I agree- great job Retire44 on building your NW! Interesting dilemma Wingfooted, I used to tell my best friend that I would retire once I hit a $10M NW.
I have one good friend who retired 2 years ago at 43. He was overly stressed with work, has a young family, NW >$10M, so he "retired". He struggled his first year of retirement without a clear plan, so he started helping a friend at a startup. He got sucked in full time and retired again 2 months ago "for good". I hope it sticks.
Another great friend of mine always planned on retiring at 50. He retired last year at 50, married with no kids and probably double the NW of my friend who retired at 43. We had dinner with him last week, he bought a small piece of land and is growing organic fruits and veggies and traveling as much as they can. He is really enjoying the retired life and wished he would have pulled the plug a couple years ago.
My take is you need to be both emotionally and financially ready. I had planned on retiring this year at 45. I am financially ready and nearly there emotionally. I have a high probability of reaching a major financial milestone if I work through April 2016. My job is much less stressful now, than it was last year. So, after realizing the financial milestone was within reach, I got infected with the OMY syndrome.