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Executive Director as the Big Apple

As I chat with organizational leaders about succession and transition, one of the questions I hear most frequently is: How do I know when it’s the right time to leave? 

My immediate answer is always: There is no right time. There will always be a crisis looming, or an exciting opportunity percolating, or too much staff turnover, or you finally got your staff stabilized… 

This is also the wrong question. The RIGHT question is: How do I know when to start planning to leave? 

That question has many answers. Generally my response is, Now. Start planning now. The moment you think it might be time to leave, start succession planning.  

Here’s the thing: being top dog in a nonprofit is tough. It’s isolating, it’s all-encompassing, it takes heart and soul and patience and sacrifice and early mornings and late nights and humility and confidence and charm and devotion. It’s also rewarding and necessary and satisfying and joyful (or can be.) But it’s tough.

I lived in New York City for almost 10 years. I loved it, and then I had to get the hell out. Living in NYC, unless you are massively wealthy, is almost impossible. But it’s completely worth it, as long as there is absolutely nowhere else you can imagine living. The moment there’s another option for you, it is time to go. 

There’s no right time to leave. It’s always the right time to plan. The organization will survive your well-planned leaving. Will it survive your planless staying?