A sample essay from a previous edition of The Afternoon Shift newsletter. Subscribe here to read on.

The word “unmoored” keeps coming up as a way to describe the feeling of a career transition.

Now, when I share the word with others, I receive a consistent ‘I feel seen’ nod.

I wasn’t completely sure how to define this word, though I knew it had something to do with boats.

I grew up in ‘The Whaling City’ of New London, Connecticut, also home to the Coast Guard Academy, so there was a fair amount of nautical speak in the air.

Well, here’s the formal definition:

Unmoored is derived from the Middle English unmooren (late 15th century), formed by combining the reversal prefix un- and the verb moor (meaning to secure a ship to a dock or anchor). Literally meaning to be loosed from anchorage, the term has evolved to describe feeling disconnected, unstable, or adrift.

This brings to mind one of the top career researchers, Herminia Ibarra, and her book, Working Identity.

In it she quotes a research subject who described career transition as “living inside a hurricane.”

It’s easy to see the connection.

What’s worse than floating aimlessly? Doing so in a massive storm.

I’m grateful to be in a season of relatively calm waters, but I’ve been through two major transitions in my own career.

The first time, after more than a decade with the same company, I felt totally unprepared for the severe weather that came with independence.

The second time, after well over five years with the same company, I was more prepared for what it would feel like to no longer have a full-time role, but it was far from smooth sailing.

That’s because even if you embrace change, prepare for change, or initiate a change, career transitions will likely rock your boat.

There are many reasons for this, but I’m convinced the “disconnection” piece of the unmoored definition represents the eye of the storm.

Isolation makes every aspect of the shift more difficult.

Because the only thing worse than floating aimlessly in a massive storm is weathering it alone.

If the best leaders start with why, the best career transitions start with hi.