I have a high school friend who retired around 40. He came from a family of money, but worked in corporate IT sales for a large, well known vendor. We had lost touch with each other until 5 years ago when he reached out to me via FB and wanted to call. We spoke for a few hours about our lives, and I realized he was a lost soul.

He had a wife and children, and had been retired for over twenty years. His kids were now all grown and out of the house, and it seemed like he was asking "what should I do now." In contrast to him, my kids were in middle school, and retirement was 15 years away, at a much lower standard of living.

My friend had spent the last two decades traveling; he would travel to a country, live there for 3-6 months and immerse himself in it. His family would stay for a while, but then return to the States when school started, while he would remain. He seemed very curious about "normal" life which he seemed to have growing up. His father was in financial services, and he had a stay at home mom.

I envied my friend's financial independence, but nothing of his retirement life other than the opportunity to travel on a whim. Life without moorings is to be adrift, forever seeking the oxytocin rush of new things, and then being disappointed when it fades.

I haven't spoken to him since, though he randomly posts to FB; I hope he's found real happiness and acceptance in his wanderings.