The simple answer is: never retire. People die within two years of retiring on average. So unless you want to die, why retire.
But transformation is another story. After spending 45 years as a janitor at the pencil factory it might be time to try something new. Presumably the entire world is open to you. Your kids are grown up. You might have some savings, etc.
The key is personal freedom. Being able to do what you want, when you want to. Assuming your health needs don’t require you to be in one specific place, pick a location where cost of living is incredibly low and live out your life doing your fantasy work. What’s your fantasy work? For me it might be scripting comic books. It might be doing these twitter Q&As. I can do these from anywhere. Maybe when I retire I’ll move to India (where I’m going in a week or so) where I can live for about $500 a month at most.
Or a friend of mine just told me about rental prices in Savannah, Georgia, which he said, “is the most beautiful place in the country”. And rents and cost of living sound about ½ of that in the NYC area.
Here’s the three step retirement method:
– Transformation. Sharpen the idea muscle and start brainstorming what else you can do. Play in a jazz band? Open a café? Open a used bookstore? Start a website? Write a novel? What the hell do you really want to do? The world is open to you.
– The world is open to you, part II. With your current savings plus what you can make in your transformed job (and assume three years of living before you make a single dime at your transformed job), where’s the cheapest place you can go that still fits your minimum needs of comfort and beauty. Explore the world a little. It’s your oyster. You can live anywhere.
– Do it.