The End of the Road: Should I Stay or Should I Go Part 2 - Medium

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It's about the US Army, but I thought some of the general principles apply (even when not in the military).  One of my former COs said it best:  "Your job won't take care of you when you're old.  Your family will."

We all face that decision in our careers, often more than once. Some make that decision early, others not until much later. In his recent post, Should I Stay or Should I Go, Major Jake Turner revisited a conversation with a disgruntled lieutenant colonel that caused him to consider when “enough was enough.” He offered four questions to gauge when the time is right to hang up the spurs, to call it a career.

https://medium.com/the-smoking-gun/the-end-of-the-road-bafafcfae6f0