Three very useful books I recommend dealing with the often overlooked qualitative side of retirement. They include some excellent self-assessments relating to preferences in retirement. Together, they cover all aspects, including health, happiness, personality, social, activities, family, housing, etc.:
"The Joy of Retirement: Finding Happiness, Freedom, and the Life You've Always Wanted":
Amazon.com: The Joy of Retirement: Finding Happiness, Freedom, and the Life You've Always Wanted (Audible Audio Edition): David C. Borchard, Patricia A. Donohoe, Sean Pratt, LLC Gildan Media: Books
"My Next Phase: The Personality-Based Guide to Your Best Retirement":
My Next Phase: The Personality-Based Guide to Your Best Retirement: Eric Sundstrom, Randy Burnham, Michael Burnham: 9780446581172: Amazon.com: Books
"Comfort Zones: Planning a Fulfilling Retirement":
Comfort Zones: Planning a Fulfilling Retirement, 5th Edition: Marion E. Haynes: 9781592009909: Amazon.com: Books
"The Joy of Retirement: Finding Happiness, Freedom, and the Life You've Always Wanted":
Amazon.com: The Joy of Retirement: Finding Happiness, Freedom, and the Life You've Always Wanted (Audible Audio Edition): David C. Borchard, Patricia A. Donohoe, Sean Pratt, LLC Gildan Media: Books
"My Next Phase: The Personality-Based Guide to Your Best Retirement":
My Next Phase: The Personality-Based Guide to Your Best Retirement: Eric Sundstrom, Randy Burnham, Michael Burnham: 9780446581172: Amazon.com: Books
"Comfort Zones: Planning a Fulfilling Retirement":
Comfort Zones: Planning a Fulfilling Retirement, 5th Edition: Marion E. Haynes: 9781592009909: Amazon.com: Books
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