We had the pleasure to go to the Paul Simon concert last month when his tour came through our city. We like to go to concerts and have gone out to a lot more since we stopped working two years ago. It’s amazing how many acts are touring now a days.

Like many musicians of his era, this tour was themed as Simon’s “Farewell Tour”. He published a retirement letter in February, saying “I’ve often wondered what it would feel like to reach the point where I’d consider bringing my performing career to a natural end.” At the concert we went to he said he was looking forward to just seeing what direction life might take him next. My wife commented that given his age (76), we ‘beat him’ to retirement by more than 25 years!

Simon is a few years younger than David Letterman – who retired a few years ago. I wrote about his retirement plans a couple years ago. In a recent interview, Letterman said that he felt a little lost outside of the spotlight. He was so focused on his career for so long, he wasn’t prepared mentally for the lifestyle change. That becomes for many people who have been so focused on their career and not on the life they want to lead.

We spent a lot of time thinking about early retired life and used Ernie Zelinski’s book as a way to help plan. Here is a link to a post that I published more than six months before I quit MegaCorp that detailed our thinking at the time. You can see that we were pretty focused on what our new life would look like and it might help you start thinking through your next chapter – even if that’s a few years away right now.

How did you / are you preparing for the lifestyle change that comes with FIRE?

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