable, and energizing—sometimes all of those things before lunch.

But when did that transition actually begin?

It wasn’t my last day. It wasn’t the day anything officially started. It probably wasn’t even the day I wrote WORK → TRANSITION in that journal.

By then, something was already underway.

That little arrow may have been less of a decision and more of an acknowledgment. And I think the same thing happens in organizations all the time. We announce a change and call that the transition. New leader. New strategy. New structure. New program. New direction. Then we build the implementation plan, assign responsibilities, create the timeline, and start checking boxes.

All of that matters. But people don’t experience transition as a checklist. Someone can be sitting in the new structure while still holding onto the old one. Someone else may have moved on months before the official announcement. A team can know something needs to change long before anyone is willing to say it out loud.

And sometimes the most important work isn’t figuring out the destination. It’s figuring out what the space in between requires from us.

What needs to be left behind? What is worth carrying forward? What assumptions no longer work? Who needs to be part of the conversation? What are we learning now that we couldn’t have learned before things started moving?

I’m not sure good leadership means making that uncertainty disappear. I think sometimes it means being willing to stand in it long enough to understand what’s actually happening. To listen. To ask better questions. To make a decision when one needs to be made. And then to move.

I keep coming back to that arrow in the journal. An arrow doesn’t tell you much about the destination. It tells you there is movement. Maybe that’s enough sometimes. We don’t always need to know exactly where a transition ends before we begin doing the work it requires. We just need to notice that we’re in one. And then decide what we’re going to do with it.

What’s a transition in your life, work, or organization that turned out to be far more significant than you realized at the time?

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Rusty McCarty

Founder | Way Ahead