April 23, 2025

Richard Eisenberg is back. And this time, we’re diving into what his unretirement looks like now. 

If you don’t know Richard’s story, he’s an “unretired” journalist who writes a column for MarketWatch and freelances for Next Avenue, Fortune, AARP, and Fodor’s. Richard calls this chapter “unretirement” — living it with purpose and intention.

Before all that, he was an editor at Next Avenue and Money magazine, and held senior roles at Yahoo! and Good Housekeeping. He’s also the author of two personal finance books and a proud Northwestern grad.

In our conversation, Richard shares his latest stories on medical debt, telehealth access, and the renewed value of travel advisors. He also opens up about caring for his mom during her dementia journey and what it taught him about starting financial conversations early.

Listen in to hear what Richard’s been up to since the last time we spoke.

We discussed:

• What “unretirement” really looks like in practice
• The importance of having early financial conversations with aging parents
• Why telehealth access matters—and what could happen if it’s rolled back
• A fresh look at travel advisors and how they’re evolving
• Richard’s book recommendations and resources for deeper learning
• The challenge of caregiving for aging parents with dementia

Resources

The View From Unretirement
Next Avenue
Fortune | Richard Eisenberg
Fodor’s Travel 

Friends Talk Money

The Friday Afternoon Club by Griffin Dunne
The Purpose Code by Jordan Grumet
Retirement Intelligence by Robert Laura