21. Leaving a little earlier
When we stay too long
One of my clients confessed that she stayed in her role too long, even though she knew it was not aligned with her talents. Her gifts were spontaneity, idea generation, and stakeholder engagement, yet she rarely used them at work. I have seen this often among Asian American clients. Cultural messages around loyalty, saving face, and hierarchy can keep them in roles that no longer fit. Many grow up believing they must succeed at everything they do, and that quitting is simply not acceptable.
I recognized myself in that pattern. During my six years as a consultant, the first half was exhilarating: fresh industries, challenging sales work, and the energy of a close team. Gradually, though, the flame dimmed. My satisfaction waned, yet I stayed longer than I should have. In hindsight, I wish I had left a year earlier, not because the job was bad, but because my energy and generosity toward the organization had quietly ebbed. In the following job, my departure was also a little late. That time, the organization left me through a reorganization. But I knew I could have chosen to leave earlier myself.
Leave sooner for growth
A close mentor of mine recently told me she was considering leaving her job. She had only been there two years, was deeply respected, and beloved on her team. She was not unhappy. Instead, she saw leadership as stewardship, passing the torch sooner rather than later. By leaving early, she would create room for others to grow and give herself space to take risks, learn, and discover new challenges. That struck me as both generous and courageous: a choice that served her organization and herself in equal measure.
Her story connected with my own experience and resonated deeply. Almost every meaningful transition in my life would have been stronger if initiated a bit earlier. Earlier, before resentment. Earlier, while I still had generosity. Earlier, so the organization could benefit from new leadership. Earlier, so I could step toward new learning.
Paul Klee, Departure of the ships
Fear, faith, and self-authoring
Still, leaving early does not come naturally to most of us. Fear is almost always present: fear of financial instability, of the unknown, of the “what if” spiral—what if three months of unemployment stretches to six or more. For those with children, health concerns, or thin safety nets, that fear is very real. Studies confirm how widespread this anxiety is. The American Psychological Association reports that 51 percent of workers say if they lost their jobs, it would take them a significant amount of time to find a new one. And yet, most people land new roles more quickly than they expect, often with better pay, more respect, or stronger alignment with their values.
My biggest shift came when I transitioned from a corporate role to executive coaching. This time I was more intentional. I shared my desire to leave with my CEO, and together we planned a four month transition to hire and onboard my successor. I am still thankful for his understanding and support. That departure felt natural, almost smooth, because the change itself felt so right. I had already been experimenting with coaching leaders for three years and knew in my gut that it fit my talents and values better than corporate life ever did.
In some ways, choosing to leave a little earlier is an act of self-authoring. It requires stepping out of the roles that others might want you to hold, and trusting your own sense of timing. It is a shift from fulfilling expectations to shaping your own path, even when the path is not yet clear.
I sense another transition may be coming for me soon. The fear is still there—fear of letting go, fear of losing stability. But alongside the fear sits conviction: that transitions, when timed with intention, create growth for others and for myself. Trusting that I will find or create something new is not recklessness. It is faith in my capacity to learn, adapt, and lead.
Maybe the art of transition is not about perfect timing. It is trusting ourselves enough to step away a bit sooner, with gratitude, with grace, and with faith that what comes next will help us grow.