…So lately, much of my age cohort seems to be unusually amenable to exploring new career opportunities. Fun fact: Within the past three months I’ve been asked for more letters of referral and/or headhunter recommendations than I’d been asked for over the entirety of the prior eighteen.

To this point, a peer recently reached out to me asking to discuss the timing of career moves. He wondered:

When is the right time to leave a company?

…I have been thinking on this question ever since he asked it, and having been with the same company for the entirety of my post business-school career I’ve come to the conclusion that I may not have the requisite perspective and experience to answer it well. With that said, here’s me taking a shot:

Almost two years ago I wrote in this space about a guiding life principle of mine, and it is as follows:

In any context, to stop learning and progressing is for me something unthinkable – a sort of death. As such, after too many days of doing the same thing over and over again, the following questions begin to take hold of me;

“____ is what’s next. Do this so you can do that. The next step lies here.”

1. The pretentiousness of quoting myself is not lost on me. I promise not to make it a regular thing.^These questions grows continually louder in my mind if unanswered 1, eventually becoming so untenably boisterous that I am forced to make a change.

…In applying this principle as a career move calculus, I don’t discount the value of doing one thing very well. But while it *is* healthy – necessary, actually – to go through the iterative process required to learn any rare and valuable skill, it is also important to be working towards something. More money, more benefits, more skills, more relationships… it is crucial to never find oneself blowing untethered in the wind. We should always have something that we’re holding onto – moving towards.

Ergo, while I think that “when” (if ever) it makes sense to leave a company is different for everyone, the table stakes requirement for staying has got to be a sense of direction. Or, put another way: When you no longer know what your efforts are moving you towards, then it’s time to divert them elsewhere.

That’s as good of an answer as I’ve got just now.

As always, please share your thoughts in the comments section below.

Happy Friday.