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I've been employed in financial services industry in NYC for decades with total compensation that puts me just into 'the 1%'. Spouse also works in NYC, earning about 60% of my total package. We have been big savers over the years, own 2 houses (primary residence & vacation home that's under 90 minutes away) with no mortgage debt and have sufficient money set aside to put both kids through college & grad school and have plenty for retirement. (Currently one in college and one in high school).
The past six months have been very stressful. My boss died suddenly in the fall and hasn't been formally replaced. The interim replacement is my former peer with less experience and whom I never had any respect for his business sense. It's a European company that has been reducing risk due to the economic climate and regulatory pressures. My job is not at risk due to these issues, but all I do these days is complete reports.
I'm quite tempted to just quit and try to enjoy life, clean out closets, volunteer a bit, and get more involved with younger child who needs more oversight on school work than the older one. I could possibly get some consulting work in my field, teach at a community college or expand another skill I have to bring in $35-45K/year gross. The spouse & I have commented frequently that we are just waiting for the younger one to finish high school and we sell the big house, buy another house in Florida and become snow birds.
When do you know it's time to get off the treadmill? I'm ony in my early 50s. It's not the annual income that concerns me, but rather disability and the other benefits you have as an employee versus being self-employed.