Key Takeaways
- The right time to leave is before you resent the thing you are leaving.
- The next chapter rarely reveals itself before you commit to ending the current one.
- The fear of leaving is a measure of how attached you are, not a measure of whether leaving is right.
Saim Abbasi has made several significant career transitions: from Scotiabank to entrepreneurship, from SA Capital to OptionsSwing, from operating companies to building Iron Key Capital. Each transition involved a specific kind of clarity about what was no longer working and what would work instead.
The Caretaker Signal
The internal signal that most reliably indicates a transition is coming for Saim is the shift from feeling like a builder to feeling like a caretaker. Building requires creating something from nothing or making something meaningfully better than it was. Caretaking requires maintaining what exists and not letting it deteriorate. Both are necessary but the builder energy and the caretaker energy are different, and Saim's energy runs on building.
When the day-to-day work of a role shifted from creation and growth to maintenance and management, it was a consistent signal that either the role needed to evolve or the person in the role needed to move.
The Next Chapter Problem
The difficulty of transitions is that the next chapter rarely reveals itself in full before you have committed to leaving the current one. The founder who waits for complete clarity about the next thing before leaving the current thing will often wait too long. Saim's experience is that closing one door with intention, rather than waiting for the next one to open fully first, creates the psychological and practical space for the next thing to emerge.
The Fear Is Not Evidence
The fear of leaving a stable situation is real but it is not evidence about whether leaving is correct. The fear measures attachment, not rightness. Separating those two things, "I am afraid to leave" from "it would be a mistake to leave," requires being honest about what is driving the fear. Is it rational concern about specific outcomes? Or is it the general human discomfort with known risk versus unknown territory?
"I have always known it was time to leave when I started to feel more like a caretaker than a builder."