Clarity from Complexity: Knowing when to stay; knowing when to leave
Harvey Belovski’s Newsletter #91
Given my Leave Well | Live Better approach to even the best jobs, one of the questions I’m asked most frequently is:
How do I know when it’s time to leave?
The answer is rarely obvious. Careers don’t come with ‘best before’ dates stamped on them. Roles evolve. We evolve. And the fit between person and position shifts gradually, often imperceptibly, until suddenly it’s not a fit at all.
My colleagues will confirm that I often talk about what is known to organisational psychologists as PoF: Person-organisation-Fit. It’s an important aspect of successful recruitment. It’s just as important throughout the life-cycle of a role itself.
There are signals, though—patterns I’ve observed across many career transitions. The work that once energised you now depletes you. Conversations you used to find stimulating feel repetitive. You’re contributing well but not really developing.
You find yourself daydreaming about other possibilities with increasing frequency. I did, despite having a wonderful rabbinic role with superb support and excellent lay-leaders.
These aren’t necessarily signs you should leave immediately. Sometimes they indicate that you need a rest, or that a particular project has become draining, or that a relationship needs repair.
But if the pattern persists across months rather than weeks, it deserves serious attention. The PoF might be shifting… Confucius is understood to have said:
When it is obvious that the goals cannot be reached, don’t adjust the goals, adjust the action steps.
Confucius offers wisdom here, though it requires interpretation. Sometimes adjusting action steps—taking on new projects, renegotiating responsibilities, addressing conflicts—resolves the misalignment. But sometimes the goal itself—thriving in this particular role—genuinely can no longer be achieved.
And then the action step that needs adjusting is your continued presence.
I’ve also learned to watch for what I call the contribution gap: the distance between what you’re capable of offering and what the role actually requires. When you’re consistently under-utilized, when your best skills sit dormant, when you’re maintaining rather than building—that gap signals it’s time to consider alternatives.
Equally telling is the growth ceiling. If you can clearly see your trajectory for the next five years and it doesn’t excite you, pay attention. If there’s no meaningful challenge ahead, if you’ve learned what this context can teach you, staying becomes a choice to plateau.
Timing matters enormously.
Leaving in anger, in exhaustion, or in reaction to a single incident rarely goes well. Leaving thoughtfully, from a position of strength, with preparation and planning—that serves everyone better. Leave Well | Live Better always means leaving at the right time and in the right way.
The question isn’t whether to leave, ultimately. It’s whether staying continues to serve your development, your values, and your contribution to your organisation. When the answer is consistently no, it’s time to plan your exit.
• Watch for persistent depletion, repetition, and the contribution gap.
• Don’t leave as a reaction; leave from reflection and planning.
• Ask regularly: is staying serving my growth and my values, as well as ensuring I am still contributing well to an organisation I care about.
If you’d like to learn more about my work in this field and what I can do for you, please contact me via the comments.
Next up: Clarity from Complexity: The ‘sunk cost’ careers fallacy