Related question from a different perspective: HOW DO I MAKE MY CEO TAKE SOME TIME OFF? I'm not a confounder, but the CEO-founder is a friend and hired me on a

Related question from a different perspective: HOW DO I MAKE MY CEO TAKE SOME TIME OFF? I'm not a confounder, but the CEO-founder is a friend and hired me on as soon as he cleared his A-round funding. (We've been confounders before on a project that flopped and he knew I wasn't in the risk position to be a dayjob-quitting early employee this time.) He's a serious workaholic -- claims to enjoy being so -- and the company is doing very well. That said, he's CLEARLY burning out. He's talked for the last year about taking some time off, but between the birth of a new child, fundraising, strategic partnerships and the continued burden of success, his "week in Florida" kept being pushed off, shrunk to "three days in Florida" to "a day off" to "I'll take some time after this next funding round. Maybe." Setting aside the fact that he's my CEO (and a ragged chief exec is bad for everybody), he's also a friend. I don't want to see him burn out. This will almost certainly NOT be the last company we work on together, and I'd like to see him survive -- mind, body, marriage and social circle intact -- past our current endeavor. So, again, how do I convince my workaholic CEO to take some time off?