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How do you know when to leave a role?

I like to make the provocative claim of being a quitter. I quit my job at KLA-Tencor in 2009 so that I could go back to business school to figure out what I wanted to do next. It was that moment that helped me find Facebook. Had I not done that, I don't think I would have been on the path that I'm on now. I joined Facebook in 2010 and stayed there until the end of 2016, when I quit again. I quit Facebook in 2016 to start Woven, a productivity software startup. We were a calendaring solution, and I ran that for about four and a half years until we sold it to Slack. So even though I joke about quitting, a big part of my life story has been about making space for what's next; when I did that in 2009, it paid off in huge dividends. And the same was true for leaving Facebook. Now I'm making space again. 

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Anonymous Author
I like to make the provocative claim of being a quitter. I quit my job at KLA-Tencor in 2009 so that I could go back to business school to figure out what I wanted to do next. It was that moment that helped me find Facebook. Had I not done that, I don't think I would have been on the path that I'm on now. I joined Facebook in 2010 and stayed there until the end of 2016, when I quit again. I quit Facebook in 2016 to start Woven, a productivity software startup. We were a calendaring solution, and I ran that for about four and a half years until we sold it to Slack. So even though I joke about quitting, a big part of my life story has been about making space for what's next; when I did that in 2009, it paid off in huge dividends. And the same was true for leaving Facebook. Now I'm making space again. 
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Anonymous Author
For me, it's when I'm not happy in the role, it could be several factors that push me to acknowledge that I'm not happy anymore. It could be that my Manager has not the same values as I do, also that there is persistent chaos & lies in the team which I'm not fond of. If I don't feel challenged anymore, to me it's time to find new ventures.
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Anonymous Author
When you are not happy anymore,m and when you stop feeling supported by your boss/company. When you stop learning and progressing.
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