Here is our eclectic selection of books and websites related to reinventing yourself at middle age and beyond. We don’t like the word retirement. It’s kind of silly. To retire suggests pulling back. We’re more interested in leaning forward to what’s next… before it’s too late to change. If you have suggestions, please let us know.

– Debbie and Sam

[B]OLDER podcast

Browse all the episodes of Debbie’s podcast. Now in Season 5.


My Top Ten Thought Leaders on Modern Aging (Chip Conley in Wisdom Well, June 9, 2021)

How to Live Forever: the Enduring Power of Connecting the Generations by Marc Freedman (Public Affairs, 2020)

The Number: What Do You Need for the Rest of Your Life and What Will It Cost? by Lee Eisenberg

How Much Money Do I Need to Retire? by Todd Tresidder [Note: this is a great little book. The author makes the point that it’s not just about “the number.” It’s about adjusting your lifestyle and cutting costs.]

The Big Shift: Navigating the New Stage Beyond Midlife by Marc Freedman

The Encore Career Handbook: How to Make a Living and a Difference in the Second Half of Life by Marci Alboher

The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future by Chris Guillebeau

New Job, New You: A Guide to Reinventing Yourself in a Bright New Career by Alexandra Levit

What Color Is Your Parachute? For Retirement by Richard N. Bolles and John E. Nelson

Retire Retirement: Career Strategies for the Boomer Generation by Tamara Erickson

How to Travel the World on $50 a Day: Travel Cheaper, Longer, Smarter by Matt Kepnes (aka

The First 20 Hours: How to Learn Anything Fast by Josh Kaufman



Wisdom Well (daily blog by Chip Conley)

The Art of Non-Conformity (Chris Guillebeau’s blog)

The New Old Age (Paula Span in the New York Times)

Road Scholar (this used to be called Elderhostel)

AARP’s Recareering

Booming – The New York Times (discontinued but a big archive)