When to Quit

I knew when I was pregnant with Abigail that I would be a stay-at-home mom. It had been in the plans. It was why I was able to work part-time in a job that I was passionate about. It was why we were careful to live on Chris's paychecks.
I planned to volunteer at the place I had worked. Having a baby didn't mean that I couldn't still be involved in the community. It didn't mean that I couldn't maintain relationships with the children I had spent three years with.

Did it?

Yes, I learned It did mean that I couldn't come back. I had been in charge. The kids saw me as the authority, the expert, the final say. My presence in that building made my replacement's job more difficult. It made the transition more difficult for the kids. It made my decision to leave more difficult.
I couldn't go back and not be in charge. I compared. I made judgments. I worried over what was no longer mine to worry over. And I felt guilty for leaving when the next person was doing things that I saw as very wrong. I'm not even claiming that they were wrong, but that I viewed what they were doing as wrong, or not the best.

I am in the middle again. Recently, the leader of an organization I am a part of stepped down. A new woman is in charge. More recently, I abdicated my role in the leadership of the organization. And I find myself in the same position. And doing the same things.

How do you know when it is time to retire more than your leadership?