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

What happens when the career you built your life around stops feeling like it fits? Today, I’m talking to Jordan Grummet about what it really looks like to wrestle with purpose—especially during big life transitions like retirement.

Jordan opens up about losing his father at a young age, pursuing medicine to honor his legacy, and eventually realizing that career wasn’t fulfilling him. We covered the struggle between societal expectations and our own authentic path, and how to find meaning after a life-altering shift.

Jordan, an author and host of the Earn & Invest podcast, brings a perspective shaped by both his work in hospice care and his own experience of stepping away from a path that no longer felt right.

It’s a conversation about what happens when we let go of old identities and start figuring out what comes next.

In this episode, you’ll hear:

Why purpose feels like such a monumental challenge in retirement

Jordan’s story of legacy, loss, and what medicine couldn’t give him

The slow burn of professional misalignment and how he woke up to it

How powerful external voices influence our life choices

The Purpose Code path forward into a more meaningful second act

Resources

jordangrumet.com

The Purpose Code

Only 5% of homes in the U.S. are moderately accessible. Stairways, sunken living rooms, poorly designed bathrooms, and trip hazards are just the start.

Greg Cantore’s journey has spanned bicycle mechanics to defense work and leading nonprofit programs. But his mother-in-law’s experience living in a house that wasn’t designed for her needs opened his eyes to the bigger issue.

After modifying her home, and later adjusting to her needs in assisted living, Greg realized there was a larger need for accessible, supportive home solutions. Today, he runs Little Deeds, a company dedicated to making homes safer and more accessible for aging individuals.

Your home should support you as you age. Find out how Greg is helping make that a reality for so many.

We discussed:

How universal design makes homes safer and more accessible as we age

Greg’s career journey—and how it led him to create Little Deeds

The challenges people face with aging in place

Simple ways to make your home safer and more accessible

Why it’s important to plan ahead with home modifications

Resources

Little Deeds